TY  - JOUR
AU  - Jovanović, Dunja
AU  - Filipović, Ana
AU  - Janjić, Goran
AU  - Lazarević-Pašti, Tamara
AU  - Džambaski, Zdravko
AU  - Bondžić, Bojan
AU  - Bondžić, Aleksandra
PY  - 2024
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7423
AB  - We have synthesized 22 C-1 functionalized-N-aryl-1,2,3,4-tetrahydroisoquinoline derivatives showing biological activities towards cholinergic enzymes. Synthesis was performed using visible-light-promoted photo-redox chemistry, starting from a common intermediate, and the application of this synthetic methodology drastically simplified synthetic routes and purification of desired compounds. All synthesized derivates were divided into four groups based on the substituents in the C-1 position, and their inhibition potencies towards two cholinergic enzymes, acetyl- and butyrylcholinesterase were evaluated. Most potent derivatives were selected, and kinetic analysis was further carried out to obtain insights into the mechanisms of inhibition of these two enzymes. Further validation of the mode of inhibition of cholinergic enzymes by the two most potent THIQ compounds, 3c and 3i, was performed using fluorescence-quenching titration studies. Molecular docking studies further confirmed the proposed mechanism of enzymes’ inhibition. In silico predictions of physicochemical properties, pharmacokinetics, drug-likeness, and medicinal chemistry friendliness of the selected most potent derivatives were performed using Swiss ADME tool. This was followed by UPLC-assisted log P determination and in vitro BBB permeability studies performed in order to assess the potential of the synthesized compounds to pass the BBB.
PB  - MDPI
T2  - International Journal of Molecular Sciences
T1  - Targeting Alzheimer’s Disease: Evaluating the Efficacy of C-1 Functionalized N-Aryl-Tetrahydroisoquinolines as Cholinergic Enzyme Inhibitors and Promising Therapeutic Candidates
VL  - 25
IS  - 2
SP  - 1033
DO  - 10.3390/ijms25021033
ER  - 

@article{
author = "Jovanović, Dunja and Filipović, Ana and Janjić, Goran and Lazarević-Pašti, Tamara and Džambaski, Zdravko and Bondžić, Bojan and Bondžić, Aleksandra",
year = "2024",
abstract = "We have synthesized 22 C-1 functionalized-N-aryl-1,2,3,4-tetrahydroisoquinoline derivatives showing biological activities towards cholinergic enzymes. Synthesis was performed using visible-light-promoted photo-redox chemistry, starting from a common intermediate, and the application of this synthetic methodology drastically simplified synthetic routes and purification of desired compounds. All synthesized derivates were divided into four groups based on the substituents in the C-1 position, and their inhibition potencies towards two cholinergic enzymes, acetyl- and butyrylcholinesterase were evaluated. Most potent derivatives were selected, and kinetic analysis was further carried out to obtain insights into the mechanisms of inhibition of these two enzymes. Further validation of the mode of inhibition of cholinergic enzymes by the two most potent THIQ compounds, 3c and 3i, was performed using fluorescence-quenching titration studies. Molecular docking studies further confirmed the proposed mechanism of enzymes’ inhibition. In silico predictions of physicochemical properties, pharmacokinetics, drug-likeness, and medicinal chemistry friendliness of the selected most potent derivatives were performed using Swiss ADME tool. This was followed by UPLC-assisted log P determination and in vitro BBB permeability studies performed in order to assess the potential of the synthesized compounds to pass the BBB.",
publisher = "MDPI",
journal = "International Journal of Molecular Sciences",
title = "Targeting Alzheimer’s Disease: Evaluating the Efficacy of C-1 Functionalized N-Aryl-Tetrahydroisoquinolines as Cholinergic Enzyme Inhibitors and Promising Therapeutic Candidates",
volume = "25",
number = "2",
pages = "1033",
doi = "10.3390/ijms25021033"
}

Jovanović, D., Filipović, A., Janjić, G., Lazarević-Pašti, T., Džambaski, Z., Bondžić, B.,& Bondžić, A.. (2024). Targeting Alzheimer’s Disease: Evaluating the Efficacy of C-1 Functionalized N-Aryl-Tetrahydroisoquinolines as Cholinergic Enzyme Inhibitors and Promising Therapeutic Candidates. in International Journal of Molecular Sciences
MDPI., 25(2), 1033.
https://doi.org/10.3390/ijms25021033

Jovanović D, Filipović A, Janjić G, Lazarević-Pašti T, Džambaski Z, Bondžić B, Bondžić A. Targeting Alzheimer’s Disease: Evaluating the Efficacy of C-1 Functionalized N-Aryl-Tetrahydroisoquinolines as Cholinergic Enzyme Inhibitors and Promising Therapeutic Candidates. in International Journal of Molecular Sciences. 2024;25(2):1033.
doi:10.3390/ijms25021033 .

Jovanović, Dunja, Filipović, Ana, Janjić, Goran, Lazarević-Pašti, Tamara, Džambaski, Zdravko, Bondžić, Bojan, Bondžić, Aleksandra, "Targeting Alzheimer’s Disease: Evaluating the Efficacy of C-1 Functionalized N-Aryl-Tetrahydroisoquinolines as Cholinergic Enzyme Inhibitors and Promising Therapeutic Candidates" in International Journal of Molecular Sciences, 25, no. 2 (2024):1033,
https://doi.org/10.3390/ijms25021033 . .

TY  - JOUR
AU  - Janjić, Goran
AU  - Marinović, Sanja
AU  - Jadranin, Milka
AU  - Ajduković, Marija
AU  - Đorđević, Ivana
AU  - Petkovic-Benazzouz, Marija
AU  - Milutinović Nikolić, Aleksandra
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6693
AB  - The catalytic degradation of hazardous organic contaminants in industrial wastewater is a promising technology. Reactions of tartrazine, the synthetic yellow azo dye, with Oxone® in the presence of catalyst in strong acidic condition (pH 2), were detected by using UV–Vis spectroscopy. In order to extend the applicability profile of Co-supported Al-pillared montmorillonite catalyst an investigation of Oxone® induced reactions were performed in extreme acidic environment. The products of the reactions were identified by liquid chromatography–mass spectrometry (LC-MS). Along with the catalytic decomposition of tartrazine induced by radical attack (confirmed as unique reaction path under neutral and alkaline conditions), the formation of tartrazine derivatives by reaction of nucleophilic addition was also detected. The presence of derivatives under acidic conditions slowed down the hydrolysis of tartrazine diazo bond in comparison to the reactions in neutral environment. Nevertheless, the reaction in acidic conditions (pH 2) is faster than the one conducted in alkaline conditions (pH 11). Theoretical calculations were used to complete and clarify the mechanisms of tartrazine derivatization and degradation, as well as to predict the UV–Vis spectra of compounds which could serve as predictors of certain reaction phases. ECOSAR program, used to estimate toxicological profile of compounds to aquatic animals, indicated an increase in the harmfulness of the compounds identified by LC-MS as degradation products from the reaction conducted for 240min. It could be concluded that an intensification of the process parameters (higher concentration of Oxone®, higher catalyst loading, increased reaction time, etc.) is needed in order to obtain only biodegradable products.
PB  - Elsevier
T2  - Environmental Pollution
T1  - Degradation of tartrazine by Oxone® in the presence of cobalt based catalyst supported on pillared montmorillonite - Efficient technology even in extreme conditions
VL  - 331
SP  - 121863
DO  - 10.1016/j.envpol.2023.121863
ER  - 

@article{
author = "Janjić, Goran and Marinović, Sanja and Jadranin, Milka and Ajduković, Marija and Đorđević, Ivana and Petkovic-Benazzouz, Marija and Milutinović Nikolić, Aleksandra",
year = "2023",
abstract = "The catalytic degradation of hazardous organic contaminants in industrial wastewater is a promising technology. Reactions of tartrazine, the synthetic yellow azo dye, with Oxone® in the presence of catalyst in strong acidic condition (pH 2), were detected by using UV–Vis spectroscopy. In order to extend the applicability profile of Co-supported Al-pillared montmorillonite catalyst an investigation of Oxone® induced reactions were performed in extreme acidic environment. The products of the reactions were identified by liquid chromatography–mass spectrometry (LC-MS). Along with the catalytic decomposition of tartrazine induced by radical attack (confirmed as unique reaction path under neutral and alkaline conditions), the formation of tartrazine derivatives by reaction of nucleophilic addition was also detected. The presence of derivatives under acidic conditions slowed down the hydrolysis of tartrazine diazo bond in comparison to the reactions in neutral environment. Nevertheless, the reaction in acidic conditions (pH 2) is faster than the one conducted in alkaline conditions (pH 11). Theoretical calculations were used to complete and clarify the mechanisms of tartrazine derivatization and degradation, as well as to predict the UV–Vis spectra of compounds which could serve as predictors of certain reaction phases. ECOSAR program, used to estimate toxicological profile of compounds to aquatic animals, indicated an increase in the harmfulness of the compounds identified by LC-MS as degradation products from the reaction conducted for 240min. It could be concluded that an intensification of the process parameters (higher concentration of Oxone®, higher catalyst loading, increased reaction time, etc.) is needed in order to obtain only biodegradable products.",
publisher = "Elsevier",
journal = "Environmental Pollution",
title = "Degradation of tartrazine by Oxone® in the presence of cobalt based catalyst supported on pillared montmorillonite - Efficient technology even in extreme conditions",
volume = "331",
pages = "121863",
doi = "10.1016/j.envpol.2023.121863"
}

Janjić, G., Marinović, S., Jadranin, M., Ajduković, M., Đorđević, I., Petkovic-Benazzouz, M.,& Milutinović Nikolić, A.. (2023). Degradation of tartrazine by Oxone® in the presence of cobalt based catalyst supported on pillared montmorillonite - Efficient technology even in extreme conditions. in Environmental Pollution
Elsevier., 331, 121863.
https://doi.org/10.1016/j.envpol.2023.121863

Janjić G, Marinović S, Jadranin M, Ajduković M, Đorđević I, Petkovic-Benazzouz M, Milutinović Nikolić A. Degradation of tartrazine by Oxone® in the presence of cobalt based catalyst supported on pillared montmorillonite - Efficient technology even in extreme conditions. in Environmental Pollution. 2023;331:121863.
doi:10.1016/j.envpol.2023.121863 .

Janjić, Goran, Marinović, Sanja, Jadranin, Milka, Ajduković, Marija, Đorđević, Ivana, Petkovic-Benazzouz, Marija, Milutinović Nikolić, Aleksandra, "Degradation of tartrazine by Oxone® in the presence of cobalt based catalyst supported on pillared montmorillonite - Efficient technology even in extreme conditions" in Environmental Pollution, 331 (2023):121863,
https://doi.org/10.1016/j.envpol.2023.121863 . .

TY  - CONF
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Trišović, Nemanja
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7350
AB  - Proučavano jedinjenje (slika 1) sintetisano je polazeći od cikloheksanona Bučerer- Bergsovom reakcijom i naknadnim acilovanjem dobijenog spirohidantoina. Izgradnja kristalne strukture ovog jedinjenja proučavana je sa aspekta doprinosa jednostavnih dimernih motiva koji se uspostavljaju preko različitih intermolekulskih interakcija.Intermolekulske interakcije dodatno su proučavane pomoću Hiršfeldovih površina i 2D grafičkih prikaza otisaka interakcija. Kristalna struktura, naime, zadržava motiv koji se često sreće kod derivata hidantoina, u kome su dva inverzano orijentisana molekula povezana parom N–H···O vodoničnih veza. Ovaj motiv formira dva tipa dvostrukih lanaca, koji dalje grade sloj (slika 2). Osim toga, slabe C–H⋯O interakcije zajedno sa disperzionim interakcijama (π-π i hidrofobne interakcije) identifikovane su u ovoj kristalnoj strukturi. Kristalografski	podaci:		C19H24N2O3, Mr = 328,4, trikliničan sistem, prostorna grupa P–1, a = 6,2810(2),	b = 12,0586(4),	c = 12,1852(5) Å,α = 77,624(3),	β = 81,039(3),	γ = 79,111(3) °,  V = 878.81(6) Å3, Z = 2, F(000) = 352, ρx = 1,380 g cm–3,µ(MoKα) = 0,084 mm–1. Utačnjavanje sa F2 (220 parametara) dalo je R1 = 0,0520, wR2 = 0,1199, S = 1,033 za sve podatke i R1 = 0,0443 za 3232 uočenih refleksija sa I ≥ 2σ(I).
AB  - The title compound (Figure 1) was prepared from cyclohexanone in the Bucherer-Bergs reaction, followed by acylation of the obtained spirohydantoin. Formation of the crystal structure of this compound was analysed in terms of a number of simple dimeric motifs which are associated with different intermolecular interactions. The crystal structure retains the motif commonly found in hydantoin derivatives, where two molecules related by inversion are linked by a pair of N–H O hydrogen bonds. This motif is involved in two types of double chains, whichfurther form a layer (Figure 2). Intermolecular interactions were also investigated using Hirshfeld surface analysis and 2D fingerprint analysis. Weak C–H⋯O interactions together with thedispersion interactions (π-π and hydrophobic) as the source of attraction are identified in this crystal structure.Crystal data: C19H24N2O3, Mr = 328.4, triclinic system, space group P–1, a = 6.2810(2), b = 12.0586(4), c = 12.1852(5) Å, a = 77.624(3), β = 81.039(3), γ = 79.111(3) °, V = 878.81(6) Å3, Z = 2, F(000) = 352,ρx = 1.380 g cm–3, µ(MoKa) == 0.084 mm–1. The refinement on F2 (220 parameters) yielded R1 = 0.0520, wR2 = 0.1199,S = 1.033 for all data, and R1 = 0.0443 for 3232 observed reflections with I ≥ 2σ(I).
PB  - Beograd : Srpsko kristalografsko društvo
C3  - 28th Conference of the Serbian Crystallographic Society, Abstracts, Čačak, Serbia / XXVIII Konferencija Srpskog kristalografskog društva, Izvodi radova, Čačak, Srbija
T1  - Uloga strukturnih motiva u izgradnji supramolekulske arhitekture 3-(4-terc-butilbenzoil)-1,3-diazaspiro[4.5]Dekan-2,4-diona
T1  - Role of structural motifs in formation of the supramolecular architecture of 3-(4-tert-butylbenzoyl)-1,3-diazaspiro[4.5]Decane-2,4-dione
SP  - 56
EP  - 57
UR  - https://hdl.handle.net/21.15107/rcub_cer_7350
ER  - 

@conference{
author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Janjić, Goran and Đorđević, Ivana and Trišović, Nemanja",
year = "2023",
abstract = "Proučavano jedinjenje (slika 1) sintetisano je polazeći od cikloheksanona Bučerer- Bergsovom reakcijom i naknadnim acilovanjem dobijenog spirohidantoina. Izgradnja kristalne strukture ovog jedinjenja proučavana je sa aspekta doprinosa jednostavnih dimernih motiva koji se uspostavljaju preko različitih intermolekulskih interakcija.Intermolekulske interakcije dodatno su proučavane pomoću Hiršfeldovih površina i 2D grafičkih prikaza otisaka interakcija. Kristalna struktura, naime, zadržava motiv koji se često sreće kod derivata hidantoina, u kome su dva inverzano orijentisana molekula povezana parom N–H···O vodoničnih veza. Ovaj motiv formira dva tipa dvostrukih lanaca, koji dalje grade sloj (slika 2). Osim toga, slabe C–H⋯O interakcije zajedno sa disperzionim interakcijama (π-π i hidrofobne interakcije) identifikovane su u ovoj kristalnoj strukturi. Kristalografski	podaci:		C19H24N2O3, Mr = 328,4, trikliničan sistem, prostorna grupa P–1, a = 6,2810(2),	b = 12,0586(4),	c = 12,1852(5) Å,α = 77,624(3),	β = 81,039(3),	γ = 79,111(3) °,  V = 878.81(6) Å3, Z = 2, F(000) = 352, ρx = 1,380 g cm–3,µ(MoKα) = 0,084 mm–1. Utačnjavanje sa F2 (220 parametara) dalo je R1 = 0,0520, wR2 = 0,1199, S = 1,033 za sve podatke i R1 = 0,0443 za 3232 uočenih refleksija sa I ≥ 2σ(I)., The title compound (Figure 1) was prepared from cyclohexanone in the Bucherer-Bergs reaction, followed by acylation of the obtained spirohydantoin. Formation of the crystal structure of this compound was analysed in terms of a number of simple dimeric motifs which are associated with different intermolecular interactions. The crystal structure retains the motif commonly found in hydantoin derivatives, where two molecules related by inversion are linked by a pair of N–H O hydrogen bonds. This motif is involved in two types of double chains, whichfurther form a layer (Figure 2). Intermolecular interactions were also investigated using Hirshfeld surface analysis and 2D fingerprint analysis. Weak C–H⋯O interactions together with thedispersion interactions (π-π and hydrophobic) as the source of attraction are identified in this crystal structure.Crystal data: C19H24N2O3, Mr = 328.4, triclinic system, space group P–1, a = 6.2810(2), b = 12.0586(4), c = 12.1852(5) Å, a = 77.624(3), β = 81.039(3), γ = 79.111(3) °, V = 878.81(6) Å3, Z = 2, F(000) = 352,ρx = 1.380 g cm–3, µ(MoKa) == 0.084 mm–1. The refinement on F2 (220 parameters) yielded R1 = 0.0520, wR2 = 0.1199,S = 1.033 for all data, and R1 = 0.0443 for 3232 observed reflections with I ≥ 2σ(I).",
publisher = "Beograd : Srpsko kristalografsko društvo",
journal = "28th Conference of the Serbian Crystallographic Society, Abstracts, Čačak, Serbia / XXVIII Konferencija Srpskog kristalografskog društva, Izvodi radova, Čačak, Srbija",
title = "Uloga strukturnih motiva u izgradnji supramolekulske arhitekture 3-(4-terc-butilbenzoil)-1,3-diazaspiro[4.5]Dekan-2,4-diona, Role of structural motifs in formation of the supramolecular architecture of 3-(4-tert-butylbenzoyl)-1,3-diazaspiro[4.5]Decane-2,4-dione",
pages = "56-57",
url = "https://hdl.handle.net/21.15107/rcub_cer_7350"
}

Lazić, A., Radovanović, L., Rogan, J., Janjić, G., Đorđević, I.,& Trišović, N.. (2023). Uloga strukturnih motiva u izgradnji supramolekulske arhitekture 3-(4-terc-butilbenzoil)-1,3-diazaspiro[4.5]Dekan-2,4-diona. in 28th Conference of the Serbian Crystallographic Society, Abstracts, Čačak, Serbia / XXVIII Konferencija Srpskog kristalografskog društva, Izvodi radova, Čačak, Srbija
Beograd : Srpsko kristalografsko društvo., 56-57.
https://hdl.handle.net/21.15107/rcub_cer_7350

Lazić A, Radovanović L, Rogan J, Janjić G, Đorđević I, Trišović N. Uloga strukturnih motiva u izgradnji supramolekulske arhitekture 3-(4-terc-butilbenzoil)-1,3-diazaspiro[4.5]Dekan-2,4-diona. in 28th Conference of the Serbian Crystallographic Society, Abstracts, Čačak, Serbia / XXVIII Konferencija Srpskog kristalografskog društva, Izvodi radova, Čačak, Srbija. 2023;:56-57.
https://hdl.handle.net/21.15107/rcub_cer_7350 .

Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Janjić, Goran, Đorđević, Ivana, Trišović, Nemanja, "Uloga strukturnih motiva u izgradnji supramolekulske arhitekture 3-(4-terc-butilbenzoil)-1,3-diazaspiro[4.5]Dekan-2,4-diona" in 28th Conference of the Serbian Crystallographic Society, Abstracts, Čačak, Serbia / XXVIII Konferencija Srpskog kristalografskog društva, Izvodi radova, Čačak, Srbija (2023):56-57,
https://hdl.handle.net/21.15107/rcub_cer_7350 .

TY  - CONF
AU  - Milojkov, Dušan
AU  - Marković, Gordana
AU  - Sokić, Miroslav
AU  - Manojlović, Vaso
AU  - Mutavdžić, Dragosav
AU  - Janjić, Goran
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7341
AB  - Fluorapatite (FAP) crystals have drawn significant interest over the last few decades as important hosts matrix for optically active trivalent rare earth ions, due to the strong crystal field splitting and large transition cross-sections. Nano-sized FAP particles doped with rare earth ions have been extensively studied as luminescent materials for biomedical applications for cell labeling and bioimaging, as well as antimicrobial agents for therapeutics.Fluorapatite nanoparticles doped with praseodymium ions (Pr3+) were prepared by the co precipitation method and characterized. The different number of Pr3+ (4f2) transitions in the ultraviolet and visible parts of the spectrum was investigated by photoluminescence spectroscopy. Multivariate Curve Resolution–Alternating Least Squares (MCR-ALS) analyses of fluorescence spectra and ab initio calculation indicated that Pr3+ ions are preferentially substituted Ca2 (6h) sites in FAP lattice. In addition to the substitution of cations, there is also the substitution of anionic species such as OH-, CO32-, and NO3-, which are confirmed by the CHNS method. The obtained samples were tested as bioimaging and antibacterial agents and can potentially be used for further biomedical research.
PB  - Belgrade : Serbian Ceramic Society
C3  - Program and the Book of Abstracts, The Eleventh Serbian Ceramic Society Conference Advanced Ceramics and Application, September 18-20, 2023
T1  - Luminescence transitions of Pr3+ (4f2) in fluorapatite nanocrystals for  potential biomedical application
SP  - 38
EP  - 39
UR  - https://hdl.handle.net/21.15107/rcub_cer_7341
ER  - 

@conference{
author = "Milojkov, Dušan and Marković, Gordana and Sokić, Miroslav and Manojlović, Vaso and Mutavdžić, Dragosav and Janjić, Goran",
year = "2023",
abstract = "Fluorapatite (FAP) crystals have drawn significant interest over the last few decades as important hosts matrix for optically active trivalent rare earth ions, due to the strong crystal field splitting and large transition cross-sections. Nano-sized FAP particles doped with rare earth ions have been extensively studied as luminescent materials for biomedical applications for cell labeling and bioimaging, as well as antimicrobial agents for therapeutics.Fluorapatite nanoparticles doped with praseodymium ions (Pr3+) were prepared by the co precipitation method and characterized. The different number of Pr3+ (4f2) transitions in the ultraviolet and visible parts of the spectrum was investigated by photoluminescence spectroscopy. Multivariate Curve Resolution–Alternating Least Squares (MCR-ALS) analyses of fluorescence spectra and ab initio calculation indicated that Pr3+ ions are preferentially substituted Ca2 (6h) sites in FAP lattice. In addition to the substitution of cations, there is also the substitution of anionic species such as OH-, CO32-, and NO3-, which are confirmed by the CHNS method. The obtained samples were tested as bioimaging and antibacterial agents and can potentially be used for further biomedical research.",
publisher = "Belgrade : Serbian Ceramic Society",
journal = "Program and the Book of Abstracts, The Eleventh Serbian Ceramic Society Conference Advanced Ceramics and Application, September 18-20, 2023",
title = "Luminescence transitions of Pr3+ (4f2) in fluorapatite nanocrystals for  potential biomedical application",
pages = "38-39",
url = "https://hdl.handle.net/21.15107/rcub_cer_7341"
}

Milojkov, D., Marković, G., Sokić, M., Manojlović, V., Mutavdžić, D.,& Janjić, G.. (2023). Luminescence transitions of Pr3+ (4f2) in fluorapatite nanocrystals for  potential biomedical application. in Program and the Book of Abstracts, The Eleventh Serbian Ceramic Society Conference Advanced Ceramics and Application, September 18-20, 2023
Belgrade : Serbian Ceramic Society., 38-39.
https://hdl.handle.net/21.15107/rcub_cer_7341

Milojkov D, Marković G, Sokić M, Manojlović V, Mutavdžić D, Janjić G. Luminescence transitions of Pr3+ (4f2) in fluorapatite nanocrystals for  potential biomedical application. in Program and the Book of Abstracts, The Eleventh Serbian Ceramic Society Conference Advanced Ceramics and Application, September 18-20, 2023. 2023;:38-39.
https://hdl.handle.net/21.15107/rcub_cer_7341 .

Milojkov, Dušan, Marković, Gordana, Sokić, Miroslav, Manojlović, Vaso, Mutavdžić, Dragosav, Janjić, Goran, "Luminescence transitions of Pr3+ (4f2) in fluorapatite nanocrystals for  potential biomedical application" in Program and the Book of Abstracts, The Eleventh Serbian Ceramic Society Conference Advanced Ceramics and Application, September 18-20, 2023 (2023):38-39,
https://hdl.handle.net/21.15107/rcub_cer_7341 .

TY  - CONF
AU  - Lazić, Anita
AU  - Đorđević, Ivana
AU  - Radovanović, Lidija
AU  - Popović, Dragan
AU  - Rogan, Jelena
AU  - Trišović, Nemanja
AU  - Janjić, Goran
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6816
AB  - The hierarchical development of the crystal structure of racemic 3-(4-methoxybenzyl)-6,7- benzo-1,3-diazaspiro[4.5]decane-2,4-dione was analyzed through cooperativity of various homo  and heterochiral dimeric motifs associated with the presence of different intermolecular  interactions, namely strong N–H···O and weaker C–H···O, C–H···π and PILOs.1 Although a  bigger number of the contacts in the environment of the tetralin unit results from its larger  contact surface, the 4-methoxybenzyl unit provides a greater contribution to the overall  stabilization. In addition, the investigated compound is identified as a potential inhibitor of  kinase enzymes and AG protein-coupled receptors, with a slightly higher affinity for the later  enzyme. An analysis of the nature of the amino acid residues around the tetralin and 4-methoxy  benzyl units revealed that interactions with nonpolar groups are the most prevalent and even  more numerous than interactions with other amino acid residues (polar, positive and negative).
PB  - COST Action CA21101 "COSY"
C3  - Book of abstracts - COST Training School, COST action CA21101 COSY, "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications," 19th - 22nd September, 2023, Belgrade
T1  - Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone
SP  - 47
EP  - 47
UR  - https://hdl.handle.net/21.15107/rcub_cer_6816
ER  - 

@conference{
author = "Lazić, Anita and Đorđević, Ivana and Radovanović, Lidija and Popović, Dragan and Rogan, Jelena and Trišović, Nemanja and Janjić, Goran",
year = "2023",
abstract = "The hierarchical development of the crystal structure of racemic 3-(4-methoxybenzyl)-6,7- benzo-1,3-diazaspiro[4.5]decane-2,4-dione was analyzed through cooperativity of various homo  and heterochiral dimeric motifs associated with the presence of different intermolecular  interactions, namely strong N–H···O and weaker C–H···O, C–H···π and PILOs.1 Although a  bigger number of the contacts in the environment of the tetralin unit results from its larger  contact surface, the 4-methoxybenzyl unit provides a greater contribution to the overall  stabilization. In addition, the investigated compound is identified as a potential inhibitor of  kinase enzymes and AG protein-coupled receptors, with a slightly higher affinity for the later  enzyme. An analysis of the nature of the amino acid residues around the tetralin and 4-methoxy  benzyl units revealed that interactions with nonpolar groups are the most prevalent and even  more numerous than interactions with other amino acid residues (polar, positive and negative).",
publisher = "COST Action CA21101 "COSY"",
journal = "Book of abstracts - COST Training School, COST action CA21101 COSY, "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications," 19th - 22nd September, 2023, Belgrade",
title = "Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone",
pages = "47-47",
url = "https://hdl.handle.net/21.15107/rcub_cer_6816"
}

Lazić, A., Đorđević, I., Radovanović, L., Popović, D., Rogan, J., Trišović, N.,& Janjić, G.. (2023). Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone. in Book of abstracts - COST Training School, COST action CA21101 COSY, "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications," 19th - 22nd September, 2023, Belgrade
COST Action CA21101 "COSY"., 47-47.
https://hdl.handle.net/21.15107/rcub_cer_6816

Lazić A, Đorđević I, Radovanović L, Popović D, Rogan J, Trišović N, Janjić G. Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone. in Book of abstracts - COST Training School, COST action CA21101 COSY, "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications," 19th - 22nd September, 2023, Belgrade. 2023;:47-47.
https://hdl.handle.net/21.15107/rcub_cer_6816 .

Lazić, Anita, Đorđević, Ivana, Radovanović, Lidija, Popović, Dragan, Rogan, Jelena, Trišović, Nemanja, Janjić, Goran, "Self-discriminating assembly and biorecognition of a spirohydantoin derived from α-tetralone" in Book of abstracts - COST Training School, COST action CA21101 COSY, "Multiscale modeling of the properties of compounds: From isolated molecules to 3D materials relevant for industrial and astrophysical applications," 19th - 22nd September, 2023, Belgrade (2023):47-47,
https://hdl.handle.net/21.15107/rcub_cer_6816 .

TY  - CONF
AU  - Suručić, Ljiljana T.
AU  - Sandić, Zvjezdana
AU  - Stanković, Aljoša
AU  - Janjić, Goran
AU  - Tadić, Tamara
AU  - Marković, Bojana
AU  - Onjia, Antonije
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7000
AB  - The contamination of water with chromium is a global issue that is especially severe in developing countries with intensive mining and heavy industry (South Africa, Pakistan, and India) [1,2]. Trivalent Cr(III) and hexavalent Cr(VI) are the most common forms found in effluent water. Whereas trivalent chromium is a micronutrient (25–35 g/day) involved in the metabolism of lipids and carbohydrates [3,4], hexavalent chromium is exceedingly toxic, teratogenic, and mutagenic. Particularly concerning are its high solubility in water, mobility in detritus, and potential for bioaccumulation in living tissues. Due to these factors, hexavalent chromium has been the subject of numerous studies, especially its removal from effluent [5,6]. These studies have demonstrated that sorption is a highly effective and relatively simple technique for chromium removal from wastewater. In terms of this, magnetic heavy metals nanosorbents derived from inorganic compounds and polymers [7-9] are incredibly intriguing, because they could have been readily extracted from the mixture using an external magnetic field. The sorption investigation of hexavalent chromium in aqueous solutions on the magnetic aminofunctionalized polymer nanocomposite based on glycidyl methacrylate, m-PGMA revealed its highly selectivity and efficiency. [10,11]. The binding mechanism of hexavalent chromium ions onto m-PGMA was investigated using kinetic, equilibrium, and thermodynamic experiments as well as molecular modeling techniques (theoretical quantum-chemical calculations) [12-15]. It was observed that the process occurs in two phases. In the first phase, electrostatic interactions attract hexavalent chromium ions to the surface of the sorbent via the active sites (amino and APTMS groups). Cr(VI) is then converted to Cr(III) ions, which can coordinate with amino or hydroxyl groups on the surface of the sorbent [16]. The trivalent chromium ions that persist in the solution or on the surface of the sorbent are less hazardous than the initial hexavalent form. The application of m-PGMA sorbent enables the transformation of the toxic form of chromium into a less hazardous form, which is significant due to the possibility of sorbent regeneration and the subsequent processing of the solution following sorption.
PB  - Banja Luka, Republic of Srpska, B&H : University PIM
C3  - The Book of Abstracts - XII International conference on Social and Technological Development – STED 2023,  June, 15-18, 2023, Trebinje / Zbornik izvoda radova - XII međunarodna konferencija o društvenom i tehnološkom razvoju – STED 2023, 15-18. juni 2023. godine, trebinje
T1  - Reductive removal of hexavalent chromium in aqueous solution by magnetic amino-functionalized polymer nanocomposite
SP  - 118
EP  - 120
UR  - https://hdl.handle.net/21.15107/rcub_cer_7000
ER  - 

@conference{
author = "Suručić, Ljiljana T. and Sandić, Zvjezdana and Stanković, Aljoša and Janjić, Goran and Tadić, Tamara and Marković, Bojana and Onjia, Antonije",
year = "2023",
abstract = "The contamination of water with chromium is a global issue that is especially severe in developing countries with intensive mining and heavy industry (South Africa, Pakistan, and India) [1,2]. Trivalent Cr(III) and hexavalent Cr(VI) are the most common forms found in effluent water. Whereas trivalent chromium is a micronutrient (25–35 g/day) involved in the metabolism of lipids and carbohydrates [3,4], hexavalent chromium is exceedingly toxic, teratogenic, and mutagenic. Particularly concerning are its high solubility in water, mobility in detritus, and potential for bioaccumulation in living tissues. Due to these factors, hexavalent chromium has been the subject of numerous studies, especially its removal from effluent [5,6]. These studies have demonstrated that sorption is a highly effective and relatively simple technique for chromium removal from wastewater. In terms of this, magnetic heavy metals nanosorbents derived from inorganic compounds and polymers [7-9] are incredibly intriguing, because they could have been readily extracted from the mixture using an external magnetic field. The sorption investigation of hexavalent chromium in aqueous solutions on the magnetic aminofunctionalized polymer nanocomposite based on glycidyl methacrylate, m-PGMA revealed its highly selectivity and efficiency. [10,11]. The binding mechanism of hexavalent chromium ions onto m-PGMA was investigated using kinetic, equilibrium, and thermodynamic experiments as well as molecular modeling techniques (theoretical quantum-chemical calculations) [12-15]. It was observed that the process occurs in two phases. In the first phase, electrostatic interactions attract hexavalent chromium ions to the surface of the sorbent via the active sites (amino and APTMS groups). Cr(VI) is then converted to Cr(III) ions, which can coordinate with amino or hydroxyl groups on the surface of the sorbent [16]. The trivalent chromium ions that persist in the solution or on the surface of the sorbent are less hazardous than the initial hexavalent form. The application of m-PGMA sorbent enables the transformation of the toxic form of chromium into a less hazardous form, which is significant due to the possibility of sorbent regeneration and the subsequent processing of the solution following sorption.",
publisher = "Banja Luka, Republic of Srpska, B&H : University PIM",
journal = "The Book of Abstracts - XII International conference on Social and Technological Development – STED 2023,  June, 15-18, 2023, Trebinje / Zbornik izvoda radova - XII međunarodna konferencija o društvenom i tehnološkom razvoju – STED 2023, 15-18. juni 2023. godine, trebinje",
title = "Reductive removal of hexavalent chromium in aqueous solution by magnetic amino-functionalized polymer nanocomposite",
pages = "118-120",
url = "https://hdl.handle.net/21.15107/rcub_cer_7000"
}

Suručić, L. T., Sandić, Z., Stanković, A., Janjić, G., Tadić, T., Marković, B.,& Onjia, A.. (2023). Reductive removal of hexavalent chromium in aqueous solution by magnetic amino-functionalized polymer nanocomposite. in The Book of Abstracts - XII International conference on Social and Technological Development – STED 2023,  June, 15-18, 2023, Trebinje / Zbornik izvoda radova - XII međunarodna konferencija o društvenom i tehnološkom razvoju – STED 2023, 15-18. juni 2023. godine, trebinje
Banja Luka, Republic of Srpska, B&H : University PIM., 118-120.
https://hdl.handle.net/21.15107/rcub_cer_7000

Suručić LT, Sandić Z, Stanković A, Janjić G, Tadić T, Marković B, Onjia A. Reductive removal of hexavalent chromium in aqueous solution by magnetic amino-functionalized polymer nanocomposite. in The Book of Abstracts - XII International conference on Social and Technological Development – STED 2023,  June, 15-18, 2023, Trebinje / Zbornik izvoda radova - XII međunarodna konferencija o društvenom i tehnološkom razvoju – STED 2023, 15-18. juni 2023. godine, trebinje. 2023;:118-120.
https://hdl.handle.net/21.15107/rcub_cer_7000 .

Suručić, Ljiljana T., Sandić, Zvjezdana, Stanković, Aljoša, Janjić, Goran, Tadić, Tamara, Marković, Bojana, Onjia, Antonije, "Reductive removal of hexavalent chromium in aqueous solution by magnetic amino-functionalized polymer nanocomposite" in The Book of Abstracts - XII International conference on Social and Technological Development – STED 2023,  June, 15-18, 2023, Trebinje / Zbornik izvoda radova - XII međunarodna konferencija o društvenom i tehnološkom razvoju – STED 2023, 15-18. juni 2023. godine, trebinje (2023):118-120,
https://hdl.handle.net/21.15107/rcub_cer_7000 .

TY  - JOUR
AU  - Zornić, Sanja
AU  - Simović Marković, Bojana
AU  - Franich, Andjela A.
AU  - Janjić, Goran
AU  - Jadranin, Milka
AU  - Avdalović, Jelena
AU  - Rajković, Snežana
AU  - Živković, Marija D.
AU  - Arsenijević, Nebojša N.
AU  - Radosavljević, Gordana D.
AU  - Pantić, Jelena
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7213
AB  - Platinum-based drugs are widely recognized efficient anti-tumor agents, but faced with multiple undesirable effects. Here, four dinuclear platinum(II) complexes, [{Pt(1,2-pn)Cl}2(μ-pydz)]Cl2 (C1), [{Pt(ibn)Cl}2(μ-pydz)]Cl2 (C2), [{Pt(1,3-pn)Cl}2(μ-pydz)]Cl2 (C3) and [{Pt(1,3-pnd)Cl}2(μ-pydz)]Cl2 (C4), were designed (pydz is pyridazine, 1,2-pn is ( ±)-1,2-propylenediamine, ibn is 1,2-diamino-2-methylpropane, 1,3-pn is 1,3-propylenediamine, and 1,3-pnd is 1,3-pentanediamine). Interactions and binding ability of C1–C4 complexes with calf thymus DNA (CT-DNA) has been monitored by viscosity measurements, UV–Vis, fluorescence emission spectroscopy and molecular docking. Binding affinities of C1–C4 complexes to the bovine serum albumin (BSA) has been monitored by fluorescence emission spectroscopy. The tested complexes exhibit variable cytotoxicity toward different mouse and human tumor cell lines. C2 shows the most potent cytotoxicity, especially against mouse (4T1) and human (MDA-MD468) breast cancer cells in the dose- and time-dependent manner. C2 induces 4T1 and MDA-MD468 cells apoptosis, further documented by the accumulation of cells at sub-G1 phase of cell cycle and increase of executive caspase 3 and caspase 9 levels in 4T1 cells. C2 exhibits anti-proliferative effect through the reduction of cyclin D3 and cyclin E expression and elevation of inhibitor p27 level. Also, C2 downregulates c-Myc and phosphorylated AKT, oncogenes involved in the control of tumor cell proliferation and death. In order to measure the amount of platinum(II) complexes taken up by the cells, the cellular platinum content were quantified. However, C2 failed to inhibit mouse breast cancer growth in vivo. Chemical modifications of tested platinum(II) complexes might be a valuable approach for the improvement of their anti-tumor activity, especially effects in vivo.
PB  - Springer
T2  - Journal of Biological Inorganic Chemistry
T1  - Characterization, modes of interactions with DNA/BSA biomolecules and anti-tumor activity of newly synthesized dinuclear platinum(II) complexes with pyridazine bridging ligand
DO  - 10.1007/s00775-023-02030-0
ER  - 

@article{
author = "Zornić, Sanja and Simović Marković, Bojana and Franich, Andjela A. and Janjić, Goran and Jadranin, Milka and Avdalović, Jelena and Rajković, Snežana and Živković, Marija D. and Arsenijević, Nebojša N. and Radosavljević, Gordana D. and Pantić, Jelena",
year = "2023",
abstract = "Platinum-based drugs are widely recognized efficient anti-tumor agents, but faced with multiple undesirable effects. Here, four dinuclear platinum(II) complexes, [{Pt(1,2-pn)Cl}2(μ-pydz)]Cl2 (C1), [{Pt(ibn)Cl}2(μ-pydz)]Cl2 (C2), [{Pt(1,3-pn)Cl}2(μ-pydz)]Cl2 (C3) and [{Pt(1,3-pnd)Cl}2(μ-pydz)]Cl2 (C4), were designed (pydz is pyridazine, 1,2-pn is ( ±)-1,2-propylenediamine, ibn is 1,2-diamino-2-methylpropane, 1,3-pn is 1,3-propylenediamine, and 1,3-pnd is 1,3-pentanediamine). Interactions and binding ability of C1–C4 complexes with calf thymus DNA (CT-DNA) has been monitored by viscosity measurements, UV–Vis, fluorescence emission spectroscopy and molecular docking. Binding affinities of C1–C4 complexes to the bovine serum albumin (BSA) has been monitored by fluorescence emission spectroscopy. The tested complexes exhibit variable cytotoxicity toward different mouse and human tumor cell lines. C2 shows the most potent cytotoxicity, especially against mouse (4T1) and human (MDA-MD468) breast cancer cells in the dose- and time-dependent manner. C2 induces 4T1 and MDA-MD468 cells apoptosis, further documented by the accumulation of cells at sub-G1 phase of cell cycle and increase of executive caspase 3 and caspase 9 levels in 4T1 cells. C2 exhibits anti-proliferative effect through the reduction of cyclin D3 and cyclin E expression and elevation of inhibitor p27 level. Also, C2 downregulates c-Myc and phosphorylated AKT, oncogenes involved in the control of tumor cell proliferation and death. In order to measure the amount of platinum(II) complexes taken up by the cells, the cellular platinum content were quantified. However, C2 failed to inhibit mouse breast cancer growth in vivo. Chemical modifications of tested platinum(II) complexes might be a valuable approach for the improvement of their anti-tumor activity, especially effects in vivo.",
publisher = "Springer",
journal = "Journal of Biological Inorganic Chemistry",
title = "Characterization, modes of interactions with DNA/BSA biomolecules and anti-tumor activity of newly synthesized dinuclear platinum(II) complexes with pyridazine bridging ligand",
doi = "10.1007/s00775-023-02030-0"
}

Zornić, S., Simović Marković, B., Franich, A. A., Janjić, G., Jadranin, M., Avdalović, J., Rajković, S., Živković, M. D., Arsenijević, N. N., Radosavljević, G. D.,& Pantić, J.. (2023). Characterization, modes of interactions with DNA/BSA biomolecules and anti-tumor activity of newly synthesized dinuclear platinum(II) complexes with pyridazine bridging ligand. in Journal of Biological Inorganic Chemistry
Springer..
https://doi.org/10.1007/s00775-023-02030-0

Zornić S, Simović Marković B, Franich AA, Janjić G, Jadranin M, Avdalović J, Rajković S, Živković MD, Arsenijević NN, Radosavljević GD, Pantić J. Characterization, modes of interactions with DNA/BSA biomolecules and anti-tumor activity of newly synthesized dinuclear platinum(II) complexes with pyridazine bridging ligand. in Journal of Biological Inorganic Chemistry. 2023;.
doi:10.1007/s00775-023-02030-0 .

Zornić, Sanja, Simović Marković, Bojana, Franich, Andjela A., Janjić, Goran, Jadranin, Milka, Avdalović, Jelena, Rajković, Snežana, Živković, Marija D., Arsenijević, Nebojša N., Radosavljević, Gordana D., Pantić, Jelena, "Characterization, modes of interactions with DNA/BSA biomolecules and anti-tumor activity of newly synthesized dinuclear platinum(II) complexes with pyridazine bridging ligand" in Journal of Biological Inorganic Chemistry (2023),
https://doi.org/10.1007/s00775-023-02030-0 . .

TY  - JOUR
AU  - Milojkov, Dušan V.
AU  - Sokić, Miroslav D.
AU  - Živković-Radovanović, Vukosava
AU  - Manojlović, Vaso D.
AU  - Mutavdžić, Dragosav R.
AU  - Janjić, Goran
AU  - Radotić, Ksenija
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5804
AB  - In this study, luminescence and antibacterial behavior of pure fluorapatite (FAp) and praseodymium-nitrate-carbonate co-doped fluorapatite (PrNCFAp) nanopowders were investigated. Uniform nanopowders were synthesized by precipitation reaction followed by centrifugation and systematically characterized by XRD, FTIR, SEM–EDS, TG and PL methods. XRD analysis revealed the formation of hexagonal FAp crystals, and FTIR spectra indicate the presence of nitrate (NO3−) and carbonate (CO32−) species. SEM analyzes confirm agglomerates composed of irregular nanometer-sized spheres. Emission of FAp nanopowder occurred in the violet-blue region of the visible part of the spectrum, with redshift to the blue-green color region when Pr3+, NO3− and CO32− co-doped in the lattice. Analysis of luminescence spectra by MCR-ALS method extract three fluorophores from the PrNCFAp sample and showed simultaneous existents of emission-reabsorption-emission between dopants in FAp lattice. Antibacterial activity against pathogen Staphylococcus aureus was investigated before and after treatment of nanopowders by UVA radiation of 365 nm. Nanopowders irradiated with UVA compared to non-irradiated reduced Staphylococcus aureus by 84.9% for PrNCFAp and 33.3% for FAp in the first 0.5 h of contact, and 76.1% and 42.9% after 24 h of contact. In addition, the obtained luminescent nanomaterials showed a low degree of hemolytic activity and could potentially be candidates for further research in dentistry.
PB  - Springer
T2  - Optical and Quantum Electronics
T1  - Cascade luminescence and antibacterial behavior of fluorapatite nanopowder co-doped with Pr3+, NO3− and CO32− ions
VL  - 55
IS  - 1
SP  - 84
DO  - 10.1007/s11082-022-04347-7
ER  - 

@article{
author = "Milojkov, Dušan V. and Sokić, Miroslav D. and Živković-Radovanović, Vukosava and Manojlović, Vaso D. and Mutavdžić, Dragosav R. and Janjić, Goran and Radotić, Ksenija",
year = "2023",
abstract = "In this study, luminescence and antibacterial behavior of pure fluorapatite (FAp) and praseodymium-nitrate-carbonate co-doped fluorapatite (PrNCFAp) nanopowders were investigated. Uniform nanopowders were synthesized by precipitation reaction followed by centrifugation and systematically characterized by XRD, FTIR, SEM–EDS, TG and PL methods. XRD analysis revealed the formation of hexagonal FAp crystals, and FTIR spectra indicate the presence of nitrate (NO3−) and carbonate (CO32−) species. SEM analyzes confirm agglomerates composed of irregular nanometer-sized spheres. Emission of FAp nanopowder occurred in the violet-blue region of the visible part of the spectrum, with redshift to the blue-green color region when Pr3+, NO3− and CO32− co-doped in the lattice. Analysis of luminescence spectra by MCR-ALS method extract three fluorophores from the PrNCFAp sample and showed simultaneous existents of emission-reabsorption-emission between dopants in FAp lattice. Antibacterial activity against pathogen Staphylococcus aureus was investigated before and after treatment of nanopowders by UVA radiation of 365 nm. Nanopowders irradiated with UVA compared to non-irradiated reduced Staphylococcus aureus by 84.9% for PrNCFAp and 33.3% for FAp in the first 0.5 h of contact, and 76.1% and 42.9% after 24 h of contact. In addition, the obtained luminescent nanomaterials showed a low degree of hemolytic activity and could potentially be candidates for further research in dentistry.",
publisher = "Springer",
journal = "Optical and Quantum Electronics",
title = "Cascade luminescence and antibacterial behavior of fluorapatite nanopowder co-doped with Pr3+, NO3− and CO32− ions",
volume = "55",
number = "1",
pages = "84",
doi = "10.1007/s11082-022-04347-7"
}

Milojkov, D. V., Sokić, M. D., Živković-Radovanović, V., Manojlović, V. D., Mutavdžić, D. R., Janjić, G.,& Radotić, K.. (2023). Cascade luminescence and antibacterial behavior of fluorapatite nanopowder co-doped with Pr3+, NO3− and CO32− ions. in Optical and Quantum Electronics
Springer., 55(1), 84.
https://doi.org/10.1007/s11082-022-04347-7

Milojkov DV, Sokić MD, Živković-Radovanović V, Manojlović VD, Mutavdžić DR, Janjić G, Radotić K. Cascade luminescence and antibacterial behavior of fluorapatite nanopowder co-doped with Pr3+, NO3− and CO32− ions. in Optical and Quantum Electronics. 2023;55(1):84.
doi:10.1007/s11082-022-04347-7 .

Milojkov, Dušan V., Sokić, Miroslav D., Živković-Radovanović, Vukosava, Manojlović, Vaso D., Mutavdžić, Dragosav R., Janjić, Goran, Radotić, Ksenija, "Cascade luminescence and antibacterial behavior of fluorapatite nanopowder co-doped with Pr3+, NO3− and CO32− ions" in Optical and Quantum Electronics, 55, no. 1 (2023):84,
https://doi.org/10.1007/s11082-022-04347-7 . .

TY  - JOUR
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Valentić, Nataša
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Trišović, Nemanja
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7119
AB  - The present study describes representative examples of supramolecular arrangement of 5-phenylhydantoins achieved through various N–H⋯O hydrogen-bonding patterns. Four derivatives, 5-ethyl-5-(4-methylphenyl)hydantoin (1) and three 5-methyl-5-(3- or 4-substituted phenyl)hydantoins (2–4), were synthesized by the Bucherer–Bergs reaction and their crystal structures were determined by the single crystal X-ray diffraction method. A racemate, racemic hydrate and conglomerate as outcomes of crystallization from racemic solutions were found here. The crystal structures were firstly subjected to Hirshfeld surfaces analysis. The development of hydrogen bonding driven two-dimensional assemblies such as tapes, ribbons and sheets was further analysed using DFT calculations in terms of contribution of dimeric motifs as building blocks, which are associated with the presence of intermolecular interactions. To explore qualitative correlations between intermolecular interactions determining the crystal structures of the investigated compounds and those underlying their biological activity, we performed a docking study on the neuronal voltage gated sodium channels, matrix metalloproteinase 12 and aldose reductase. The supramolecular profiles of the investigated compounds are also maintained in biological systems and as such are responsible for differences in their biological activities.
PB  - Royal Society of Chemistry
T2  - CrystEngComm
T1  - Exploring the supramolecular profile of 5-phenylhydantoins
VL  - 25
SP  - 3637
EP  - 3654
DO  - 10.1039/D3CE00213F
ER  - 

@article{
author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Valentić, Nataša and Janjić, Goran and Đorđević, Ivana and Trišović, Nemanja",
year = "2023",
abstract = "The present study describes representative examples of supramolecular arrangement of 5-phenylhydantoins achieved through various N–H⋯O hydrogen-bonding patterns. Four derivatives, 5-ethyl-5-(4-methylphenyl)hydantoin (1) and three 5-methyl-5-(3- or 4-substituted phenyl)hydantoins (2–4), were synthesized by the Bucherer–Bergs reaction and their crystal structures were determined by the single crystal X-ray diffraction method. A racemate, racemic hydrate and conglomerate as outcomes of crystallization from racemic solutions were found here. The crystal structures were firstly subjected to Hirshfeld surfaces analysis. The development of hydrogen bonding driven two-dimensional assemblies such as tapes, ribbons and sheets was further analysed using DFT calculations in terms of contribution of dimeric motifs as building blocks, which are associated with the presence of intermolecular interactions. To explore qualitative correlations between intermolecular interactions determining the crystal structures of the investigated compounds and those underlying their biological activity, we performed a docking study on the neuronal voltage gated sodium channels, matrix metalloproteinase 12 and aldose reductase. The supramolecular profiles of the investigated compounds are also maintained in biological systems and as such are responsible for differences in their biological activities.",
publisher = "Royal Society of Chemistry",
journal = "CrystEngComm",
title = "Exploring the supramolecular profile of 5-phenylhydantoins",
volume = "25",
pages = "3637-3654",
doi = "10.1039/D3CE00213F"
}

Lazić, A., Radovanović, L., Rogan, J., Valentić, N., Janjić, G., Đorđević, I.,& Trišović, N.. (2023). Exploring the supramolecular profile of 5-phenylhydantoins. in CrystEngComm
Royal Society of Chemistry., 25, 3637-3654.
https://doi.org/10.1039/D3CE00213F

Lazić A, Radovanović L, Rogan J, Valentić N, Janjić G, Đorđević I, Trišović N. Exploring the supramolecular profile of 5-phenylhydantoins. in CrystEngComm. 2023;25:3637-3654.
doi:10.1039/D3CE00213F .

Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Valentić, Nataša, Janjić, Goran, Đorđević, Ivana, Trišović, Nemanja, "Exploring the supramolecular profile of 5-phenylhydantoins" in CrystEngComm, 25 (2023):3637-3654,
https://doi.org/10.1039/D3CE00213F . .

TY  - JOUR
AU  - Dimitrijević, Jelena
AU  - Solovjova, Natalija
AU  - Bukonjić, Andriana M.
AU  - Tomović, Dušan Lj.
AU  - Milinković, Mirjana
AU  - Caković, Angelina
AU  - Bogojeski, Jovana
AU  - Ratković, Zoran R.
AU  - Janjić, Goran
AU  - Rakić, Aleksandra
AU  - Arsenijević, Nebojša N.
AU  - Milovanović, Marija Z.
AU  - Milovanović, Jelena Z.
AU  - Radić, Gordana P.
AU  - Jevtić, Verica V.
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7060
AB  - The numerous side effects of platinum based chemotherapy has led to the design of new therapeutics with platinum replaced by another transition metal. Here, we investigated the interactions of previously reported copper(II) complexes containing S-isoalkyl derivatives, the salicylic acid with guanosine-5′-monophosphate and calf thymus DNA (CT-DNA) and their antitumor effects, in a colon carcinoma model. All three copper(II) complexes exhibited an affinity for binding to CT-DNA, but there was no indication of intercalation or the displacement of ethidium bromide. Molecular docking studies revealed a significant affinity of the complexes for binding to the minor groove of B-form DNA, which coincided with DNA elongation, and a higher affinity for binding to Z-form DNA, supporting the hypothesis that the complex binding to CT-DNA induces a local transition from B-form to Z-form DNA. These complexes show a moderate, but selective cytotoxic effect toward colon cancer cells in vitro. Binuclear complex of copper(II) with S-isoamyl derivative of thiosalicylic acid showed the highest cytotoxic effect, arrested tumor cells in the G2/M phase of the cell cycle, and significantly reduced the expression of inflammatory molecules pro-IL-1β, TNF-α, ICAM-1, and VCAM-1 in the tissue of primary heterotopic murine colon cancer, which was accompanied by a significantly reduced tumor growth and metastases in the lung and liver.
PB  - MDPI
T2  - International Journal of Molecular Sciences
T1  - Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules
VL  - 24
IS  - 15
SP  - 12504
DO  - 10.3390/ijms241512504
ER  - 

@article{
author = "Dimitrijević, Jelena and Solovjova, Natalija and Bukonjić, Andriana M. and Tomović, Dušan Lj. and Milinković, Mirjana and Caković, Angelina and Bogojeski, Jovana and Ratković, Zoran R. and Janjić, Goran and Rakić, Aleksandra and Arsenijević, Nebojša N. and Milovanović, Marija Z. and Milovanović, Jelena Z. and Radić, Gordana P. and Jevtić, Verica V.",
year = "2023",
abstract = "The numerous side effects of platinum based chemotherapy has led to the design of new therapeutics with platinum replaced by another transition metal. Here, we investigated the interactions of previously reported copper(II) complexes containing S-isoalkyl derivatives, the salicylic acid with guanosine-5′-monophosphate and calf thymus DNA (CT-DNA) and their antitumor effects, in a colon carcinoma model. All three copper(II) complexes exhibited an affinity for binding to CT-DNA, but there was no indication of intercalation or the displacement of ethidium bromide. Molecular docking studies revealed a significant affinity of the complexes for binding to the minor groove of B-form DNA, which coincided with DNA elongation, and a higher affinity for binding to Z-form DNA, supporting the hypothesis that the complex binding to CT-DNA induces a local transition from B-form to Z-form DNA. These complexes show a moderate, but selective cytotoxic effect toward colon cancer cells in vitro. Binuclear complex of copper(II) with S-isoamyl derivative of thiosalicylic acid showed the highest cytotoxic effect, arrested tumor cells in the G2/M phase of the cell cycle, and significantly reduced the expression of inflammatory molecules pro-IL-1β, TNF-α, ICAM-1, and VCAM-1 in the tissue of primary heterotopic murine colon cancer, which was accompanied by a significantly reduced tumor growth and metastases in the lung and liver.",
publisher = "MDPI",
journal = "International Journal of Molecular Sciences",
title = "Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules",
volume = "24",
number = "15",
pages = "12504",
doi = "10.3390/ijms241512504"
}

Dimitrijević, J., Solovjova, N., Bukonjić, A. M., Tomović, D. Lj., Milinković, M., Caković, A., Bogojeski, J., Ratković, Z. R., Janjić, G., Rakić, A., Arsenijević, N. N., Milovanović, M. Z., Milovanović, J. Z., Radić, G. P.,& Jevtić, V. V.. (2023). Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules. in International Journal of Molecular Sciences
MDPI., 24(15), 12504.
https://doi.org/10.3390/ijms241512504

Dimitrijević J, Solovjova N, Bukonjić AM, Tomović DL, Milinković M, Caković A, Bogojeski J, Ratković ZR, Janjić G, Rakić A, Arsenijević NN, Milovanović MZ, Milovanović JZ, Radić GP, Jevtić VV. Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules. in International Journal of Molecular Sciences. 2023;24(15):12504.
doi:10.3390/ijms241512504 .

Dimitrijević, Jelena, Solovjova, Natalija, Bukonjić, Andriana M., Tomović, Dušan Lj., Milinković, Mirjana, Caković, Angelina, Bogojeski, Jovana, Ratković, Zoran R., Janjić, Goran, Rakić, Aleksandra, Arsenijević, Nebojša N., Milovanović, Marija Z., Milovanović, Jelena Z., Radić, Gordana P., Jevtić, Verica V., "Docking studies, cytotoxicity evaluation and interactions of binuclear copper(ii) complexes with s-isoalkyl derivatives of thiosalicylic acid with some relevant biomolecules" in International Journal of Molecular Sciences, 24, no. 15 (2023):12504,
https://doi.org/10.3390/ijms241512504 . .

TY  - JOUR
AU  - Konovalov, Bata
AU  - Đorđević, Ivana
AU  - Franich, Andjela A.
AU  - Šmit, Biljana
AU  - Živković, Marija D.
AU  - Djuran, Miloš I.
AU  - Janjić, Goran
AU  - Rajković, Snežana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7061
AB  - The hydrolysis of N-acetylated L-methionylglycine dipeptide (Ac-L-Met-Gly) in the presence of dinuclear platinum(II)-aqua complexes with general formula [{Pt(L)(H2O)}2(μ-1,5-nphe)]4+ (1,5-nphe is 1,5-naphthyridine; L is bidentately coordinated ethylenediamine (1w), (±)-1,2-propylenediamine (2w) and 1,3-propylenediamine (3w)) is described in detail. The hydrolytic activity of these complexes was monitored by 1H NMR spectroscopy, which confirmed the regioselective cleavage of the Met-Gly-amide bond in this peptide. Quantum-chemical calculations revealed the primary reaction path with coordination of dipeptide via the terminal amide nitrogen of methionine followed by its coordination for the sulphur atom, in which the decomposition of the resulted platinum(II)-dipeptide complex and the coordination of its glycine residue precedes the hydrolytic cleavage of the Met-Gly amide bond. In the secondary reaction path, in which Ac-L-Met-Gly is coordinated via the methionine sulphur atom, the decomposition of the starting [{Pt(L)(H2O)}2(μ-1,5-nphe)]4+ complex is followed by the regioselective hydrolysis of the investigated dipeptide. The binding affinity of the chloride derivatives of the corresponding dinuclear platinum(II)-aqua complexes, [{Pt(L)Cl}2(μ-1,5-nphe)]2+ (1–3) towards the human serum albumin (HSA), a transport protein, was investigated using electronic absorption and fluorescence emission measurements, and results indicated the static interactions between these complexes and HSA. A docking study revealed a unique binding site on HSA, based on the electrostatic and the hydrogen bonding, which does not have a methionine residue nearby, therefore does not exist danger of HSA hydrolysis by these complexes.
PB  - Elsevier
T2  - Journal of Molecular Structure
T1  - Dinuclear platinum(II) complexes with 1,5-nphe bridging ligand: Spectroscopic and molecular docking study of the interactions with N-acetylated L-methionylglycine and human serum albumin
VL  - 1288
SP  - 135810
DO  - 10.1016/j.molstruc.2023.135810
ER  - 

@article{
author = "Konovalov, Bata and Đorđević, Ivana and Franich, Andjela A. and Šmit, Biljana and Živković, Marija D. and Djuran, Miloš I. and Janjić, Goran and Rajković, Snežana",
year = "2023",
abstract = "The hydrolysis of N-acetylated L-methionylglycine dipeptide (Ac-L-Met-Gly) in the presence of dinuclear platinum(II)-aqua complexes with general formula [{Pt(L)(H2O)}2(μ-1,5-nphe)]4+ (1,5-nphe is 1,5-naphthyridine; L is bidentately coordinated ethylenediamine (1w), (±)-1,2-propylenediamine (2w) and 1,3-propylenediamine (3w)) is described in detail. The hydrolytic activity of these complexes was monitored by 1H NMR spectroscopy, which confirmed the regioselective cleavage of the Met-Gly-amide bond in this peptide. Quantum-chemical calculations revealed the primary reaction path with coordination of dipeptide via the terminal amide nitrogen of methionine followed by its coordination for the sulphur atom, in which the decomposition of the resulted platinum(II)-dipeptide complex and the coordination of its glycine residue precedes the hydrolytic cleavage of the Met-Gly amide bond. In the secondary reaction path, in which Ac-L-Met-Gly is coordinated via the methionine sulphur atom, the decomposition of the starting [{Pt(L)(H2O)}2(μ-1,5-nphe)]4+ complex is followed by the regioselective hydrolysis of the investigated dipeptide. The binding affinity of the chloride derivatives of the corresponding dinuclear platinum(II)-aqua complexes, [{Pt(L)Cl}2(μ-1,5-nphe)]2+ (1–3) towards the human serum albumin (HSA), a transport protein, was investigated using electronic absorption and fluorescence emission measurements, and results indicated the static interactions between these complexes and HSA. A docking study revealed a unique binding site on HSA, based on the electrostatic and the hydrogen bonding, which does not have a methionine residue nearby, therefore does not exist danger of HSA hydrolysis by these complexes.",
publisher = "Elsevier",
journal = "Journal of Molecular Structure",
title = "Dinuclear platinum(II) complexes with 1,5-nphe bridging ligand: Spectroscopic and molecular docking study of the interactions with N-acetylated L-methionylglycine and human serum albumin",
volume = "1288",
pages = "135810",
doi = "10.1016/j.molstruc.2023.135810"
}

Konovalov, B., Đorđević, I., Franich, A. A., Šmit, B., Živković, M. D., Djuran, M. I., Janjić, G.,& Rajković, S.. (2023). Dinuclear platinum(II) complexes with 1,5-nphe bridging ligand: Spectroscopic and molecular docking study of the interactions with N-acetylated L-methionylglycine and human serum albumin. in Journal of Molecular Structure
Elsevier., 1288, 135810.
https://doi.org/10.1016/j.molstruc.2023.135810

Konovalov B, Đorđević I, Franich AA, Šmit B, Živković MD, Djuran MI, Janjić G, Rajković S. Dinuclear platinum(II) complexes with 1,5-nphe bridging ligand: Spectroscopic and molecular docking study of the interactions with N-acetylated L-methionylglycine and human serum albumin. in Journal of Molecular Structure. 2023;1288:135810.
doi:10.1016/j.molstruc.2023.135810 .

Konovalov, Bata, Đorđević, Ivana, Franich, Andjela A., Šmit, Biljana, Živković, Marija D., Djuran, Miloš I., Janjić, Goran, Rajković, Snežana, "Dinuclear platinum(II) complexes with 1,5-nphe bridging ligand: Spectroscopic and molecular docking study of the interactions with N-acetylated L-methionylglycine and human serum albumin" in Journal of Molecular Structure, 1288 (2023):135810,
https://doi.org/10.1016/j.molstruc.2023.135810 . .

TY  - JOUR
AU  - Suručić, Ljiljana
AU  - Janjić, Goran
AU  - Marković, Bojana
AU  - Tadić, Tamara
AU  - Vuković, Zorica
AU  - Nastasović, Aleksandra
AU  - Onjia, Antonije
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/6329
AB  - A new magnetic amino-functionalized polymeric sorbent based on glycidyl methacrylate was synthesized and used in the separation of chromium Cr(VI) oxyanions sorption from aqueous solutions in a static batch system. The kinetic and isothermal parameters of the sorption process were determined. The experimental data were best fitted by a pseudo-second-order model with R2 = 0.994 and χ2 = 0.004. The sorption process of Cr(VI) removal by amino-functionalized sorbent was controlled by both intraparticle diffusion and liquid film diffusion. The equilibrium results showed that the sorption process is best described by the Freundlich model, followed closely by the Sips isotherm model, with a maximum sorption capacity of 64 mg/g. Quantum chemical modeling revealed that the sorption sites on the sorbent surface are fragments with diethylenetriamine and aminopropyl silane groups that coated the magnetic nanoparticles. The calculations showed that Cr(VI) oxyanions (Cr2O72−, CrO42− and HCrO4−) bind to both sorption sites, with diethylenetriamine centers slightly favored. The X-ray photoelectron spectroscopy (XPS) spectra demonstrate that the chromium bound to the sorbent in the form of Cr(III), indicating that the Cr(VI) can be converted on the surface of the sorbent to a less harmful form Cr(III) due to the sorbent’s chemical composition.
PB  - Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)
T2  - Materials
T1  - Speciation of Hexavalent Chromium in Aqueous Solutions Using a Magnetic Silica-Coated Amino-Modified Glycidyl Methacrylate Polymer Nanocomposite
VL  - 16
IS  - 6
SP  - 2233
DO  - 10.3390/ma16062233
ER  - 

@article{
author = "Suručić, Ljiljana and Janjić, Goran and Marković, Bojana and Tadić, Tamara and Vuković, Zorica and Nastasović, Aleksandra and Onjia, Antonije",
year = "2023",
abstract = "A new magnetic amino-functionalized polymeric sorbent based on glycidyl methacrylate was synthesized and used in the separation of chromium Cr(VI) oxyanions sorption from aqueous solutions in a static batch system. The kinetic and isothermal parameters of the sorption process were determined. The experimental data were best fitted by a pseudo-second-order model with R2 = 0.994 and χ2 = 0.004. The sorption process of Cr(VI) removal by amino-functionalized sorbent was controlled by both intraparticle diffusion and liquid film diffusion. The equilibrium results showed that the sorption process is best described by the Freundlich model, followed closely by the Sips isotherm model, with a maximum sorption capacity of 64 mg/g. Quantum chemical modeling revealed that the sorption sites on the sorbent surface are fragments with diethylenetriamine and aminopropyl silane groups that coated the magnetic nanoparticles. The calculations showed that Cr(VI) oxyanions (Cr2O72−, CrO42− and HCrO4−) bind to both sorption sites, with diethylenetriamine centers slightly favored. The X-ray photoelectron spectroscopy (XPS) spectra demonstrate that the chromium bound to the sorbent in the form of Cr(III), indicating that the Cr(VI) can be converted on the surface of the sorbent to a less harmful form Cr(III) due to the sorbent’s chemical composition.",
publisher = "Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)",
journal = "Materials",
title = "Speciation of Hexavalent Chromium in Aqueous Solutions Using a Magnetic Silica-Coated Amino-Modified Glycidyl Methacrylate Polymer Nanocomposite",
volume = "16",
number = "6",
pages = "2233",
doi = "10.3390/ma16062233"
}

Suručić, L., Janjić, G., Marković, B., Tadić, T., Vuković, Z., Nastasović, A.,& Onjia, A.. (2023). Speciation of Hexavalent Chromium in Aqueous Solutions Using a Magnetic Silica-Coated Amino-Modified Glycidyl Methacrylate Polymer Nanocomposite. in Materials
Switzerland : Multidisciplinary Digital Publishing Institute (MDPI)., 16(6), 2233.
https://doi.org/10.3390/ma16062233

Suručić L, Janjić G, Marković B, Tadić T, Vuković Z, Nastasović A, Onjia A. Speciation of Hexavalent Chromium in Aqueous Solutions Using a Magnetic Silica-Coated Amino-Modified Glycidyl Methacrylate Polymer Nanocomposite. in Materials. 2023;16(6):2233.
doi:10.3390/ma16062233 .

Suručić, Ljiljana, Janjić, Goran, Marković, Bojana, Tadić, Tamara, Vuković, Zorica, Nastasović, Aleksandra, Onjia, Antonije, "Speciation of Hexavalent Chromium in Aqueous Solutions Using a Magnetic Silica-Coated Amino-Modified Glycidyl Methacrylate Polymer Nanocomposite" in Materials, 16, no. 6 (2023):2233,
https://doi.org/10.3390/ma16062233 . .

TY  - CONF
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Trišović, Nemanja
AU  - Đorđević, Ivana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7542
AB  - Derivat cikloheksan-5-spirohidantoina (Slika 1) je sintetisan, određena je njegova kristalnastruktura i urađena kvantno-hemijska analiza. Kristalno pakovanje grade mrežesupramolekulskih R64(32) prstenova postavljenih međusobno paralelno, pri čemu seformiraju linearni kanali. Određene su vrednosti energije intermolekulskih interakcija zarazličite dimerne motive dobijene iz kristalne strukture. Uzimajući u razmatranjeprethodno strukturno okarakterisane srodne spirohidantoine [1], dobijena je serijajedinjenja koja je omogućila procenu uticaja supstituenata na njihovu molekulsku ikristalnu strukturu.
AB  - A spirohydantoin derivative (Figure 1) was synthesized and its crystal structure wasdetermined by single crystal X-ray diffraction and analysed by DFT calculations. Thecrystal packing is made of supramolecular nets of R64(32) rings linked together to formstacks that enclose linear channels. The intermolecular interaction energies are quantifiedfor various dimeric motifs. By including the previously reported structurally-relatedspirohydantoins [1], we created a set of compounds that enabled us to evaluate substituenteffects on both molecular and crystal structures.
PB  - Beograd : Srpsko hemijsko društvo
C3  - Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine
T1  - Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina
T1  - Insights into conformational and cristal structure features of selected cyclohexane-5-spirohydantoin derivatives
SP  - 138
EP  - 138
UR  - https://hdl.handle.net/21.15107/rcub_cer_7542
ER  - 

@conference{
author = "Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Janjić, Goran and Trišović, Nemanja and Đorđević, Ivana",
year = "2022",
abstract = "Derivat cikloheksan-5-spirohidantoina (Slika 1) je sintetisan, određena je njegova kristalnastruktura i urađena kvantno-hemijska analiza. Kristalno pakovanje grade mrežesupramolekulskih R64(32) prstenova postavljenih međusobno paralelno, pri čemu seformiraju linearni kanali. Određene su vrednosti energije intermolekulskih interakcija zarazličite dimerne motive dobijene iz kristalne strukture. Uzimajući u razmatranjeprethodno strukturno okarakterisane srodne spirohidantoine [1], dobijena je serijajedinjenja koja je omogućila procenu uticaja supstituenata na njihovu molekulsku ikristalnu strukturu., A spirohydantoin derivative (Figure 1) was synthesized and its crystal structure wasdetermined by single crystal X-ray diffraction and analysed by DFT calculations. Thecrystal packing is made of supramolecular nets of R64(32) rings linked together to formstacks that enclose linear channels. The intermolecular interaction energies are quantifiedfor various dimeric motifs. By including the previously reported structurally-relatedspirohydantoins [1], we created a set of compounds that enabled us to evaluate substituenteffects on both molecular and crystal structures.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine",
title = "Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina, Insights into conformational and cristal structure features of selected cyclohexane-5-spirohydantoin derivatives",
pages = "138-138",
url = "https://hdl.handle.net/21.15107/rcub_cer_7542"
}

Lazić, A., Radovanović, L., Rogan, J., Janjić, G., Trišović, N.,& Đorđević, I.. (2022). Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina. in Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine
Beograd : Srpsko hemijsko društvo., 138-138.
https://hdl.handle.net/21.15107/rcub_cer_7542

Lazić A, Radovanović L, Rogan J, Janjić G, Trišović N, Đorđević I. Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina. in Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine. 2022;:138-138.
https://hdl.handle.net/21.15107/rcub_cer_7542 .

Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Janjić, Goran, Trišović, Nemanja, Đorđević, Ivana, "Proučavanje konformacije i kristalne strukture odabranih derivata cikloheksan-5-spirohidantoina" in Kratki izvodi radova ; Knjiga radova / 58. savetovanje Srpskog hemijskog društva, Beograd, 9. i 10. jun 2022. godine (2022):138-138,
https://hdl.handle.net/21.15107/rcub_cer_7542 .

TY  - JOUR
AU  - Kokanov, Sanja B.
AU  - Filipović, Nenad R.
AU  - Višnjevac, Aleksandar
AU  - Nikolić, Milan
AU  - Novaković, Irena
AU  - Janjić, Goran
AU  - Holló, Berta Barta
AU  - Ramotowska, Sandra
AU  - Nowicka, Paulina
AU  - Makowski, Mariusz
AU  - Uğuz, Özlem
AU  - Koca, Atıf
AU  - Todorović, Tamara
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5474
AB  - Interest in Cd complexes has been growing in recent years. Cd complexes are considered a potential solution in the search for novel antibiotics that can fight antimicrobial resistance. In addition, Cd complexes draw attention to material chemistry. The main objective of this work was to prepare the first Cd(II) complexes with anionic forms of pyridine-based thiazolyl hydrazone (THs) ligands HLS2 [(E)-4-(4-methoxyphenyl)-2-(2-[pyridine-2-ylmethylene]hydrazinyl)thiazole] and HLS3 [(E)-2-(2-[pyridine-2-ylmethylene]hydrazinyl)-4-(p-tolyl)thiazole] and perform their structural and spectroscopic characterization, as well as stability in solution and upon heating. Studies related to their biological activities and possible electrochromic applications are also being conducted. Complexes [Cd(HLS2)2] (1) and [Cd(HLS3)2] (2) have been characterized by a single-crystal X-ray diffraction and computational analysis of intermolecular interactions responsible for their solid-state structures was performed. Thermal stability of 1 and 2 in the solid-state was analyzed by TGA/MS, where as their solution stability was determined by the spectrophotometric titration method. Electrochemical and in situ UV–Vis spectroelectrochemical analyses of 1 and 2 were carried out to determine redox mechanisms and the influence of the substituents and electrolytes on their redox responses. The antioxidant capacity of both complexes was tested in antioxidant assays, while their antimicrobial activity was tested against five Gram-positive and four Gram-negative bacteria, as well as against three fungi. The obtained results indicate their potent antioxidant capacity. The antimicrobial activity of investigated compounds on almost all tested bacterial strains was stronger than that of the standard antibiotic erythromycin. The results of docking studies indicate that the minor groove DNA is the possible biological target of 1 and 2.
PB  - Wiley
T2  - Applied Organometallic Chemistry
T1  - A detailed experimental and computational study of Cd complexes with pyridyl-based thiazolyl hydrazones
DO  - 10.1002/aoc.6942
ER  - 

@article{
author = "Kokanov, Sanja B. and Filipović, Nenad R. and Višnjevac, Aleksandar and Nikolić, Milan and Novaković, Irena and Janjić, Goran and Holló, Berta Barta and Ramotowska, Sandra and Nowicka, Paulina and Makowski, Mariusz and Uğuz, Özlem and Koca, Atıf and Todorović, Tamara",
year = "2022",
abstract = "Interest in Cd complexes has been growing in recent years. Cd complexes are considered a potential solution in the search for novel antibiotics that can fight antimicrobial resistance. In addition, Cd complexes draw attention to material chemistry. The main objective of this work was to prepare the first Cd(II) complexes with anionic forms of pyridine-based thiazolyl hydrazone (THs) ligands HLS2 [(E)-4-(4-methoxyphenyl)-2-(2-[pyridine-2-ylmethylene]hydrazinyl)thiazole] and HLS3 [(E)-2-(2-[pyridine-2-ylmethylene]hydrazinyl)-4-(p-tolyl)thiazole] and perform their structural and spectroscopic characterization, as well as stability in solution and upon heating. Studies related to their biological activities and possible electrochromic applications are also being conducted. Complexes [Cd(HLS2)2] (1) and [Cd(HLS3)2] (2) have been characterized by a single-crystal X-ray diffraction and computational analysis of intermolecular interactions responsible for their solid-state structures was performed. Thermal stability of 1 and 2 in the solid-state was analyzed by TGA/MS, where as their solution stability was determined by the spectrophotometric titration method. Electrochemical and in situ UV–Vis spectroelectrochemical analyses of 1 and 2 were carried out to determine redox mechanisms and the influence of the substituents and electrolytes on their redox responses. The antioxidant capacity of both complexes was tested in antioxidant assays, while their antimicrobial activity was tested against five Gram-positive and four Gram-negative bacteria, as well as against three fungi. The obtained results indicate their potent antioxidant capacity. The antimicrobial activity of investigated compounds on almost all tested bacterial strains was stronger than that of the standard antibiotic erythromycin. The results of docking studies indicate that the minor groove DNA is the possible biological target of 1 and 2.",
publisher = "Wiley",
journal = "Applied Organometallic Chemistry",
title = "A detailed experimental and computational study of Cd complexes with pyridyl-based thiazolyl hydrazones",
doi = "10.1002/aoc.6942"
}

Kokanov, S. B., Filipović, N. R., Višnjevac, A., Nikolić, M., Novaković, I., Janjić, G., Holló, B. B., Ramotowska, S., Nowicka, P., Makowski, M., Uğuz, Ö., Koca, A.,& Todorović, T.. (2022). A detailed experimental and computational study of Cd complexes with pyridyl-based thiazolyl hydrazones. in Applied Organometallic Chemistry
Wiley..
https://doi.org/10.1002/aoc.6942

Kokanov SB, Filipović NR, Višnjevac A, Nikolić M, Novaković I, Janjić G, Holló BB, Ramotowska S, Nowicka P, Makowski M, Uğuz Ö, Koca A, Todorović T. A detailed experimental and computational study of Cd complexes with pyridyl-based thiazolyl hydrazones. in Applied Organometallic Chemistry. 2022;.
doi:10.1002/aoc.6942 .

Kokanov, Sanja B., Filipović, Nenad R., Višnjevac, Aleksandar, Nikolić, Milan, Novaković, Irena, Janjić, Goran, Holló, Berta Barta, Ramotowska, Sandra, Nowicka, Paulina, Makowski, Mariusz, Uğuz, Özlem, Koca, Atıf, Todorović, Tamara, "A detailed experimental and computational study of Cd complexes with pyridyl-based thiazolyl hydrazones" in Applied Organometallic Chemistry (2022),
https://doi.org/10.1002/aoc.6942 . .

TY  - JOUR
AU  - Franich, Andjela
AU  - Đorđević, Ivana S.
AU  - Živković, Marija D.
AU  - Rajković, Snežana
AU  - Janjić, Goran
AU  - Đuran, Miloš
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4832
AB  - The mechanism of action of most approved drugs in use today is based on their binding to specific proteins or DNA. One
of the achievements of this research is a new perspective for recognition of binding modes to DNA by monitoring of
changes in measured and stoichiometric values of absorbance at 260 nm. UV–Vis and IR spectroscopy, gel electrophoresis
and docking study were used for investigation of binding properties of three dinuclear platinum(II) complexes containing
different pyridine-based bridging ligands, [{Pt(en)Cl}2(μ-4,4’-bipy)]Cl2・2H2O (Pt1), [{Pt(en)Cl}2(μ-bpa)]Cl2・4H2O (Pt2)
and [{Pt(en)Cl}2(μ-bpe)]Cl2・4H2O (Pt3) to DNA (4,4’-bipy, bpa and bpe are 4,4′-bipyridine, 1,2-bis(4-pyridyl)ethane and
1,2-bis(4-pyridyl)ethene, respectively). In contrast to the system with well-known intercalated ligand (EtBr), covalently bound
ligand (cis-Pt) and with minor groove binder (Hoechst 33258), which do not have significant differences in measured and
stoichiometric values, the most pronounced deviations are recorded for two dinuclear platinum(II) complexes (Pt1 and Pt2),
as a consequence of complex binding to the phosphate backbone and bending of DNA helix. The hydrolysis of complexes
and changes in DNA conformation were also analysed as phenomena that may have an impact on the changes in absorbance.
PB  - Springer
T2  - Journal of Biological Inorganic Chemistry
T1  - Dinuclear platinum(II) complexes as the pattern for phosphate backbone binding: a new perspective for recognition of binding modes to DNA
VL  - 27
SP  - 65
EP  - 79
DO  - 10.1007/s00775-021-01911-6
ER  - 

@article{
author = "Franich, Andjela and Đorđević, Ivana S. and Živković, Marija D. and Rajković, Snežana and Janjić, Goran and Đuran, Miloš",
year = "2022",
abstract = "The mechanism of action of most approved drugs in use today is based on their binding to specific proteins or DNA. One
of the achievements of this research is a new perspective for recognition of binding modes to DNA by monitoring of
changes in measured and stoichiometric values of absorbance at 260 nm. UV–Vis and IR spectroscopy, gel electrophoresis
and docking study were used for investigation of binding properties of three dinuclear platinum(II) complexes containing
different pyridine-based bridging ligands, [{Pt(en)Cl}2(μ-4,4’-bipy)]Cl2・2H2O (Pt1), [{Pt(en)Cl}2(μ-bpa)]Cl2・4H2O (Pt2)
and [{Pt(en)Cl}2(μ-bpe)]Cl2・4H2O (Pt3) to DNA (4,4’-bipy, bpa and bpe are 4,4′-bipyridine, 1,2-bis(4-pyridyl)ethane and
1,2-bis(4-pyridyl)ethene, respectively). In contrast to the system with well-known intercalated ligand (EtBr), covalently bound
ligand (cis-Pt) and with minor groove binder (Hoechst 33258), which do not have significant differences in measured and
stoichiometric values, the most pronounced deviations are recorded for two dinuclear platinum(II) complexes (Pt1 and Pt2),
as a consequence of complex binding to the phosphate backbone and bending of DNA helix. The hydrolysis of complexes
and changes in DNA conformation were also analysed as phenomena that may have an impact on the changes in absorbance.",
publisher = "Springer",
journal = "Journal of Biological Inorganic Chemistry",
title = "Dinuclear platinum(II) complexes as the pattern for phosphate backbone binding: a new perspective for recognition of binding modes to DNA",
volume = "27",
pages = "65-79",
doi = "10.1007/s00775-021-01911-6"
}

Franich, A., Đorđević, I. S., Živković, M. D., Rajković, S., Janjić, G.,& Đuran, M.. (2022). Dinuclear platinum(II) complexes as the pattern for phosphate backbone binding: a new perspective for recognition of binding modes to DNA. in Journal of Biological Inorganic Chemistry
Springer., 27, 65-79.
https://doi.org/10.1007/s00775-021-01911-6

Franich A, Đorđević IS, Živković MD, Rajković S, Janjić G, Đuran M. Dinuclear platinum(II) complexes as the pattern for phosphate backbone binding: a new perspective for recognition of binding modes to DNA. in Journal of Biological Inorganic Chemistry. 2022;27:65-79.
doi:10.1007/s00775-021-01911-6 .

Franich, Andjela, Đorđević, Ivana S., Živković, Marija D., Rajković, Snežana, Janjić, Goran, Đuran, Miloš, "Dinuclear platinum(II) complexes as the pattern for phosphate backbone binding: a new perspective for recognition of binding modes to DNA" in Journal of Biological Inorganic Chemistry, 27 (2022):65-79,
https://doi.org/10.1007/s00775-021-01911-6 . .

TY  - CONF
AU  - Suručić, Ljiljana T.
AU  - Nastasović, Aleksandra
AU  - Marković, Bojana
AU  - Tadić, Tamara
AU  - Onjia, Antonije
AU  - Janjić, Goran
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7001
AB  - Improving the affinity and selectivity of polymeric materials for sorbing ionic species, particularly
heavy metals that pose a high environmental risk, is crucial from an environmental standpoint.
Research on the mechanism of sorption can aid in selecting the optimal sorbent for a given
application. Sorption occurs as a result of various interactions. Sorption includes diffusion of ions
through solution (typically the quickest), diffusion of ions through the boundary layer surrounding
the sorbent surface, diffusion through the porous structure of the sorbent (intra-particle diffusion),
and binding to active sites on sorbent surfaces. Kinetic and equilibrium models explain the sorption
mechanism but not the nature of interactions, which is essential for predicting the selectivity and
efficiency of the sorbent based on particular ionic species. As a result, we were compelled to
approach the molecular level. Active sites on the surface of the magnetic aminofunctionalized
polymer, which are amino functional groups, are used to bind ions to the magnetic nanocomposite.
The sorption process can be viewed as the sum of ion-ligand unit interactions. Unit complex
formation and stability can be studied with statistical analysis and quantum chemical calculations.
The Cambridge database (CSD) improves the crystal structure of complex ion-ligand. Based on
binding energy, DFT (Density Functional Theory) predicts the stability of complex molecules (unit
ion-ligand interactions). To ensure an accurate calculation, it is essential to include all system
parameters, including sorbent structure, ligand properties, ligand charge under specific conditions,
ion forms and charges, and solvatation effects. In the early stages of research, defining the system's model lets researchers make theoretical predictions about the magnetic aminofunctionalized polymer sorbent's affinity and selectivity for certain ionic species.
PB  - University in Banjaluka, Faculty of Technology
C3  - Book of Abstracts - XIV Conference of  Chemists, Technologists and Environmentalists of Republic of Srpska, October 21-22, 2022, Banja Luka
T1  - Theoretical prediction of magnetic aminofunctionalized polymer sorbent performance using molecular modeling methods
SP  - 20
EP  - 20
UR  - https://hdl.handle.net/21.15107/rcub_cer_7001
ER  - 

@conference{
author = "Suručić, Ljiljana T. and Nastasović, Aleksandra and Marković, Bojana and Tadić, Tamara and Onjia, Antonije and Janjić, Goran",
year = "2022",
abstract = "Improving the affinity and selectivity of polymeric materials for sorbing ionic species, particularly
heavy metals that pose a high environmental risk, is crucial from an environmental standpoint.
Research on the mechanism of sorption can aid in selecting the optimal sorbent for a given
application. Sorption occurs as a result of various interactions. Sorption includes diffusion of ions
through solution (typically the quickest), diffusion of ions through the boundary layer surrounding
the sorbent surface, diffusion through the porous structure of the sorbent (intra-particle diffusion),
and binding to active sites on sorbent surfaces. Kinetic and equilibrium models explain the sorption
mechanism but not the nature of interactions, which is essential for predicting the selectivity and
efficiency of the sorbent based on particular ionic species. As a result, we were compelled to
approach the molecular level. Active sites on the surface of the magnetic aminofunctionalized
polymer, which are amino functional groups, are used to bind ions to the magnetic nanocomposite.
The sorption process can be viewed as the sum of ion-ligand unit interactions. Unit complex
formation and stability can be studied with statistical analysis and quantum chemical calculations.
The Cambridge database (CSD) improves the crystal structure of complex ion-ligand. Based on
binding energy, DFT (Density Functional Theory) predicts the stability of complex molecules (unit
ion-ligand interactions). To ensure an accurate calculation, it is essential to include all system
parameters, including sorbent structure, ligand properties, ligand charge under specific conditions,
ion forms and charges, and solvatation effects. In the early stages of research, defining the system's model lets researchers make theoretical predictions about the magnetic aminofunctionalized polymer sorbent's affinity and selectivity for certain ionic species.",
publisher = "University in Banjaluka, Faculty of Technology",
journal = "Book of Abstracts - XIV Conference of  Chemists, Technologists and Environmentalists of Republic of Srpska, October 21-22, 2022, Banja Luka",
title = "Theoretical prediction of magnetic aminofunctionalized polymer sorbent performance using molecular modeling methods",
pages = "20-20",
url = "https://hdl.handle.net/21.15107/rcub_cer_7001"
}

Suručić, L. T., Nastasović, A., Marković, B., Tadić, T., Onjia, A.,& Janjić, G.. (2022). Theoretical prediction of magnetic aminofunctionalized polymer sorbent performance using molecular modeling methods. in Book of Abstracts - XIV Conference of  Chemists, Technologists and Environmentalists of Republic of Srpska, October 21-22, 2022, Banja Luka
University in Banjaluka, Faculty of Technology., 20-20.
https://hdl.handle.net/21.15107/rcub_cer_7001

Suručić LT, Nastasović A, Marković B, Tadić T, Onjia A, Janjić G. Theoretical prediction of magnetic aminofunctionalized polymer sorbent performance using molecular modeling methods. in Book of Abstracts - XIV Conference of  Chemists, Technologists and Environmentalists of Republic of Srpska, October 21-22, 2022, Banja Luka. 2022;:20-20.
https://hdl.handle.net/21.15107/rcub_cer_7001 .

Suručić, Ljiljana T., Nastasović, Aleksandra, Marković, Bojana, Tadić, Tamara, Onjia, Antonije, Janjić, Goran, "Theoretical prediction of magnetic aminofunctionalized polymer sorbent performance using molecular modeling methods" in Book of Abstracts - XIV Conference of  Chemists, Technologists and Environmentalists of Republic of Srpska, October 21-22, 2022, Banja Luka (2022):20-20,
https://hdl.handle.net/21.15107/rcub_cer_7001 .

TY  - JOUR
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Gak Simić, Kristina
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Trišović, Nemanja
AU  - Đorđević, Ivana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5427
AB  - Two spirohydantoin derivatives, 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-bromobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), were synthesized and analyzed by single crystal X-ray diffraction, DFT and QTAIM calculations. Simple substitution of the benzoyl unit gave rise to different crystal structures. In 1, a parallel stack along the b-axis with alternating perpendicular separation is formed, while in 2 the R46(32) nets are joined together to form stacks which enclose linear channels. Hierarchical development of these crystal structures was analyzed through dimeric motifs associated with the presence of intermolecular interactions. By including the previously reported structurally-related spirohydantoin derivatives, we created a set of structures which enabled us to evaluate substituent effects on their conformational preferences, i.e., widening of the dihedral angle between the hydantoin and substituted benzoyl unit when going from F to Br. A conformational search revealed that the value of the torsion angle N3-C11-C12-C13 can be regarded as a compromise between the extended conjugation between the carbonyl and phenyl group and intramolecular C-H⋯O interaction between these two groups. This intramolecular effect is more pronounced on the torsion angle C2-N3-C11-C12, which defines the relative orientation between the hydantoin ring and the carbonyl bridge. The present work may provide a basis for design of new cyclohexane-5-spirohydantoins with potential for pharmaceutical applications both at the molecular and supramolecular level.
PB  - USA : Royal Society of Chemistry
T2  - CrystEngComm
T1  - Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group
VL  - 24
IS  - 22
SP  - 4106
EP  - 4119
DO  - 10.1039/d2ce00376g
ER  - 

@article{
author = "Lazić, Anita and Radovanović, Lidija and Gak Simić, Kristina and Rogan, Jelena and Janjić, Goran and Trišović, Nemanja and Đorđević, Ivana",
year = "2022",
abstract = "Two spirohydantoin derivatives, 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (1) and 3-(4-bromobenzoyl)-1,3-diazaspiro[4.5]decane-2,4-dione (2), were synthesized and analyzed by single crystal X-ray diffraction, DFT and QTAIM calculations. Simple substitution of the benzoyl unit gave rise to different crystal structures. In 1, a parallel stack along the b-axis with alternating perpendicular separation is formed, while in 2 the R46(32) nets are joined together to form stacks which enclose linear channels. Hierarchical development of these crystal structures was analyzed through dimeric motifs associated with the presence of intermolecular interactions. By including the previously reported structurally-related spirohydantoin derivatives, we created a set of structures which enabled us to evaluate substituent effects on their conformational preferences, i.e., widening of the dihedral angle between the hydantoin and substituted benzoyl unit when going from F to Br. A conformational search revealed that the value of the torsion angle N3-C11-C12-C13 can be regarded as a compromise between the extended conjugation between the carbonyl and phenyl group and intramolecular C-H⋯O interaction between these two groups. This intramolecular effect is more pronounced on the torsion angle C2-N3-C11-C12, which defines the relative orientation between the hydantoin ring and the carbonyl bridge. The present work may provide a basis for design of new cyclohexane-5-spirohydantoins with potential for pharmaceutical applications both at the molecular and supramolecular level.",
publisher = "USA : Royal Society of Chemistry",
journal = "CrystEngComm",
title = "Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group",
volume = "24",
number = "22",
pages = "4106-4119",
doi = "10.1039/d2ce00376g"
}

Lazić, A., Radovanović, L., Gak Simić, K., Rogan, J., Janjić, G., Trišović, N.,& Đorđević, I.. (2022). Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group. in CrystEngComm
USA : Royal Society of Chemistry., 24(22), 4106-4119.
https://doi.org/10.1039/d2ce00376g

Lazić A, Radovanović L, Gak Simić K, Rogan J, Janjić G, Trišović N, Đorđević I. Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group. in CrystEngComm. 2022;24(22):4106-4119.
doi:10.1039/d2ce00376g .

Lazić, Anita, Radovanović, Lidija, Gak Simić, Kristina, Rogan, Jelena, Janjić, Goran, Trišović, Nemanja, Đorđević, Ivana, "Unravelling conformational and crystal packing preferences of cyclohexane-5-spirohydantoin derivatives incorporating a halogenated benzoyl group" in CrystEngComm, 24, no. 22 (2022):4106-4119,
https://doi.org/10.1039/d2ce00376g . .

TY  - JOUR
AU  - Bondžić, Aleksandra M.
AU  - Žakula, Jelena J.
AU  - Korićanac, Lela
AU  - Keta, Otilija D.
AU  - Janjić, Goran
AU  - Đorđević, Ivana S.
AU  - Rajković, Snežana
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5412
AB  - Herein, the stability, lipophilicity, in vitro cytotoxicity, and influence on acetylcholinesterase of five dinuclear platinum(II) complexes with the general formula [{Pt(en)Cl}2(μ-L)]2+ (L is a different aromatic nitrogen-containing heterocyclic bridging ligands pyrazine (pz, Pt1), pyridazine (pydz, Pt2), quinoxaline (qx, Pt3), phthalazine (phtz, Pt4) and quinazoline (qz, Pt5), while en is bidentate coordinated ethylenediamine) were evaluated. The most active analyzed platinum complexes induced time-dependent growth inhibition of A375, HeLa, PANC-1, and MRC-5 cells. The best efficiency was achieved on HeLa and PANC-1 cells for Pt1, Pt2, and Pt3 at the highest concentration, while Pt1 was significantly more potent than cisplatin at a lower concentration. Additionally, a lower effect on normal cells was observed compared to cisplatin, which may indicate potentially fewer side effects of these complexes. Selected complexes induce reactive oxygen species and apoptosis on tumor cell lines. The most potent reversible acetylcholinesterase (AChE) inhibitors were Pt2, Pt4, and Pt5. Pt1 showed similar inhibitory potential toward AChE as cisplatin, but a different type of inhibition, which could contribute to lower neurotoxicity. Docking studies revealed that Pt2 and Pt4 were bound to the active gorge above the catalytic triad. In contrast, the other complexes were bound to the edge of the active gorge without impeding the approach to the catalytic triad. According to this, Pt1 represents a promising compound with potent anticancer properties, high selectivity, and low neurotoxicity.
PB  - Elsevier
T2  - Chemico-Biological Interactions
T1  - Cytotoxic activity and influence on acetylcholinesterase of series dinuclear platinum(II) complexes with aromatic nitrogen-containing heterocyclic bridging ligands: Insights in the mechanisms of action
VL  - 351
SP  - 109708
DO  - 10.1016/j.cbi.2021.109708
ER  - 

@article{
author = "Bondžić, Aleksandra M. and Žakula, Jelena J. and Korićanac, Lela and Keta, Otilija D. and Janjić, Goran and Đorđević, Ivana S. and Rajković, Snežana",
year = "2022",
abstract = "Herein, the stability, lipophilicity, in vitro cytotoxicity, and influence on acetylcholinesterase of five dinuclear platinum(II) complexes with the general formula [{Pt(en)Cl}2(μ-L)]2+ (L is a different aromatic nitrogen-containing heterocyclic bridging ligands pyrazine (pz, Pt1), pyridazine (pydz, Pt2), quinoxaline (qx, Pt3), phthalazine (phtz, Pt4) and quinazoline (qz, Pt5), while en is bidentate coordinated ethylenediamine) were evaluated. The most active analyzed platinum complexes induced time-dependent growth inhibition of A375, HeLa, PANC-1, and MRC-5 cells. The best efficiency was achieved on HeLa and PANC-1 cells for Pt1, Pt2, and Pt3 at the highest concentration, while Pt1 was significantly more potent than cisplatin at a lower concentration. Additionally, a lower effect on normal cells was observed compared to cisplatin, which may indicate potentially fewer side effects of these complexes. Selected complexes induce reactive oxygen species and apoptosis on tumor cell lines. The most potent reversible acetylcholinesterase (AChE) inhibitors were Pt2, Pt4, and Pt5. Pt1 showed similar inhibitory potential toward AChE as cisplatin, but a different type of inhibition, which could contribute to lower neurotoxicity. Docking studies revealed that Pt2 and Pt4 were bound to the active gorge above the catalytic triad. In contrast, the other complexes were bound to the edge of the active gorge without impeding the approach to the catalytic triad. According to this, Pt1 represents a promising compound with potent anticancer properties, high selectivity, and low neurotoxicity.",
publisher = "Elsevier",
journal = "Chemico-Biological Interactions",
title = "Cytotoxic activity and influence on acetylcholinesterase of series dinuclear platinum(II) complexes with aromatic nitrogen-containing heterocyclic bridging ligands: Insights in the mechanisms of action",
volume = "351",
pages = "109708",
doi = "10.1016/j.cbi.2021.109708"
}

Bondžić, A. M., Žakula, J. J., Korićanac, L., Keta, O. D., Janjić, G., Đorđević, I. S.,& Rajković, S.. (2022). Cytotoxic activity and influence on acetylcholinesterase of series dinuclear platinum(II) complexes with aromatic nitrogen-containing heterocyclic bridging ligands: Insights in the mechanisms of action. in Chemico-Biological Interactions
Elsevier., 351, 109708.
https://doi.org/10.1016/j.cbi.2021.109708

Bondžić AM, Žakula JJ, Korićanac L, Keta OD, Janjić G, Đorđević IS, Rajković S. Cytotoxic activity and influence on acetylcholinesterase of series dinuclear platinum(II) complexes with aromatic nitrogen-containing heterocyclic bridging ligands: Insights in the mechanisms of action. in Chemico-Biological Interactions. 2022;351:109708.
doi:10.1016/j.cbi.2021.109708 .

Bondžić, Aleksandra M., Žakula, Jelena J., Korićanac, Lela, Keta, Otilija D., Janjić, Goran, Đorđević, Ivana S., Rajković, Snežana, "Cytotoxic activity and influence on acetylcholinesterase of series dinuclear platinum(II) complexes with aromatic nitrogen-containing heterocyclic bridging ligands: Insights in the mechanisms of action" in Chemico-Biological Interactions, 351 (2022):109708,
https://doi.org/10.1016/j.cbi.2021.109708 . .

TY  - JOUR
AU  - Petković-Benazzouz, Marija M.
AU  - Rakić, Aleksandra
AU  - Trišović, Nemanja
AU  - Zarić, Božidarka
AU  - Janjić, Goran
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7120
AB  - Coordination effects have been considered through the most common interactions in the crystal structures of fluoro compounds (C–H/F and F/F interactions). The supramolecular profile of these effects is based on quantum-chemical calculations for the assessment of the interaction strength and electrostatic potential maps, which provide a qualitative insight into the examined effect. Coordination of aliphatic fluorides leads to an increase of the negative potential of the F atoms, and, hence, an increase in the hydrogen-bonding acceptor ability (strengthening of C–H/F interactions) and a weakening of the F/F interactions, due to an increase in repulsive interactions between the F atoms. There is no significant change in the potential of the F atoms due to coordination of C6-aromatic fluorides, as in the case of aliphatic ones. This results in slight changes in the strengths of the C–H/F and F/F interactions (coupled with parallel interaction at large offsets, PILO), in a noticeable enhancement of stacking interactions, as well as in a significant enhancement of interactions involving the π-system (F/π and C–H/π interactions). It has also been shown that a decrease in the charge of the metal ions leads to a decrease in the negative potential of the F atom and also that the nature of the metal ion has a significant influence on the value of the potential of the F atoms.
PB  - American Chemical Society (ACS)
T2  - Crystal Growth and Design
T1  - Supramolecular Perspective of Coordination Effects on Fluorine Interactions
VL  - 21
VL  - 6142
IS  - 11
SP  - 6129
DO  - 10.1021/acs.cgd.1c00584
ER  - 

@article{
author = "Petković-Benazzouz, Marija M. and Rakić, Aleksandra and Trišović, Nemanja and Zarić, Božidarka and Janjić, Goran",
year = "2021",
abstract = "Coordination effects have been considered through the most common interactions in the crystal structures of fluoro compounds (C–H/F and F/F interactions). The supramolecular profile of these effects is based on quantum-chemical calculations for the assessment of the interaction strength and electrostatic potential maps, which provide a qualitative insight into the examined effect. Coordination of aliphatic fluorides leads to an increase of the negative potential of the F atoms, and, hence, an increase in the hydrogen-bonding acceptor ability (strengthening of C–H/F interactions) and a weakening of the F/F interactions, due to an increase in repulsive interactions between the F atoms. There is no significant change in the potential of the F atoms due to coordination of C6-aromatic fluorides, as in the case of aliphatic ones. This results in slight changes in the strengths of the C–H/F and F/F interactions (coupled with parallel interaction at large offsets, PILO), in a noticeable enhancement of stacking interactions, as well as in a significant enhancement of interactions involving the π-system (F/π and C–H/π interactions). It has also been shown that a decrease in the charge of the metal ions leads to a decrease in the negative potential of the F atom and also that the nature of the metal ion has a significant influence on the value of the potential of the F atoms.",
publisher = "American Chemical Society (ACS)",
journal = "Crystal Growth and Design",
title = "Supramolecular Perspective of Coordination Effects on Fluorine Interactions",
volume = "21, 6142",
number = "11",
pages = "6129",
doi = "10.1021/acs.cgd.1c00584"
}

Petković-Benazzouz, M. M., Rakić, A., Trišović, N., Zarić, B.,& Janjić, G.. (2021). Supramolecular Perspective of Coordination Effects on Fluorine Interactions. in Crystal Growth and Design
American Chemical Society (ACS)., 21(11), 6129.
https://doi.org/10.1021/acs.cgd.1c00584

Petković-Benazzouz MM, Rakić A, Trišović N, Zarić B, Janjić G. Supramolecular Perspective of Coordination Effects on Fluorine Interactions. in Crystal Growth and Design. 2021;21(11):6129.
doi:10.1021/acs.cgd.1c00584 .

Petković-Benazzouz, Marija M., Rakić, Aleksandra, Trišović, Nemanja, Zarić, Božidarka, Janjić, Goran, "Supramolecular Perspective of Coordination Effects on Fluorine Interactions" in Crystal Growth and Design, 21, no. 11 (2021):6129,
https://doi.org/10.1021/acs.cgd.1c00584 . .

TY  - CONF
AU  - Lazić, Anita
AU  - Đorđević, Ivana
AU  - Radovanović, Lidija
AU  - Popović, Dragan
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Trišović, Nemanja
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7124
AB  - A racemic spirohydantoin derivative bearing a tetralin and 4-methoxybenzyl group was synthesized
and its crystal structure was determined. The hierarchical development of the crystal packing was
discussed through cooperativity of various homo and heterohiral dimeric motifs associated with the
presence of different intermolecular interactions. A hallmark structural feature of the investigated
compound was alternation of double layers. A larger number of the contact fragments in the
environment of the tetralin unit results from its larger contact surface, while the 4-methoxybenzyl
unit provides a slightly greater contribution to the overall stabilization. Regarding the
pharmacological potential of the investigated compound, we performed a docking study on the
dopamine D3 receptor and IRAK 4 (Interleukin-1 Receptor-Associated Kinase 4) enzyme. The total
number of amino acid, which interact with the 4-methoxybenzyl unit, was slightly larger than the
number of amino acids in the neighborhood of the tetralin unit as a result of its greater flexibility. It
made the 4-methoxybenzyl unit more adaptable for interactions with the biological targets.
PB  - Belgrade : Serbian Chemical Society
C3  - Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia
T1  - Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative
T1  - Улога интермолекулских интеракција у супрамолекулској организацији и биолошком препознавању деривата спирохидантоина
SP  - 93
EP  - 93
UR  - https://hdl.handle.net/21.15107/rcub_cer_7124
ER  - 

@conference{
author = "Lazić, Anita and Đorđević, Ivana and Radovanović, Lidija and Popović, Dragan and Rogan, Jelena and Janjić, Goran and Trišović, Nemanja",
year = "2021",
abstract = "A racemic spirohydantoin derivative bearing a tetralin and 4-methoxybenzyl group was synthesized
and its crystal structure was determined. The hierarchical development of the crystal packing was
discussed through cooperativity of various homo and heterohiral dimeric motifs associated with the
presence of different intermolecular interactions. A hallmark structural feature of the investigated
compound was alternation of double layers. A larger number of the contact fragments in the
environment of the tetralin unit results from its larger contact surface, while the 4-methoxybenzyl
unit provides a slightly greater contribution to the overall stabilization. Regarding the
pharmacological potential of the investigated compound, we performed a docking study on the
dopamine D3 receptor and IRAK 4 (Interleukin-1 Receptor-Associated Kinase 4) enzyme. The total
number of amino acid, which interact with the 4-methoxybenzyl unit, was slightly larger than the
number of amino acids in the neighborhood of the tetralin unit as a result of its greater flexibility. It
made the 4-methoxybenzyl unit more adaptable for interactions with the biological targets.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia",
title = "Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative, Улога интермолекулских интеракција у супрамолекулској организацији и биолошком препознавању деривата спирохидантоина",
pages = "93-93",
url = "https://hdl.handle.net/21.15107/rcub_cer_7124"
}

Lazić, A., Đorđević, I., Radovanović, L., Popović, D., Rogan, J., Janjić, G.,& Trišović, N.. (2021). Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative. in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia
Belgrade : Serbian Chemical Society., 93-93.
https://hdl.handle.net/21.15107/rcub_cer_7124

Lazić A, Đorđević I, Radovanović L, Popović D, Rogan J, Janjić G, Trišović N. Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative. in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia. 2021;:93-93.
https://hdl.handle.net/21.15107/rcub_cer_7124 .

Lazić, Anita, Đorđević, Ivana, Radovanović, Lidija, Popović, Dragan, Rogan, Jelena, Janjić, Goran, Trišović, Nemanja, "Role of intermolecular interactions in the self-assembly and biorecognition of a spirohydantoin derivative" in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia (2021):93-93,
https://hdl.handle.net/21.15107/rcub_cer_7124 .

TY  - CONF
AU  - Rakić, Aleksandra
AU  - Petković-Benazzouz, Marija
AU  - Trišović, Nemanja
AU  - Janjić, Goran
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7125
AB  - Statistical analysis of crystal structures from CSD (Crystallographic database) has shown the 
F...F contacts are the second group of interactions (23050 structures), immediately after the 
hydrogen bonds (43397 structures), that are mainly of aliphatic C−H...F type. There is no clear 
tendency of F...F contacts toward some certain values of d parameter, but it is possible to notice noticeable clear tendency of numerous structures to d values greater than 2.9 Å. There is a pronounced maximum in the range of torsion angle T from 160 to 180° corresponding to trans orientation of interacting C−F and X−Y fragments.
AB  - На основу анализе кристалних структура преузетих из Кембричке базе кристалографских података (CSD) показано је да се алифтичне C−H...F водоничне везе издвајају као најбројније интеракције флуорованих алифатичних група (43397 стуктура).  Далеко испод (23050 структура), на другом месту су F...F интеракције. Уочљиво је да су вредности F...F растојања (d параметар) претежно изнад 2,9 Å. Међутим, не постоји јасно изражена тенденција према одређеној вредности d параметра. Пошто се за највећи број структура вредности торзионог угла C-F-X-Y (Т параметар) крећу између 160 и 180° може се закључити да интерагујуће C−F и X−Y групе међусобно заузимају trans оријентацију
PB  - Serbian Crystallographic Society
C3  - Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
T1  - Fluorovanje alifatičnih jedinjenja. Pokretačka sila u kristalnim strukturama
T1  - Fluorination of aliphatic compounds. Driving force in crystal structures
SP  - 12
EP  - 13
UR  - https://hdl.handle.net/21.15107/rcub_cer_7125
ER  - 

@conference{
author = "Rakić, Aleksandra and Petković-Benazzouz, Marija and Trišović, Nemanja and Janjić, Goran",
year = "2021",
abstract = "Statistical analysis of crystal structures from CSD (Crystallographic database) has shown the 
F...F contacts are the second group of interactions (23050 structures), immediately after the 
hydrogen bonds (43397 structures), that are mainly of aliphatic C−H...F type. There is no clear 
tendency of F...F contacts toward some certain values of d parameter, but it is possible to notice noticeable clear tendency of numerous structures to d values greater than 2.9 Å. There is a pronounced maximum in the range of torsion angle T from 160 to 180° corresponding to trans orientation of interacting C−F and X−Y fragments., На основу анализе кристалних структура преузетих из Кембричке базе кристалографских података (CSD) показано је да се алифтичне C−H...F водоничне везе издвајају као најбројније интеракције флуорованих алифатичних група (43397 стуктура).  Далеко испод (23050 структура), на другом месту су F...F интеракције. Уочљиво је да су вредности F...F растојања (d параметар) претежно изнад 2,9 Å. Међутим, не постоји јасно изражена тенденција према одређеној вредности d параметра. Пошто се за највећи број структура вредности торзионог угла C-F-X-Y (Т параметар) крећу између 160 и 180° може се закључити да интерагујуће C−F и X−Y групе међусобно заузимају trans оријентацију",
publisher = "Serbian Crystallographic Society",
journal = "Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac",
title = "Fluorovanje alifatičnih jedinjenja. Pokretačka sila u kristalnim strukturama, Fluorination of aliphatic compounds. Driving force in crystal structures",
pages = "12-13",
url = "https://hdl.handle.net/21.15107/rcub_cer_7125"
}

Rakić, A., Petković-Benazzouz, M., Trišović, N.,& Janjić, G.. (2021). Fluorovanje alifatičnih jedinjenja. Pokretačka sila u kristalnim strukturama. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
Serbian Crystallographic Society., 12-13.
https://hdl.handle.net/21.15107/rcub_cer_7125

Rakić A, Petković-Benazzouz M, Trišović N, Janjić G. Fluorovanje alifatičnih jedinjenja. Pokretačka sila u kristalnim strukturama. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac. 2021;:12-13.
https://hdl.handle.net/21.15107/rcub_cer_7125 .

Rakić, Aleksandra, Petković-Benazzouz, Marija, Trišović, Nemanja, Janjić, Goran, "Fluorovanje alifatičnih jedinjenja. Pokretačka sila u kristalnim strukturama" in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac (2021):12-13,
https://hdl.handle.net/21.15107/rcub_cer_7125 .

TY  - CONF
AU  - Gak Simić, Kristina
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Rogan, Jelena
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Trišović, Nemanja
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7126
AB  - Синтетисан је дериват циклохексан-5-спирохидантоина и одређена је његова кристална
структура. Хијерархијски развој кристалног паковања дискутован је са аспекта кооперативности димерних мотива који настају преко различитих интермолекулских
интеракција, и то: јаких N–H···O водоничних веза и слабих C–H···O, C–H···Cl и C–H···π
интеракција. Кристално паковање задржава мотив, који се обично среће код деривата
хидантоина, у коме су два инверзано оријентисана молекула повезана паром N–H···O
водоничних веза. Специфична структурна карактеристика јесу паралелни слојеви дуж ac-равни. Пошто овај мотив повезује сваки други слој, растојање између слојева се наизменично мења. Накнадна анализа Хиршфелдове површине омогућила је
разраду квалитативних и квантитативних доприноса интермолекулских интеракција
проучаваном кристалном паковању.
AB  - A derivative of cyclohexane-5-spirohydantoin was synthesized and its crystal structure was determined. The hierarchical development of the crystal packing was discussed through cooperativity of various dimeric motifs associated with the presence of different intermolecular interactions, namely strong N–H···O, and weaker C–H···O, C–H···Cl and C–H···π interactions. The crystal packing retained the motif commonly found in hydantoin derivatives where two molecules related by inversion are linked by a pair of N–H∙∙∙O hydrogen bonds. A hallmark structural feature was a parallel layer arrangement to the ac-plane with alternating perpendicular separation, whereby this motif connect every second layer. An analysis of the Hirshfeld surface further elaborated the qualitative and quantitative contributions of intermolecular interactions to the crystal packing.
PB  - Serbian Crystallographic Society
C3  - Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
T1  - Supramolekulska organizacija 3-(4-hlorbenzoil)-1,3- diazaspiro[4.5]dekan-2,4-diona
T1  - Supramolecular association in 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4- dione
SP  - 24
EP  - 25
UR  - https://hdl.handle.net/21.15107/rcub_cer_7126
ER  - 

@conference{
author = "Gak Simić, Kristina and Lazić, Anita and Radovanović, Lidija and Rogan, Jelena and Janjić, Goran and Đorđević, Ivana and Trišović, Nemanja",
year = "2021",
abstract = "Синтетисан је дериват циклохексан-5-спирохидантоина и одређена је његова кристална
структура. Хијерархијски развој кристалног паковања дискутован је са аспекта кооперативности димерних мотива који настају преко различитих интермолекулских
интеракција, и то: јаких N–H···O водоничних веза и слабих C–H···O, C–H···Cl и C–H···π
интеракција. Кристално паковање задржава мотив, који се обично среће код деривата
хидантоина, у коме су два инверзано оријентисана молекула повезана паром N–H···O
водоничних веза. Специфична структурна карактеристика јесу паралелни слојеви дуж ac-равни. Пошто овај мотив повезује сваки други слој, растојање између слојева се наизменично мења. Накнадна анализа Хиршфелдове површине омогућила је
разраду квалитативних и квантитативних доприноса интермолекулских интеракција
проучаваном кристалном паковању., A derivative of cyclohexane-5-spirohydantoin was synthesized and its crystal structure was determined. The hierarchical development of the crystal packing was discussed through cooperativity of various dimeric motifs associated with the presence of different intermolecular interactions, namely strong N–H···O, and weaker C–H···O, C–H···Cl and C–H···π interactions. The crystal packing retained the motif commonly found in hydantoin derivatives where two molecules related by inversion are linked by a pair of N–H∙∙∙O hydrogen bonds. A hallmark structural feature was a parallel layer arrangement to the ac-plane with alternating perpendicular separation, whereby this motif connect every second layer. An analysis of the Hirshfeld surface further elaborated the qualitative and quantitative contributions of intermolecular interactions to the crystal packing.",
publisher = "Serbian Crystallographic Society",
journal = "Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac",
title = "Supramolekulska organizacija 3-(4-hlorbenzoil)-1,3- diazaspiro[4.5]dekan-2,4-diona, Supramolecular association in 3-(4-chlorobenzoyl)-1,3-diazaspiro[4.5]decane-2,4- dione",
pages = "24-25",
url = "https://hdl.handle.net/21.15107/rcub_cer_7126"
}

Gak Simić, K., Lazić, A., Radovanović, L., Rogan, J., Janjić, G., Đorđević, I.,& Trišović, N.. (2021). Supramolekulska organizacija 3-(4-hlorbenzoil)-1,3- diazaspiro[4.5]dekan-2,4-diona. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
Serbian Crystallographic Society., 24-25.
https://hdl.handle.net/21.15107/rcub_cer_7126

Gak Simić K, Lazić A, Radovanović L, Rogan J, Janjić G, Đorđević I, Trišović N. Supramolekulska organizacija 3-(4-hlorbenzoil)-1,3- diazaspiro[4.5]dekan-2,4-diona. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac. 2021;:24-25.
https://hdl.handle.net/21.15107/rcub_cer_7126 .

Gak Simić, Kristina, Lazić, Anita, Radovanović, Lidija, Rogan, Jelena, Janjić, Goran, Đorđević, Ivana, Trišović, Nemanja, "Supramolekulska organizacija 3-(4-hlorbenzoil)-1,3- diazaspiro[4.5]dekan-2,4-diona" in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac (2021):24-25,
https://hdl.handle.net/21.15107/rcub_cer_7126 .

TY  - CONF
AU  - Janjić, Goran
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7123
AB  - The supramolecular approach is based on statistical analysis of data from crystal structures extracted
from the Cambridge Structural Database (CSD), quantum-chemical calculations for assess the
strength of typical interactions, and docking study for determination of the binding of S/Se
compounds to selected biomolecules. The statistical analysis has shown that S and Se atoms, in
fragments that corresponds to the side chains of cysteine (Cys), methionine (Met) selenocysteine
(Sec) and selenomethionine (Mse), display a similar tendency towards specific types of interaction.
The most numerous are structures with C-H/Se and C-H/S interactions (∼80%). The structures with
Se/Se and S/S interactions are notably less numerous (∼5%), although the C-H/Se and C-H/S
interactions (∼−0.8 kcal/mol) are weaker than the most stable parallel Se/Se and S/S interactions
(∼−3.3 kcal/mol) and electrostatic interactions of σ/π type (∼−2.6 kcal/mol). The significant
difference in numerosity can be explained by the abundance of C-H groups in analyzed crystal
structures. Docking studies revealed that S and Se rarely participate in interactions with the amino
acid residues of target enzymes, but the differences in the number and positions of their binding
sites between Se and S compounds are more pronounced if the substituents of S/Se atom are polar
and if there are more Se/S atoms in the ligand.
AB  - Supramolekulski pristup zasnovan je na statističkoj analizi podataka dobijenih iz kristalnih struktura, ekstrahovanih iz CSD-a (od eng. Cambridge Structural Database), kvantno-hemijskim proračunima za procenu jačine tipičnih interakcija, i na doking studiji za određivanje vezivanja S/Se jedinjenja za odabrane biomolekule. Statistička analiza je pokazala da atomi S i Se, u fragmentima koji odgovaraju bočnim lancima cisteina (Cis), metionina (Met), selenocisteina (Sec) i
selenometionina (Mse), pokazuju sličnu tendenciju ka određenim vrstama interakcija. Najbrojnije su 
strukture sa C-H/Se i C-H/S interakcijama (~ 80%). Strukture sa Se/Se i S/S interakcijama su znatno 
manje zastupljene u kristalnim strukturama (∼5%), iako su C-H/Se i C-H/S interakcije (∼ -0,8 kcal/mol) slabije od najstabilnijih Se/Se i S/S interakcija sa paralelnih orientacijom (∼ -3,3 kcal/mol) i njihovih elektrostatičkih interakcija σ/π tipa (∼ -2,6 kcal/mol). Značajna razlika u brojnosti može se objasniti obiljem C-H grupa u analiziranim kristalnim strukturama. Doking studija je pokazala da S i Se atomi retko uključeni u interakcijama sa amino-kiselinskim ostacima ciljanih enzima, ali su razlike u broju i položajima vezivnih mesta izraženije ako su supstituenti vezani za S/Se polarni, ali i ako ligand poseduje više od jednog Se ili S atoma.
PB  - Belgrade : Serbian Chemical Society
C3  - Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia
T1  - Zamena sumpora selenom; Supramolekulski pristup
T1  - Substitution of sulfur by selenium; The supramolecular insight
SP  - 25
EP  - 25
UR  - https://hdl.handle.net/21.15107/rcub_cer_7123
ER  - 

@conference{
author = "Janjić, Goran",
year = "2021",
abstract = "The supramolecular approach is based on statistical analysis of data from crystal structures extracted
from the Cambridge Structural Database (CSD), quantum-chemical calculations for assess the
strength of typical interactions, and docking study for determination of the binding of S/Se
compounds to selected biomolecules. The statistical analysis has shown that S and Se atoms, in
fragments that corresponds to the side chains of cysteine (Cys), methionine (Met) selenocysteine
(Sec) and selenomethionine (Mse), display a similar tendency towards specific types of interaction.
The most numerous are structures with C-H/Se and C-H/S interactions (∼80%). The structures with
Se/Se and S/S interactions are notably less numerous (∼5%), although the C-H/Se and C-H/S
interactions (∼−0.8 kcal/mol) are weaker than the most stable parallel Se/Se and S/S interactions
(∼−3.3 kcal/mol) and electrostatic interactions of σ/π type (∼−2.6 kcal/mol). The significant
difference in numerosity can be explained by the abundance of C-H groups in analyzed crystal
structures. Docking studies revealed that S and Se rarely participate in interactions with the amino
acid residues of target enzymes, but the differences in the number and positions of their binding
sites between Se and S compounds are more pronounced if the substituents of S/Se atom are polar
and if there are more Se/S atoms in the ligand., Supramolekulski pristup zasnovan je na statističkoj analizi podataka dobijenih iz kristalnih struktura, ekstrahovanih iz CSD-a (od eng. Cambridge Structural Database), kvantno-hemijskim proračunima za procenu jačine tipičnih interakcija, i na doking studiji za određivanje vezivanja S/Se jedinjenja za odabrane biomolekule. Statistička analiza je pokazala da atomi S i Se, u fragmentima koji odgovaraju bočnim lancima cisteina (Cis), metionina (Met), selenocisteina (Sec) i
selenometionina (Mse), pokazuju sličnu tendenciju ka određenim vrstama interakcija. Najbrojnije su 
strukture sa C-H/Se i C-H/S interakcijama (~ 80%). Strukture sa Se/Se i S/S interakcijama su znatno 
manje zastupljene u kristalnim strukturama (∼5%), iako su C-H/Se i C-H/S interakcije (∼ -0,8 kcal/mol) slabije od najstabilnijih Se/Se i S/S interakcija sa paralelnih orientacijom (∼ -3,3 kcal/mol) i njihovih elektrostatičkih interakcija σ/π tipa (∼ -2,6 kcal/mol). Značajna razlika u brojnosti može se objasniti obiljem C-H grupa u analiziranim kristalnim strukturama. Doking studija je pokazala da S i Se atomi retko uključeni u interakcijama sa amino-kiselinskim ostacima ciljanih enzima, ali su razlike u broju i položajima vezivnih mesta izraženije ako su supstituenti vezani za S/Se polarni, ali i ako ligand poseduje više od jednog Se ili S atoma.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia",
title = "Zamena sumpora selenom; Supramolekulski pristup, Substitution of sulfur by selenium; The supramolecular insight",
pages = "25-25",
url = "https://hdl.handle.net/21.15107/rcub_cer_7123"
}

Janjić, G.. (2021). Zamena sumpora selenom; Supramolekulski pristup. in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia
Belgrade : Serbian Chemical Society., 25-25.
https://hdl.handle.net/21.15107/rcub_cer_7123

Janjić G. Zamena sumpora selenom; Supramolekulski pristup. in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia. 2021;:25-25.
https://hdl.handle.net/21.15107/rcub_cer_7123 .

Janjić, Goran, "Zamena sumpora selenom; Supramolekulski pristup" in Kratki izvodi radova, Knjiga radova 57. Savetovanje Srpskog hemijskog društva, 18. i 19. juni 2021, Kragujevac / Book of abstracts, Proceedings - 57th Meeting of the Serbian Chemical Society, June 18-19, 2021, Kragujevac, Serbia (2021):25-25,
https://hdl.handle.net/21.15107/rcub_cer_7123 .

TY  - CONF
AU  - Petković-Benazzouz, Marija
AU  - Rakić, Aleksandra
AU  - Trišović, Nemanja
AU  - Janjić, Goran
AU  - Sarvan, Mirjana
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7128
AB  - Statistical analysis of crystal structures obtained from Cambridge Structural Database (CSD) 
showed that the most numerous are structures in which carbon atom is bound to interacting fluorine atom.
AB  - Statistička analiza kristalnih struktura iz Kembričke baze strukturnih podataka pokazuje da su 
najbrojnije one strukture kod kojih je ugljenikov atom vezan za interagujući atom fluora. One u 
kojima je fluor vezan za aromatičnu grupu su malo manje zastupljene.
PB  - Serbian Crystallographic Society
C3  - Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
T1  - Fluorinacija aromatičnih grupa. Efekat koordinovanja na atom fluora
T1  - Fluorination of aromatic groups. The effects of coordination on fluorine interactions
SP  - 48
EP  - 49
UR  - https://hdl.handle.net/21.15107/rcub_cer_7128
ER  - 

@conference{
author = "Petković-Benazzouz, Marija and Rakić, Aleksandra and Trišović, Nemanja and Janjić, Goran and Sarvan, Mirjana",
year = "2021",
abstract = "Statistical analysis of crystal structures obtained from Cambridge Structural Database (CSD) 
showed that the most numerous are structures in which carbon atom is bound to interacting fluorine atom., Statistička analiza kristalnih struktura iz Kembričke baze strukturnih podataka pokazuje da su 
najbrojnije one strukture kod kojih je ugljenikov atom vezan za interagujući atom fluora. One u 
kojima je fluor vezan za aromatičnu grupu su malo manje zastupljene.",
publisher = "Serbian Crystallographic Society",
journal = "Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac",
title = "Fluorinacija aromatičnih grupa. Efekat koordinovanja na atom fluora, Fluorination of aromatic groups. The effects of coordination on fluorine interactions",
pages = "48-49",
url = "https://hdl.handle.net/21.15107/rcub_cer_7128"
}

Petković-Benazzouz, M., Rakić, A., Trišović, N., Janjić, G.,& Sarvan, M.. (2021). Fluorinacija aromatičnih grupa. Efekat koordinovanja na atom fluora. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
Serbian Crystallographic Society., 48-49.
https://hdl.handle.net/21.15107/rcub_cer_7128

Petković-Benazzouz M, Rakić A, Trišović N, Janjić G, Sarvan M. Fluorinacija aromatičnih grupa. Efekat koordinovanja na atom fluora. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac. 2021;:48-49.
https://hdl.handle.net/21.15107/rcub_cer_7128 .

Petković-Benazzouz, Marija, Rakić, Aleksandra, Trišović, Nemanja, Janjić, Goran, Sarvan, Mirjana, "Fluorinacija aromatičnih grupa. Efekat koordinovanja na atom fluora" in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac (2021):48-49,
https://hdl.handle.net/21.15107/rcub_cer_7128 .

TY  - CONF
AU  - Janjić, Goran
AU  - Đorđević, Ivana
AU  - Lazić, Anita
AU  - Radovanović, Lidija
AU  - Petković-Benazzouz, Marija
AU  - Rogan, Jelena
AU  - Trišović, Nemanja
PY  - 2021
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7127
AB  - Kristalografska i kvantnohemijska studija, koja je usmerena na proučavanje efekata fluorovanja benzoil-grupe vezane za cikloheksan-5-spirohidantoin, pokazala je da aromatični prsten ima najveći afinitet prema cikloheksanskom prstenu (nepolarnim grupama), sa kojim gradi C–H∙∙∙π i 
paralelne interakcije sa velikim pomakom. Uvođenje atoma fluora na aromatični prsten dovodi do 
povećanog afiniteta, usled stvaranja dodatnih C–H∙∙∙F interakcija. Dodatno, ova studija je 
proširena na hlorovane i bromovane derivate. Analizom kristalnog pakovanja četiri derivata spirohidantoina (slika) pokazano je da orijentacija aromatičnog prstena, koja je preko rotabilne 
C(aromatični)–C(karbonilni) veze odvojena od rigidnog spirohidantoinskog jezgra, određuje
trodimenzionalnu supramolekulsku arhitekturu. Energijski profil rotabilne veze (slika) jako zavisi 
od vrste halogenog atoma vezanog za aromatični prsten (X). Najvišu barijeru (najmanju rotacionu 
slobodu) ima aromatični prsten sa Br atomom (oko 36 kcal/mol), dok najnižu barijeru imaju 
prstenovi sa vezanim Cl ili F atomom (oko 7 kcal/mol). Izmerene vrednosti torzionog ugla T 
(slika) u kristalnim stukturama, koji definiše rotabilnost ove veze, odgovaraju minimumima energije na energijskim profilima. Kod ovih orijentacija aromatični prstenovi istovremeno grade C–
H...π interakcije sa hidantoinskim prstenom i C–H...O interakciju sa karbonilnom grupom koja 
premošćuje dva prstena. Na osnovu ovih rezultata može se zaključiti da su orijentacije aromatičnog prstena određene unutarmolekulskim interakcijama, a ne međumolekulskim interakcijama, kao i da su konformacione razlike uzrok razlika u kristalnom pakovanju ovih jedinjenja.
AB  - The crystallographic and quantum chemical study, focused on the effects of fluorination of the 
benzoyl group bound to the spirohydantoin moiety, showed that the aromatic ring has the highest 
affinity towards the cyclohexene ring (nonpolar groups), thus forming C–H∙∙∙π and parallel interactions at large offset. Introduction of a fluorine atom into the aromatic ring leads to higher affinity, due to formation of additional C–H∙∙∙F interactions. Subsequently, the present study has been extended to chlorinated and brominated derivatives. An analysis of the crystal packaging of four spirohydantoin derivatives has shown that the orientation of the aromatic ring, bound to the rigid spirohydantoin moiety by the rotatable C(aromatic)–C(carbonyl) bond, determines the three-dimensional supramolecular architecture. The energy profile of the rotatable bond (Figure) strongly depends on the halogen atom bound to the aromatic ring (X). The highest barrier (the lowest rotational freedom) has been found for the aromatic ring with the Br atom (36 kcal/mol), while the rings with the Cl or F atom have the lowest barrier (7 kcal/mol). The measured values of the torsion angle T in the crystal structures which defines the rotability of the mentioned bond, correspond to the energy minima on the energy profiles. In these orientations, the aromatic ring simultaneously forms C–H...π interactions with the hydantoin ring and C–H...O interaction with the carbonyl spacer group. Based on these results, one can conclude that the orientation of the aromatic ring is defined by intramolecular interactions, not by intermolecular interactions, as well as that the conformational differences further cause differences in the crystal packaging of these compounds.
PB  - Serbian Crystallographic Society
C3  - Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
T1  - Uticaj halogenovanja aromatičnog prstena na konformaciju spirohidantoinskih jedinjenja
T1  - Influence of halogenation of aromatic ring on the conformation of spirohydantoin compounds
SP  - 34
EP  - 35
UR  - https://hdl.handle.net/21.15107/rcub_cer_7127
ER  - 

@conference{
author = "Janjić, Goran and Đorđević, Ivana and Lazić, Anita and Radovanović, Lidija and Petković-Benazzouz, Marija and Rogan, Jelena and Trišović, Nemanja",
year = "2021",
abstract = "Kristalografska i kvantnohemijska studija, koja je usmerena na proučavanje efekata fluorovanja benzoil-grupe vezane za cikloheksan-5-spirohidantoin, pokazala je da aromatični prsten ima najveći afinitet prema cikloheksanskom prstenu (nepolarnim grupama), sa kojim gradi C–H∙∙∙π i 
paralelne interakcije sa velikim pomakom. Uvođenje atoma fluora na aromatični prsten dovodi do 
povećanog afiniteta, usled stvaranja dodatnih C–H∙∙∙F interakcija. Dodatno, ova studija je 
proširena na hlorovane i bromovane derivate. Analizom kristalnog pakovanja četiri derivata spirohidantoina (slika) pokazano je da orijentacija aromatičnog prstena, koja je preko rotabilne 
C(aromatični)–C(karbonilni) veze odvojena od rigidnog spirohidantoinskog jezgra, određuje
trodimenzionalnu supramolekulsku arhitekturu. Energijski profil rotabilne veze (slika) jako zavisi 
od vrste halogenog atoma vezanog za aromatični prsten (X). Najvišu barijeru (najmanju rotacionu 
slobodu) ima aromatični prsten sa Br atomom (oko 36 kcal/mol), dok najnižu barijeru imaju 
prstenovi sa vezanim Cl ili F atomom (oko 7 kcal/mol). Izmerene vrednosti torzionog ugla T 
(slika) u kristalnim stukturama, koji definiše rotabilnost ove veze, odgovaraju minimumima energije na energijskim profilima. Kod ovih orijentacija aromatični prstenovi istovremeno grade C–
H...π interakcije sa hidantoinskim prstenom i C–H...O interakciju sa karbonilnom grupom koja 
premošćuje dva prstena. Na osnovu ovih rezultata može se zaključiti da su orijentacije aromatičnog prstena određene unutarmolekulskim interakcijama, a ne međumolekulskim interakcijama, kao i da su konformacione razlike uzrok razlika u kristalnom pakovanju ovih jedinjenja., The crystallographic and quantum chemical study, focused on the effects of fluorination of the 
benzoyl group bound to the spirohydantoin moiety, showed that the aromatic ring has the highest 
affinity towards the cyclohexene ring (nonpolar groups), thus forming C–H∙∙∙π and parallel interactions at large offset. Introduction of a fluorine atom into the aromatic ring leads to higher affinity, due to formation of additional C–H∙∙∙F interactions. Subsequently, the present study has been extended to chlorinated and brominated derivatives. An analysis of the crystal packaging of four spirohydantoin derivatives has shown that the orientation of the aromatic ring, bound to the rigid spirohydantoin moiety by the rotatable C(aromatic)–C(carbonyl) bond, determines the three-dimensional supramolecular architecture. The energy profile of the rotatable bond (Figure) strongly depends on the halogen atom bound to the aromatic ring (X). The highest barrier (the lowest rotational freedom) has been found for the aromatic ring with the Br atom (36 kcal/mol), while the rings with the Cl or F atom have the lowest barrier (7 kcal/mol). The measured values of the torsion angle T in the crystal structures which defines the rotability of the mentioned bond, correspond to the energy minima on the energy profiles. In these orientations, the aromatic ring simultaneously forms C–H...π interactions with the hydantoin ring and C–H...O interaction with the carbonyl spacer group. Based on these results, one can conclude that the orientation of the aromatic ring is defined by intramolecular interactions, not by intermolecular interactions, as well as that the conformational differences further cause differences in the crystal packaging of these compounds.",
publisher = "Serbian Crystallographic Society",
journal = "Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac",
title = "Uticaj halogenovanja aromatičnog prstena na konformaciju spirohidantoinskih jedinjenja, Influence of halogenation of aromatic ring on the conformation of spirohydantoin compounds",
pages = "34-35",
url = "https://hdl.handle.net/21.15107/rcub_cer_7127"
}

Janjić, G., Đorđević, I., Lazić, A., Radovanović, L., Petković-Benazzouz, M., Rogan, J.,& Trišović, N.. (2021). Uticaj halogenovanja aromatičnog prstena na konformaciju spirohidantoinskih jedinjenja. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac
Serbian Crystallographic Society., 34-35.
https://hdl.handle.net/21.15107/rcub_cer_7127

Janjić G, Đorđević I, Lazić A, Radovanović L, Petković-Benazzouz M, Rogan J, Trišović N. Uticaj halogenovanja aromatičnog prstena na konformaciju spirohidantoinskih jedinjenja. in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac. 2021;:34-35.
https://hdl.handle.net/21.15107/rcub_cer_7127 .

Janjić, Goran, Đorđević, Ivana, Lazić, Anita, Radovanović, Lidija, Petković-Benazzouz, Marija, Rogan, Jelena, Trišović, Nemanja, "Uticaj halogenovanja aromatičnog prstena na konformaciju spirohidantoinskih jedinjenja" in Изводи радова - XXVII Конференција Српског кристалографског друштва, Крагујевац / Abstracts - 27th Conference of the Serbian crystallographic society , Kragujevac (2021):34-35,
https://hdl.handle.net/21.15107/rcub_cer_7127 .