TY  - JOUR
AU  - Kop, Tatjana
AU  - Pavlović, Radoslav
AU  - Nešić, Marko
AU  - Stepanović, Olivera
AU  - Wang, Xiuze
AU  - Todorović, Nina
AU  - Rodić, Marko
AU  - Šmit, Biljana
PY  - 2023
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7113
AB  - Fluorinated piperidines find wide applications, most notably in the development of novel therapies and agrochemicals. Cyclization of alkenyl N-tosylamides promoted by BF3-activated aryliodine(III) carboxylates is an attractive strategy to construct 3-fluoropiperidines, but it suffers from selectivity issues arising from competitive oxoaminations and the inability to easily modulate the reactions diastereoselectivity. Herein, we report an itemized optimization of the reaction conditions carried out on both cyclic and acyclic substrates and outline the origins of substrate- and reagent-based stereo-, regio-, and chemoselectivity. Extensive mechanistic studies encompassing multinuclear NMR spectroscopy, deuterium labeling, rearrangements on stereodefined substrates, and careful structural analyses (NMR and X-ray) of the reaction products are performed. This revealed the processes and interactions crucial for achieving controlled preparation of 3-fluoropiperidines using I(III) chemistry and has provided an advanced understanding of the reaction mechanism. In brief, we propose that BF3-coordinated I(III) reagents attack C═C to produce the corresponding iodiranium(III) ion, which then undergoes diastereodetermining 5-exo-cyclization. Transiently formed pyrrolidines with an exocyclic σ-alkyl-I(III) moiety can further undergo aziridinium ion formation or reductive ligand coupling processes, which dictate not only the final product’s ring size but also the chemoselectivity. Importantly, the selectivity of the reaction depends on the nature of the ligand bound to I(III) and the presence of electrolytes such as TBABF4. Reported findings will facilitate the usage of ArI(III)-dicarboxylates in the reliable construction of fluorinated azaheterocycles.
PB  - American Chemical Society (ACS)
T2  - The Journal of Organic Chemistry
T1  - On the Selectivity in the Synthesis of 3-Fluoropiperidines Using BF3-Activated Hypervalent Iodine Reagents
VL  - 88
IS  - 15
SP  - 10946
EP  - 10959
DO  - 10.1021/acs.joc.3c00944
ER  - 

@article{
author = "Kop, Tatjana and Pavlović, Radoslav and Nešić, Marko and Stepanović, Olivera and Wang, Xiuze and Todorović, Nina and Rodić, Marko and Šmit, Biljana",
year = "2023",
abstract = "Fluorinated piperidines find wide applications, most notably in the development of novel therapies and agrochemicals. Cyclization of alkenyl N-tosylamides promoted by BF3-activated aryliodine(III) carboxylates is an attractive strategy to construct 3-fluoropiperidines, but it suffers from selectivity issues arising from competitive oxoaminations and the inability to easily modulate the reactions diastereoselectivity. Herein, we report an itemized optimization of the reaction conditions carried out on both cyclic and acyclic substrates and outline the origins of substrate- and reagent-based stereo-, regio-, and chemoselectivity. Extensive mechanistic studies encompassing multinuclear NMR spectroscopy, deuterium labeling, rearrangements on stereodefined substrates, and careful structural analyses (NMR and X-ray) of the reaction products are performed. This revealed the processes and interactions crucial for achieving controlled preparation of 3-fluoropiperidines using I(III) chemistry and has provided an advanced understanding of the reaction mechanism. In brief, we propose that BF3-coordinated I(III) reagents attack C═C to produce the corresponding iodiranium(III) ion, which then undergoes diastereodetermining 5-exo-cyclization. Transiently formed pyrrolidines with an exocyclic σ-alkyl-I(III) moiety can further undergo aziridinium ion formation or reductive ligand coupling processes, which dictate not only the final product’s ring size but also the chemoselectivity. Importantly, the selectivity of the reaction depends on the nature of the ligand bound to I(III) and the presence of electrolytes such as TBABF4. Reported findings will facilitate the usage of ArI(III)-dicarboxylates in the reliable construction of fluorinated azaheterocycles.",
publisher = "American Chemical Society (ACS)",
journal = "The Journal of Organic Chemistry",
title = "On the Selectivity in the Synthesis of 3-Fluoropiperidines Using BF3-Activated Hypervalent Iodine Reagents",
volume = "88",
number = "15",
pages = "10946-10959",
doi = "10.1021/acs.joc.3c00944"
}

Kop, T., Pavlović, R., Nešić, M., Stepanović, O., Wang, X., Todorović, N., Rodić, M.,& Šmit, B.. (2023). On the Selectivity in the Synthesis of 3-Fluoropiperidines Using BF3-Activated Hypervalent Iodine Reagents. in The Journal of Organic Chemistry
American Chemical Society (ACS)., 88(15), 10946-10959.
https://doi.org/10.1021/acs.joc.3c00944

Kop T, Pavlović R, Nešić M, Stepanović O, Wang X, Todorović N, Rodić M, Šmit B. On the Selectivity in the Synthesis of 3-Fluoropiperidines Using BF3-Activated Hypervalent Iodine Reagents. in The Journal of Organic Chemistry. 2023;88(15):10946-10959.
doi:10.1021/acs.joc.3c00944 .

Kop, Tatjana, Pavlović, Radoslav, Nešić, Marko, Stepanović, Olivera, Wang, Xiuze, Todorović, Nina, Rodić, Marko, Šmit, Biljana, "On the Selectivity in the Synthesis of 3-Fluoropiperidines Using BF3-Activated Hypervalent Iodine Reagents" in The Journal of Organic Chemistry, 88, no. 15 (2023):10946-10959,
https://doi.org/10.1021/acs.joc.3c00944 . .

TY  - CONF
AU  - Pavlović, Pavle
AU  - Rodić, Marko
AU  - Novaković, Irena
AU  - Filipović, Nenad
AU  - Todorović, Tamara
PY  - 2022
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/5784
AB  - Kompleks Cu(II) sa kondenzacionim derivatom 2-acetilpiridina i dihidrazida malonske  kiseline (H2L) je dobijen direktnom sintezom. Prekristalizacijom je dobijen monokristalni  proizvod te je struktura kompleksa rešena primenom rendgenske strukturne analize. U  unutrašnjoj sferi binuklearnog simetrinog kompleksa, sa distorgovanom oktaedarskom  geometrijom oko jona Cu(II), jedan molekul liganda je koordinovan u anjonskom, a drugi  u neutralnom obliku, oba bis-tridentatno preko N,N,O seta donorskih atoma. U spoljašnjoj  sferi kompleksa se nalaze perhloratni joni i molekuli vode. Kompleks je pokazao  antimikrobnu aktivnost u niskom mikromolarnom opsegu na svim testiranim  mikroorganizmima.
AB  - The Cu(II) complex with the ligand H2L, which is a condensation derivative of  2-acetylpyridine and malonic acid dihydrazide, was obtained by direct synthesis.  Recrystallization gave a single crystal product, and the structure of the complex was solved  by X-ray structural analysis. In the inner sphere of the binuclear symmetrical complex,  with distorted octahedral geometry around Cu(II) ions, one ligand molecule is coordinated  in anionic and the other in neutral form, both bis-tridentaly via the N, N, O set of donor  atoms. Perchlorate ions and water molecules are located in the outer sphere of the  complex. The complex showed antimicrobial activity in the low micromolar range on all  tested microorganisms.
PB  - Belgrade: Serbian Chemical Society
C3  - Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine
T1  - Sinteza, karakterizacija i antimikrobna aktivnost kompleksa  Cu(II) sa kondenzacionim derivatom 2-acetilpiridina i dihidrazida  malonske kiseline
T1  - Synthesis, characterization and antimicrobial activity of Cu(II)  complex with condensation derivative of  2-acetylpyridine and malonic acid dihydrazide
SP  - 120
EP  - 120
UR  - https://hdl.handle.net/21.15107/rcub_cer_5784
ER  - 

@conference{
author = "Pavlović, Pavle and Rodić, Marko and Novaković, Irena and Filipović, Nenad and Todorović, Tamara",
year = "2022",
abstract = "Kompleks Cu(II) sa kondenzacionim derivatom 2-acetilpiridina i dihidrazida malonske  kiseline (H2L) je dobijen direktnom sintezom. Prekristalizacijom je dobijen monokristalni  proizvod te je struktura kompleksa rešena primenom rendgenske strukturne analize. U  unutrašnjoj sferi binuklearnog simetrinog kompleksa, sa distorgovanom oktaedarskom  geometrijom oko jona Cu(II), jedan molekul liganda je koordinovan u anjonskom, a drugi  u neutralnom obliku, oba bis-tridentatno preko N,N,O seta donorskih atoma. U spoljašnjoj  sferi kompleksa se nalaze perhloratni joni i molekuli vode. Kompleks je pokazao  antimikrobnu aktivnost u niskom mikromolarnom opsegu na svim testiranim  mikroorganizmima., The Cu(II) complex with the ligand H2L, which is a condensation derivative of  2-acetylpyridine and malonic acid dihydrazide, was obtained by direct synthesis.  Recrystallization gave a single crystal product, and the structure of the complex was solved  by X-ray structural analysis. In the inner sphere of the binuclear symmetrical complex,  with distorted octahedral geometry around Cu(II) ions, one ligand molecule is coordinated  in anionic and the other in neutral form, both bis-tridentaly via the N, N, O set of donor  atoms. Perchlorate ions and water molecules are located in the outer sphere of the  complex. The complex showed antimicrobial activity in the low micromolar range on all  tested microorganisms.",
publisher = "Belgrade: Serbian Chemical Society",
journal = "Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine",
title = "Sinteza, karakterizacija i antimikrobna aktivnost kompleksa  Cu(II) sa kondenzacionim derivatom 2-acetilpiridina i dihidrazida  malonske kiseline, Synthesis, characterization and antimicrobial activity of Cu(II)  complex with condensation derivative of  2-acetylpyridine and malonic acid dihydrazide",
pages = "120-120",
url = "https://hdl.handle.net/21.15107/rcub_cer_5784"
}

Pavlović, P., Rodić, M., Novaković, I., Filipović, N.,& Todorović, T.. (2022). Sinteza, karakterizacija i antimikrobna aktivnost kompleksa  Cu(II) sa kondenzacionim derivatom 2-acetilpiridina i dihidrazida  malonske kiseline. in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine
Belgrade: Serbian Chemical Society., 120-120.
https://hdl.handle.net/21.15107/rcub_cer_5784

Pavlović P, Rodić M, Novaković I, Filipović N, Todorović T. Sinteza, karakterizacija i antimikrobna aktivnost kompleksa  Cu(II) sa kondenzacionim derivatom 2-acetilpiridina i dihidrazida  malonske kiseline. in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine. 2022;:120-120.
https://hdl.handle.net/21.15107/rcub_cer_5784 .

Pavlović, Pavle, Rodić, Marko, Novaković, Irena, Filipović, Nenad, Todorović, Tamara, "Sinteza, karakterizacija i antimikrobna aktivnost kompleksa  Cu(II) sa kondenzacionim derivatom 2-acetilpiridina i dihidrazida  malonske kiseline" in Book of Abstracts, Proceedings - 58th Meeting of the Serbian Chemical Society, Belgrade, Serbia, June 9-10, 2022 / Kratki izvodi radova, kjniga radova - 58. Savetovanje Srpskog hemijskog društva, Beograd 9. i 10. jun 2022. godine (2022):120-120,
https://hdl.handle.net/21.15107/rcub_cer_5784 .

TY  - JOUR
AU  - Dimitrijević, Teodora
AU  - Novaković, Irena
AU  - Radanović, Dušanka
AU  - Novaković, Sladjana B.
AU  - Rodić, Marko V.
AU  - Anđelković, Katarina
AU  - Šumar-Ristović, Maja
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4025
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3643
AB  - In this article, synthesis, spectral and X-ray structure characterization, antimicrobial activity and Brine shrimp test of two new Cu(II) complexes with a salicylaldehyde derivative have been reported. Complexes [Cu(L)(bipy)]BF4·0.5H2O and [Cu2(L)2(phen)2](BF4)2 were obtained in the reaction of Cu(BF4)2·6H2O, deprotonated 4-(diethylamino)−2-hydroxybenzaldehyde ligand (L) and α-diimine (2,2’-bipyridine or 1,10-phenanthroline). The complex with bipyridine is mononuclear, containing one L and one bipyridine ligand in a distorted square-planar cation with a BF4 − anion and lattice water molecule, whereas the complex with phenanthroline is a dinuclear centrosymmetric dimeric cation, containing two L ligands along with two phenanthroline ligands and BF4 − anions. The coordination geometry of each Cu(II) ion can be described as an elongated square pyramid. MS-ESI spectroscopy indicated that [Cu2(L)2(phen)2](BF4)2 is mononuclear in DMSO solution. In vitro antibacterial and antifungal activity was tested against four Gram-positive, four Gram-negative bacteria and three fungal strains. Complexes showed significantly stronger antibacterial activities than parent ligands. The mononuclear phenanthroline complex in solution showed very good antimicrobial activity, which is comparable to the activity of the standard antibiotic amikacin against all tested bacterial strains. The same complex has better antifungal activity than fluconazole, which was used as a standard. Results of the brine shrimp test indicate that both complexes have good toxicity against Artemia nauplii.
PB  - Taylor & Francis
T2  - Journal of Coordination Chemistry
T1  - Synthesis, spectral and structural characterization and biological activity of Cu(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines
VL  - 73
IS  - 4
SP  - 702
EP  - 716
DO  - 10.1080/00958972.2020.1740212
ER  - 

@article{
author = "Dimitrijević, Teodora and Novaković, Irena and Radanović, Dušanka and Novaković, Sladjana B. and Rodić, Marko V. and Anđelković, Katarina and Šumar-Ristović, Maja",
year = "2020",
abstract = "In this article, synthesis, spectral and X-ray structure characterization, antimicrobial activity and Brine shrimp test of two new Cu(II) complexes with a salicylaldehyde derivative have been reported. Complexes [Cu(L)(bipy)]BF4·0.5H2O and [Cu2(L)2(phen)2](BF4)2 were obtained in the reaction of Cu(BF4)2·6H2O, deprotonated 4-(diethylamino)−2-hydroxybenzaldehyde ligand (L) and α-diimine (2,2’-bipyridine or 1,10-phenanthroline). The complex with bipyridine is mononuclear, containing one L and one bipyridine ligand in a distorted square-planar cation with a BF4 − anion and lattice water molecule, whereas the complex with phenanthroline is a dinuclear centrosymmetric dimeric cation, containing two L ligands along with two phenanthroline ligands and BF4 − anions. The coordination geometry of each Cu(II) ion can be described as an elongated square pyramid. MS-ESI spectroscopy indicated that [Cu2(L)2(phen)2](BF4)2 is mononuclear in DMSO solution. In vitro antibacterial and antifungal activity was tested against four Gram-positive, four Gram-negative bacteria and three fungal strains. Complexes showed significantly stronger antibacterial activities than parent ligands. The mononuclear phenanthroline complex in solution showed very good antimicrobial activity, which is comparable to the activity of the standard antibiotic amikacin against all tested bacterial strains. The same complex has better antifungal activity than fluconazole, which was used as a standard. Results of the brine shrimp test indicate that both complexes have good toxicity against Artemia nauplii.",
publisher = "Taylor & Francis",
journal = "Journal of Coordination Chemistry",
title = "Synthesis, spectral and structural characterization and biological activity of Cu(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines",
volume = "73",
number = "4",
pages = "702-716",
doi = "10.1080/00958972.2020.1740212"
}

Dimitrijević, T., Novaković, I., Radanović, D., Novaković, S. B., Rodić, M. V., Anđelković, K.,& Šumar-Ristović, M.. (2020). Synthesis, spectral and structural characterization and biological activity of Cu(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines. in Journal of Coordination Chemistry
Taylor & Francis., 73(4), 702-716.
https://doi.org/10.1080/00958972.2020.1740212

Dimitrijević T, Novaković I, Radanović D, Novaković SB, Rodić MV, Anđelković K, Šumar-Ristović M. Synthesis, spectral and structural characterization and biological activity of Cu(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines. in Journal of Coordination Chemistry. 2020;73(4):702-716.
doi:10.1080/00958972.2020.1740212 .

Dimitrijević, Teodora, Novaković, Irena, Radanović, Dušanka, Novaković, Sladjana B., Rodić, Marko V., Anđelković, Katarina, Šumar-Ristović, Maja, "Synthesis, spectral and structural characterization and biological activity of Cu(II) complexes with 4-(diethylamino)salicylaldehyde and α-diimines" in Journal of Coordination Chemistry, 73, no. 4 (2020):702-716,
https://doi.org/10.1080/00958972.2020.1740212 . .

TY  - JOUR
AU  - Ristić, Predrag
AU  - Blagojević, Vladimir
AU  - Janjić, Goran
AU  - Rodić, Marko
AU  - Vulić, Predrag
AU  - Donnard, Morgan
AU  - Gulea, Mihaela
AU  - Chylewska, Agnieszka
AU  - Makowski, Mariusz
AU  - Todorović, Tamara
AU  - Filipović, Nenad
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4028
AB  - Pt(II) and Pd(II) complexes (1 and 2, respectively) with thiomorpholine-4-carbonitrile (TM-CN), an N-substituted thiomorpholine derivative, were synthesized from tetrachlorido precursors in water. Structural analysis has shown that 1 represents the first monomeric metal complex with this ligand type with an axial M–S bond with respect to the TM-CN ring chair conformation, while in 2 a typical equatorial M–S bond position with respect to the ring chair conformation was observed. A detailed DFT investigation revealed that axial conformers are more stable for molecular forms of both metals, while intermolecular interactions in the crystals stabilize the axial conformer for Pt(II) and the equatorial conformer for Pd(II). The magnitude of this stabilization in the case of 2 is large enough to change the most stable axial conformer in the molecular form to the equatorial conformer in the crystal. Further investigation of the strength of individual intermolecular interactions revealed significant differences of some interactions between the two structures. The likely cause of the difference in the crystal structures of experimentally obtained complexes is the fact that 1 and 2 exhibit different dominant interactions: C–H/M and C–H/S are more dominant in 1 and C–H/Cl interactions are more dominant in 2. In addition, DFT calculations have shown that while the axial position of the Pt–S bond with respect to the ring chair conformation results in a significantly shorter C–H/Pt interaction distance than that in the hypothetical equatorial conformer, there is very little difference in C–H/Pd interaction distances in conformers with axial and equatorial positions of Pd–S bond with respect to the ring chair conformation.
PB  - American Chemical Society (ACS)
T2  - Crystal Growth & Design
T1  - Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study
VL  - 20
IS  - 5
SP  - 3018
EP  - 3033
DO  - 10.1021/acs.cgd.9b01661
ER  - 

@article{
author = "Ristić, Predrag and Blagojević, Vladimir and Janjić, Goran and Rodić, Marko and Vulić, Predrag and Donnard, Morgan and Gulea, Mihaela and Chylewska, Agnieszka and Makowski, Mariusz and Todorović, Tamara and Filipović, Nenad",
year = "2020",
abstract = "Pt(II) and Pd(II) complexes (1 and 2, respectively) with thiomorpholine-4-carbonitrile (TM-CN), an N-substituted thiomorpholine derivative, were synthesized from tetrachlorido precursors in water. Structural analysis has shown that 1 represents the first monomeric metal complex with this ligand type with an axial M–S bond with respect to the TM-CN ring chair conformation, while in 2 a typical equatorial M–S bond position with respect to the ring chair conformation was observed. A detailed DFT investigation revealed that axial conformers are more stable for molecular forms of both metals, while intermolecular interactions in the crystals stabilize the axial conformer for Pt(II) and the equatorial conformer for Pd(II). The magnitude of this stabilization in the case of 2 is large enough to change the most stable axial conformer in the molecular form to the equatorial conformer in the crystal. Further investigation of the strength of individual intermolecular interactions revealed significant differences of some interactions between the two structures. The likely cause of the difference in the crystal structures of experimentally obtained complexes is the fact that 1 and 2 exhibit different dominant interactions: C–H/M and C–H/S are more dominant in 1 and C–H/Cl interactions are more dominant in 2. In addition, DFT calculations have shown that while the axial position of the Pt–S bond with respect to the ring chair conformation results in a significantly shorter C–H/Pt interaction distance than that in the hypothetical equatorial conformer, there is very little difference in C–H/Pd interaction distances in conformers with axial and equatorial positions of Pd–S bond with respect to the ring chair conformation.",
publisher = "American Chemical Society (ACS)",
journal = "Crystal Growth & Design",
title = "Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study",
volume = "20",
number = "5",
pages = "3018-3033",
doi = "10.1021/acs.cgd.9b01661"
}

Ristić, P., Blagojević, V., Janjić, G., Rodić, M., Vulić, P., Donnard, M., Gulea, M., Chylewska, A., Makowski, M., Todorović, T.,& Filipović, N.. (2020). Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study. in Crystal Growth & Design
American Chemical Society (ACS)., 20(5), 3018-3033.
https://doi.org/10.1021/acs.cgd.9b01661

Ristić P, Blagojević V, Janjić G, Rodić M, Vulić P, Donnard M, Gulea M, Chylewska A, Makowski M, Todorović T, Filipović N. Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study. in Crystal Growth & Design. 2020;20(5):3018-3033.
doi:10.1021/acs.cgd.9b01661 .

Ristić, Predrag, Blagojević, Vladimir, Janjić, Goran, Rodić, Marko, Vulić, Predrag, Donnard, Morgan, Gulea, Mihaela, Chylewska, Agnieszka, Makowski, Mariusz, Todorović, Tamara, Filipović, Nenad, "Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study" in Crystal Growth & Design, 20, no. 5 (2020):3018-3033,
https://doi.org/10.1021/acs.cgd.9b01661 . .

TY  - JOUR
AU  - Ristić, Predrag
AU  - Blagojević, Vladimir
AU  - Janjić, Goran
AU  - Rodić, Marko
AU  - Vulić, Predrag
AU  - Donnard, Morgan
AU  - Gulea, Mihaela
AU  - Chylewska, Agnieszka
AU  - Makowski, Mariusz
AU  - Todorović, Tamara
AU  - Filipović, Nenad
PY  - 2020
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4029
AB  - Pt(II) and Pd(II) complexes (1 and 2, respectively) with thiomorpholine-4-carbonitrile (TM-CN), an N-substituted thiomorpholine derivative, were synthesized from tetrachlorido precursors in water. Structural analysis has shown that 1 represents the first monomeric metal complex with this ligand type with an axial M–S bond with respect to the TM-CN ring chair conformation, while in 2 a typical equatorial M–S bond position with respect to the ring chair conformation was observed. A detailed DFT investigation revealed that axial conformers are more stable for molecular forms of both metals, while intermolecular interactions in the crystals stabilize the axial conformer for Pt(II) and the equatorial conformer for Pd(II). The magnitude of this stabilization in the case of 2 is large enough to change the most stable axial conformer in the molecular form to the equatorial conformer in the crystal. Further investigation of the strength of individual intermolecular interactions revealed significant differences of some interactions between the two structures. The likely cause of the difference in the crystal structures of experimentally obtained complexes is the fact that 1 and 2 exhibit different dominant interactions: C–H/M and C–H/S are more dominant in 1 and C–H/Cl interactions are more dominant in 2. In addition, DFT calculations have shown that while the axial position of the Pt–S bond with respect to the ring chair conformation results in a significantly shorter C–H/Pt interaction distance than that in the hypothetical equatorial conformer, there is very little difference in C–H/Pd interaction distances in conformers with axial and equatorial positions of Pd–S bond with respect to the ring chair conformation.
PB  - American Chemical Society (ACS)
T2  - Crystal Growth & Design
T1  - Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study
VL  - 20
IS  - 5
SP  - 3018
EP  - 3033
DO  - 10.1021/acs.cgd.9b01661
ER  - 

@article{
author = "Ristić, Predrag and Blagojević, Vladimir and Janjić, Goran and Rodić, Marko and Vulić, Predrag and Donnard, Morgan and Gulea, Mihaela and Chylewska, Agnieszka and Makowski, Mariusz and Todorović, Tamara and Filipović, Nenad",
year = "2020",
abstract = "Pt(II) and Pd(II) complexes (1 and 2, respectively) with thiomorpholine-4-carbonitrile (TM-CN), an N-substituted thiomorpholine derivative, were synthesized from tetrachlorido precursors in water. Structural analysis has shown that 1 represents the first monomeric metal complex with this ligand type with an axial M–S bond with respect to the TM-CN ring chair conformation, while in 2 a typical equatorial M–S bond position with respect to the ring chair conformation was observed. A detailed DFT investigation revealed that axial conformers are more stable for molecular forms of both metals, while intermolecular interactions in the crystals stabilize the axial conformer for Pt(II) and the equatorial conformer for Pd(II). The magnitude of this stabilization in the case of 2 is large enough to change the most stable axial conformer in the molecular form to the equatorial conformer in the crystal. Further investigation of the strength of individual intermolecular interactions revealed significant differences of some interactions between the two structures. The likely cause of the difference in the crystal structures of experimentally obtained complexes is the fact that 1 and 2 exhibit different dominant interactions: C–H/M and C–H/S are more dominant in 1 and C–H/Cl interactions are more dominant in 2. In addition, DFT calculations have shown that while the axial position of the Pt–S bond with respect to the ring chair conformation results in a significantly shorter C–H/Pt interaction distance than that in the hypothetical equatorial conformer, there is very little difference in C–H/Pd interaction distances in conformers with axial and equatorial positions of Pd–S bond with respect to the ring chair conformation.",
publisher = "American Chemical Society (ACS)",
journal = "Crystal Growth & Design",
title = "Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study",
volume = "20",
number = "5",
pages = "3018-3033",
doi = "10.1021/acs.cgd.9b01661"
}

Ristić, P., Blagojević, V., Janjić, G., Rodić, M., Vulić, P., Donnard, M., Gulea, M., Chylewska, A., Makowski, M., Todorović, T.,& Filipović, N.. (2020). Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study. in Crystal Growth & Design
American Chemical Society (ACS)., 20(5), 3018-3033.
https://doi.org/10.1021/acs.cgd.9b01661

Ristić P, Blagojević V, Janjić G, Rodić M, Vulić P, Donnard M, Gulea M, Chylewska A, Makowski M, Todorović T, Filipović N. Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study. in Crystal Growth & Design. 2020;20(5):3018-3033.
doi:10.1021/acs.cgd.9b01661 .

Ristić, Predrag, Blagojević, Vladimir, Janjić, Goran, Rodić, Marko, Vulić, Predrag, Donnard, Morgan, Gulea, Mihaela, Chylewska, Agnieszka, Makowski, Mariusz, Todorović, Tamara, Filipović, Nenad, "Influence of C–H/X (X = S, Cl, N, Pt/Pd) Interactions on the Molecular and Crystal Structures of Pt(II) and Pd(II) Complexes with Thiomorpholine-4-carbonitrile: Crystallographic, Thermal, and DFT Study" in Crystal Growth & Design, 20, no. 5 (2020):3018-3033,
https://doi.org/10.1021/acs.cgd.9b01661 . .

TY  - JOUR
AU  - Bjelogrlić, Snežana K.
AU  - Todorović, Tamara
AU  - Cvijetić, Ilija
AU  - Rodić, Marko V.
AU  - Vujčić, Miroslava
AU  - Marković, Sanja
AU  - Araskov, Jovana
AU  - Janović, Barbara
AU  - Emhemmed, Fathi
AU  - Muller, Christian D.
AU  - Filipovic, Nenad R.
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2493
AB  - A novel binuclear Cd complex (1) with hydrazone-based ligand was prepared and characterized by spectroscopy and single crystal X-ray diffraction techniques. Complex 1 reveals a strong pro-apoptotic activity in both human, mammary adenocarcinoma cells (MCF-7) and pancreatic AsPC-1 cancer stem cells (CSCs). While apoptosis undergoes mostly caspase-independent, 1 stimulates the activation of intrinsic pathway with noteworthy down regulation of caspase-8 activity in respect to non-treated controls. Distribution of cells over mitotic division indicates that 1 caused DNA damage in both cell lines, which is confirmed in DNA interaction studies. Compared to 1, cisplatin (CDDP) does not achieve cell death in 2D cultured AsPC-1 cells, while induces different pattern of cell cycle changes and caspase activation in 2D cultured MCF-7 cells, implying that these two compounds do not share similar mechanism of action. Additionally, 1 acts as a powerful inducer of mitochondrial superoxide production with dissipated trans-membrane potential in the majority of the treated cells already after 6 h of incubation. On 3D tumors, 1 displays a superior activity against CSC model, and at 100 M induces disintegration of spheroids within 2 days of incubation. Fluorescence spectroscopy, along with molecular docking show that compound 1 binds to the minor groove of DNA. Compound 1 binds to the human serum albumin (HSA) showing that the HSA can effectively transport and store 1 in the human body. Thus, our current study strongly supports further investigations on antitumor activity of 1 as a drug candidate for the treatment of highly resistant pancreatic cancer.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells
VL  - 190
SP  - 45
EP  - 66
DO  - 10.1016/j.jinorgbio.2018.10.002
ER  - 

@article{
author = "Bjelogrlić, Snežana K. and Todorović, Tamara and Cvijetić, Ilija and Rodić, Marko V. and Vujčić, Miroslava and Marković, Sanja and Araskov, Jovana and Janović, Barbara and Emhemmed, Fathi and Muller, Christian D. and Filipovic, Nenad R.",
year = "2019",
abstract = "A novel binuclear Cd complex (1) with hydrazone-based ligand was prepared and characterized by spectroscopy and single crystal X-ray diffraction techniques. Complex 1 reveals a strong pro-apoptotic activity in both human, mammary adenocarcinoma cells (MCF-7) and pancreatic AsPC-1 cancer stem cells (CSCs). While apoptosis undergoes mostly caspase-independent, 1 stimulates the activation of intrinsic pathway with noteworthy down regulation of caspase-8 activity in respect to non-treated controls. Distribution of cells over mitotic division indicates that 1 caused DNA damage in both cell lines, which is confirmed in DNA interaction studies. Compared to 1, cisplatin (CDDP) does not achieve cell death in 2D cultured AsPC-1 cells, while induces different pattern of cell cycle changes and caspase activation in 2D cultured MCF-7 cells, implying that these two compounds do not share similar mechanism of action. Additionally, 1 acts as a powerful inducer of mitochondrial superoxide production with dissipated trans-membrane potential in the majority of the treated cells already after 6 h of incubation. On 3D tumors, 1 displays a superior activity against CSC model, and at 100 M induces disintegration of spheroids within 2 days of incubation. Fluorescence spectroscopy, along with molecular docking show that compound 1 binds to the minor groove of DNA. Compound 1 binds to the human serum albumin (HSA) showing that the HSA can effectively transport and store 1 in the human body. Thus, our current study strongly supports further investigations on antitumor activity of 1 as a drug candidate for the treatment of highly resistant pancreatic cancer.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells",
volume = "190",
pages = "45-66",
doi = "10.1016/j.jinorgbio.2018.10.002"
}

Bjelogrlić, S. K., Todorović, T., Cvijetić, I., Rodić, M. V., Vujčić, M., Marković, S., Araskov, J., Janović, B., Emhemmed, F., Muller, C. D.,& Filipovic, N. R.. (2019). A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 190, 45-66.
https://doi.org/10.1016/j.jinorgbio.2018.10.002

Bjelogrlić SK, Todorović T, Cvijetić I, Rodić MV, Vujčić M, Marković S, Araskov J, Janović B, Emhemmed F, Muller CD, Filipovic NR. A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells. in Journal of Inorganic Biochemistry. 2019;190:45-66.
doi:10.1016/j.jinorgbio.2018.10.002 .

Bjelogrlić, Snežana K., Todorović, Tamara, Cvijetić, Ilija, Rodić, Marko V., Vujčić, Miroslava, Marković, Sanja, Araskov, Jovana, Janović, Barbara, Emhemmed, Fathi, Muller, Christian D., Filipovic, Nenad R., "A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells" in Journal of Inorganic Biochemistry, 190 (2019):45-66,
https://doi.org/10.1016/j.jinorgbio.2018.10.002 . .

TY  - JOUR
AU  - Bjelogrlić, Snežana K.
AU  - Todorović, Tamara
AU  - Cvijetić, Ilija
AU  - Rodić, Marko V.
AU  - Vujčić, Miroslava
AU  - Marković, Sanja
AU  - Araskov, Jovana
AU  - Janović, Barbara
AU  - Emhemmed, Fathi
AU  - Muller, Christian D.
AU  - Filipović, Nenad R.
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2623
AB  - A novel binuclear Cd complex (1) with hydrazone-based ligand was prepared and characterized by spectroscopy and single crystal X-ray diffraction techniques. Complex 1 reveals a strong pro-apoptotic activity in both human, mammary adenocarcinoma cells (MCF-7) and pancreatic AsPC-1 cancer stem cells (CSCs). While apoptosis undergoes mostly caspase-independent, 1 stimulates the activation of intrinsic pathway with noteworthy down regulation of caspase-8 activity in respect to non-treated controls. Distribution of cells over mitotic division indicates that 1 caused DNA damage in both cell lines, which is confirmed in DNA interaction studies. Compared to 1, cisplatin (CDDP) does not achieve cell death in 2D cultured AsPC-1 cells, while induces different pattern of cell cycle changes and caspase activation in 2D cultured MCF-7 cells, implying that these two compounds do not share similar mechanism of action. Additionally, 1 acts as a powerful inducer of mitochondrial superoxide production with dissipated trans-membrane potential in the majority of the treated cells already after 6 h of incubation. On 3D tumors, 1 displays a superior activity against CSC model, and at 100 M induces disintegration of spheroids within 2 days of incubation. Fluorescence spectroscopy, along with molecular docking show that compound 1 binds to the minor groove of DNA. Compound 1 binds to the human serum albumin (HSA) showing that the HSA can effectively transport and store 1 in the human body. Thus, our current study strongly supports further investigations on antitumor activity of 1 as a drug candidate for the treatment of highly resistant pancreatic cancer.
PB  - Elsevier Science Inc, New York
T2  - Journal of Inorganic Biochemistry
T1  - A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells
VL  - 190
SP  - 45
EP  - 66
DO  - 10.1016/j.jinorgbio.2018.10.002
ER  - 

@article{
author = "Bjelogrlić, Snežana K. and Todorović, Tamara and Cvijetić, Ilija and Rodić, Marko V. and Vujčić, Miroslava and Marković, Sanja and Araskov, Jovana and Janović, Barbara and Emhemmed, Fathi and Muller, Christian D. and Filipović, Nenad R.",
year = "2019",
abstract = "A novel binuclear Cd complex (1) with hydrazone-based ligand was prepared and characterized by spectroscopy and single crystal X-ray diffraction techniques. Complex 1 reveals a strong pro-apoptotic activity in both human, mammary adenocarcinoma cells (MCF-7) and pancreatic AsPC-1 cancer stem cells (CSCs). While apoptosis undergoes mostly caspase-independent, 1 stimulates the activation of intrinsic pathway with noteworthy down regulation of caspase-8 activity in respect to non-treated controls. Distribution of cells over mitotic division indicates that 1 caused DNA damage in both cell lines, which is confirmed in DNA interaction studies. Compared to 1, cisplatin (CDDP) does not achieve cell death in 2D cultured AsPC-1 cells, while induces different pattern of cell cycle changes and caspase activation in 2D cultured MCF-7 cells, implying that these two compounds do not share similar mechanism of action. Additionally, 1 acts as a powerful inducer of mitochondrial superoxide production with dissipated trans-membrane potential in the majority of the treated cells already after 6 h of incubation. On 3D tumors, 1 displays a superior activity against CSC model, and at 100 M induces disintegration of spheroids within 2 days of incubation. Fluorescence spectroscopy, along with molecular docking show that compound 1 binds to the minor groove of DNA. Compound 1 binds to the human serum albumin (HSA) showing that the HSA can effectively transport and store 1 in the human body. Thus, our current study strongly supports further investigations on antitumor activity of 1 as a drug candidate for the treatment of highly resistant pancreatic cancer.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Inorganic Biochemistry",
title = "A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells",
volume = "190",
pages = "45-66",
doi = "10.1016/j.jinorgbio.2018.10.002"
}

Bjelogrlić, S. K., Todorović, T., Cvijetić, I., Rodić, M. V., Vujčić, M., Marković, S., Araskov, J., Janović, B., Emhemmed, F., Muller, C. D.,& Filipović, N. R.. (2019). A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells. in Journal of Inorganic Biochemistry
Elsevier Science Inc, New York., 190, 45-66.
https://doi.org/10.1016/j.jinorgbio.2018.10.002

Bjelogrlić SK, Todorović T, Cvijetić I, Rodić MV, Vujčić M, Marković S, Araskov J, Janović B, Emhemmed F, Muller CD, Filipović NR. A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells. in Journal of Inorganic Biochemistry. 2019;190:45-66.
doi:10.1016/j.jinorgbio.2018.10.002 .

Bjelogrlić, Snežana K., Todorović, Tamara, Cvijetić, Ilija, Rodić, Marko V., Vujčić, Miroslava, Marković, Sanja, Araskov, Jovana, Janović, Barbara, Emhemmed, Fathi, Muller, Christian D., Filipović, Nenad R., "A novel binuclear hydrazone-based Cd(II) complex is a strong pro-apoptotic inducer with significant activity against 2D and 3D pancreatic cancer stem cells" in Journal of Inorganic Biochemistry, 190 (2019):45-66,
https://doi.org/10.1016/j.jinorgbio.2018.10.002 . .

TY  - JOUR
AU  - Živković, Marijana
AU  - Matić, Ivana Z.
AU  - Rodić, Marko V.
AU  - Novaković, Irena
AU  - Krivokuca, Ana M.
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2089
AB  - The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro
VL  - 174
SP  - 72
EP  - 85
DO  - 10.1016/j.jsbmb.2017.07.031
ER  - 

@article{
author = "Živković, Marijana and Matić, Ivana Z. and Rodić, Marko V. and Novaković, Irena and Krivokuca, Ana M. and Sladić, Dušan and Krstić, Natalija",
year = "2017",
abstract = "The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro",
volume = "174",
pages = "72-85",
doi = "10.1016/j.jsbmb.2017.07.031"
}

Živković, M., Matić, I. Z., Rodić, M. V., Novaković, I., Krivokuca, A. M., Sladić, D.,& Krstić, N.. (2017). Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology
Oxford : Pergamon-Elsevier Science Ltd., 174, 72-85.
https://doi.org/10.1016/j.jsbmb.2017.07.031

Živković M, Matić IZ, Rodić MV, Novaković I, Krivokuca AM, Sladić D, Krstić N. Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology. 2017;174:72-85.
doi:10.1016/j.jsbmb.2017.07.031 .

Živković, Marijana, Matić, Ivana Z., Rodić, Marko V., Novaković, Irena, Krivokuca, Ana M., Sladić, Dušan, Krstić, Natalija, "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro" in Journal of Steroid Biochemistry and Molecular Biology, 174 (2017):72-85,
https://doi.org/10.1016/j.jsbmb.2017.07.031 . .

TY  - JOUR
AU  - Đorđević, Ivana
AU  - Vukasinovic, Jelena
AU  - Todorović, Tamara
AU  - Filipovic, Nenad R.
AU  - Rodić, Marko V.
AU  - Lolić, Aleksandar
AU  - Portalone, Gustavo
AU  - Zlatović, Mario
AU  - Grubišić, Sonja
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2166
AB  - Cobalt(III) complexes derived from thio-and selenosemicarbazone ligands have been studied to elucidate the nature and consequences of S to Se substitution on their possible biological activity. Solid state structures of cobalt(III) complexes with bis-tridentate coordinated 2-quinolinecarboxaldehyde thio-and selenosemicarbazone were determined by single crystal X-ray diffraction analysis. The complexes were also characterized by spectroscopic methods and cyclic voltammetry. Electronic properties of the complexes were studied using DFT and TD-DFT methods. Finally, evident in vitro antioxidant activity of the complexes was demonstrated.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study
VL  - 82
IS  - 7-8
SP  - 825
EP  - 839
DO  - 10.2298/JSC170412062D
ER  - 

@article{
author = "Đorđević, Ivana and Vukasinovic, Jelena and Todorović, Tamara and Filipovic, Nenad R. and Rodić, Marko V. and Lolić, Aleksandar and Portalone, Gustavo and Zlatović, Mario and Grubišić, Sonja",
year = "2017",
abstract = "Cobalt(III) complexes derived from thio-and selenosemicarbazone ligands have been studied to elucidate the nature and consequences of S to Se substitution on their possible biological activity. Solid state structures of cobalt(III) complexes with bis-tridentate coordinated 2-quinolinecarboxaldehyde thio-and selenosemicarbazone were determined by single crystal X-ray diffraction analysis. The complexes were also characterized by spectroscopic methods and cyclic voltammetry. Electronic properties of the complexes were studied using DFT and TD-DFT methods. Finally, evident in vitro antioxidant activity of the complexes was demonstrated.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study",
volume = "82",
number = "7-8",
pages = "825-839",
doi = "10.2298/JSC170412062D"
}

Đorđević, I., Vukasinovic, J., Todorović, T., Filipovic, N. R., Rodić, M. V., Lolić, A., Portalone, G., Zlatović, M.,& Grubišić, S.. (2017). Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 82(7-8), 825-839.
https://doi.org/10.2298/JSC170412062D

Đorđević I, Vukasinovic J, Todorović T, Filipovic NR, Rodić MV, Lolić A, Portalone G, Zlatović M, Grubišić S. Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study. in Journal of the Serbian Chemical Society. 2017;82(7-8):825-839.
doi:10.2298/JSC170412062D .

Đorđević, Ivana, Vukasinovic, Jelena, Todorović, Tamara, Filipovic, Nenad R., Rodić, Marko V., Lolić, Aleksandar, Portalone, Gustavo, Zlatović, Mario, Grubišić, Sonja, "Synthesis, structures and electronic properties of Co(III) complexes with 2-quinolinecarboxaldehyde thio- and selenosemicarbazone: A combined experimental and theoretical study" in Journal of the Serbian Chemical Society, 82, no. 7-8 (2017):825-839,
https://doi.org/10.2298/JSC170412062D . .

TY  - JOUR
AU  - Filipovic, Nenad R.
AU  - Elshaflu, Hana
AU  - Grubišić, Sonja
AU  - Jovanović, Ljiljana S.
AU  - Rodić, Marko V.
AU  - Novaković, Irena
AU  - Malešević, Aleksandar S.
AU  - Đorđević, Ivana
AU  - Li, Haidong
AU  - Šojić, Nešo
AU  - Marinković, Aleksandar D.
AU  - Todorović, Tamara
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2188
AB  - The first Co(III) complexes with (1,3-selenazol-2-yl)hydrazones as an unexplored class of ligands were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis. The novel ligands act as NNN tridentate chelators forming octahedral Co(III) complexes. The impact of structural changes on ligands' periphery as well as that of isosteric replacement of sulphur with selenium on the electrochemical and electronic absorption features of complexes are explored. To support the experimental data, density functional theory (DFT) calculations were also conducted. Theoretical NMR chemical shifts, the relative energies and natural bond orbital (NBO) analysis are calculated within the DFT approach, while the singlet excited state energies and HOMO-LUMO energy gap were calculated with time-dependent density functional theory (TD-DFT). The electrophilic f(-) and nucleophilic f(+) Fukui functions are well adapted to find the electrophile and nucleophile centres in the molecules. Both (1,3-selenazol-2-yl)- and (1,3-thiazol-2-yl) hydrazone Co(III) complexes showed potent antimicrobial and antioxidant activity. A significant difference among them was a smaller cytotoxicity of selenium compounds.
PB  - Royal Soc Chemistry, Cambridge
T2  - Dalton Transactions
T1  - Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues
VL  - 46
IS  - 9
SP  - 2910
EP  - 2924
DO  - 10.1039/c6dt04785h
ER  - 

@article{
author = "Filipovic, Nenad R. and Elshaflu, Hana and Grubišić, Sonja and Jovanović, Ljiljana S. and Rodić, Marko V. and Novaković, Irena and Malešević, Aleksandar S. and Đorđević, Ivana and Li, Haidong and Šojić, Nešo and Marinković, Aleksandar D. and Todorović, Tamara",
year = "2017",
abstract = "The first Co(III) complexes with (1,3-selenazol-2-yl)hydrazones as an unexplored class of ligands were prepared and characterized by NMR spectroscopy and X-ray diffraction analysis. The novel ligands act as NNN tridentate chelators forming octahedral Co(III) complexes. The impact of structural changes on ligands' periphery as well as that of isosteric replacement of sulphur with selenium on the electrochemical and electronic absorption features of complexes are explored. To support the experimental data, density functional theory (DFT) calculations were also conducted. Theoretical NMR chemical shifts, the relative energies and natural bond orbital (NBO) analysis are calculated within the DFT approach, while the singlet excited state energies and HOMO-LUMO energy gap were calculated with time-dependent density functional theory (TD-DFT). The electrophilic f(-) and nucleophilic f(+) Fukui functions are well adapted to find the electrophile and nucleophile centres in the molecules. Both (1,3-selenazol-2-yl)- and (1,3-thiazol-2-yl) hydrazone Co(III) complexes showed potent antimicrobial and antioxidant activity. A significant difference among them was a smaller cytotoxicity of selenium compounds.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Dalton Transactions",
title = "Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues",
volume = "46",
number = "9",
pages = "2910-2924",
doi = "10.1039/c6dt04785h"
}

Filipovic, N. R., Elshaflu, H., Grubišić, S., Jovanović, L. S., Rodić, M. V., Novaković, I., Malešević, A. S., Đorđević, I., Li, H., Šojić, N., Marinković, A. D.,& Todorović, T.. (2017). Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues. in Dalton Transactions
Royal Soc Chemistry, Cambridge., 46(9), 2910-2924.
https://doi.org/10.1039/c6dt04785h

Filipovic NR, Elshaflu H, Grubišić S, Jovanović LS, Rodić MV, Novaković I, Malešević AS, Đorđević I, Li H, Šojić N, Marinković AD, Todorović T. Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues. in Dalton Transactions. 2017;46(9):2910-2924.
doi:10.1039/c6dt04785h .

Filipovic, Nenad R., Elshaflu, Hana, Grubišić, Sonja, Jovanović, Ljiljana S., Rodić, Marko V., Novaković, Irena, Malešević, Aleksandar S., Đorđević, Ivana, Li, Haidong, Šojić, Nešo, Marinković, Aleksandar D., Todorović, Tamara, "Co(III) complexes of (1,3-selenazol-2-yl)hydrazones and their sulphur analogues" in Dalton Transactions, 46, no. 9 (2017):2910-2924,
https://doi.org/10.1039/c6dt04785h . .

TY  - JOUR
AU  - Živković, Marijana
AU  - Matić, Ivana Z.
AU  - Rodić, Marko V.
AU  - Novaković, Irena
AU  - Krivokuca, Ana M.
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2017
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3009
AB  - The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Journal of Steroid Biochemistry and Molecular Biology
T1  - Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro
VL  - 174
SP  - 72
EP  - 85
DO  - 10.1016/j.jsbmb.2017.07.031
ER  - 

@article{
author = "Živković, Marijana and Matić, Ivana Z. and Rodić, Marko V. and Novaković, Irena and Krivokuca, Ana M. and Sladić, Dušan and Krstić, Natalija",
year = "2017",
abstract = "The synthesis and cytotoxic activities determination of new steroidal mono- and bis(thiazolidin-4-ones) 4a-f and 5a-f have been performed. Their anticancer action was also evaluated in comparison to previously synthesized and reported corresponding steroidal thiosemicarbazones. All compounds were obtained as stereoisomeric mixtures with different configuration (E or Z) in the hydrazone moiety at the C-3 position. After several consecutive crystallizations diastereomerically pure major (5)-isomers of mono-thiazolidin-4-ones were isolated. The structure and stereochemistry of 2,4-thiazolidinedione,2-[(17-oxoandrost-4-en-3-ylidene)hydrazone] were confirmed by X-ray analysis. A pathway for the formation of thiazolidin-4-one ring was proposed. The steroid thiazolidinone derivatives examined in this study exerted selective concentration-dependent cytotoxic activities on six tested malignant cell lines. Ten out of twelve examined compounds exhibited strong cytotoxic effects on K562 cells (IC50 values from 8.5 mu M to 14.9 mu M), eight on HeLa cells (IC50 values ranging from 8.9 mu M to 15.1 mu M) while against MDA-MB-361 cells six compouds exerted similar or even higher cytotoxic action (IC50 values from 12.7 mu M to 25.6 mu M) than cisplatin (21.5 mu M) which served as a positive control. Eight of these ten compounds showed high selectivity in the cytotoxic action against HeLa and K562 cancer cell lines when compared with normal human fibroblasts MRC-5 and normal human PBMC. The study of mechanisms of the anticancer activity of the two selected compounds, mono- and bis(thiazolidin-4-one) derivatives of 19-norandrost-4-ene-3,17-dione 4a and 5a, revealed that both of these compounds induced apoptosis in HeLa cells through extrinsic and intrinsic signalling pathways. Treatment of EA.hy926 cells with sub-toxic concentrations of these compounds led to the inhibition of cell connecting and sprouting, and tube formation. The synthesized compounds exhibited poor antioxidant activity.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Journal of Steroid Biochemistry and Molecular Biology",
title = "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro",
volume = "174",
pages = "72-85",
doi = "10.1016/j.jsbmb.2017.07.031"
}

Živković, M., Matić, I. Z., Rodić, M. V., Novaković, I., Krivokuca, A. M., Sladić, D.,& Krstić, N.. (2017). Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology
Oxford : Pergamon-Elsevier Science Ltd., 174, 72-85.
https://doi.org/10.1016/j.jsbmb.2017.07.031

Živković M, Matić IZ, Rodić MV, Novaković I, Krivokuca AM, Sladić D, Krstić N. Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro. in Journal of Steroid Biochemistry and Molecular Biology. 2017;174:72-85.
doi:10.1016/j.jsbmb.2017.07.031 .

Živković, Marijana, Matić, Ivana Z., Rodić, Marko V., Novaković, Irena, Krivokuca, Ana M., Sladić, Dušan, Krstić, Natalija, "Anticancer potential of new steroidal thiazolidin-4-one derivatives. Mechanisms of cytotoxic action and effects on angiogenesis in vitro" in Journal of Steroid Biochemistry and Molecular Biology, 174 (2017):72-85,
https://doi.org/10.1016/j.jsbmb.2017.07.031 . .

TY  - JOUR
AU  - Živković, Marijana
AU  - Matić, Ivana Z.
AU  - Rodić, Marko V.
AU  - Novaković, Irena
AU  - Sladić, Dušan
AU  - Krstić, Natalija
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2028
AB  - A series of new steroidal mono- and bis(thiosemicarbazones) (2a-e and 3a-e) and corresponding mono- and bis(1,3,4-thiadiazolines) (4a-e and 5a-e) was synthesized, characterized and evaluated for their anticancer activity. Detailed NMR analysis of the mono-and bis(thiosemicarbazones) revealed the presence of two stereoisomers (Z and E) with different configurations in the hydrazone moiety at the C-3 position, where the substituents on the C(3)]=N double bond in the main isomers adopted the E configuration. The configurations at C-3 and C-17 in thiadiazolines 4a-e and 5a-e were deduced by detailed NMR analysis as well as by the examination of Dreiding molecular models and X-ray analysis of 3-thiadiazoline 4a, which confirmed the structure and absolute configuration at C-3. The synthesized compounds were tested against six cancer cell lines (HeLa, K562, MDA-MB-361, MDA-MB-453, LS174 and A549), the normal human cell line MRC-5 and peripheral blood mononuclear cells (PBMC) isolated from healthy donors. The best activity was exhibited by 3-thiosemicarbazones 2a, 2b, 2c and 2e and 3,17-bis(thiadiazolines) 5a and 5d. Examination of the mechanisms of cytotoxicity on cervical adenocarcinoma HeLa cells revealed the pro-apoptotic action of these compounds, which triggered both extrinsic and intrinsic apoptotic pathways. These compounds also showed the ability to decrease angiogenesis in vitro. In addition, 3,17-bis(thiadiazolines) 5a and 5d showed high selectivity in anticancer activity against all the examined malignant cell lines. Compound 5a displayed prominent anticancer potential. The tested compounds showed poor antimicrobial activity.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines
VL  - 6
IS  - 41
SP  - 34312
EP  - 34333
DO  - 10.1039/c6ra01516f
ER  - 

@article{
author = "Živković, Marijana and Matić, Ivana Z. and Rodić, Marko V. and Novaković, Irena and Sladić, Dušan and Krstić, Natalija",
year = "2016",
abstract = "A series of new steroidal mono- and bis(thiosemicarbazones) (2a-e and 3a-e) and corresponding mono- and bis(1,3,4-thiadiazolines) (4a-e and 5a-e) was synthesized, characterized and evaluated for their anticancer activity. Detailed NMR analysis of the mono-and bis(thiosemicarbazones) revealed the presence of two stereoisomers (Z and E) with different configurations in the hydrazone moiety at the C-3 position, where the substituents on the C(3)]=N double bond in the main isomers adopted the E configuration. The configurations at C-3 and C-17 in thiadiazolines 4a-e and 5a-e were deduced by detailed NMR analysis as well as by the examination of Dreiding molecular models and X-ray analysis of 3-thiadiazoline 4a, which confirmed the structure and absolute configuration at C-3. The synthesized compounds were tested against six cancer cell lines (HeLa, K562, MDA-MB-361, MDA-MB-453, LS174 and A549), the normal human cell line MRC-5 and peripheral blood mononuclear cells (PBMC) isolated from healthy donors. The best activity was exhibited by 3-thiosemicarbazones 2a, 2b, 2c and 2e and 3,17-bis(thiadiazolines) 5a and 5d. Examination of the mechanisms of cytotoxicity on cervical adenocarcinoma HeLa cells revealed the pro-apoptotic action of these compounds, which triggered both extrinsic and intrinsic apoptotic pathways. These compounds also showed the ability to decrease angiogenesis in vitro. In addition, 3,17-bis(thiadiazolines) 5a and 5d showed high selectivity in anticancer activity against all the examined malignant cell lines. Compound 5a displayed prominent anticancer potential. The tested compounds showed poor antimicrobial activity.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines",
volume = "6",
number = "41",
pages = "34312-34333",
doi = "10.1039/c6ra01516f"
}

Živković, M., Matić, I. Z., Rodić, M. V., Novaković, I., Sladić, D.,& Krstić, N.. (2016). Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines. in RSC Advances
Royal Soc Chemistry, Cambridge., 6(41), 34312-34333.
https://doi.org/10.1039/c6ra01516f

Živković M, Matić IZ, Rodić MV, Novaković I, Sladić D, Krstić N. Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines. in RSC Advances. 2016;6(41):34312-34333.
doi:10.1039/c6ra01516f .

Živković, Marijana, Matić, Ivana Z., Rodić, Marko V., Novaković, Irena, Sladić, Dušan, Krstić, Natalija, "Synthesis, characterization and in vitro cytotoxic activities of new steroidal thiosemicarbazones and thiadiazolines" in RSC Advances, 6, no. 41 (2016):34312-34333,
https://doi.org/10.1039/c6ra01516f . .

TY  - JOUR
AU  - Filipovic, Nenad R.
AU  - Bjelogrlić, Snežana K.
AU  - Marinković, Aleksandar D.
AU  - Verbić, Tatjana
AU  - Cvijetić, Ilija
AU  - Senćanski, Milan
AU  - Rodić, Marko V.
AU  - Vujčić, Miroslava
AU  - Sladić, Dušan
AU  - Strikovic, Zlatko
AU  - Todorović, Tamara
AU  - Muller, Christian D.
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1830
AB  - A new Zn(II)-based potential chemotherapeutic agent was synthesized from the ligand 2-quinolinecarboxaldehyde selenosemicarbazone (Hqasesc). Single crystal X-ray diffraction analysis showed that the Zn(II) complex consists of a cation [Zn(Hqasesc)(2)](2+), two perchlorate anions and one ethanol solvent molecule. The interaction of calf thymus (CT) DNA and human serum albumin (HSA) with the Zn(II) complex was explored using absorption and emission spectral methods, and also has been supported by molecular docking studies. The complex has more affinity to minor DNA groove than major, with no significant intercalation. The HSA interaction studies of the complex revealed the quenching of the intrinsic fluorescence of the HSA through a static quenching mechanism. The antitumor activity of the ligand and the complex against pancreatic adenocarcinoma cell line (AsPC-1) and acute monocytic leukemia (THP-1) cells was evaluated. Both compounds are strong concentration-dependent apoptosis inducers in THP-1 cells. While Hqasesc in AsPC-1 cells induces apoptosis only at the highest concentration, treatment with the Zn complex shows a concentration-dependent apoptotic response, where the treated cells are arrested in the G1-to-S phase accompanied with extensive activation of caspase-8 and -9. These results indicate that the ligand and Zn(II) complex display cell phenotype specific activity.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction
VL  - 5
IS  - 115
SP  - 95191
EP  - 95211
DO  - 10.1039/c5ra19849f
ER  - 

@article{
author = "Filipovic, Nenad R. and Bjelogrlić, Snežana K. and Marinković, Aleksandar D. and Verbić, Tatjana and Cvijetić, Ilija and Senćanski, Milan and Rodić, Marko V. and Vujčić, Miroslava and Sladić, Dušan and Strikovic, Zlatko and Todorović, Tamara and Muller, Christian D.",
year = "2015",
abstract = "A new Zn(II)-based potential chemotherapeutic agent was synthesized from the ligand 2-quinolinecarboxaldehyde selenosemicarbazone (Hqasesc). Single crystal X-ray diffraction analysis showed that the Zn(II) complex consists of a cation [Zn(Hqasesc)(2)](2+), two perchlorate anions and one ethanol solvent molecule. The interaction of calf thymus (CT) DNA and human serum albumin (HSA) with the Zn(II) complex was explored using absorption and emission spectral methods, and also has been supported by molecular docking studies. The complex has more affinity to minor DNA groove than major, with no significant intercalation. The HSA interaction studies of the complex revealed the quenching of the intrinsic fluorescence of the HSA through a static quenching mechanism. The antitumor activity of the ligand and the complex against pancreatic adenocarcinoma cell line (AsPC-1) and acute monocytic leukemia (THP-1) cells was evaluated. Both compounds are strong concentration-dependent apoptosis inducers in THP-1 cells. While Hqasesc in AsPC-1 cells induces apoptosis only at the highest concentration, treatment with the Zn complex shows a concentration-dependent apoptotic response, where the treated cells are arrested in the G1-to-S phase accompanied with extensive activation of caspase-8 and -9. These results indicate that the ligand and Zn(II) complex display cell phenotype specific activity.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction",
volume = "5",
number = "115",
pages = "95191-95211",
doi = "10.1039/c5ra19849f"
}

Filipovic, N. R., Bjelogrlić, S. K., Marinković, A. D., Verbić, T., Cvijetić, I., Senćanski, M., Rodić, M. V., Vujčić, M., Sladić, D., Strikovic, Z., Todorović, T.,& Muller, C. D.. (2015). Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction. in RSC Advances
Royal Soc Chemistry, Cambridge., 5(115), 95191-95211.
https://doi.org/10.1039/c5ra19849f

Filipovic NR, Bjelogrlić SK, Marinković AD, Verbić T, Cvijetić I, Senćanski M, Rodić MV, Vujčić M, Sladić D, Strikovic Z, Todorović T, Muller CD. Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction. in RSC Advances. 2015;5(115):95191-95211.
doi:10.1039/c5ra19849f .

Filipovic, Nenad R., Bjelogrlić, Snežana K., Marinković, Aleksandar D., Verbić, Tatjana, Cvijetić, Ilija, Senćanski, Milan, Rodić, Marko V., Vujčić, Miroslava, Sladić, Dušan, Strikovic, Zlatko, Todorović, Tamara, Muller, Christian D., "Zn(II) complex with 2-quinolinecarboxaldehyde selenosemicarbazone: synthesis, structure, interaction studies with DNA/HSA, molecular docking and caspase-8 and-9 independent apoptose induction" in RSC Advances, 5, no. 115 (2015):95191-95211,
https://doi.org/10.1039/c5ra19849f . .

TY  - JOUR
AU  - Leovac, Vukadin
AU  - Rodić, Marko V.
AU  - Jovanović, Ljiljana S.
AU  - Joksovic, Milan D.
AU  - Stanojković, Tatjana
AU  - Vujčić, Miroslava
AU  - Sladić, Dušan
AU  - Markovic, Violeta
AU  - Vojinovic-Jesic, Ljiljana S
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1735
AB  - Five pentacoordinate copper(II) complexes with 2-acetylpyridine or di(2-pyridyl) ketone 1-adamantoyl hydrazone ligands (Adpy and Addpy, respectively) of the formulae [CuCl2(Adpy)] (1), [Cu-2(-Cl)(2)(Adpy-H)(2)] (2), [Cu(NCS)(2)(Adpy)] (3), [Cu-2(-Cl)(2)(Addpy-H)(2)] (4), and [Cu-2(NCS)(2)(-Addpy-H)(2)] (5) were synthesized and characterized by spectral, electrochemical, and X-ray structural analysis. Flow cytometry and morphological analysis confirmed that the copper(II) complexes 2 and 5 induced accumulation of a sub-G1 phase population, and fluorescence microscopy indicated the presence of large cells in apoptosis. The interaction of the copper(II) complexes with calf thymus DNA (CT-DNA) was monitored by changes in their UV/Vis spectra. The observed intrinsic binding constants for 2 and 5 (K-b = 1.77x10(6) and 3.58x10(6) M-1, respectively) together with ethidium displacement fluorescence experiments indicate intercalative binding. Complexes 2 and 5 showed nuclease activity against pUC19 plasmid DNA.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Inorganic Chemistry
T1  - Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System
IS  - 5
SP  - 882
EP  - 895
DO  - 10.1002/ejic.201403050
ER  - 

@article{
author = "Leovac, Vukadin and Rodić, Marko V. and Jovanović, Ljiljana S. and Joksovic, Milan D. and Stanojković, Tatjana and Vujčić, Miroslava and Sladić, Dušan and Markovic, Violeta and Vojinovic-Jesic, Ljiljana S",
year = "2015",
abstract = "Five pentacoordinate copper(II) complexes with 2-acetylpyridine or di(2-pyridyl) ketone 1-adamantoyl hydrazone ligands (Adpy and Addpy, respectively) of the formulae [CuCl2(Adpy)] (1), [Cu-2(-Cl)(2)(Adpy-H)(2)] (2), [Cu(NCS)(2)(Adpy)] (3), [Cu-2(-Cl)(2)(Addpy-H)(2)] (4), and [Cu-2(NCS)(2)(-Addpy-H)(2)] (5) were synthesized and characterized by spectral, electrochemical, and X-ray structural analysis. Flow cytometry and morphological analysis confirmed that the copper(II) complexes 2 and 5 induced accumulation of a sub-G1 phase population, and fluorescence microscopy indicated the presence of large cells in apoptosis. The interaction of the copper(II) complexes with calf thymus DNA (CT-DNA) was monitored by changes in their UV/Vis spectra. The observed intrinsic binding constants for 2 and 5 (K-b = 1.77x10(6) and 3.58x10(6) M-1, respectively) together with ethidium displacement fluorescence experiments indicate intercalative binding. Complexes 2 and 5 showed nuclease activity against pUC19 plasmid DNA.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Inorganic Chemistry",
title = "Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System",
number = "5",
pages = "882-895",
doi = "10.1002/ejic.201403050"
}

Leovac, V., Rodić, M. V., Jovanović, L. S., Joksovic, M. D., Stanojković, T., Vujčić, M., Sladić, D., Markovic, V.,& Vojinovic-Jesic, L. S.. (2015). Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System. in European Journal of Inorganic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(5), 882-895.
https://doi.org/10.1002/ejic.201403050

Leovac V, Rodić MV, Jovanović LS, Joksovic MD, Stanojković T, Vujčić M, Sladić D, Markovic V, Vojinovic-Jesic LS. Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System. in European Journal of Inorganic Chemistry. 2015;(5):882-895.
doi:10.1002/ejic.201403050 .

Leovac, Vukadin, Rodić, Marko V., Jovanović, Ljiljana S., Joksovic, Milan D., Stanojković, Tatjana, Vujčić, Miroslava, Sladić, Dušan, Markovic, Violeta, Vojinovic-Jesic, Ljiljana S, "Transition Metal Complexes with 1-Adamantoyl Hydrazones - Cytotoxic Copper(II) Complexes of Tri- and Tetradentate Pyridine Chelators Containing an Adamantane Ring System" in European Journal of Inorganic Chemistry, no. 5 (2015):882-895,
https://doi.org/10.1002/ejic.201403050 . .

TY  - JOUR
AU  - Novkovic, L
AU  - Trmcic, M
AU  - Rodić, Marko V.
AU  - Bihelović, Filip
AU  - Zlatar, Matija
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1796
AB  - Domino reactions of ketones with molecular oxygen in the presence of potassium hydroxide and potassium t-butoxide afford cyclic hydroperoxy acetals (3,5-dihydroxy-1,2-dioxanes). Mixed endoperoxides can also be obtained in a three-component reaction of two ketones and oxygen.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen
VL  - 5
IS  - 120
SP  - 99577
EP  - 99584
DO  - 10.1039/c5ra13476e
ER  - 

@article{
author = "Novkovic, L and Trmcic, M and Rodić, Marko V. and Bihelović, Filip and Zlatar, Matija and Matović, Radomir and Saičić, Radomir N.",
year = "2015",
abstract = "Domino reactions of ketones with molecular oxygen in the presence of potassium hydroxide and potassium t-butoxide afford cyclic hydroperoxy acetals (3,5-dihydroxy-1,2-dioxanes). Mixed endoperoxides can also be obtained in a three-component reaction of two ketones and oxygen.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen",
volume = "5",
number = "120",
pages = "99577-99584",
doi = "10.1039/c5ra13476e"
}

Novkovic, L., Trmcic, M., Rodić, M. V., Bihelović, F., Zlatar, M., Matović, R.,& Saičić, R. N.. (2015). Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen. in RSC Advances
Royal Soc Chemistry, Cambridge., 5(120), 99577-99584.
https://doi.org/10.1039/c5ra13476e

Novkovic L, Trmcic M, Rodić MV, Bihelović F, Zlatar M, Matović R, Saičić RN. Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen. in RSC Advances. 2015;5(120):99577-99584.
doi:10.1039/c5ra13476e .

Novkovic, L, Trmcic, M, Rodić, Marko V., Bihelović, Filip, Zlatar, Matija, Matović, Radomir, Saičić, Radomir N., "Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen" in RSC Advances, 5, no. 120 (2015):99577-99584,
https://doi.org/10.1039/c5ra13476e . .

TY  - CONF
AU  - Petrović, Vladimir
AU  - Rodić, Marko V.
AU  - Vidović, Milka
AU  - Rogan, S.
AU  - Gordanic, V.
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1610
AB  - The quality of surface waters is a very important problem incorporated in the environment protection. Water reservoir “Grliste” was formed with the aim of water supplies of Zajecar and surrounding villages in Eastern Serbia. In this paper, the measured values of nutrient concentrations, were analysed in the water reservoir and its tributaries Lenovacka and Lasovacka river. The influence of anthropogenic factors of degradation on the water reservoir, during the exploitation was analysed. Sampling was performed in according to seasonal changes, and results were analyzed for the period (May - October). Defined by the law of areas sanitary protection, the basis for the purpose of prevention of the degradation (organic and other pollutants) of the water reservoir was formed. Special attention is given to the structural characteristics of the geological terrain, mineral occurrences and mines in the hydro accumulation basin. The research results will be shown with tables, charts and maps.
PB  - International Multidisciplinary Scientific Geoconference
C3  - International Multidisciplinary Scientific GeoConference Surveying Geology and Mining Ecology Manage
T1  - The influence of natural and anthropogenic factors on the degradation of water in “Grliste” Reservoir
VL  - 1
IS  - 5
SP  - 735
EP  - 741
UR  - https://hdl.handle.net/21.15107/rcub_cer_1610
ER  - 

@conference{
author = "Petrović, Vladimir and Rodić, Marko V. and Vidović, Milka and Rogan, S. and Gordanic, V.",
year = "2014",
abstract = "The quality of surface waters is a very important problem incorporated in the environment protection. Water reservoir “Grliste” was formed with the aim of water supplies of Zajecar and surrounding villages in Eastern Serbia. In this paper, the measured values of nutrient concentrations, were analysed in the water reservoir and its tributaries Lenovacka and Lasovacka river. The influence of anthropogenic factors of degradation on the water reservoir, during the exploitation was analysed. Sampling was performed in according to seasonal changes, and results were analyzed for the period (May - October). Defined by the law of areas sanitary protection, the basis for the purpose of prevention of the degradation (organic and other pollutants) of the water reservoir was formed. Special attention is given to the structural characteristics of the geological terrain, mineral occurrences and mines in the hydro accumulation basin. The research results will be shown with tables, charts and maps.",
publisher = "International Multidisciplinary Scientific Geoconference",
journal = "International Multidisciplinary Scientific GeoConference Surveying Geology and Mining Ecology Manage",
title = "The influence of natural and anthropogenic factors on the degradation of water in “Grliste” Reservoir",
volume = "1",
number = "5",
pages = "735-741",
url = "https://hdl.handle.net/21.15107/rcub_cer_1610"
}

Petrović, V., Rodić, M. V., Vidović, M., Rogan, S.,& Gordanic, V.. (2014). The influence of natural and anthropogenic factors on the degradation of water in “Grliste” Reservoir. in International Multidisciplinary Scientific GeoConference Surveying Geology and Mining Ecology Manage
International Multidisciplinary Scientific Geoconference., 1(5), 735-741.
https://hdl.handle.net/21.15107/rcub_cer_1610

Petrović V, Rodić MV, Vidović M, Rogan S, Gordanic V. The influence of natural and anthropogenic factors on the degradation of water in “Grliste” Reservoir. in International Multidisciplinary Scientific GeoConference Surveying Geology and Mining Ecology Manage. 2014;1(5):735-741.
https://hdl.handle.net/21.15107/rcub_cer_1610 .

Petrović, Vladimir, Rodić, Marko V., Vidović, Milka, Rogan, S., Gordanic, V., "The influence of natural and anthropogenic factors on the degradation of water in “Grliste” Reservoir" in International Multidisciplinary Scientific GeoConference Surveying Geology and Mining Ecology Manage, 1, no. 5 (2014):735-741,
https://hdl.handle.net/21.15107/rcub_cer_1610 .

TY  - JOUR
AU  - Markovic, Violeta
AU  - Marković, Svetlana
AU  - Janicijevic, Ana
AU  - Rodić, Marko V.
AU  - Leovac, Vukadin
AU  - Todorović, Nina
AU  - Trifunović, Snežana
AU  - Joksovic, Milan D.
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1225
AB  - A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate
VL  - 24
IS  - 6
SP  - 2127
EP  - 2136
DO  - 10.1007/s11224-013-0223-3
ER  - 

@article{
author = "Markovic, Violeta and Marković, Svetlana and Janicijevic, Ana and Rodić, Marko V. and Leovac, Vukadin and Todorović, Nina and Trifunović, Snežana and Joksovic, Milan D.",
year = "2013",
abstract = "A study on the synthesis and mechanistical aspects of formation of 3-methyl-5-oxo-3-pyrazolin-1-carboxamide (MOPC) starting from S-methylisothiosemicarbazide hydrogen iodide and methyl acetoacetate was performed. In the alkaline aqueous solution, the intermediate methyl acetoacetate S-methylisothiosemicarbazone undergoes substitution of CH3S- anion by hydroxide anion, cyclization, carbanion formation, and elimination of methanol, thus yielding corresponding Na-enolate salt of pyrazol-5-one derivative. The structure of the compound obtained after protonation of the formed enolate salt was determined by means of spectroscopic techniques and single-crystal X-ray diffraction analysis. The mechanism of conversion of methyl acetoacetate S-methylisothiosemicarbazone into MOPC was investigated by means of the B3LYP functional, and it was found that the reaction is thermodynamically controlled.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate",
volume = "24",
number = "6",
pages = "2127-2136",
doi = "10.1007/s11224-013-0223-3"
}

Markovic, V., Marković, S., Janicijevic, A., Rodić, M. V., Leovac, V., Todorović, N., Trifunović, S.,& Joksovic, M. D.. (2013). Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate. in Structural Chemistry
Springer/Plenum Publishers, New York., 24(6), 2127-2136.
https://doi.org/10.1007/s11224-013-0223-3

Markovic V, Marković S, Janicijevic A, Rodić MV, Leovac V, Todorović N, Trifunović S, Joksovic MD. Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate. in Structural Chemistry. 2013;24(6):2127-2136.
doi:10.1007/s11224-013-0223-3 .

Markovic, Violeta, Marković, Svetlana, Janicijevic, Ana, Rodić, Marko V., Leovac, Vukadin, Todorović, Nina, Trifunović, Snežana, Joksovic, Milan D., "Mechanistic investigation and DFT calculation of the new reaction between S-methylisothiosemicarbazide and methyl acetoacetate" in Structural Chemistry, 24, no. 6 (2013):2127-2136,
https://doi.org/10.1007/s11224-013-0223-3 . .

TY  - CONF
AU  - Vidović, Milka
AU  - Trajković, Ivana
AU  - Rodić, Marko
AU  - Rogan, Saša
AU  - Petrović, Vladimir
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/7092
AB  - Flaširanu vodu koja se koristi u konzumacione svrhe, a nalazi se na tržištu, zakonska regulativa obično svrstava u tri grupe: prirodnu mineralnu, prirodnu izvorsku i stonu vodu. Flaširane vode su prema sadržaju mineralnih materija, jonskom sastavu i sadržaju ugljen-dioksida svrstane u tačno određene grupe, na osnovu kojih je određivana i njihova pripadnost prema važećoj zakonskoj regulativi. 
Kod ovako deklarisanih voda su zanemarene fiziološke karakteristike vode, oksido-redukcioni status i posledice lošeg uticaja na zdravlje usled prekomernog konzumiranja voda sa bogatim sadržajem mineralnih materija. Sa fiziološkog aspekta oksido-redukcioni status vode predstavlja zdravstveni faktor, a njega u potpunosti definišu pH vrednost, redox potencijal i rH2 faktor koji su mereni i prikazani u ovom radu.
AB  - Bottled water used in consummation purposes, which is placed on the market, legislation usually classified into three groups: natural mineral, a natural spring and table water. According to the mineral content, ionic composition and content of carbon dioxide, bottled waters are classified precisely in certain groups on which their affiliation to the current legislation was determined.  
In such a declared water, physiological characteristics of water, redox status and the consequences of bad health effects, are neglected due to excessive consumption of waters with high minereral content. From the physiological point, redox status of water represents a health factor, and it is completely defines by the pH value, redox potential and rH2 factor which were measured and presented in this paper.
PB  - Udruženje za tehnologiju vode i sanitarno inženjerstvo / Association for water technology and sanitary engineering
C3  - Zbornik radova - Peti međunarodni kongres "Ekologija, zdravlje, rad i sport," 06-09.09.2012, Banja Luka
T1  - Kvalitet flaširanih voda kao indikator njihove zdravstvene ispravnosti
T1  - Bottled water quality and redox potential as an indicator of their health safety
VL  - 1
SP  - 309
EP  - 318
UR  - https://hdl.handle.net/21.15107/rcub_cer_7092
ER  - 

@conference{
author = "Vidović, Milka and Trajković, Ivana and Rodić, Marko and Rogan, Saša and Petrović, Vladimir",
year = "2012",
abstract = "Flaširanu vodu koja se koristi u konzumacione svrhe, a nalazi se na tržištu, zakonska regulativa obično svrstava u tri grupe: prirodnu mineralnu, prirodnu izvorsku i stonu vodu. Flaširane vode su prema sadržaju mineralnih materija, jonskom sastavu i sadržaju ugljen-dioksida svrstane u tačno određene grupe, na osnovu kojih je određivana i njihova pripadnost prema važećoj zakonskoj regulativi. 
Kod ovako deklarisanih voda su zanemarene fiziološke karakteristike vode, oksido-redukcioni status i posledice lošeg uticaja na zdravlje usled prekomernog konzumiranja voda sa bogatim sadržajem mineralnih materija. Sa fiziološkog aspekta oksido-redukcioni status vode predstavlja zdravstveni faktor, a njega u potpunosti definišu pH vrednost, redox potencijal i rH2 faktor koji su mereni i prikazani u ovom radu., Bottled water used in consummation purposes, which is placed on the market, legislation usually classified into three groups: natural mineral, a natural spring and table water. According to the mineral content, ionic composition and content of carbon dioxide, bottled waters are classified precisely in certain groups on which their affiliation to the current legislation was determined.  
In such a declared water, physiological characteristics of water, redox status and the consequences of bad health effects, are neglected due to excessive consumption of waters with high minereral content. From the physiological point, redox status of water represents a health factor, and it is completely defines by the pH value, redox potential and rH2 factor which were measured and presented in this paper.",
publisher = "Udruženje za tehnologiju vode i sanitarno inženjerstvo / Association for water technology and sanitary engineering",
journal = "Zbornik radova - Peti međunarodni kongres "Ekologija, zdravlje, rad i sport," 06-09.09.2012, Banja Luka",
title = "Kvalitet flaširanih voda kao indikator njihove zdravstvene ispravnosti, Bottled water quality and redox potential as an indicator of their health safety",
volume = "1",
pages = "309-318",
url = "https://hdl.handle.net/21.15107/rcub_cer_7092"
}

Vidović, M., Trajković, I., Rodić, M., Rogan, S.,& Petrović, V.. (2012). Kvalitet flaširanih voda kao indikator njihove zdravstvene ispravnosti. in Zbornik radova - Peti međunarodni kongres "Ekologija, zdravlje, rad i sport," 06-09.09.2012, Banja Luka
Udruženje za tehnologiju vode i sanitarno inženjerstvo / Association for water technology and sanitary engineering., 1, 309-318.
https://hdl.handle.net/21.15107/rcub_cer_7092

Vidović M, Trajković I, Rodić M, Rogan S, Petrović V. Kvalitet flaširanih voda kao indikator njihove zdravstvene ispravnosti. in Zbornik radova - Peti međunarodni kongres "Ekologija, zdravlje, rad i sport," 06-09.09.2012, Banja Luka. 2012;1:309-318.
https://hdl.handle.net/21.15107/rcub_cer_7092 .

Vidović, Milka, Trajković, Ivana, Rodić, Marko, Rogan, Saša, Petrović, Vladimir, "Kvalitet flaširanih voda kao indikator njihove zdravstvene ispravnosti" in Zbornik radova - Peti međunarodni kongres "Ekologija, zdravlje, rad i sport," 06-09.09.2012, Banja Luka, 1 (2012):309-318,
https://hdl.handle.net/21.15107/rcub_cer_7092 .