TY  - JOUR
AU  - Trifunović-Macedoljan, Jelena
AU  - Pantelić, Nebojša Đ.
AU  - Jadranin, Milka
AU  - Juranić, Ivan
PY  - 2019
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3261
AB  - The biosynthetic pathway of biogenic amines is very active during the growth of many tumour cells. Non-Hodgkin lymphoma represents a very heterogeneous group of malignancies. The concentration level of some biogenic amines (putrescine, histamine, spermidine, epinephrine, and spermine) was investigated to elucidate whether they could be observed as markers for the patients with non-Hodgkin’s lymphoma. In this study, the method of acidic extraction of five biogenic amines from human serum, dansyl chloride pre-column derivatization, and LC/DAD analysis were used to determine the content of biogenic amines in biological fluids. The results indicate that statistically significant differences exist in putrescine, spermidine and histamine contents in non-Hodgkin’s patients versus healthy controls. The concentrations of putrescine, spermidine and epinephrine were elevated, and histamine was lower compared to controls. Based on their content, serum biogenic amines could be considered as potential tumour markers.
PB  - Editura Academiei Romane
T2  - Revue Roumaine de Chimie
T1  - Biogenic amines content in the serum of patients with non-Hodgkin’s lymphoma
VL  - 64
IS  - 8
SP  - 681
EP  - 686
DO  - 10.3224/rrch.2019.64.8.05
ER  - 

@article{
author = "Trifunović-Macedoljan, Jelena and Pantelić, Nebojša Đ. and Jadranin, Milka and Juranić, Ivan",
year = "2019",
abstract = "The biosynthetic pathway of biogenic amines is very active during the growth of many tumour cells. Non-Hodgkin lymphoma represents a very heterogeneous group of malignancies. The concentration level of some biogenic amines (putrescine, histamine, spermidine, epinephrine, and spermine) was investigated to elucidate whether they could be observed as markers for the patients with non-Hodgkin’s lymphoma. In this study, the method of acidic extraction of five biogenic amines from human serum, dansyl chloride pre-column derivatization, and LC/DAD analysis were used to determine the content of biogenic amines in biological fluids. The results indicate that statistically significant differences exist in putrescine, spermidine and histamine contents in non-Hodgkin’s patients versus healthy controls. The concentrations of putrescine, spermidine and epinephrine were elevated, and histamine was lower compared to controls. Based on their content, serum biogenic amines could be considered as potential tumour markers.",
publisher = "Editura Academiei Romane",
journal = "Revue Roumaine de Chimie",
title = "Biogenic amines content in the serum of patients with non-Hodgkin’s lymphoma",
volume = "64",
number = "8",
pages = "681-686",
doi = "10.3224/rrch.2019.64.8.05"
}

Trifunović-Macedoljan, J., Pantelić, N. Đ., Jadranin, M.,& Juranić, I.. (2019). Biogenic amines content in the serum of patients with non-Hodgkin’s lymphoma. in Revue Roumaine de Chimie
Editura Academiei Romane., 64(8), 681-686.
https://doi.org/10.3224/rrch.2019.64.8.05

Trifunović-Macedoljan J, Pantelić NĐ, Jadranin M, Juranić I. Biogenic amines content in the serum of patients with non-Hodgkin’s lymphoma. in Revue Roumaine de Chimie. 2019;64(8):681-686.
doi:10.3224/rrch.2019.64.8.05 .

Trifunović-Macedoljan, Jelena, Pantelić, Nebojša Đ., Jadranin, Milka, Juranić, Ivan, "Biogenic amines content in the serum of patients with non-Hodgkin’s lymphoma" in Revue Roumaine de Chimie, 64, no. 8 (2019):681-686,
https://doi.org/10.3224/rrch.2019.64.8.05 . .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Pešić, Miloš P.
AU  - Todorov, Miljana D.
AU  - Drakulić, Branko
AU  - Juranić, Ivan
AU  - Verbić, Tatjana
AU  - Zloh, Mire
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2693
AB  - Aryldiketo acids (ADKs) exhibit the variety of biological activities, mainly due to large affinity toward divalent metal ions. Metal complexation ability of ADKs, as well as interactions with proteins, depend on tautomeric form present in solution. The main aim of this study was to fully explore the tautomeric preferences of 4-phenyl-2,4-dioxobutanoic acid (4PDA), as ADKs representative, in aqueous media at different pH values. 1D and 2D NMR spectroscopy in combination with quantum chemical calculations was applied in order to better understand the tautomeric preferences of 4PDA. The data in highly acidic media are especially interesting since there are no such findings in the literature due to low solubility of ADKs in molecular form. At low pH values, where 4PDA is unionized, the most abundant tautomeric form is enol with keto group closer to phenyl ring. At higher pH values, mixture of two 4PDA ionic forms coexists in solution. Their ratio calculated according to NMR data fits the values predicted using two experimentally determined pK (a) values. Based on the complexity of H-1 NMR spectrum of monoanionic 4PDA form, coexistence of two stable rotamers was assumed. In an alkaline media, 4PDA is mostly present in dianionic form. As pi-electrons of dianion are delocalized over an entire keto-enol moiety, spectral distinction between tautomers was not possible. Quantum chemical calculations were used to predict relative stability of tautomers. The predictions were in good accordance with experimental results only in case when explicit water molecule was included in calculations.
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - Tautomerism of 4-phenyl-2,4-dioxobutanoic acid. Insights from pH ramping NMR study and quantum chemical calculations
VL  - 29
IS  - 2
SP  - 423
EP  - 434
DO  - 10.1007/s11224-017-1039-3
ER  - 

@article{
author = "Cvijetić, Ilija and Pešić, Miloš P. and Todorov, Miljana D. and Drakulić, Branko and Juranić, Ivan and Verbić, Tatjana and Zloh, Mire",
year = "2018",
abstract = "Aryldiketo acids (ADKs) exhibit the variety of biological activities, mainly due to large affinity toward divalent metal ions. Metal complexation ability of ADKs, as well as interactions with proteins, depend on tautomeric form present in solution. The main aim of this study was to fully explore the tautomeric preferences of 4-phenyl-2,4-dioxobutanoic acid (4PDA), as ADKs representative, in aqueous media at different pH values. 1D and 2D NMR spectroscopy in combination with quantum chemical calculations was applied in order to better understand the tautomeric preferences of 4PDA. The data in highly acidic media are especially interesting since there are no such findings in the literature due to low solubility of ADKs in molecular form. At low pH values, where 4PDA is unionized, the most abundant tautomeric form is enol with keto group closer to phenyl ring. At higher pH values, mixture of two 4PDA ionic forms coexists in solution. Their ratio calculated according to NMR data fits the values predicted using two experimentally determined pK (a) values. Based on the complexity of H-1 NMR spectrum of monoanionic 4PDA form, coexistence of two stable rotamers was assumed. In an alkaline media, 4PDA is mostly present in dianionic form. As pi-electrons of dianion are delocalized over an entire keto-enol moiety, spectral distinction between tautomers was not possible. Quantum chemical calculations were used to predict relative stability of tautomers. The predictions were in good accordance with experimental results only in case when explicit water molecule was included in calculations.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "Tautomerism of 4-phenyl-2,4-dioxobutanoic acid. Insights from pH ramping NMR study and quantum chemical calculations",
volume = "29",
number = "2",
pages = "423-434",
doi = "10.1007/s11224-017-1039-3"
}

Cvijetić, I., Pešić, M. P., Todorov, M. D., Drakulić, B., Juranić, I., Verbić, T.,& Zloh, M.. (2018). Tautomerism of 4-phenyl-2,4-dioxobutanoic acid. Insights from pH ramping NMR study and quantum chemical calculations. in Structural Chemistry
Springer/Plenum Publishers, New York., 29(2), 423-434.
https://doi.org/10.1007/s11224-017-1039-3

Cvijetić I, Pešić MP, Todorov MD, Drakulić B, Juranić I, Verbić T, Zloh M. Tautomerism of 4-phenyl-2,4-dioxobutanoic acid. Insights from pH ramping NMR study and quantum chemical calculations. in Structural Chemistry. 2018;29(2):423-434.
doi:10.1007/s11224-017-1039-3 .

Cvijetić, Ilija, Pešić, Miloš P., Todorov, Miljana D., Drakulić, Branko, Juranić, Ivan, Verbić, Tatjana, Zloh, Mire, "Tautomerism of 4-phenyl-2,4-dioxobutanoic acid. Insights from pH ramping NMR study and quantum chemical calculations" in Structural Chemistry, 29, no. 2 (2018):423-434,
https://doi.org/10.1007/s11224-017-1039-3 . .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Pešić, Miloš P.
AU  - Todorov, Miljana D.
AU  - Drakulić, Branko
AU  - Juranić, Ivan
AU  - Verbić, Tatjana
AU  - Zloh, Mire
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2694
AB  - Aryldiketo acids (ADKs) exhibit the variety of biological activities, mainly due to large affinity toward divalent metal ions. Metal complexation ability of ADKs, as well as interactions with proteins, depend on tautomeric form present in solution. The main aim of this study was to fully explore the tautomeric preferences of 4-phenyl-2,4-dioxobutanoic acid (4PDA), as ADKs representative, in aqueous media at different pH values. 1D and 2D NMR spectroscopy in combination with quantum chemical calculations was applied in order to better understand the tautomeric preferences of 4PDA. The data in highly acidic media are especially interesting since there are no such findings in the literature due to low solubility of ADKs in molecular form. At low pH values, where 4PDA is unionized, the most abundant tautomeric form is enol with keto group closer to phenyl ring. At higher pH values, mixture of two 4PDA ionic forms coexists in solution. Their ratio calculated according to NMR data fits the values predicted using two experimentally determined pK (a) values. Based on the complexity of H-1 NMR spectrum of monoanionic 4PDA form, coexistence of two stable rotamers was assumed. In an alkaline media, 4PDA is mostly present in dianionic form. As pi-electrons of dianion are delocalized over an entire keto-enol moiety, spectral distinction between tautomers was not possible. Quantum chemical calculations were used to predict relative stability of tautomers. The predictions were in good accordance with experimental results only in case when explicit water molecule was included in calculations.
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - Tautomerism of 4-phenyl-2,4-dioxobutanoic acid. Insights from pH ramping NMR study and quantum chemical calculations
VL  - 29
IS  - 2
SP  - 423
EP  - 434
DO  - 10.1007/s11224-017-1039-3
ER  - 

@article{
author = "Cvijetić, Ilija and Pešić, Miloš P. and Todorov, Miljana D. and Drakulić, Branko and Juranić, Ivan and Verbić, Tatjana and Zloh, Mire",
year = "2018",
abstract = "Aryldiketo acids (ADKs) exhibit the variety of biological activities, mainly due to large affinity toward divalent metal ions. Metal complexation ability of ADKs, as well as interactions with proteins, depend on tautomeric form present in solution. The main aim of this study was to fully explore the tautomeric preferences of 4-phenyl-2,4-dioxobutanoic acid (4PDA), as ADKs representative, in aqueous media at different pH values. 1D and 2D NMR spectroscopy in combination with quantum chemical calculations was applied in order to better understand the tautomeric preferences of 4PDA. The data in highly acidic media are especially interesting since there are no such findings in the literature due to low solubility of ADKs in molecular form. At low pH values, where 4PDA is unionized, the most abundant tautomeric form is enol with keto group closer to phenyl ring. At higher pH values, mixture of two 4PDA ionic forms coexists in solution. Their ratio calculated according to NMR data fits the values predicted using two experimentally determined pK (a) values. Based on the complexity of H-1 NMR spectrum of monoanionic 4PDA form, coexistence of two stable rotamers was assumed. In an alkaline media, 4PDA is mostly present in dianionic form. As pi-electrons of dianion are delocalized over an entire keto-enol moiety, spectral distinction between tautomers was not possible. Quantum chemical calculations were used to predict relative stability of tautomers. The predictions were in good accordance with experimental results only in case when explicit water molecule was included in calculations.",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "Tautomerism of 4-phenyl-2,4-dioxobutanoic acid. Insights from pH ramping NMR study and quantum chemical calculations",
volume = "29",
number = "2",
pages = "423-434",
doi = "10.1007/s11224-017-1039-3"
}

Cvijetić, I., Pešić, M. P., Todorov, M. D., Drakulić, B., Juranić, I., Verbić, T.,& Zloh, M.. (2018). Tautomerism of 4-phenyl-2,4-dioxobutanoic acid. Insights from pH ramping NMR study and quantum chemical calculations. in Structural Chemistry
Springer/Plenum Publishers, New York., 29(2), 423-434.
https://doi.org/10.1007/s11224-017-1039-3

Cvijetić I, Pešić MP, Todorov MD, Drakulić B, Juranić I, Verbić T, Zloh M. Tautomerism of 4-phenyl-2,4-dioxobutanoic acid. Insights from pH ramping NMR study and quantum chemical calculations. in Structural Chemistry. 2018;29(2):423-434.
doi:10.1007/s11224-017-1039-3 .

Cvijetić, Ilija, Pešić, Miloš P., Todorov, Miljana D., Drakulić, Branko, Juranić, Ivan, Verbić, Tatjana, Zloh, Mire, "Tautomerism of 4-phenyl-2,4-dioxobutanoic acid. Insights from pH ramping NMR study and quantum chemical calculations" in Structural Chemistry, 29, no. 2 (2018):423-434,
https://doi.org/10.1007/s11224-017-1039-3 . .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Verbić, Tatjana
AU  - de Resende, Pedro Ernesto
AU  - Stapleton, Paul
AU  - Gibbons, Simon
AU  - Juranić, Ivan
AU  - Drakulić, Branko
AU  - Zloh, Mire
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2690
AB  - Antimicrobial resistance (AMR) is a major health problem worldwide, because of ability of bacteria, fungi and viruses to evade known therapeutic agents used in treatment of infections. Aryldiketo acids (ADK) have shown antimicrobial activity against several resistant strains including Gram-positive Staphylococcus aureus bacteria. Our previous studies revealed that ADK analogues having bulky alkyl group in ortho position on a phenyl ring have up to ten times better activity than norfloxacin against the same strains. Rational modifications of analogues by introduction of hydrophobic substituents on the aromatic ring has led to more than tenfold increase in antibacterial activity against multidrug resistant Gram positive strains. To elucidate a potential mechanism of action for this potentially novel class of antimicrobials, several bacterial enzymes were identified as putative targets according to literature data and pharmacophoric similarity searches for potent ADK analogues. Among the seven bacterial targets chosen, the strongest favorable binding interactions were observed between most active analogue and S. aureus dehydrosqualene synthase and DNA gyrase. Furthermore, the docking results in combination with literature data suggest that these novel molecules could also target several other bacterial enzymes, including prenyl-transferases and methionine aminopeptidase. These results and our statistically significant 3D QSAR model could be used to guide the further design of more potent derivatives as well as in virtual screening for novel antibacterial agents. (C) 2017 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier
T2  - European Journal of Medicinal Chemistry
T1  - Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains
VL  - 143
SP  - 1474
EP  - 1488
DO  - 10.1016/j.ejmech.2017.10.045
ER  - 

@article{
author = "Cvijetić, Ilija and Verbić, Tatjana and de Resende, Pedro Ernesto and Stapleton, Paul and Gibbons, Simon and Juranić, Ivan and Drakulić, Branko and Zloh, Mire",
year = "2018",
abstract = "Antimicrobial resistance (AMR) is a major health problem worldwide, because of ability of bacteria, fungi and viruses to evade known therapeutic agents used in treatment of infections. Aryldiketo acids (ADK) have shown antimicrobial activity against several resistant strains including Gram-positive Staphylococcus aureus bacteria. Our previous studies revealed that ADK analogues having bulky alkyl group in ortho position on a phenyl ring have up to ten times better activity than norfloxacin against the same strains. Rational modifications of analogues by introduction of hydrophobic substituents on the aromatic ring has led to more than tenfold increase in antibacterial activity against multidrug resistant Gram positive strains. To elucidate a potential mechanism of action for this potentially novel class of antimicrobials, several bacterial enzymes were identified as putative targets according to literature data and pharmacophoric similarity searches for potent ADK analogues. Among the seven bacterial targets chosen, the strongest favorable binding interactions were observed between most active analogue and S. aureus dehydrosqualene synthase and DNA gyrase. Furthermore, the docking results in combination with literature data suggest that these novel molecules could also target several other bacterial enzymes, including prenyl-transferases and methionine aminopeptidase. These results and our statistically significant 3D QSAR model could be used to guide the further design of more potent derivatives as well as in virtual screening for novel antibacterial agents. (C) 2017 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier",
journal = "European Journal of Medicinal Chemistry",
title = "Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains",
volume = "143",
pages = "1474-1488",
doi = "10.1016/j.ejmech.2017.10.045"
}

Cvijetić, I., Verbić, T., de Resende, P. E., Stapleton, P., Gibbons, S., Juranić, I., Drakulić, B.,& Zloh, M.. (2018). Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains. in European Journal of Medicinal Chemistry
Elsevier., 143, 1474-1488.
https://doi.org/10.1016/j.ejmech.2017.10.045

Cvijetić I, Verbić T, de Resende PE, Stapleton P, Gibbons S, Juranić I, Drakulić B, Zloh M. Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains. in European Journal of Medicinal Chemistry. 2018;143:1474-1488.
doi:10.1016/j.ejmech.2017.10.045 .

Cvijetić, Ilija, Verbić, Tatjana, de Resende, Pedro Ernesto, Stapleton, Paul, Gibbons, Simon, Juranić, Ivan, Drakulić, Branko, Zloh, Mire, "Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains" in European Journal of Medicinal Chemistry, 143 (2018):1474-1488,
https://doi.org/10.1016/j.ejmech.2017.10.045 . .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Verbić, Tatjana
AU  - de Resende, Pedro Ernesto
AU  - Stapleton, Paul
AU  - Gibbons, Simon
AU  - Juranić, Ivan
AU  - Drakulić, Branko
AU  - Zloh, Mire
PY  - 2018
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2690
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2691
AB  - Antimicrobial resistance (AMR) is a major health problem worldwide, because of ability of bacteria, fungi and viruses to evade known therapeutic agents used in treatment of infections. Aryldiketo acids (ADK) have shown antimicrobial activity against several resistant strains including Gram-positive Staphylococcus aureus bacteria. Our previous studies revealed that ADK analogues having bulky alkyl group in ortho position on a phenyl ring have up to ten times better activity than norfloxacin against the same strains. Rational modifications of analogues by introduction of hydrophobic substituents on the aromatic ring has led to more than tenfold increase in antibacterial activity against multidrug resistant Gram positive strains. To elucidate a potential mechanism of action for this potentially novel class of antimicrobials, several bacterial enzymes were identified as putative targets according to literature data and pharmacophoric similarity searches for potent ADK analogues. Among the seven bacterial targets chosen, the strongest favorable binding interactions were observed between most active analogue and S. aureus dehydrosqualene synthase and DNA gyrase. Furthermore, the docking results in combination with literature data suggest that these novel molecules could also target several other bacterial enzymes, including prenyl-transferases and methionine aminopeptidase. These results and our statistically significant 3D QSAR model could be used to guide the further design of more potent derivatives as well as in virtual screening for novel antibacterial agents. (C) 2017 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2  - European Journal of Medicinal Chemistry
T1  - Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains
VL  - 143
SP  - 1474
EP  - 1488
DO  - 10.1016/j.ejmech.2017.10.045
ER  - 

@article{
author = "Cvijetić, Ilija and Verbić, Tatjana and de Resende, Pedro Ernesto and Stapleton, Paul and Gibbons, Simon and Juranić, Ivan and Drakulić, Branko and Zloh, Mire",
year = "2018",
abstract = "Antimicrobial resistance (AMR) is a major health problem worldwide, because of ability of bacteria, fungi and viruses to evade known therapeutic agents used in treatment of infections. Aryldiketo acids (ADK) have shown antimicrobial activity against several resistant strains including Gram-positive Staphylococcus aureus bacteria. Our previous studies revealed that ADK analogues having bulky alkyl group in ortho position on a phenyl ring have up to ten times better activity than norfloxacin against the same strains. Rational modifications of analogues by introduction of hydrophobic substituents on the aromatic ring has led to more than tenfold increase in antibacterial activity against multidrug resistant Gram positive strains. To elucidate a potential mechanism of action for this potentially novel class of antimicrobials, several bacterial enzymes were identified as putative targets according to literature data and pharmacophoric similarity searches for potent ADK analogues. Among the seven bacterial targets chosen, the strongest favorable binding interactions were observed between most active analogue and S. aureus dehydrosqualene synthase and DNA gyrase. Furthermore, the docking results in combination with literature data suggest that these novel molecules could also target several other bacterial enzymes, including prenyl-transferases and methionine aminopeptidase. These results and our statistically significant 3D QSAR model could be used to guide the further design of more potent derivatives as well as in virtual screening for novel antibacterial agents. (C) 2017 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains",
volume = "143",
pages = "1474-1488",
doi = "10.1016/j.ejmech.2017.10.045"
}

Cvijetić, I., Verbić, T., de Resende, P. E., Stapleton, P., Gibbons, S., Juranić, I., Drakulić, B.,& Zloh, M.. (2018). Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 143, 1474-1488.
https://doi.org/10.1016/j.ejmech.2017.10.045

Cvijetić I, Verbić T, de Resende PE, Stapleton P, Gibbons S, Juranić I, Drakulić B, Zloh M. Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains. in European Journal of Medicinal Chemistry. 2018;143:1474-1488.
doi:10.1016/j.ejmech.2017.10.045 .

Cvijetić, Ilija, Verbić, Tatjana, de Resende, Pedro Ernesto, Stapleton, Paul, Gibbons, Simon, Juranić, Ivan, Drakulić, Branko, Zloh, Mire, "Design, synthesis and biological evaluation of novel aryldiketo acids with enhanced antibacterial activity against multidrug resistant bacterial strains" in European Journal of Medicinal Chemistry, 143 (2018):1474-1488,
https://doi.org/10.1016/j.ejmech.2017.10.045 . .

TY  - JOUR
AU  - Juranić, Ivan
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4399
AB  - For the prediction of material's properties and of interaction of molecules with the surroundings, one needs to know their properties. Usually, the molecular properties are revealed through experimental measurements. It can be a tedious, time-consuming, and costly work. On the other hand, computational chemistry readily generates a huge number of data which can provide various molecular descriptors. These can be various observable properties (bond lengths and angles, dipole moments, etc...), but also the unobservable properties (partial atomic charges, electronegativity, various latent variables ....). There is an urgent need to develop accurate and economical screening tools that predict potential toxicity and environmental burden of various chemicals. Equally important is the design of safer alternatives. Molecular modeling methods offer one of several complementary approaches to evaluate the risk to human health and the environment as a result of exposure to environmental chemicals. These tools can streamline the hazard assessment process by simulating possible modes of action and providing virtual screening tools that can help prioritize bioassay requirements. Tailoring these strategies to the particular challenges presented by environmental chemical interactions make them even more effective. Advances in the fields of computational chemistry and molecular toxicology in recent decades allow the development of predictive models that inform the design of molecules with reduced potential to be toxic to humans or to the environment. As an example we present the novel methodology for the computational evaluation of pKa values of various organic bases, based on calculation of partial atomic charges by a simple semiempirical QM method.
AB  - Za predviđanje osobina materijala i njihove interakcije sa okolinom, treba poznavati njihove
osobine. Obično se osobine molekula otkrivaju eksperimentalnim merenjima. To može biti
mukotrpan dugotrajan i skup posao. Sa druge strane, računarska hemija lako daje veliki broj
podataka koji mogu da obezbede različite deskriptore molekula. To mogu biti razne merljive
veličine (dužine i uglovi veza, dipolni momenti, i sl...), ali i nemerljive osobine (parcijalna atomska
naelektrisanja, elektronegativnost, razne latentne varijable ....).
Postoji velika potreba za razvijanjem pouzdanih i ekonomičnih načina za skrininge kojima se
predskazuje potencijalna otrovnost i opterećenje životne okoline raznim hemikalijama. Jednako
važan je i dizajn bezbednijih alternativa.
Metode molekulskog modelovanja nude jedan od nekoliko komplementarnih pristupa za procenu
rizika za zdravlje ljudi i životne sredine kao posledicu izlaganja hemikalijama u okolišu. Ovim
postupcima se može neprekidno vršiti procena opasnosti simuliranjem mogućih načina delovanja,
a obezbeđivanje virtualnog skrininga može pomoći u određivanju prioriteta kod bio-eseja.
Ukrajanjem ovih strategija u određene izazove interakcija hemikalija i životne sredine može iste
učiniti efikasnijima.
Napredak u računarskoj hemiji i molekulskoj toksikologiji postignut poslednjih decenija dozvoljava
razvoj prediktivnih modela za racionalni dizajn molekula sa umanjenim potencijalom otrovnosti za
ljude ili za životnu sredinu.
Kao primer predstavljamo novu metodologiju za računarsko procenjivanje pKa vrednosti različitih
organskih baza na osnovu izračunavanja parcijalnih atomskih naelektrisanja prostim
semiempirijskim QM metodom.
PB  - Belgrade : Engineering Society for Corrosion
T2  - Zaštita materijala
T1  - Molecular descriptors as proxies for the modeling of the materials and their environmental impact
T1  - Računarski generisani molekulski deskriptori kao proxi-ji za modelovanje materijala i njihovog uticaja
VL  - 57
IS  - 3
SP  - 359
EP  - 369
DO  - 10.5937/ZasMat1603359J
ER  - 

@article{
author = "Juranić, Ivan",
year = "2016",
abstract = "For the prediction of material's properties and of interaction of molecules with the surroundings, one needs to know their properties. Usually, the molecular properties are revealed through experimental measurements. It can be a tedious, time-consuming, and costly work. On the other hand, computational chemistry readily generates a huge number of data which can provide various molecular descriptors. These can be various observable properties (bond lengths and angles, dipole moments, etc...), but also the unobservable properties (partial atomic charges, electronegativity, various latent variables ....). There is an urgent need to develop accurate and economical screening tools that predict potential toxicity and environmental burden of various chemicals. Equally important is the design of safer alternatives. Molecular modeling methods offer one of several complementary approaches to evaluate the risk to human health and the environment as a result of exposure to environmental chemicals. These tools can streamline the hazard assessment process by simulating possible modes of action and providing virtual screening tools that can help prioritize bioassay requirements. Tailoring these strategies to the particular challenges presented by environmental chemical interactions make them even more effective. Advances in the fields of computational chemistry and molecular toxicology in recent decades allow the development of predictive models that inform the design of molecules with reduced potential to be toxic to humans or to the environment. As an example we present the novel methodology for the computational evaluation of pKa values of various organic bases, based on calculation of partial atomic charges by a simple semiempirical QM method., Za predviđanje osobina materijala i njihove interakcije sa okolinom, treba poznavati njihove
osobine. Obično se osobine molekula otkrivaju eksperimentalnim merenjima. To može biti
mukotrpan dugotrajan i skup posao. Sa druge strane, računarska hemija lako daje veliki broj
podataka koji mogu da obezbede različite deskriptore molekula. To mogu biti razne merljive
veličine (dužine i uglovi veza, dipolni momenti, i sl...), ali i nemerljive osobine (parcijalna atomska
naelektrisanja, elektronegativnost, razne latentne varijable ....).
Postoji velika potreba za razvijanjem pouzdanih i ekonomičnih načina za skrininge kojima se
predskazuje potencijalna otrovnost i opterećenje životne okoline raznim hemikalijama. Jednako
važan je i dizajn bezbednijih alternativa.
Metode molekulskog modelovanja nude jedan od nekoliko komplementarnih pristupa za procenu
rizika za zdravlje ljudi i životne sredine kao posledicu izlaganja hemikalijama u okolišu. Ovim
postupcima se može neprekidno vršiti procena opasnosti simuliranjem mogućih načina delovanja,
a obezbeđivanje virtualnog skrininga može pomoći u određivanju prioriteta kod bio-eseja.
Ukrajanjem ovih strategija u određene izazove interakcija hemikalija i životne sredine može iste
učiniti efikasnijima.
Napredak u računarskoj hemiji i molekulskoj toksikologiji postignut poslednjih decenija dozvoljava
razvoj prediktivnih modela za racionalni dizajn molekula sa umanjenim potencijalom otrovnosti za
ljude ili za životnu sredinu.
Kao primer predstavljamo novu metodologiju za računarsko procenjivanje pKa vrednosti različitih
organskih baza na osnovu izračunavanja parcijalnih atomskih naelektrisanja prostim
semiempirijskim QM metodom.",
publisher = "Belgrade : Engineering Society for Corrosion",
journal = "Zaštita materijala",
title = "Molecular descriptors as proxies for the modeling of the materials and their environmental impact, Računarski generisani molekulski deskriptori kao proxi-ji za modelovanje materijala i njihovog uticaja",
volume = "57",
number = "3",
pages = "359-369",
doi = "10.5937/ZasMat1603359J"
}

Juranić, I.. (2016). Molecular descriptors as proxies for the modeling of the materials and their environmental impact. in Zaštita materijala
Belgrade : Engineering Society for Corrosion., 57(3), 359-369.
https://doi.org/10.5937/ZasMat1603359J

Juranić I. Molecular descriptors as proxies for the modeling of the materials and their environmental impact. in Zaštita materijala. 2016;57(3):359-369.
doi:10.5937/ZasMat1603359J .

Juranić, Ivan, "Molecular descriptors as proxies for the modeling of the materials and their environmental impact" in Zaštita materijala, 57, no. 3 (2016):359-369,
https://doi.org/10.5937/ZasMat1603359J . .

TY  - JOUR
AU  - Trifunovic-Macedoljan, Jelena
AU  - Pantelić, Nebojša Đ.
AU  - Damjanovic, Ana
AU  - Raskovic, Sanvila
AU  - Nikolic-Durovic, Marina
AU  - Pudar, Georgina
AU  - Jadranin, Milka
AU  - Juranić, Ivan
AU  - Juranić, Zorica
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1865
AB  - Biogenic amines are integral part of nearly every cell. In the present study, the method of acidic extraction of histamine (His), of polyamines putrescine (Put), spermidine (Spd) and catecholamines epinephrine (Epi) and norepinephrine (NE) from human serum, precolumn derivatization with dansyl chloride, and LC/DAD analysis of the biogenic amines was used with the aim of monitoring differences of their levels in patients with diabetes mellitus, chronic urticaria, and Hashimoto's thyroiditis, compared to healthy subjects, and to observe them as possible markers for immune mediated diseases. The retention times were used for the determination of serum biogenic amines. Statistically significant differences were found in the levels of putrescine and histamine in diabetes mellitus patients, of the levels of putrescine, histamine, spermidine and epinephrine in chronic urticaria patients and of the levels of putrescine and spermidine levels in Hashimoto's thyroiditis patients, compared to those of healthy controls. Norepinephrine was found only in the serum of patients with chronic urticaria. The values of recovery, evaluated in controls, varied between 85.7 and 106.7 %. The statistically significant changes in putrescine, histamine, spermidine and epinephrine levels in patients compared with those in healthy people reflects the existence of biochemical disturbances in the mentioned immune-mediated diseases.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - LC/DAD determination of biogenic amines in serum of patients with diabetes mellitus, chronic urticaria or Hashimoto's thyroiditis
VL  - 81
IS  - 5
SP  - 487
EP  - 498
DO  - 10.2298/JSC150910020T
ER  - 

@article{
author = "Trifunovic-Macedoljan, Jelena and Pantelić, Nebojša Đ. and Damjanovic, Ana and Raskovic, Sanvila and Nikolic-Durovic, Marina and Pudar, Georgina and Jadranin, Milka and Juranić, Ivan and Juranić, Zorica",
year = "2016",
abstract = "Biogenic amines are integral part of nearly every cell. In the present study, the method of acidic extraction of histamine (His), of polyamines putrescine (Put), spermidine (Spd) and catecholamines epinephrine (Epi) and norepinephrine (NE) from human serum, precolumn derivatization with dansyl chloride, and LC/DAD analysis of the biogenic amines was used with the aim of monitoring differences of their levels in patients with diabetes mellitus, chronic urticaria, and Hashimoto's thyroiditis, compared to healthy subjects, and to observe them as possible markers for immune mediated diseases. The retention times were used for the determination of serum biogenic amines. Statistically significant differences were found in the levels of putrescine and histamine in diabetes mellitus patients, of the levels of putrescine, histamine, spermidine and epinephrine in chronic urticaria patients and of the levels of putrescine and spermidine levels in Hashimoto's thyroiditis patients, compared to those of healthy controls. Norepinephrine was found only in the serum of patients with chronic urticaria. The values of recovery, evaluated in controls, varied between 85.7 and 106.7 %. The statistically significant changes in putrescine, histamine, spermidine and epinephrine levels in patients compared with those in healthy people reflects the existence of biochemical disturbances in the mentioned immune-mediated diseases.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "LC/DAD determination of biogenic amines in serum of patients with diabetes mellitus, chronic urticaria or Hashimoto's thyroiditis",
volume = "81",
number = "5",
pages = "487-498",
doi = "10.2298/JSC150910020T"
}

Trifunovic-Macedoljan, J., Pantelić, N. Đ., Damjanovic, A., Raskovic, S., Nikolic-Durovic, M., Pudar, G., Jadranin, M., Juranić, I.,& Juranić, Z.. (2016). LC/DAD determination of biogenic amines in serum of patients with diabetes mellitus, chronic urticaria or Hashimoto's thyroiditis. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 81(5), 487-498.
https://doi.org/10.2298/JSC150910020T

Trifunovic-Macedoljan J, Pantelić NĐ, Damjanovic A, Raskovic S, Nikolic-Durovic M, Pudar G, Jadranin M, Juranić I, Juranić Z. LC/DAD determination of biogenic amines in serum of patients with diabetes mellitus, chronic urticaria or Hashimoto's thyroiditis. in Journal of the Serbian Chemical Society. 2016;81(5):487-498.
doi:10.2298/JSC150910020T .

Trifunovic-Macedoljan, Jelena, Pantelić, Nebojša Đ., Damjanovic, Ana, Raskovic, Sanvila, Nikolic-Durovic, Marina, Pudar, Georgina, Jadranin, Milka, Juranić, Ivan, Juranić, Zorica, "LC/DAD determination of biogenic amines in serum of patients with diabetes mellitus, chronic urticaria or Hashimoto's thyroiditis" in Journal of the Serbian Chemical Society, 81, no. 5 (2016):487-498,
https://doi.org/10.2298/JSC150910020T . .

TY  - JOUR
AU  - Markovic, Jelena M.
AU  - Trišović, Nemanja
AU  - Mutavdžić, Dragosav
AU  - Radotić, Ksenija
AU  - Juranić, Ivan
AU  - Drakulić, Branko
AU  - Marinković, Aleksandar D.
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3431
AB  - Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogenbond
acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization
was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified
using the Kamlet–Taft and Catalán approach. The obtained results were rationalized by comparison of
electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier
molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HF, DFT,
MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions
on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silico obtained conformational
assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used
to estimate population of conformers and to deconvolute the UV-Vis spectrum of representative derivative;
inferring that the conformational assembly is more complex than was assumed in so far published
literature data for this class of compounds. Along with this, the emission spectra of the representative
compounds were decomposed by the Multivariate Curve Resolution analysis.
PB  - Amsterdam : Elsevier
T2  - Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
T1  - Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study
VL  - 135
SP  - 435
EP  - 446
DO  - 10.1016/j.saa.2014.07.023
ER  - 

@article{
author = "Markovic, Jelena M. and Trišović, Nemanja and Mutavdžić, Dragosav and Radotić, Ksenija and Juranić, Ivan and Drakulić, Branko and Marinković, Aleksandar D.",
year = "2015",
abstract = "Seven symmetrical 2,6-distyrylpyridines, phenyl-substituted with hydrogen-bond donors, hydrogenbond
acceptors, halogens and hydrophobic moieties were synthesized and their spectroscopic characterization
was done. Solvent effects on the absorption and fluorescence spectra were analyzed and quantified
using the Kamlet–Taft and Catalán approach. The obtained results were rationalized by comparison of
electrostatic potentials of the molecules in the ground and in excited state and by comparison of the frontier
molecular orbitals (HOMO and LUMO), derived from quantum-mechanical calculations (HF, DFT,
MP2). Analysis of the results revealed an important influence of non-specific (dispersive) interactions
on the solvatochromic behavior of the compounds. 1D and 2D NMR data, in silico obtained conformational
assembly of the compound, and the NMR analysis of molecular flexibility in solution (NAMFIS), were used
to estimate population of conformers and to deconvolute the UV-Vis spectrum of representative derivative;
inferring that the conformational assembly is more complex than was assumed in so far published
literature data for this class of compounds. Along with this, the emission spectra of the representative
compounds were decomposed by the Multivariate Curve Resolution analysis.",
publisher = "Amsterdam : Elsevier",
journal = "Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy",
title = "Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study",
volume = "135",
pages = "435-446",
doi = "10.1016/j.saa.2014.07.023"
}

Markovic, J. M., Trišović, N., Mutavdžić, D., Radotić, K., Juranić, I., Drakulić, B.,& Marinković, A. D.. (2015). Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study. in Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy
Amsterdam : Elsevier., 135, 435-446.
https://doi.org/10.1016/j.saa.2014.07.023

Markovic JM, Trišović N, Mutavdžić D, Radotić K, Juranić I, Drakulić B, Marinković AD. Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study. in Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2015;135:435-446.
doi:10.1016/j.saa.2014.07.023 .

Markovic, Jelena M., Trišović, Nemanja, Mutavdžić, Dragosav, Radotić, Ksenija, Juranić, Ivan, Drakulić, Branko, Marinković, Aleksandar D., "Solvatochromism of symmetrical 2,6-distyrylpyridines. An experimental and theoretical study" in Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 135 (2015):435-446,
https://doi.org/10.1016/j.saa.2014.07.023 . .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Tanc, Muhammet
AU  - Juranić, Ivan
AU  - Verbić, Tatjana
AU  - Supuran, Claudiu T.
AU  - Drakulić, Branko
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2668
AB  - Inhibitory activity of a congeneric set of 23 phenyl-substituted 5-phenyl-pyrazole-3-carboxylic acids toward human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II, IX and XII was evaluated by a stopped-flow CO2 hydrase assay. These compounds exerted a clear, selective inhibition of hCA IX and XII over hCAI and II, with Ki in two to one digit micromolar concentrations (4-50 mu M). Derivatives bearing bulkier substituents in para-position of the phenyl ring inhibited hCA XII at one-digit micromolar concentrations, while derivatives having alkyl substituents in both ortho-and meta-positions inhibited hCA IX with Kis ranging between 5 and 25 mu M. Results of docking experiments offered a rational explanation on the selectivity of these compounds toward CA IX and XII, as well as on the substitution patterns leading to best CA IX or CA XII inhibitors. By examining the active sites of these four isoforms with GRID generated molecular-interaction fields, striking differences between hCA XII and the other three isoforms were observed. The field of hydrophobic probe (DRY) appeared significantly different in CA XII active site, comparing to other three isoforms studied. To the best of our knowledge such an observation was not reported in literature so far. Considering the selectivity of these carboxylates towards membrane-associated over cytosolic CA isoforms, the title compounds could be useful for the development of isoform-specific non-sulfonamide CA inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Bioorganic and Medicinal Chemistry
T1  - 5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII
VL  - 23
IS  - 15
SP  - 4649
EP  - 4659
DO  - 10.1016/j.bmc.2015.05.052
ER  - 

@article{
author = "Cvijetić, Ilija and Tanc, Muhammet and Juranić, Ivan and Verbić, Tatjana and Supuran, Claudiu T. and Drakulić, Branko",
year = "2015",
abstract = "Inhibitory activity of a congeneric set of 23 phenyl-substituted 5-phenyl-pyrazole-3-carboxylic acids toward human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II, IX and XII was evaluated by a stopped-flow CO2 hydrase assay. These compounds exerted a clear, selective inhibition of hCA IX and XII over hCAI and II, with Ki in two to one digit micromolar concentrations (4-50 mu M). Derivatives bearing bulkier substituents in para-position of the phenyl ring inhibited hCA XII at one-digit micromolar concentrations, while derivatives having alkyl substituents in both ortho-and meta-positions inhibited hCA IX with Kis ranging between 5 and 25 mu M. Results of docking experiments offered a rational explanation on the selectivity of these compounds toward CA IX and XII, as well as on the substitution patterns leading to best CA IX or CA XII inhibitors. By examining the active sites of these four isoforms with GRID generated molecular-interaction fields, striking differences between hCA XII and the other three isoforms were observed. The field of hydrophobic probe (DRY) appeared significantly different in CA XII active site, comparing to other three isoforms studied. To the best of our knowledge such an observation was not reported in literature so far. Considering the selectivity of these carboxylates towards membrane-associated over cytosolic CA isoforms, the title compounds could be useful for the development of isoform-specific non-sulfonamide CA inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Bioorganic and Medicinal Chemistry",
title = "5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII",
volume = "23",
number = "15",
pages = "4649-4659",
doi = "10.1016/j.bmc.2015.05.052"
}

Cvijetić, I., Tanc, M., Juranić, I., Verbić, T., Supuran, C. T.,& Drakulić, B.. (2015). 5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII. in Bioorganic and Medicinal Chemistry
Oxford : Pergamon-Elsevier Science Ltd., 23(15), 4649-4659.
https://doi.org/10.1016/j.bmc.2015.05.052

Cvijetić I, Tanc M, Juranić I, Verbić T, Supuran CT, Drakulić B. 5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII. in Bioorganic and Medicinal Chemistry. 2015;23(15):4649-4659.
doi:10.1016/j.bmc.2015.05.052 .

Cvijetić, Ilija, Tanc, Muhammet, Juranić, Ivan, Verbić, Tatjana, Supuran, Claudiu T., Drakulić, Branko, "5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII" in Bioorganic and Medicinal Chemistry, 23, no. 15 (2015):4649-4659,
https://doi.org/10.1016/j.bmc.2015.05.052 . .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Tanc, Muhammet
AU  - Juranić, Ivan
AU  - Verbić, Tatjana
AU  - Supuran, Claudiu T.
AU  - Drakulić, Branko
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2668
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2872
AB  - Inhibitory activity of a congeneric set of 23 phenyl-substituted 5-phenyl-pyrazole-3-carboxylic acids toward human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II, IX and XII was evaluated by a stopped-flow CO2 hydrase assay. These compounds exerted a clear, selective inhibition of hCA IX and XII over hCAI and II, with Ki in two to one digit micromolar concentrations (4-50 mu M). Derivatives bearing bulkier substituents in para-position of the phenyl ring inhibited hCA XII at one-digit micromolar concentrations, while derivatives having alkyl substituents in both ortho-and meta-positions inhibited hCA IX with Kis ranging between 5 and 25 mu M. Results of docking experiments offered a rational explanation on the selectivity of these compounds toward CA IX and XII, as well as on the substitution patterns leading to best CA IX or CA XII inhibitors. By examining the active sites of these four isoforms with GRID generated molecular-interaction fields, striking differences between hCA XII and the other three isoforms were observed. The field of hydrophobic probe (DRY) appeared significantly different in CA XII active site, comparing to other three isoforms studied. To the best of our knowledge such an observation was not reported in literature so far. Considering the selectivity of these carboxylates towards membrane-associated over cytosolic CA isoforms, the title compounds could be useful for the development of isoform-specific non-sulfonamide CA inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Bioorganic and Medicinal Chemistry
T1  - 5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII
VL  - 23
IS  - 15
SP  - 4649
EP  - 4659
DO  - 10.1016/j.bmc.2015.05.052
ER  - 

@article{
author = "Cvijetić, Ilija and Tanc, Muhammet and Juranić, Ivan and Verbić, Tatjana and Supuran, Claudiu T. and Drakulić, Branko",
year = "2015",
abstract = "Inhibitory activity of a congeneric set of 23 phenyl-substituted 5-phenyl-pyrazole-3-carboxylic acids toward human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II, IX and XII was evaluated by a stopped-flow CO2 hydrase assay. These compounds exerted a clear, selective inhibition of hCA IX and XII over hCAI and II, with Ki in two to one digit micromolar concentrations (4-50 mu M). Derivatives bearing bulkier substituents in para-position of the phenyl ring inhibited hCA XII at one-digit micromolar concentrations, while derivatives having alkyl substituents in both ortho-and meta-positions inhibited hCA IX with Kis ranging between 5 and 25 mu M. Results of docking experiments offered a rational explanation on the selectivity of these compounds toward CA IX and XII, as well as on the substitution patterns leading to best CA IX or CA XII inhibitors. By examining the active sites of these four isoforms with GRID generated molecular-interaction fields, striking differences between hCA XII and the other three isoforms were observed. The field of hydrophobic probe (DRY) appeared significantly different in CA XII active site, comparing to other three isoforms studied. To the best of our knowledge such an observation was not reported in literature so far. Considering the selectivity of these carboxylates towards membrane-associated over cytosolic CA isoforms, the title compounds could be useful for the development of isoform-specific non-sulfonamide CA inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Bioorganic and Medicinal Chemistry",
title = "5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII",
volume = "23",
number = "15",
pages = "4649-4659",
doi = "10.1016/j.bmc.2015.05.052"
}

Cvijetić, I., Tanc, M., Juranić, I., Verbić, T., Supuran, C. T.,& Drakulić, B.. (2015). 5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII. in Bioorganic and Medicinal Chemistry
Oxford : Pergamon-Elsevier Science Ltd., 23(15), 4649-4659.
https://doi.org/10.1016/j.bmc.2015.05.052

Cvijetić I, Tanc M, Juranić I, Verbić T, Supuran CT, Drakulić B. 5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII. in Bioorganic and Medicinal Chemistry. 2015;23(15):4649-4659.
doi:10.1016/j.bmc.2015.05.052 .

Cvijetić, Ilija, Tanc, Muhammet, Juranić, Ivan, Verbić, Tatjana, Supuran, Claudiu T., Drakulić, Branko, "5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII" in Bioorganic and Medicinal Chemistry, 23, no. 15 (2015):4649-4659,
https://doi.org/10.1016/j.bmc.2015.05.052 . .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Petrović, D.D.
AU  - Verbić, Tatjana
AU  - Juranić, Ivan
AU  - Drakulić, Branko
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2669
AB  - Interactions of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic acid (compound 1) and its mono-Me ester (compound 2) with the human serum albumin (HSA) have been studied by fluorescence spectroscopy. Comp. 1 exerts antiproliferative activity toward human tumor cells and significant selectivity (tumor vs. healthy cells) in vitro. Competitive binding study with warfarin and ibuprofen as binding site probes, revealed that one molecule of comp. 1 selectively binds to HSA Sudlow site I (warfarin site) with moderate binding constant (Kb = (2.8 ± 0.5) × 104 M-1 at 37 ± 1 °C), while comp. 2 binds to Sudlow site II (Kb = (3.2 ± 0.9) × 104 M-1 at 37 ± 1 °C). Fluorescence quenching at different temperatures was analyzed using classical Stern-Volmer equation, and a static quenching mechanism was proposed. Energy resonance transfer between HSA and comp. 1 was examined according to Förster's non-radiative energy transfer theory. Distance of about 10 Å between ligand and Trp214 (HSA) was obtained. Docking studies confirmed HSA Sudlow site I as a preferable comp. 1 binding site, and Sudlow site II as comp. 2 binding site. Molecular dynamics simulations proved the stability of comp. 1/HSA complex. © 2014 by the authors.
T2  - ADMET and DMPK
T1  - Human Serum Albumin Binding of 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic Acid and its Mono-Me Esters
VL  - 2
IS  - 2
SP  - 126
EP  - 142
DO  - 10.5599/admet.2.2.28
ER  - 

@article{
author = "Cvijetić, Ilija and Petrović, D.D. and Verbić, Tatjana and Juranić, Ivan and Drakulić, Branko",
year = "2014",
abstract = "Interactions of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic acid (compound 1) and its mono-Me ester (compound 2) with the human serum albumin (HSA) have been studied by fluorescence spectroscopy. Comp. 1 exerts antiproliferative activity toward human tumor cells and significant selectivity (tumor vs. healthy cells) in vitro. Competitive binding study with warfarin and ibuprofen as binding site probes, revealed that one molecule of comp. 1 selectively binds to HSA Sudlow site I (warfarin site) with moderate binding constant (Kb = (2.8 ± 0.5) × 104 M-1 at 37 ± 1 °C), while comp. 2 binds to Sudlow site II (Kb = (3.2 ± 0.9) × 104 M-1 at 37 ± 1 °C). Fluorescence quenching at different temperatures was analyzed using classical Stern-Volmer equation, and a static quenching mechanism was proposed. Energy resonance transfer between HSA and comp. 1 was examined according to Förster's non-radiative energy transfer theory. Distance of about 10 Å between ligand and Trp214 (HSA) was obtained. Docking studies confirmed HSA Sudlow site I as a preferable comp. 1 binding site, and Sudlow site II as comp. 2 binding site. Molecular dynamics simulations proved the stability of comp. 1/HSA complex. © 2014 by the authors.",
journal = "ADMET and DMPK",
title = "Human Serum Albumin Binding of 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic Acid and its Mono-Me Esters",
volume = "2",
number = "2",
pages = "126-142",
doi = "10.5599/admet.2.2.28"
}

Cvijetić, I., Petrović, D.D., Verbić, T., Juranić, I.,& Drakulić, B.. (2014). Human Serum Albumin Binding of 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic Acid and its Mono-Me Esters. in ADMET and DMPK, 2(2), 126-142.
https://doi.org/10.5599/admet.2.2.28

Cvijetić I, Petrović D, Verbić T, Juranić I, Drakulić B. Human Serum Albumin Binding of 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic Acid and its Mono-Me Esters. in ADMET and DMPK. 2014;2(2):126-142.
doi:10.5599/admet.2.2.28 .

Cvijetić, Ilija, Petrović, D.D., Verbić, Tatjana, Juranić, Ivan, Drakulić, Branko, "Human Serum Albumin Binding of 2-[(Carboxymethyl)sulfanyl]-4-oxo-4-(4-tert-butylphenyl)butanoic Acid and its Mono-Me Esters" in ADMET and DMPK, 2, no. 2 (2014):126-142,
https://doi.org/10.5599/admet.2.2.28 . .

TY  - JOUR
AU  - Juranić, Ivan
AU  - Tošić, Ana V.
AU  - Kolundžija, Branka
AU  - Drakulić, Branko
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2670
AB  - Antiproliferative activity of twenty one Michael adducts of aroylacrylic acids and cyclic amines (  N -Me-piperazine, imidazole, 2-Me-imidazole, and indole) was tested toward five human tumor cell lines (HeLa, LS174, K562, FemX, MDA-MB-361) in vitro. Compounds exerted antiproliferative activity in the high to the single-digit micromolar concentrations, causing increase of the cell population fraction in S phase and apoptosis.   N -Me-piperazine and imidazole derivatives of aroylacrylic acids substituted with bulky alkyl substituents (2,4-di-  i -Pr-Ph-, 2,4,6-tri-Et-Ph-, or   β -tetrahydronaphthyl-) showed the best potency, while indole adducts were proved as the inferior antiproliferative agents. Few compounds showed significant selectivity, tumor versus healthy cells, with selectivity index   ∼60  for the most selective congener. An unbiased in silico distinction between more and less potent compounds was obtained from 3D QSAR models derived by alignment-independent GRIND-2 descriptors.
PB  - Springer
T2  - Molecular Diversity
T1  - Antiproliferative activity of the Michael adducts of aroylacrylic acids and cyclic amines
VL  - 18
IS  - 3
SP  - 577
EP  - 592
DO  - 10.1007/s11030-014-9528-4
ER  - 

@article{
author = "Juranić, Ivan and Tošić, Ana V. and Kolundžija, Branka and Drakulić, Branko",
year = "2014",
abstract = "Antiproliferative activity of twenty one Michael adducts of aroylacrylic acids and cyclic amines (  N -Me-piperazine, imidazole, 2-Me-imidazole, and indole) was tested toward five human tumor cell lines (HeLa, LS174, K562, FemX, MDA-MB-361) in vitro. Compounds exerted antiproliferative activity in the high to the single-digit micromolar concentrations, causing increase of the cell population fraction in S phase and apoptosis.   N -Me-piperazine and imidazole derivatives of aroylacrylic acids substituted with bulky alkyl substituents (2,4-di-  i -Pr-Ph-, 2,4,6-tri-Et-Ph-, or   β -tetrahydronaphthyl-) showed the best potency, while indole adducts were proved as the inferior antiproliferative agents. Few compounds showed significant selectivity, tumor versus healthy cells, with selectivity index   ∼60  for the most selective congener. An unbiased in silico distinction between more and less potent compounds was obtained from 3D QSAR models derived by alignment-independent GRIND-2 descriptors.",
publisher = "Springer",
journal = "Molecular Diversity",
title = "Antiproliferative activity of the Michael adducts of aroylacrylic acids and cyclic amines",
volume = "18",
number = "3",
pages = "577-592",
doi = "10.1007/s11030-014-9528-4"
}

Juranić, I., Tošić, A. V., Kolundžija, B.,& Drakulić, B.. (2014). Antiproliferative activity of the Michael adducts of aroylacrylic acids and cyclic amines. in Molecular Diversity
Springer., 18(3), 577-592.
https://doi.org/10.1007/s11030-014-9528-4

Juranić I, Tošić AV, Kolundžija B, Drakulić B. Antiproliferative activity of the Michael adducts of aroylacrylic acids and cyclic amines. in Molecular Diversity. 2014;18(3):577-592.
doi:10.1007/s11030-014-9528-4 .

Juranić, Ivan, Tošić, Ana V., Kolundžija, Branka, Drakulić, Branko, "Antiproliferative activity of the Michael adducts of aroylacrylic acids and cyclic amines" in Molecular Diversity, 18, no. 3 (2014):577-592,
https://doi.org/10.1007/s11030-014-9528-4 . .

TY  - JOUR
AU  - Vitorović-Todorović, Maja D.
AU  - Koukoulitsa, Catherine
AU  - Juranić, Ivan
AU  - Mandić, Ljuba M.
AU  - Drakulić, Branko
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2688
AB  - Congeneric set of thirty-eight 4-aryl-4-oxo-2-(N-aryl/cycloalkyl)butanamides has been designed, synthesized and evaluated for acetyl- and butyrylcholinesterase inhibitory activity. Structural variations included cycloalkylamino group attached to C2 position of butanoyl moiety, and variation of amido moiety of molecules. Twelve compounds, mostly piperidino and imidazolo derivatives, inhibited AChE in low micromolar range, and were inactive toward BChE. Several N-methylpiperazino derivatives showed inhibition of BChE in low micromolar or submicromolar concentrations, and were inactive toward AChE. Therefore, the nature of the cycloalkylamino moiety governs the AChE/BChE selectivity profile of compounds. The most active AChE inhibitor showed mixed-type inhibition modality, indicating its binding to free enzyme and to enzyme-substrate complex. Thorough docking calculations of the seven most potent AChE inhibitors from the set, showed that the hydrogen bond can be formed between amide -NH- moiety of compounds and -OH group of Tyr 124. The 10 ns unconstrained molecular dynamic simulation of the AChE- compound 18 complex shows that this interaction is the most persistent. This is, probably, the major anchoring point for the binding. (C) 2014 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations
VL  - 81
SP  - 158
EP  - 175
DO  - 10.1016/j.ejmech.2014.05.008
ER  - 

@article{
author = "Vitorović-Todorović, Maja D. and Koukoulitsa, Catherine and Juranić, Ivan and Mandić, Ljuba M. and Drakulić, Branko",
year = "2014",
abstract = "Congeneric set of thirty-eight 4-aryl-4-oxo-2-(N-aryl/cycloalkyl)butanamides has been designed, synthesized and evaluated for acetyl- and butyrylcholinesterase inhibitory activity. Structural variations included cycloalkylamino group attached to C2 position of butanoyl moiety, and variation of amido moiety of molecules. Twelve compounds, mostly piperidino and imidazolo derivatives, inhibited AChE in low micromolar range, and were inactive toward BChE. Several N-methylpiperazino derivatives showed inhibition of BChE in low micromolar or submicromolar concentrations, and were inactive toward AChE. Therefore, the nature of the cycloalkylamino moiety governs the AChE/BChE selectivity profile of compounds. The most active AChE inhibitor showed mixed-type inhibition modality, indicating its binding to free enzyme and to enzyme-substrate complex. Thorough docking calculations of the seven most potent AChE inhibitors from the set, showed that the hydrogen bond can be formed between amide -NH- moiety of compounds and -OH group of Tyr 124. The 10 ns unconstrained molecular dynamic simulation of the AChE- compound 18 complex shows that this interaction is the most persistent. This is, probably, the major anchoring point for the binding. (C) 2014 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations",
volume = "81",
pages = "158-175",
doi = "10.1016/j.ejmech.2014.05.008"
}

Vitorović-Todorović, M. D., Koukoulitsa, C., Juranić, I., Mandić, L. M.,& Drakulić, B.. (2014). Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 81, 158-175.
https://doi.org/10.1016/j.ejmech.2014.05.008

Vitorović-Todorović MD, Koukoulitsa C, Juranić I, Mandić LM, Drakulić B. Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations. in European Journal of Medicinal Chemistry. 2014;81:158-175.
doi:10.1016/j.ejmech.2014.05.008 .

Vitorović-Todorović, Maja D., Koukoulitsa, Catherine, Juranić, Ivan, Mandić, Ljuba M., Drakulić, Branko, "Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations" in European Journal of Medicinal Chemistry, 81 (2014):158-175,
https://doi.org/10.1016/j.ejmech.2014.05.008 . .

TY  - JOUR
AU  - Vitorović-Todorović, Maja D.
AU  - Koukoulitsa, Catherine
AU  - Juranić, Ivan
AU  - Mandić, Ljuba M.
AU  - Drakulić, Branko
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3134
AB  - Congeneric set of thirty-eight 4-aryl-4-oxo-2-(N-aryl/cycloalkyl)butanamides has been designed, synthesized and evaluated for acetyl- and butyrylcholinesterase inhibitory activity. Structural variations included cycloalkylamino group attached to C2 position of butanoyl moiety, and variation of amido moiety of molecules. Twelve compounds, mostly piperidino and imidazolo derivatives, inhibited AChE in low micromolar range, and were inactive toward BChE. Several N-methylpiperazino derivatives showed inhibition of BChE in low micromolar or submicromolar concentrations, and were inactive toward AChE. Therefore, the nature of the cycloalkylamino moiety governs the AChE/BChE selectivity profile of compounds. The most active AChE inhibitor showed mixed-type inhibition modality, indicating its binding to free enzyme and to enzyme-substrate complex. Thorough docking calculations of the seven most potent AChE inhibitors from the set, showed that the hydrogen bond can be formed between amide -NH- moiety of compounds and -OH group of Tyr 124. The 10 ns unconstrained molecular dynamic simulation of the AChE- compound 18 complex shows that this interaction is the most persistent. This is, probably, the major anchoring point for the binding. (C) 2014 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations
VL  - 81
SP  - 158
EP  - 175
DO  - 10.1016/j.ejmech.2014.05.008
ER  - 

@article{
author = "Vitorović-Todorović, Maja D. and Koukoulitsa, Catherine and Juranić, Ivan and Mandić, Ljuba M. and Drakulić, Branko",
year = "2014",
abstract = "Congeneric set of thirty-eight 4-aryl-4-oxo-2-(N-aryl/cycloalkyl)butanamides has been designed, synthesized and evaluated for acetyl- and butyrylcholinesterase inhibitory activity. Structural variations included cycloalkylamino group attached to C2 position of butanoyl moiety, and variation of amido moiety of molecules. Twelve compounds, mostly piperidino and imidazolo derivatives, inhibited AChE in low micromolar range, and were inactive toward BChE. Several N-methylpiperazino derivatives showed inhibition of BChE in low micromolar or submicromolar concentrations, and were inactive toward AChE. Therefore, the nature of the cycloalkylamino moiety governs the AChE/BChE selectivity profile of compounds. The most active AChE inhibitor showed mixed-type inhibition modality, indicating its binding to free enzyme and to enzyme-substrate complex. Thorough docking calculations of the seven most potent AChE inhibitors from the set, showed that the hydrogen bond can be formed between amide -NH- moiety of compounds and -OH group of Tyr 124. The 10 ns unconstrained molecular dynamic simulation of the AChE- compound 18 complex shows that this interaction is the most persistent. This is, probably, the major anchoring point for the binding. (C) 2014 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations",
volume = "81",
pages = "158-175",
doi = "10.1016/j.ejmech.2014.05.008"
}

Vitorović-Todorović, M. D., Koukoulitsa, C., Juranić, I., Mandić, L. M.,& Drakulić, B.. (2014). Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 81, 158-175.
https://doi.org/10.1016/j.ejmech.2014.05.008

Vitorović-Todorović MD, Koukoulitsa C, Juranić I, Mandić LM, Drakulić B. Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations. in European Journal of Medicinal Chemistry. 2014;81:158-175.
doi:10.1016/j.ejmech.2014.05.008 .

Vitorović-Todorović, Maja D., Koukoulitsa, Catherine, Juranić, Ivan, Mandić, Ljuba M., Drakulić, Branko, "Structural modifications of 4-aryl-4-oxo-2-aminylbutanamides and their acetyl- and butyrylcholinesterase inhibitory activity. Investigation of AChE-ligand interactions by docking calculations and molecular dynamics simulations" in European Journal of Medicinal Chemistry, 81 (2014):158-175,
https://doi.org/10.1016/j.ejmech.2014.05.008 . .

TY  - JOUR
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Banjac, Nebojša R.
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
AU  - Juranić, Ivan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3160
AB  - This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wave-number showed very good agreement with the experimental values. The H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the sigma* and pi* antibonding orbitals and second order delocalization energies E(2) confirm the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide
VL  - 117
SP  - 42
EP  - 53
DO  - 10.1016/j.saa.2013.07.099
ER  - 

@article{
author = "Vitnik, Vesna and Vitnik, Željko and Banjac, Nebojša R. and Valentić, Nataša V. and Ušćumlić, Gordana and Juranić, Ivan",
year = "2014",
abstract = "This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wave-number showed very good agreement with the experimental values. The H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the sigma* and pi* antibonding orbitals and second order delocalization energies E(2) confirm the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide",
volume = "117",
pages = "42-53",
doi = "10.1016/j.saa.2013.07.099"
}

Vitnik, V., Vitnik, Ž., Banjac, N. R., Valentić, N. V., Ušćumlić, G.,& Juranić, I.. (2014). Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
Oxford : Pergamon-Elsevier Science Ltd., 117, 42-53.
https://doi.org/10.1016/j.saa.2013.07.099

Vitnik V, Vitnik Ž, Banjac NR, Valentić NV, Ušćumlić G, Juranić I. Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2014;117:42-53.
doi:10.1016/j.saa.2013.07.099 .

Vitnik, Vesna, Vitnik, Željko, Banjac, Nebojša R., Valentić, Nataša V., Ušćumlić, Gordana, Juranić, Ivan, "Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 117 (2014):42-53,
https://doi.org/10.1016/j.saa.2013.07.099 . .

TY  - JOUR
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Banjac, Nebojša R.
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
AU  - Juranić, Ivan
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1496
AB  - This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wave-number showed very good agreement with the experimental values. The H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the sigma* and pi* antibonding orbitals and second order delocalization energies E(2) confirm the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
T1  - Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide
VL  - 117
SP  - 42
EP  - 53
DO  - 10.1016/j.saa.2013.07.099
ER  - 

@article{
author = "Vitnik, Vesna and Vitnik, Željko and Banjac, Nebojša R. and Valentić, Nataša V. and Ušćumlić, Gordana and Juranić, Ivan",
year = "2014",
abstract = "This study represents an integrated approach towards understanding the vibrational, electronic, NMR, and structural aspects, and reactivity of 1-(4-chloro-phenyl)-3-phenyl-succinimide (CPPS). A detailed interpretation of the FT-IR, UV and NMR spectra were reported. The equilibrium geometry, bonding features, and harmonic vibrational frequencies have been investigated with the help of density functional theory (DFT) B3LYP method using 6-31G(d,p) and 6-311++G(d,p) basis set. The scaled theoretical wave-number showed very good agreement with the experimental values. The H-1 and C-13 nuclear magnetic resonance (NMR) chemical shifts of the molecule were calculated by the Gauge-Invariant Atomic Orbital (GIAO) method. Stability of the molecule, arising from hyperconjugative interactions and charge delocalization, has been analyzed using Natural Bond Orbital (NBO) analysis. The results show that ED in the sigma* and pi* antibonding orbitals and second order delocalization energies E(2) confirm the occurrence of intramolecular charge transfer (ICT) within the molecule. UV-Vis spectrum of the compound was recorded and the electronic properties, such as HOMO and LUMO energies, were calculated by Time-Dependent (TD-DFT) approach. To estimate chemical reactivity of the molecule, the molecular electrostatic potential (MEP) surface map is calculated for the optimized geometry of the molecule.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy",
title = "Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide",
volume = "117",
pages = "42-53",
doi = "10.1016/j.saa.2013.07.099"
}

Vitnik, V., Vitnik, Ž., Banjac, N. R., Valentić, N. V., Ušćumlić, G.,& Juranić, I.. (2014). Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy
Oxford : Pergamon-Elsevier Science Ltd., 117, 42-53.
https://doi.org/10.1016/j.saa.2013.07.099

Vitnik V, Vitnik Ž, Banjac NR, Valentić NV, Ušćumlić G, Juranić I. Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide. in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy. 2014;117:42-53.
doi:10.1016/j.saa.2013.07.099 .

Vitnik, Vesna, Vitnik, Željko, Banjac, Nebojša R., Valentić, Nataša V., Ušćumlić, Gordana, Juranić, Ivan, "Quantum mechanical and spectroscopic (FT-IR, C-13, H-1 NMR and UV) investigations of potent antiepileptic drug 1-(4-chloro-phenyl)-3-phenyl-succinimide" in Spectrochimica Acta Part A-Molecular and Biomolecular Spectroscopy, 117 (2014):42-53,
https://doi.org/10.1016/j.saa.2013.07.099 . .

TY  - JOUR
AU  - Juranić, Ivan
PY  - 2014
UR  - https://jepm.tfzv.ues.rs.ba/index.php/Journal/article/view/53
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3907
AB  - A review on advanced photochemical processes influencing properties of materials is presented. Particular emphasis is given on photolytic processes for the removal of pollutants. Separately are presented methods for the removal of biological pollution. Major concern is paid to the methods for removal of persistent chemical pollutants. Two major groups of processes are known: homogenous and heterogeneous photocatalytic methods. The heterogeneous photocatalysis is usually done with semiconductor nanoparticles, capable to absorb light. In semiconductor the absorption of light quanta is connected with the promotion of electron(s) from valence to conduction band, leaving a positively charged hole(s) in CB. Electrons and holes can react with adsorbed molecules including water molecules. In this way the reactive intermediates are produced, which upon the sequence of reactions end with complete mineralization of ingredients. The scaling-up of heterogeneous photocatalytic process is closely connected with efficacy of them. As a matter of fact, many factors are involved in kinetics of photocatalysis: concentration of pollutants; concentration of catalyst; temperature; radiant flux; quantum yield; dopants; etc. The interrelations among various parameters are mostly nonlinear, and construction of the photoreactor is very demanding task. In last 30 years a lot of study was done, and general conclusion is that TiO2 (mostly anatase) is most efficient photocatalyst, but there is a lot of work needed on improvement of such processes.
PB  - Bosnia and Herzegovina : University of East Sarajevo, Faculty of Technology
T2  - Journal of Engineering & Processing Management
T1  - Effect of light on the aging, corrosion, and degradation of materials, in relation to the enhanced removal of organic pollutants
VL  - 6
IS  - 1
SP  - 15
EP  - 48
DO  - 10.7251/JEPMEN1406015J
ER  - 

@article{
author = "Juranić, Ivan",
year = "2014",
abstract = "A review on advanced photochemical processes influencing properties of materials is presented. Particular emphasis is given on photolytic processes for the removal of pollutants. Separately are presented methods for the removal of biological pollution. Major concern is paid to the methods for removal of persistent chemical pollutants. Two major groups of processes are known: homogenous and heterogeneous photocatalytic methods. The heterogeneous photocatalysis is usually done with semiconductor nanoparticles, capable to absorb light. In semiconductor the absorption of light quanta is connected with the promotion of electron(s) from valence to conduction band, leaving a positively charged hole(s) in CB. Electrons and holes can react with adsorbed molecules including water molecules. In this way the reactive intermediates are produced, which upon the sequence of reactions end with complete mineralization of ingredients. The scaling-up of heterogeneous photocatalytic process is closely connected with efficacy of them. As a matter of fact, many factors are involved in kinetics of photocatalysis: concentration of pollutants; concentration of catalyst; temperature; radiant flux; quantum yield; dopants; etc. The interrelations among various parameters are mostly nonlinear, and construction of the photoreactor is very demanding task. In last 30 years a lot of study was done, and general conclusion is that TiO2 (mostly anatase) is most efficient photocatalyst, but there is a lot of work needed on improvement of such processes.",
publisher = "Bosnia and Herzegovina : University of East Sarajevo, Faculty of Technology",
journal = "Journal of Engineering & Processing Management",
title = "Effect of light on the aging, corrosion, and degradation of materials, in relation to the enhanced removal of organic pollutants",
volume = "6",
number = "1",
pages = "15-48",
doi = "10.7251/JEPMEN1406015J"
}

Juranić, I.. (2014). Effect of light on the aging, corrosion, and degradation of materials, in relation to the enhanced removal of organic pollutants. in Journal of Engineering & Processing Management
Bosnia and Herzegovina : University of East Sarajevo, Faculty of Technology., 6(1), 15-48.
https://doi.org/10.7251/JEPMEN1406015J

Juranić I. Effect of light on the aging, corrosion, and degradation of materials, in relation to the enhanced removal of organic pollutants. in Journal of Engineering & Processing Management. 2014;6(1):15-48.
doi:10.7251/JEPMEN1406015J .

Juranić, Ivan, "Effect of light on the aging, corrosion, and degradation of materials, in relation to the enhanced removal of organic pollutants" in Journal of Engineering & Processing Management, 6, no. 1 (2014):15-48,
https://doi.org/10.7251/JEPMEN1406015J . .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Vitorović-Todorović, Maja D.
AU  - Juranić, Ivan
AU  - Drakulić, Branko
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2689
AB  - The reactivity of fifteen (E)-4-aryl-4-oxo-2-butenoic (aroylacrylic) acid arylamides toward thiols was studied, measuring the rate constants of the addition of model thiol nucleophile, 2-mercaptoethanol. The influence of the variation of the substituents on the phenyl rings on the rate of reaction was quantified using the Hammett substituent constants and descriptors derived from ab initio or semiempirical calculations (atomic charges, HOMO, and LUMO). Statistically significant linear correlations between second-order rate constants and Hammett substituent constants, as well as energies of LUMO orbitals, were obtained. Substituents on both aroyl and arylamido moieties were shown to influence the reactivity of studied compounds toward thiols. The regioselectivity of reaction was confirmed by NMR spectroscopy. Exclusively beta-addition product with respect to the aroyl keto group was obtained. The determined enthalpy and entropy of activation were found to be in agreement with the proposed reaction mechanism, which includes a highly ordered transition state.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study
VL  - 144
IS  - 12
SP  - 1815
EP  - 1824
DO  - 10.1007/s00706-013-1084-6
ER  - 

@article{
author = "Cvijetić, Ilija and Vitorović-Todorović, Maja D. and Juranić, Ivan and Drakulić, Branko",
year = "2013",
abstract = "The reactivity of fifteen (E)-4-aryl-4-oxo-2-butenoic (aroylacrylic) acid arylamides toward thiols was studied, measuring the rate constants of the addition of model thiol nucleophile, 2-mercaptoethanol. The influence of the variation of the substituents on the phenyl rings on the rate of reaction was quantified using the Hammett substituent constants and descriptors derived from ab initio or semiempirical calculations (atomic charges, HOMO, and LUMO). Statistically significant linear correlations between second-order rate constants and Hammett substituent constants, as well as energies of LUMO orbitals, were obtained. Substituents on both aroyl and arylamido moieties were shown to influence the reactivity of studied compounds toward thiols. The regioselectivity of reaction was confirmed by NMR spectroscopy. Exclusively beta-addition product with respect to the aroyl keto group was obtained. The determined enthalpy and entropy of activation were found to be in agreement with the proposed reaction mechanism, which includes a highly ordered transition state.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study",
volume = "144",
number = "12",
pages = "1815-1824",
doi = "10.1007/s00706-013-1084-6"
}

Cvijetić, I., Vitorović-Todorović, M. D., Juranić, I.,& Drakulić, B.. (2013). Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study. in Monatshefte Fur Chemie
Springer Wien, Wien., 144(12), 1815-1824.
https://doi.org/10.1007/s00706-013-1084-6

Cvijetić I, Vitorović-Todorović MD, Juranić I, Drakulić B. Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study. in Monatshefte Fur Chemie. 2013;144(12):1815-1824.
doi:10.1007/s00706-013-1084-6 .

Cvijetić, Ilija, Vitorović-Todorović, Maja D., Juranić, Ivan, Drakulić, Branko, "Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid arylamides toward 2-mercaptoethanol. A LFER study" in Monatshefte Fur Chemie, 144, no. 12 (2013):1815-1824,
https://doi.org/10.1007/s00706-013-1084-6 . .

TY  - JOUR
AU  - Vitorović-Todorović, Maja D.
AU  - Erić-Nikolić, Aleksandra
AU  - Kolundžija, Branka
AU  - Hamel, Ernest
AU  - Ristić, Slavica S.
AU  - Juranić, Ivan
AU  - Drakulić, Branko
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2873
AB  - Antiproliferative activity of twenty-nine (E)-4-aryl-4-oxo-2-butenoic acid amides against three human
tumor cell lines (HeLa, FemX, and K562) is reported. Compounds showed antiproliferative activity in
one-digit micromolar to submicromolar concentrations. The most active derivatives toward all the cell
lines tested bear alkyl substituents on the aroyl moiety of the molecules. Fourteen compounds showed
tubulin assembly inhibition at concentrations <20 mM. The most potent inhibitor of tubulin assembly
was unsubstituted compound 1, with IC50 ¼ 2.9 mM. Compound 23 had an oral LD50 in vivo of 45 mg/kg in
mice. Cell cycle analysis on K562 cells showed that compounds 1, 2 and 23 caused accumulation of cells
in the G2/M phase, but inhibition of microtubule polymerization is not the principal mode of action of
the compounds. Nevertheless, they may be useful leads for the design of a new class of antitubulin
agents.
PB  - Elsevier Masson SAS.
T2  - European Journal of Medicinal Chemistry
T1  - (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalconeearoylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization
VL  - 62
SP  - 40
EP  - 50
DO  - 10.1016/j.ejmech.2013.01.006
ER  - 

@article{
author = "Vitorović-Todorović, Maja D. and Erić-Nikolić, Aleksandra and Kolundžija, Branka and Hamel, Ernest and Ristić, Slavica S. and Juranić, Ivan and Drakulić, Branko",
year = "2013",
abstract = "Antiproliferative activity of twenty-nine (E)-4-aryl-4-oxo-2-butenoic acid amides against three human
tumor cell lines (HeLa, FemX, and K562) is reported. Compounds showed antiproliferative activity in
one-digit micromolar to submicromolar concentrations. The most active derivatives toward all the cell
lines tested bear alkyl substituents on the aroyl moiety of the molecules. Fourteen compounds showed
tubulin assembly inhibition at concentrations <20 mM. The most potent inhibitor of tubulin assembly
was unsubstituted compound 1, with IC50 ¼ 2.9 mM. Compound 23 had an oral LD50 in vivo of 45 mg/kg in
mice. Cell cycle analysis on K562 cells showed that compounds 1, 2 and 23 caused accumulation of cells
in the G2/M phase, but inhibition of microtubule polymerization is not the principal mode of action of
the compounds. Nevertheless, they may be useful leads for the design of a new class of antitubulin
agents.",
publisher = "Elsevier Masson SAS.",
journal = "European Journal of Medicinal Chemistry",
title = "(E)-4-Aryl-4-oxo-2-butenoic acid amides, chalconeearoylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization",
volume = "62",
pages = "40-50",
doi = "10.1016/j.ejmech.2013.01.006"
}

Vitorović-Todorović, M. D., Erić-Nikolić, A., Kolundžija, B., Hamel, E., Ristić, S. S., Juranić, I.,& Drakulić, B.. (2013). (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalconeearoylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization. in European Journal of Medicinal Chemistry
Elsevier Masson SAS.., 62, 40-50.
https://doi.org/10.1016/j.ejmech.2013.01.006

Vitorović-Todorović MD, Erić-Nikolić A, Kolundžija B, Hamel E, Ristić SS, Juranić I, Drakulić B. (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalconeearoylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization. in European Journal of Medicinal Chemistry. 2013;62:40-50.
doi:10.1016/j.ejmech.2013.01.006 .

Vitorović-Todorović, Maja D., Erić-Nikolić, Aleksandra, Kolundžija, Branka, Hamel, Ernest, Ristić, Slavica S., Juranić, Ivan, Drakulić, Branko, "(E)-4-Aryl-4-oxo-2-butenoic acid amides, chalconeearoylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization" in European Journal of Medicinal Chemistry, 62 (2013):40-50,
https://doi.org/10.1016/j.ejmech.2013.01.006 . .

TY  - JOUR
AU  - Banjac, Nebojša R.
AU  - Trišović, Nemanja
AU  - Vitnik, Željko
AU  - Vitnik, Vesna
AU  - Valentić, Nataša V.
AU  - Ušćumlić, Gordana
AU  - Juranić, Ivan
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1173
AB  - Two series of 1-aryl-3-phenyl- and 1-aryl-3,3-diphenylpyrrolidine-2,5-diones were synthesized and their solvatochromic properties were studied in a set of 15 solvents of different polarity. The effect of specific and non-specific solvent-solute interactions on the position of their absorption bands was evaluated by using the solvent parameter sets of Kamlet and Taft. The interpretation of the effect of different substituent patterns on the solvatochromic properties of the investigated compounds was based on quantum chemical calculations performed by the density functional theory (DFT)/CAM-B3LYP method using the 6-311G(d,p) basis set. The theoretical absorption frequencies show very good agreement with the experimental values. The energy gaps between the HOMO and LUMO orbitals were also analyzed. It is demonstrated that different substituents change the conjugation effect and further determine the pathways of intramolecular charge transfer.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer
VL  - 144
IS  - 10
SP  - 1525
EP  - 1535
DO  - 10.1007/s00706-013-1052-1
ER  - 

@article{
author = "Banjac, Nebojša R. and Trišović, Nemanja and Vitnik, Željko and Vitnik, Vesna and Valentić, Nataša V. and Ušćumlić, Gordana and Juranić, Ivan",
year = "2013",
abstract = "Two series of 1-aryl-3-phenyl- and 1-aryl-3,3-diphenylpyrrolidine-2,5-diones were synthesized and their solvatochromic properties were studied in a set of 15 solvents of different polarity. The effect of specific and non-specific solvent-solute interactions on the position of their absorption bands was evaluated by using the solvent parameter sets of Kamlet and Taft. The interpretation of the effect of different substituent patterns on the solvatochromic properties of the investigated compounds was based on quantum chemical calculations performed by the density functional theory (DFT)/CAM-B3LYP method using the 6-311G(d,p) basis set. The theoretical absorption frequencies show very good agreement with the experimental values. The energy gaps between the HOMO and LUMO orbitals were also analyzed. It is demonstrated that different substituents change the conjugation effect and further determine the pathways of intramolecular charge transfer.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer",
volume = "144",
number = "10",
pages = "1525-1535",
doi = "10.1007/s00706-013-1052-1"
}

Banjac, N. R., Trišović, N., Vitnik, Ž., Vitnik, V., Valentić, N. V., Ušćumlić, G.,& Juranić, I.. (2013). Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer. in Monatshefte Fur Chemie
Springer Wien, Wien., 144(10), 1525-1535.
https://doi.org/10.1007/s00706-013-1052-1

Banjac NR, Trišović N, Vitnik Ž, Vitnik V, Valentić NV, Ušćumlić G, Juranić I. Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer. in Monatshefte Fur Chemie. 2013;144(10):1525-1535.
doi:10.1007/s00706-013-1052-1 .

Banjac, Nebojša R., Trišović, Nemanja, Vitnik, Željko, Vitnik, Vesna, Valentić, Nataša V., Ušćumlić, Gordana, Juranić, Ivan, "Solvatochromic and quantum chemical investigations of newly synthesized succinimides: substituent effect on intramolecular charge transfer" in Monatshefte Fur Chemie, 144, no. 10 (2013):1525-1535,
https://doi.org/10.1007/s00706-013-1052-1 . .

TY  - JOUR
AU  - Simić, Aleksandra Z.
AU  - Verbić, Tatjana
AU  - Sentić, Milica
AU  - Vojic, Mirjana P.
AU  - Juranić, Ivan
AU  - Manojlović, Dragan
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1319
AB  - Ellagic acid is a biologically active polyphenol found in numerous fruits and vegetables. However, not many papers dealing with the electrochemical properties and protolytic equilibria of ellagic acid have been published so far. The electro-oxidation mechanism of ellagic acid was studied in methanol aqueous media (1:1, v/v) within the pH range of 1.5-9.0, t = 25 +/- A 1 A degrees C, using cyclic voltammetry on a glassy carbon electrode, and by semiempirical calculations. Results show that oxidation of ellagic acid is a pH-dependent, two-step quasireversible process. The slope of peak 1 indicates the exchange of the same number of electrons and protons within the whole studied pH range; the slope of peak 2 changes with the increase of pH, and three different regions are visible. As protolytic equilibria studies revealed that ellagic acid acts as a diprotic acid in the studied conditions (acidity constants were potentiometrically determined as pK (a1) = 5.42 +/- A 0.01 and pK (a2) = 6.76 +/- A 0.01), it is obvious that the electro-oxidation occurs at the hydroxyl group subjected to dissociation. The three different regions are therefore recognized as regions with different dominating species: unionized molecule (H(4)A), monoanion (H(3)A(-)), and dianion (H(2)A(2-)). UV/Vis spectral changes confirmed the proposed equilibria. Heat of formation and electron densities calculated at semiempirical level were used to propose the hydrogen and electron abstraction sites. According to the obtained results, a new mechanism of ellagic acid electro-oxidation is proposed.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - Study of ellagic acid electro-oxidation mechanism
VL  - 144
IS  - 2
SP  - 121
EP  - 128
DO  - 10.1007/s00706-012-0856-8
ER  - 

@article{
author = "Simić, Aleksandra Z. and Verbić, Tatjana and Sentić, Milica and Vojic, Mirjana P. and Juranić, Ivan and Manojlović, Dragan",
year = "2013",
abstract = "Ellagic acid is a biologically active polyphenol found in numerous fruits and vegetables. However, not many papers dealing with the electrochemical properties and protolytic equilibria of ellagic acid have been published so far. The electro-oxidation mechanism of ellagic acid was studied in methanol aqueous media (1:1, v/v) within the pH range of 1.5-9.0, t = 25 +/- A 1 A degrees C, using cyclic voltammetry on a glassy carbon electrode, and by semiempirical calculations. Results show that oxidation of ellagic acid is a pH-dependent, two-step quasireversible process. The slope of peak 1 indicates the exchange of the same number of electrons and protons within the whole studied pH range; the slope of peak 2 changes with the increase of pH, and three different regions are visible. As protolytic equilibria studies revealed that ellagic acid acts as a diprotic acid in the studied conditions (acidity constants were potentiometrically determined as pK (a1) = 5.42 +/- A 0.01 and pK (a2) = 6.76 +/- A 0.01), it is obvious that the electro-oxidation occurs at the hydroxyl group subjected to dissociation. The three different regions are therefore recognized as regions with different dominating species: unionized molecule (H(4)A), monoanion (H(3)A(-)), and dianion (H(2)A(2-)). UV/Vis spectral changes confirmed the proposed equilibria. Heat of formation and electron densities calculated at semiempirical level were used to propose the hydrogen and electron abstraction sites. According to the obtained results, a new mechanism of ellagic acid electro-oxidation is proposed.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "Study of ellagic acid electro-oxidation mechanism",
volume = "144",
number = "2",
pages = "121-128",
doi = "10.1007/s00706-012-0856-8"
}

Simić, A. Z., Verbić, T., Sentić, M., Vojic, M. P., Juranić, I.,& Manojlović, D.. (2013). Study of ellagic acid electro-oxidation mechanism. in Monatshefte Fur Chemie
Springer Wien, Wien., 144(2), 121-128.
https://doi.org/10.1007/s00706-012-0856-8

Simić AZ, Verbić T, Sentić M, Vojic MP, Juranić I, Manojlović D. Study of ellagic acid electro-oxidation mechanism. in Monatshefte Fur Chemie. 2013;144(2):121-128.
doi:10.1007/s00706-012-0856-8 .

Simić, Aleksandra Z., Verbić, Tatjana, Sentić, Milica, Vojic, Mirjana P., Juranić, Ivan, Manojlović, Dragan, "Study of ellagic acid electro-oxidation mechanism" in Monatshefte Fur Chemie, 144, no. 2 (2013):121-128,
https://doi.org/10.1007/s00706-012-0856-8 . .

TY  - JOUR
AU  - Drakulić, Branko
AU  - Marinković, Aleksandar D.
AU  - Juranić, Ivan
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3438
AB  - Rate constants for the esterification of eleven 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids
with diphenyldiazomethane in ethanol at 30  C were determined, and correlated with substituent constants
using classical Hammett and related methods. Statistically valid results for the para-substituted
compounds were obtained by the Swain–Lupton approach. The compounds studied had significant conformational
mobility due to seven rotatable bonds in their backbone. Going beyond the classical Hammett
approach, we established a relatively fast procedure to find the optimal conformations that can
be used in linear free-energy relationships, combining molecular dynamics with semiempirical calculations,
and calculations using a higher level of theory (DFT and MP2). Fair correlations were observed with
frontier orbitals, allowing inclusion of ortho-substituted derivatives and clarifying artifact-like data, as
perceived by the Hammett-type approach.
PB  - Amsterdam : Elsevier
T2  - Tetrahedron Letters
T1  - On the choice of optimal conformation in linear free-energy relationships. Reactivity of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane
VL  - 53
IS  - 5
SP  - 553
EP  - 556
DO  - 10.1016/j.tetlet.2011.11.097
ER  - 

@article{
author = "Drakulić, Branko and Marinković, Aleksandar D. and Juranić, Ivan",
year = "2012",
abstract = "Rate constants for the esterification of eleven 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids
with diphenyldiazomethane in ethanol at 30  C were determined, and correlated with substituent constants
using classical Hammett and related methods. Statistically valid results for the para-substituted
compounds were obtained by the Swain–Lupton approach. The compounds studied had significant conformational
mobility due to seven rotatable bonds in their backbone. Going beyond the classical Hammett
approach, we established a relatively fast procedure to find the optimal conformations that can
be used in linear free-energy relationships, combining molecular dynamics with semiempirical calculations,
and calculations using a higher level of theory (DFT and MP2). Fair correlations were observed with
frontier orbitals, allowing inclusion of ortho-substituted derivatives and clarifying artifact-like data, as
perceived by the Hammett-type approach.",
publisher = "Amsterdam : Elsevier",
journal = "Tetrahedron Letters",
title = "On the choice of optimal conformation in linear free-energy relationships. Reactivity of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane",
volume = "53",
number = "5",
pages = "553-556",
doi = "10.1016/j.tetlet.2011.11.097"
}

Drakulić, B., Marinković, A. D.,& Juranić, I.. (2012). On the choice of optimal conformation in linear free-energy relationships. Reactivity of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane. in Tetrahedron Letters
Amsterdam : Elsevier., 53(5), 553-556.
https://doi.org/10.1016/j.tetlet.2011.11.097

Drakulić B, Marinković AD, Juranić I. On the choice of optimal conformation in linear free-energy relationships. Reactivity of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane. in Tetrahedron Letters. 2012;53(5):553-556.
doi:10.1016/j.tetlet.2011.11.097 .

Drakulić, Branko, Marinković, Aleksandar D., Juranić, Ivan, "On the choice of optimal conformation in linear free-energy relationships. Reactivity of 2-[(carboxymethyl)sulfanyl]-4-oxo-4-arylbutanoic acids with diphenyldiazomethane" in Tetrahedron Letters, 53, no. 5 (2012):553-556,
https://doi.org/10.1016/j.tetlet.2011.11.097 . .

TY  - CONF
AU  - Cvijetić, Ilija
AU  - Vitorović-Todorović, Maja D.
AU  - Juranić, Ivan O.
AU  - Drakulić, Branko
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4672
AB  - Title molecule, recently prepared in our laboratory comprises the pharmacophoric pattern of the BH3 domain inhibitors. Such compounds were extensively studied as the antiproliferative agents. In this communication we present its conformational preferences in the solvents of different polarity and HBD/HBA abilities. NOESY spectra of compound were recorded in DMSO-d6 and CDCl3. NOESY cross-peaks and coupling constants were processed by NAMFIS analysis and results compared with the conformational assembly and the free-energy surfaces of compound obtained by molecular dynamics simulations in the corresponding explicit solvents. Adaptive biasing force was used to map free-energy surfaces. Janocchio program was used for the NAMFIS analysis, molecular dynamics simulations (30 ns, each) were performed in NAMD 2.9 using CHARMm22 force field on the multi-node Linux cluster. Conformations of the compound were generated by OMEGA program.
PB  - Belgrade : Serbian Chemical Society
C3  - Програм и кратки изводи радова - Прва конференција младих хемичара Србије
T1  - Conformational preferences of 2-[(2-hydroxyethyl)sulfanyl]-4-oxo-4-(2,4-diisopropylphenyl)- butanoic acid phenylamide. The NMR/MD study
UR  - https://hdl.handle.net/21.15107/rcub_cer_4672
ER  - 

@conference{
author = "Cvijetić, Ilija and Vitorović-Todorović, Maja D. and Juranić, Ivan O. and Drakulić, Branko",
year = "2012",
abstract = "Title molecule, recently prepared in our laboratory comprises the pharmacophoric pattern of the BH3 domain inhibitors. Such compounds were extensively studied as the antiproliferative agents. In this communication we present its conformational preferences in the solvents of different polarity and HBD/HBA abilities. NOESY spectra of compound were recorded in DMSO-d6 and CDCl3. NOESY cross-peaks and coupling constants were processed by NAMFIS analysis and results compared with the conformational assembly and the free-energy surfaces of compound obtained by molecular dynamics simulations in the corresponding explicit solvents. Adaptive biasing force was used to map free-energy surfaces. Janocchio program was used for the NAMFIS analysis, molecular dynamics simulations (30 ns, each) were performed in NAMD 2.9 using CHARMm22 force field on the multi-node Linux cluster. Conformations of the compound were generated by OMEGA program.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Програм и кратки изводи радова - Прва конференција младих хемичара Србије",
title = "Conformational preferences of 2-[(2-hydroxyethyl)sulfanyl]-4-oxo-4-(2,4-diisopropylphenyl)- butanoic acid phenylamide. The NMR/MD study",
url = "https://hdl.handle.net/21.15107/rcub_cer_4672"
}

Cvijetić, I., Vitorović-Todorović, M. D., Juranić, I. O.,& Drakulić, B.. (2012). Conformational preferences of 2-[(2-hydroxyethyl)sulfanyl]-4-oxo-4-(2,4-diisopropylphenyl)- butanoic acid phenylamide. The NMR/MD study. in Програм и кратки изводи радова - Прва конференција младих хемичара Србије
Belgrade : Serbian Chemical Society..
https://hdl.handle.net/21.15107/rcub_cer_4672

Cvijetić I, Vitorović-Todorović MD, Juranić IO, Drakulić B. Conformational preferences of 2-[(2-hydroxyethyl)sulfanyl]-4-oxo-4-(2,4-diisopropylphenyl)- butanoic acid phenylamide. The NMR/MD study. in Програм и кратки изводи радова - Прва конференција младих хемичара Србије. 2012;.
https://hdl.handle.net/21.15107/rcub_cer_4672 .

Cvijetić, Ilija, Vitorović-Todorović, Maja D., Juranić, Ivan O., Drakulić, Branko, "Conformational preferences of 2-[(2-hydroxyethyl)sulfanyl]-4-oxo-4-(2,4-diisopropylphenyl)- butanoic acid phenylamide. The NMR/MD study" in Програм и кратки изводи радова - Прва конференција младих хемичара Србије (2012),
https://hdl.handle.net/21.15107/rcub_cer_4672 .

TY  - JOUR
AU  - Vitnik, Vesna
AU  - Vitnik, Željko
AU  - Juranić, Ivan
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1135
AB  - The extensive computation study was done to elucidate the mechanism of formation dibromoepoxide from cyclohexanone and bromoform. In this reaction, the formation of dihaloepoxide 2 is postulated as a key step that determines the distribution and stereochemistry of products. Two mechanistic paths of reaction were investigated: the addition of dibromocarbene to carbonyl group of ketone, and the addition of tribromomethyl carbanion to the same (C=O) group. The mechanisms for the addition reactions of dibromocarbenes and tribromomethyl carbanions with cyclohexanone have been investigated using ab initio HF/6-311++G** and MP2/6-311+G* level of theory. Solvent effects on these reactions have been explored by calculations which included a continuum polarizable conductor model (CPCM) for the solvent (H2O). The calculations showed that both mechanisms are possible and are exothermic, but have markedly different activation energies.
PB  - Springer, New York
T2  - Journal of Molecular Modeling
T1  - Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform
VL  - 18
IS  - 10
SP  - 4721
EP  - 4728
DO  - 10.1007/s00894-012-1468-2
ER  - 

@article{
author = "Vitnik, Vesna and Vitnik, Željko and Juranić, Ivan",
year = "2012",
abstract = "The extensive computation study was done to elucidate the mechanism of formation dibromoepoxide from cyclohexanone and bromoform. In this reaction, the formation of dihaloepoxide 2 is postulated as a key step that determines the distribution and stereochemistry of products. Two mechanistic paths of reaction were investigated: the addition of dibromocarbene to carbonyl group of ketone, and the addition of tribromomethyl carbanion to the same (C=O) group. The mechanisms for the addition reactions of dibromocarbenes and tribromomethyl carbanions with cyclohexanone have been investigated using ab initio HF/6-311++G** and MP2/6-311+G* level of theory. Solvent effects on these reactions have been explored by calculations which included a continuum polarizable conductor model (CPCM) for the solvent (H2O). The calculations showed that both mechanisms are possible and are exothermic, but have markedly different activation energies.",
publisher = "Springer, New York",
journal = "Journal of Molecular Modeling",
title = "Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform",
volume = "18",
number = "10",
pages = "4721-4728",
doi = "10.1007/s00894-012-1468-2"
}

Vitnik, V., Vitnik, Ž.,& Juranić, I.. (2012). Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform. in Journal of Molecular Modeling
Springer, New York., 18(10), 4721-4728.
https://doi.org/10.1007/s00894-012-1468-2

Vitnik V, Vitnik Ž, Juranić I. Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform. in Journal of Molecular Modeling. 2012;18(10):4721-4728.
doi:10.1007/s00894-012-1468-2 .

Vitnik, Vesna, Vitnik, Željko, Juranić, Ivan, "Carbenic vs. ionic mechanistic pathway in reaction of cyclohexanone with bromoform" in Journal of Molecular Modeling, 18, no. 10 (2012):4721-4728,
https://doi.org/10.1007/s00894-012-1468-2 . .

TY  - JOUR
AU  - Vitnik, Vesna
AU  - Milenković, Marina
AU  - Dilber, Sanda P.
AU  - Vitnik, Željko
AU  - Juranić, Ivan
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/964
AB  - A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst.
AB  - U ovom radu je prikazano in vitro ispitivanje antimikrobnog dejstva serije α,β-nezasićenih i α-bromkarboksilnih kiselina i pokazano je da su one potencijalno dobri antimikrobni agensi. Sve kiseline 1-12 pokazale su značajnu aktivnost prema devet sojeva bakterija i dva soja gljivica Candida albicans. Ispitivane kiseline sintetisane su u optimizovanoj reakciji ketona sa bromoformom i litijum-hidroksidom u smesi rastvarača (terc-butanol/voda). Kao katalizator za prenos između faza upotrebljen je trietilbenzilamonijum-hlorid (TEBA).
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids
T1  - Optimizacija sinteze i in vitro proučavanje antimikrobnog dejstva α,β-nezasićenih i α-bromkarboksilnih kiselina
VL  - 77
IS  - 6
SP  - 741
EP  - 750
DO  - 10.2298/JSC111104016V
ER  - 

@article{
author = "Vitnik, Vesna and Milenković, Marina and Dilber, Sanda P. and Vitnik, Željko and Juranić, Ivan",
year = "2012",
abstract = "A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst., U ovom radu je prikazano in vitro ispitivanje antimikrobnog dejstva serije α,β-nezasićenih i α-bromkarboksilnih kiselina i pokazano je da su one potencijalno dobri antimikrobni agensi. Sve kiseline 1-12 pokazale su značajnu aktivnost prema devet sojeva bakterija i dva soja gljivica Candida albicans. Ispitivane kiseline sintetisane su u optimizovanoj reakciji ketona sa bromoformom i litijum-hidroksidom u smesi rastvarača (terc-butanol/voda). Kao katalizator za prenos između faza upotrebljen je trietilbenzilamonijum-hlorid (TEBA).",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids, Optimizacija sinteze i in vitro proučavanje antimikrobnog dejstva α,β-nezasićenih i α-bromkarboksilnih kiselina",
volume = "77",
number = "6",
pages = "741-750",
doi = "10.2298/JSC111104016V"
}

Vitnik, V., Milenković, M., Dilber, S. P., Vitnik, Ž.,& Juranić, I.. (2012). Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 77(6), 741-750.
https://doi.org/10.2298/JSC111104016V

Vitnik V, Milenković M, Dilber SP, Vitnik Ž, Juranić I. Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids. in Journal of the Serbian Chemical Society. 2012;77(6):741-750.
doi:10.2298/JSC111104016V .

Vitnik, Vesna, Milenković, Marina, Dilber, Sanda P., Vitnik, Željko, Juranić, Ivan, "Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids" in Journal of the Serbian Chemical Society, 77, no. 6 (2012):741-750,
https://doi.org/10.2298/JSC111104016V . .