TY  - JOUR
AU  - Trifunović-Macedoljan, Jelena
AU  - Pantelić, Nebojša Đ.
AU  - Jadranin, Milka
AU  - Juranić, Ivan O.
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3724
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 O.",
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. O.. (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 IO. 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 O., "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  - DATA
AU  - Pešić, Miloš P.
AU  - Todorov, Miljana D.
AU  - Drakulić, Branko J.
AU  - Juranić, Ivan O.
AU  - Verbić, Tatjana
AU  - Zloh, Mire
AU  - Cvijetić, Ilija
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3050
PB  - Springer/Plenum Publishers, New York
T2  - Structural Chemistry
T1  - Supplementary material for the article: Cvijetić, I. N.; Pešić, M. P.; Todorov, M. D.; Drakulić, B. J.; Juranić, I. O.; Verbić, T. Ž.; Zloh, M. Tautomerism of 4-Phenyl-2,4-Dioxobutanoic Acid. Insights from PH Ramping NMR Study and Quantum Chemical Calculations. Structural Chemistry 2018, 29 (2), 423–434. https://doi.org/10.1007/s11224-017-1039-3
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3050
ER  - 

@misc{
author = "Pešić, Miloš P. and Todorov, Miljana D. and Drakulić, Branko J. and Juranić, Ivan O. and Verbić, Tatjana and Zloh, Mire and Cvijetić, Ilija",
year = "2018",
publisher = "Springer/Plenum Publishers, New York",
journal = "Structural Chemistry",
title = "Supplementary material for the article: Cvijetić, I. N.; Pešić, M. P.; Todorov, M. D.; Drakulić, B. J.; Juranić, I. O.; Verbić, T. Ž.; Zloh, M. Tautomerism of 4-Phenyl-2,4-Dioxobutanoic Acid. Insights from PH Ramping NMR Study and Quantum Chemical Calculations. Structural Chemistry 2018, 29 (2), 423–434. https://doi.org/10.1007/s11224-017-1039-3",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3050"
}

Pešić, M. P., Todorov, M. D., Drakulić, B. J., Juranić, I. O., Verbić, T., Zloh, M.,& Cvijetić, I.. (2018). Supplementary material for the article: Cvijetić, I. N.; Pešić, M. P.; Todorov, M. D.; Drakulić, B. J.; Juranić, I. O.; Verbić, T. Ž.; Zloh, M. Tautomerism of 4-Phenyl-2,4-Dioxobutanoic Acid. Insights from PH Ramping NMR Study and Quantum Chemical Calculations. Structural Chemistry 2018, 29 (2), 423–434. https://doi.org/10.1007/s11224-017-1039-3. in Structural Chemistry
Springer/Plenum Publishers, New York..
https://hdl.handle.net/21.15107/rcub_cherry_3050

Pešić MP, Todorov MD, Drakulić BJ, Juranić IO, Verbić T, Zloh M, Cvijetić I. Supplementary material for the article: Cvijetić, I. N.; Pešić, M. P.; Todorov, M. D.; Drakulić, B. J.; Juranić, I. O.; Verbić, T. Ž.; Zloh, M. Tautomerism of 4-Phenyl-2,4-Dioxobutanoic Acid. Insights from PH Ramping NMR Study and Quantum Chemical Calculations. Structural Chemistry 2018, 29 (2), 423–434. https://doi.org/10.1007/s11224-017-1039-3. in Structural Chemistry. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3050 .

Pešić, Miloš P., Todorov, Miljana D., Drakulić, Branko J., Juranić, Ivan O., Verbić, Tatjana, Zloh, Mire, Cvijetić, Ilija, "Supplementary material for the article: Cvijetić, I. N.; Pešić, M. P.; Todorov, M. D.; Drakulić, B. J.; Juranić, I. O.; Verbić, T. Ž.; Zloh, M. Tautomerism of 4-Phenyl-2,4-Dioxobutanoic Acid. Insights from PH Ramping NMR Study and Quantum Chemical Calculations. Structural Chemistry 2018, 29 (2), 423–434. https://doi.org/10.1007/s11224-017-1039-3" in Structural Chemistry (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3050 .

TY  - DATA
AU  - Cvijetić, Ilija
AU  - Verbić, Tatjana
AU  - de Resende, Pedro Ernesto
AU  - Stapleton, Paul
AU  - Gibbons, Simon
AU  - Juranić, Ivan O.
AU  - Drakulić, Branko J.
AU  - Zloh, Mire
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3195
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2  - European Journal of Medicinal Chemistry
T1  - Supplementary material for the article: Cvijetić, I. N.; Verbić, T. Ž.; Ernesto de Resende, P.; Stapleton, P.; Gibbons, S.; Juranić, I.  O.; Drakulić, B. J.; Zloh, M. Design, Synthesis and Biological Evaluation of Novel  Aryldiketo Acids with Enhanced Antibacterial Activity against Multidrug Resistant Bacterial  Strains. European Journal of Medicinal Chemistry 2018, 143, 1474–1488.  https://doi.org/10.1016/j.ejmech.2017.10.045
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3195
ER  - 

@misc{
author = "Cvijetić, Ilija and Verbić, Tatjana and de Resende, Pedro Ernesto and Stapleton, Paul and Gibbons, Simon and Juranić, Ivan O. and Drakulić, Branko J. and Zloh, Mire",
year = "2018",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "Supplementary material for the article: Cvijetić, I. N.; Verbić, T. Ž.; Ernesto de Resende, P.; Stapleton, P.; Gibbons, S.; Juranić, I.  O.; Drakulić, B. J.; Zloh, M. Design, Synthesis and Biological Evaluation of Novel  Aryldiketo Acids with Enhanced Antibacterial Activity against Multidrug Resistant Bacterial  Strains. European Journal of Medicinal Chemistry 2018, 143, 1474–1488.  https://doi.org/10.1016/j.ejmech.2017.10.045",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3195"
}

Cvijetić, I., Verbić, T., de Resende, P. E., Stapleton, P., Gibbons, S., Juranić, I. O., Drakulić, B. J.,& Zloh, M.. (2018). Supplementary material for the article: Cvijetić, I. N.; Verbić, T. Ž.; Ernesto de Resende, P.; Stapleton, P.; Gibbons, S.; Juranić, I.  O.; Drakulić, B. J.; Zloh, M. Design, Synthesis and Biological Evaluation of Novel  Aryldiketo Acids with Enhanced Antibacterial Activity against Multidrug Resistant Bacterial  Strains. European Journal of Medicinal Chemistry 2018, 143, 1474–1488.  https://doi.org/10.1016/j.ejmech.2017.10.045. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux..
https://hdl.handle.net/21.15107/rcub_cherry_3195

Cvijetić I, Verbić T, de Resende PE, Stapleton P, Gibbons S, Juranić IO, Drakulić BJ, Zloh M. Supplementary material for the article: Cvijetić, I. N.; Verbić, T. Ž.; Ernesto de Resende, P.; Stapleton, P.; Gibbons, S.; Juranić, I.  O.; Drakulić, B. J.; Zloh, M. Design, Synthesis and Biological Evaluation of Novel  Aryldiketo Acids with Enhanced Antibacterial Activity against Multidrug Resistant Bacterial  Strains. European Journal of Medicinal Chemistry 2018, 143, 1474–1488.  https://doi.org/10.1016/j.ejmech.2017.10.045. in European Journal of Medicinal Chemistry. 2018;.
https://hdl.handle.net/21.15107/rcub_cherry_3195 .

Cvijetić, Ilija, Verbić, Tatjana, de Resende, Pedro Ernesto, Stapleton, Paul, Gibbons, Simon, Juranić, Ivan O., Drakulić, Branko J., Zloh, Mire, "Supplementary material for the article: Cvijetić, I. N.; Verbić, T. Ž.; Ernesto de Resende, P.; Stapleton, P.; Gibbons, S.; Juranić, I.  O.; Drakulić, B. J.; Zloh, M. Design, Synthesis and Biological Evaluation of Novel  Aryldiketo Acids with Enhanced Antibacterial Activity against Multidrug Resistant Bacterial  Strains. European Journal of Medicinal Chemistry 2018, 143, 1474–1488.  https://doi.org/10.1016/j.ejmech.2017.10.045" in European Journal of Medicinal Chemistry (2018),
https://hdl.handle.net/21.15107/rcub_cherry_3195 .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Pešić, Miloš P.
AU  - Todorov, Miljana D.
AU  - Drakulić, Branko J.
AU  - Juranić, Ivan O.
AU  - Verbić, Tatjana
AU  - Zloh, Mire
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2111
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 J. and Juranić, Ivan O. 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. J., Juranić, I. O., 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 BJ, Juranić IO, 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 J., Juranić, Ivan O., 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 O.
AU  - Drakulić, Branko J.
AU  - Zloh, Mire
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2075
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 O. and Drakulić, Branko J. 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. O., Drakulić, B. J.,& 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 IO, Drakulić BJ, 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 O., Drakulić, Branko J., 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  - Drakulić, Branko J.
AU  - Stanković, Dalibor
AU  - Juranić, Ivan O.
AU  - Manojlović, Dragan D.
AU  - Zloh, Mire
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2458
AB  - Redox properties of a set of aryldiketo acids (ADKs), small organic molecules that comprise 2,4-dioxobutanoic acid moiety, were studied. Along with well-known HIV-1 integrase (IN) inhibition, ADKs exert widespread biological activities. The aim of this work was to evaluate the effects of aryl substitutions on the properties of the dioxobutanoic moiety that is involved in key interactions with metal ions within the active sites of target enzymes. The effect of pH on the electronic properties of nine congeners was examined using cyclic voltammetry and differential pulse polarography. The compounds were chosen as a simple set of congeners bearing Me-groups on the phenyl ring, which should not be involved in electrochemical reactions, leaving the diketo moiety as the sole electrophore. The substitution pattern was systematically varied, yielding a set having different torsion between the phenyl ring and the aryl keto group (Ar-C(O)). The protonation state of the ADKs at different pH values was determined from the experimentally obtained pK(a) values. The results showed that an equal number of protons and electrons were involved in the oxidation and reduction reactions at the surface of the electrode. Quantitative linear correlations were found between the reduction potentials and the energies of the frontier orbitals, calculated for neutral, mono-anionic and the corresponding radical anionic species, and the steric parameter as two independent variables.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids
VL  - 82
IS  - 3
SP  - 303
EP  - 316
DO  - 10.2298/JSC161118021C
ER  - 

@article{
author = "Cvijetić, Ilija and Verbić, Tatjana and Drakulić, Branko J. and Stanković, Dalibor and Juranić, Ivan O. and Manojlović, Dragan D. and Zloh, Mire",
year = "2017",
abstract = "Redox properties of a set of aryldiketo acids (ADKs), small organic molecules that comprise 2,4-dioxobutanoic acid moiety, were studied. Along with well-known HIV-1 integrase (IN) inhibition, ADKs exert widespread biological activities. The aim of this work was to evaluate the effects of aryl substitutions on the properties of the dioxobutanoic moiety that is involved in key interactions with metal ions within the active sites of target enzymes. The effect of pH on the electronic properties of nine congeners was examined using cyclic voltammetry and differential pulse polarography. The compounds were chosen as a simple set of congeners bearing Me-groups on the phenyl ring, which should not be involved in electrochemical reactions, leaving the diketo moiety as the sole electrophore. The substitution pattern was systematically varied, yielding a set having different torsion between the phenyl ring and the aryl keto group (Ar-C(O)). The protonation state of the ADKs at different pH values was determined from the experimentally obtained pK(a) values. The results showed that an equal number of protons and electrons were involved in the oxidation and reduction reactions at the surface of the electrode. Quantitative linear correlations were found between the reduction potentials and the energies of the frontier orbitals, calculated for neutral, mono-anionic and the corresponding radical anionic species, and the steric parameter as two independent variables.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids",
volume = "82",
number = "3",
pages = "303-316",
doi = "10.2298/JSC161118021C"
}

Cvijetić, I., Verbić, T., Drakulić, B. J., Stanković, D., Juranić, I. O., Manojlović, D. D.,& Zloh, M.. (2017). Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 82(3), 303-316.
https://doi.org/10.2298/JSC161118021C

Cvijetić I, Verbić T, Drakulić BJ, Stanković D, Juranić IO, Manojlović DD, Zloh M. Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids. in Journal of the Serbian Chemical Society. 2017;82(3):303-316.
doi:10.2298/JSC161118021C .

Cvijetić, Ilija, Verbić, Tatjana, Drakulić, Branko J., Stanković, Dalibor, Juranić, Ivan O., Manojlović, Dragan D., Zloh, Mire, "Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids" in Journal of the Serbian Chemical Society, 82, no. 3 (2017):303-316,
https://doi.org/10.2298/JSC161118021C . .

TY  - DATA
AU  - Cvijetić, Ilija
AU  - Tanç, Muhammet
AU  - Juranić, Ivan O.
AU  - Verbić, Tatjana
AU  - Supuran, Claudiu T.
AU  - Drakulić, Branko J.
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3328
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic and Medicinal Chemistry
T1  - Supplementary data for the article: Cvijetić, I. N.; Tanç, M.; Juranić, I. O.; Verbić, T. Ž.; Supuran, C. T.; Drakulić, B. J. 5-Aryl-1H-Pyrazole-3-Carboxylic Acids as Selective Inhibitors of Human Carbonic Anhydrases IX and XII. Bioorganic and Medicinal Chemistry 2015, 23 (15), 4649–4659. https://doi.org/10.1016/j.bmc.2015.05.052
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3328
ER  - 

@misc{
author = "Cvijetić, Ilija and Tanç, Muhammet and Juranić, Ivan O. and Verbić, Tatjana and Supuran, Claudiu T. and Drakulić, Branko J.",
year = "2015",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry",
title = "Supplementary data for the article: Cvijetić, I. N.; Tanç, M.; Juranić, I. O.; Verbić, T. Ž.; Supuran, C. T.; Drakulić, B. J. 5-Aryl-1H-Pyrazole-3-Carboxylic Acids as Selective Inhibitors of Human Carbonic Anhydrases IX and XII. Bioorganic and Medicinal Chemistry 2015, 23 (15), 4649–4659. https://doi.org/10.1016/j.bmc.2015.05.052",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3328"
}

Cvijetić, I., Tanç, M., Juranić, I. O., Verbić, T., Supuran, C. T.,& Drakulić, B. J.. (2015). Supplementary data for the article: Cvijetić, I. N.; Tanç, M.; Juranić, I. O.; Verbić, T. Ž.; Supuran, C. T.; Drakulić, B. J. 5-Aryl-1H-Pyrazole-3-Carboxylic Acids as Selective Inhibitors of Human Carbonic Anhydrases IX and XII. Bioorganic and Medicinal Chemistry 2015, 23 (15), 4649–4659. https://doi.org/10.1016/j.bmc.2015.05.052. in Bioorganic and Medicinal Chemistry
Pergamon-Elsevier Science Ltd, Oxford..
https://hdl.handle.net/21.15107/rcub_cherry_3328

Cvijetić I, Tanç M, Juranić IO, Verbić T, Supuran CT, Drakulić BJ. Supplementary data for the article: Cvijetić, I. N.; Tanç, M.; Juranić, I. O.; Verbić, T. Ž.; Supuran, C. T.; Drakulić, B. J. 5-Aryl-1H-Pyrazole-3-Carboxylic Acids as Selective Inhibitors of Human Carbonic Anhydrases IX and XII. Bioorganic and Medicinal Chemistry 2015, 23 (15), 4649–4659. https://doi.org/10.1016/j.bmc.2015.05.052. in Bioorganic and Medicinal Chemistry. 2015;.
https://hdl.handle.net/21.15107/rcub_cherry_3328 .

Cvijetić, Ilija, Tanç, Muhammet, Juranić, Ivan O., Verbić, Tatjana, Supuran, Claudiu T., Drakulić, Branko J., "Supplementary data for the article: Cvijetić, I. N.; Tanç, M.; Juranić, I. O.; Verbić, T. Ž.; Supuran, C. T.; Drakulić, B. J. 5-Aryl-1H-Pyrazole-3-Carboxylic Acids as Selective Inhibitors of Human Carbonic Anhydrases IX and XII. Bioorganic and Medicinal Chemistry 2015, 23 (15), 4649–4659. https://doi.org/10.1016/j.bmc.2015.05.052" in Bioorganic and Medicinal Chemistry (2015),
https://hdl.handle.net/21.15107/rcub_cherry_3328 .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Tanç, Muhammet
AU  - Juranić, Ivan O.
AU  - Verbić, Tatjana
AU  - Supuran, Claudiu T.
AU  - Drakulić, Branko J.
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3327
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.
PB  - Pergamon-Elsevier Science Ltd, Oxford
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 Tanç, Muhammet and Juranić, Ivan O. and Verbić, Tatjana and Supuran, Claudiu T. and Drakulić, Branko J.",
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.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
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., Tanç, M., Juranić, I. O., Verbić, T., Supuran, C. T.,& Drakulić, B. J.. (2015). 5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII. in Bioorganic and Medicinal Chemistry
Pergamon-Elsevier Science Ltd, Oxford., 23(15), 4649-4659.
https://doi.org/10.1016/j.bmc.2015.05.052

Cvijetić I, Tanç M, Juranić IO, Verbić T, Supuran CT, Drakulić BJ. 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, Tanç, Muhammet, Juranić, Ivan O., Verbić, Tatjana, Supuran, Claudiu T., Drakulić, Branko J., "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  - Tanç, Muhammet
AU  - Juranić, Ivan O.
AU  - Verbić, Tatjana
AU  - Supuran, Claudiu T.
AU  - Drakulić, Branko J.
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1742
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.
PB  - Pergamon-Elsevier Science Ltd, Oxford
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 Tanç, Muhammet and Juranić, Ivan O. and Verbić, Tatjana and Supuran, Claudiu T. and Drakulić, Branko J.",
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.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
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., Tanç, M., Juranić, I. O., Verbić, T., Supuran, C. T.,& Drakulić, B. J.. (2015). 5-Aryl-1H-pyrazole-3-carboxylic acids as selective inhibitors of human carbonic anhydrases IX and XII. in Bioorganic and Medicinal Chemistry
Pergamon-Elsevier Science Ltd, Oxford., 23(15), 4649-4659.
https://doi.org/10.1016/j.bmc.2015.05.052

Cvijetić I, Tanç M, Juranić IO, Verbić T, Supuran CT, Drakulić BJ. 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, Tanç, Muhammet, Juranić, Ivan O., Verbić, Tatjana, Supuran, Claudiu T., Drakulić, Branko J., "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  - Vitorović-Todorović, Maja D.
AU  - Koukoulitsa, Catherine
AU  - Juranić, Ivan O.
AU  - Mandić, Ljuba M.
AU  - Drakulić, Branko J.
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1808
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 O. and Mandić, Ljuba M. and Drakulić, Branko J.",
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. O., Mandić, L. M.,& Drakulić, B. J.. (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 IO, Mandić LM, Drakulić BJ. 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 O., Mandić, Ljuba M., Drakulić, Branko J., "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  - Cvijetić, Ilija
AU  - Vitorović-Todorović, Maja D.
AU  - Juranić, Ivan O.
AU  - Nakarada, Dura J.
AU  - Milosavljević, Milica D.
AU  - Drakulić, Branko J.
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1816
AB  - Rates of the aza-Michael addition of piperidine and benzylamine to thirteen (E)-4-aryl-4-oxo-2-butenoic acid phenylamides (AACPs) are reported. Progress of the reaction was monitored by UV/Vis spectroscopy. The 2D NMR spectra confirmed regioselectivity of the reactions. Piperidine and benzylamine provide exclusively beta-adducts in respect to the aroyl keto group. Influence of the substituents of the aroyl phenyl ring of AACPs on the rate of the reaction was quantified by Hammett substituent constants, partial atomic charges, and the energies of frontier orbitals. Good correlations between second-order rate constants and the Hammett substituent constants were obtained (r = 0.98, piperidine; r = 0.94, benzylamine) for para-, and meta-, para-substituted derivatives. Best correlations were obtained with the energies of the lowest unoccupied molecular orbitals of compounds, derived from the MP2 level of theory. Calculated UV/Vis spectra of representative AACPs and their Michael adduct with piperidine and benzylamine are in fair agreement with experimentally obtained data.
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid phenylamides with piperidine and benzylamine: kinetic and theoretical study
VL  - 145
IS  - 8
SP  - 1297
EP  - 1306
DO  - 10.1007/s00706-014-1223-8
ER  - 

@article{
author = "Cvijetić, Ilija and Vitorović-Todorović, Maja D. and Juranić, Ivan O. and Nakarada, Dura J. and Milosavljević, Milica D. and Drakulić, Branko J.",
year = "2014",
abstract = "Rates of the aza-Michael addition of piperidine and benzylamine to thirteen (E)-4-aryl-4-oxo-2-butenoic acid phenylamides (AACPs) are reported. Progress of the reaction was monitored by UV/Vis spectroscopy. The 2D NMR spectra confirmed regioselectivity of the reactions. Piperidine and benzylamine provide exclusively beta-adducts in respect to the aroyl keto group. Influence of the substituents of the aroyl phenyl ring of AACPs on the rate of the reaction was quantified by Hammett substituent constants, partial atomic charges, and the energies of frontier orbitals. Good correlations between second-order rate constants and the Hammett substituent constants were obtained (r = 0.98, piperidine; r = 0.94, benzylamine) for para-, and meta-, para-substituted derivatives. Best correlations were obtained with the energies of the lowest unoccupied molecular orbitals of compounds, derived from the MP2 level of theory. Calculated UV/Vis spectra of representative AACPs and their Michael adduct with piperidine and benzylamine are in fair agreement with experimentally obtained data.",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid phenylamides with piperidine and benzylamine: kinetic and theoretical study",
volume = "145",
number = "8",
pages = "1297-1306",
doi = "10.1007/s00706-014-1223-8"
}

Cvijetić, I., Vitorović-Todorović, M. D., Juranić, I. O., Nakarada, D. J., Milosavljević, M. D.,& Drakulić, B. J.. (2014). Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid phenylamides with piperidine and benzylamine: kinetic and theoretical study. in Monatshefte Fur Chemie
Springer Wien, Wien., 145(8), 1297-1306.
https://doi.org/10.1007/s00706-014-1223-8

Cvijetić I, Vitorović-Todorović MD, Juranić IO, Nakarada DJ, Milosavljević MD, Drakulić BJ. Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid phenylamides with piperidine and benzylamine: kinetic and theoretical study. in Monatshefte Fur Chemie. 2014;145(8):1297-1306.
doi:10.1007/s00706-014-1223-8 .

Cvijetić, Ilija, Vitorović-Todorović, Maja D., Juranić, Ivan O., Nakarada, Dura J., Milosavljević, Milica D., Drakulić, Branko J., "Reactivity of (E)-4-aryl-4-oxo-2-butenoic acid phenylamides with piperidine and benzylamine: kinetic and theoretical study" in Monatshefte Fur Chemie, 145, no. 8 (2014):1297-1306,
https://doi.org/10.1007/s00706-014-1223-8 . .

TY  - DATA
AU  - Vitorović-Todorović, Maja D.
AU  - Koukoulitsa, Catherine
AU  - Juranić, Ivan O.
AU  - Mandić, Ljuba M.
AU  - Drakulić, Branko J.
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2906
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Supplementary data for the article: Vitorović-Todorović, M. D.; Koukoulitsa, C.; Juranić, I. O.; Mandić, L. M.; Drakulić, B. J. 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. European Journal of Medicinal Chemistry 2014, 81, 158–175. https://doi.org/10.1016/j.ejmech.2014.05.008
UR  - https://hdl.handle.net/21.15107/rcub_cherry_2906
ER  - 

@misc{
author = "Vitorović-Todorović, Maja D. and Koukoulitsa, Catherine and Juranić, Ivan O. and Mandić, Ljuba M. and Drakulić, Branko J.",
year = "2014",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Supplementary data for the article: Vitorović-Todorović, M. D.; Koukoulitsa, C.; Juranić, I. O.; Mandić, L. M.; Drakulić, B. J. 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. European Journal of Medicinal Chemistry 2014, 81, 158–175. https://doi.org/10.1016/j.ejmech.2014.05.008",
url = "https://hdl.handle.net/21.15107/rcub_cherry_2906"
}

Vitorović-Todorović, M. D., Koukoulitsa, C., Juranić, I. O., Mandić, L. M.,& Drakulić, B. J.. (2014). Supplementary data for the article: Vitorović-Todorović, M. D.; Koukoulitsa, C.; Juranić, I. O.; Mandić, L. M.; Drakulić, B. J. 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. European Journal of Medicinal Chemistry 2014, 81, 158–175. https://doi.org/10.1016/j.ejmech.2014.05.008. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris..
https://hdl.handle.net/21.15107/rcub_cherry_2906

Vitorović-Todorović MD, Koukoulitsa C, Juranić IO, Mandić LM, Drakulić BJ. Supplementary data for the article: Vitorović-Todorović, M. D.; Koukoulitsa, C.; Juranić, I. O.; Mandić, L. M.; Drakulić, B. J. 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. European Journal of Medicinal Chemistry 2014, 81, 158–175. https://doi.org/10.1016/j.ejmech.2014.05.008. in European Journal of Medicinal Chemistry. 2014;.
https://hdl.handle.net/21.15107/rcub_cherry_2906 .

Vitorović-Todorović, Maja D., Koukoulitsa, Catherine, Juranić, Ivan O., Mandić, Ljuba M., Drakulić, Branko J., "Supplementary data for the article: Vitorović-Todorović, M. D.; Koukoulitsa, C.; Juranić, I. O.; Mandić, L. M.; Drakulić, B. J. 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. European Journal of Medicinal Chemistry 2014, 81, 158–175. https://doi.org/10.1016/j.ejmech.2014.05.008" in European Journal of Medicinal Chemistry (2014),
https://hdl.handle.net/21.15107/rcub_cherry_2906 .

TY  - JOUR
AU  - Vitorović-Todorović, Maja D.
AU  - Koukoulitsa, Catherine
AU  - Juranić, Ivan O.
AU  - Mandić, Ljuba M.
AU  - Drakulić, Branko J.
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2907
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 O. and Mandić, Ljuba M. and Drakulić, Branko J.",
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. O., Mandić, L. M.,& Drakulić, B. J.. (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 IO, Mandić LM, Drakulić BJ. 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 O., Mandić, Ljuba M., Drakulić, Branko J., "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  - Cvijetić, Ilija
AU  - Petrović, D.D.
AU  - Verbić, Tatjana
AU  - Juranić, Ivan O.
AU  - Drakulić, B.J.
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/333
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 O. and Drakulić, B.J.",
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. O.,& Drakulić, B.J.. (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 IO, 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 O., Drakulić, B.J., "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  - DATA
AU  - Cvijetić, Ilija
AU  - Vitorović-Todorović, Maja D.
AU  - Juranić, Ivan O.
AU  - Drakulić, Branko J.
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3515
PB  - Springer Wien, Wien
T2  - Monatshefte Fur Chemie
T1  - Supplementary data for article: Cvijetić, I.; Vitorović-Todorović, M. D.; Juranić, I. O.; Drakulić, B. J. Reactivity of (E)-4-Aryl-4-Oxo-2-Butenoic Acid Arylamides toward 2-Mercaptoethanol. A LFER Study. Monatshefte Fur Chemie 2013, 144 (12), 1815–1824. https://doi.org/10.1007/s00706-013-1084-6
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3515
ER  - 

@misc{
author = "Cvijetić, Ilija and Vitorović-Todorović, Maja D. and Juranić, Ivan O. and Drakulić, Branko J.",
year = "2013",
publisher = "Springer Wien, Wien",
journal = "Monatshefte Fur Chemie",
title = "Supplementary data for article: Cvijetić, I.; Vitorović-Todorović, M. D.; Juranić, I. O.; Drakulić, B. J. Reactivity of (E)-4-Aryl-4-Oxo-2-Butenoic Acid Arylamides toward 2-Mercaptoethanol. A LFER Study. Monatshefte Fur Chemie 2013, 144 (12), 1815–1824. https://doi.org/10.1007/s00706-013-1084-6",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3515"
}

Cvijetić, I., Vitorović-Todorović, M. D., Juranić, I. O.,& Drakulić, B. J.. (2013). Supplementary data for article: Cvijetić, I.; Vitorović-Todorović, M. D.; Juranić, I. O.; Drakulić, B. J. Reactivity of (E)-4-Aryl-4-Oxo-2-Butenoic Acid Arylamides toward 2-Mercaptoethanol. A LFER Study. Monatshefte Fur Chemie 2013, 144 (12), 1815–1824. https://doi.org/10.1007/s00706-013-1084-6. in Monatshefte Fur Chemie
Springer Wien, Wien..
https://hdl.handle.net/21.15107/rcub_cherry_3515

Cvijetić I, Vitorović-Todorović MD, Juranić IO, Drakulić BJ. Supplementary data for article: Cvijetić, I.; Vitorović-Todorović, M. D.; Juranić, I. O.; Drakulić, B. J. Reactivity of (E)-4-Aryl-4-Oxo-2-Butenoic Acid Arylamides toward 2-Mercaptoethanol. A LFER Study. Monatshefte Fur Chemie 2013, 144 (12), 1815–1824. https://doi.org/10.1007/s00706-013-1084-6. in Monatshefte Fur Chemie. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3515 .

Cvijetić, Ilija, Vitorović-Todorović, Maja D., Juranić, Ivan O., Drakulić, Branko J., "Supplementary data for article: Cvijetić, I.; Vitorović-Todorović, M. D.; Juranić, I. O.; Drakulić, B. J. Reactivity of (E)-4-Aryl-4-Oxo-2-Butenoic Acid Arylamides toward 2-Mercaptoethanol. A LFER Study. Monatshefte Fur Chemie 2013, 144 (12), 1815–1824. https://doi.org/10.1007/s00706-013-1084-6" in Monatshefte Fur Chemie (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3515 .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Vitorović-Todorović, Maja D.
AU  - Juranić, Ivan O.
AU  - Drakulić, Branko J.
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1441
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 O. and Drakulić, Branko J.",
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. O.,& Drakulić, B. J.. (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 IO, Drakulić BJ. 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 O., Drakulić, Branko J., "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  - Simic, Aleksandra Z.
AU  - Verbić, Tatjana
AU  - Sentić, Milica N.
AU  - Vojic, Mirjana P.
AU  - Juranić, Ivan O.
AU  - Manojlović, Dragan D.
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1593
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 = "Simic, Aleksandra Z. and Verbić, Tatjana and Sentić, Milica N. and Vojic, Mirjana P. and Juranić, Ivan O. and Manojlović, Dragan D.",
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"
}

Simic, A. Z., Verbić, T., Sentić, M. N., Vojic, M. P., Juranić, I. O.,& Manojlović, D. 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

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

Simic, Aleksandra Z., Verbić, Tatjana, Sentić, Milica N., Vojic, Mirjana P., Juranić, Ivan O., Manojlović, Dragan D., "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  - CONF
AU  - Trifunović, Jelena
AU  - Jadranin, Milka
AU  - Damjanović, Ana
AU  - Rašković, Sanvila S.
AU  - Djurovic, M. N.
AU  - Draskovic, D.
AU  - Pudar, G.
AU  - Tešević, Vele
AU  - Juranić, Ivan O.
AU  - Juranić, Z.
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1535
PB  - Wiley-Blackwell, Hoboken
C3  - Immunology
T1  - LC/DAD analysis of serum biogenic amines in patients with diabetes mellitus, chronic urticaria and Hashimoto's thyroiditis
VL  - 137
SP  - 673
EP  - 673
UR  - https://hdl.handle.net/21.15107/rcub_cherry_1535
ER  - 

@conference{
author = "Trifunović, Jelena and Jadranin, Milka and Damjanović, Ana and Rašković, Sanvila S. and Djurovic, M. N. and Draskovic, D. and Pudar, G. and Tešević, Vele and Juranić, Ivan O. and Juranić, Z.",
year = "2012",
publisher = "Wiley-Blackwell, Hoboken",
journal = "Immunology",
title = "LC/DAD analysis of serum biogenic amines in patients with diabetes mellitus, chronic urticaria and Hashimoto's thyroiditis",
volume = "137",
pages = "673-673",
url = "https://hdl.handle.net/21.15107/rcub_cherry_1535"
}

Trifunović, J., Jadranin, M., Damjanović, A., Rašković, S. S., Djurovic, M. N., Draskovic, D., Pudar, G., Tešević, V., Juranić, I. O.,& Juranić, Z.. (2012). LC/DAD analysis of serum biogenic amines in patients with diabetes mellitus, chronic urticaria and Hashimoto's thyroiditis. in Immunology
Wiley-Blackwell, Hoboken., 137, 673-673.
https://hdl.handle.net/21.15107/rcub_cherry_1535

Trifunović J, Jadranin M, Damjanović A, Rašković SS, Djurovic MN, Draskovic D, Pudar G, Tešević V, Juranić IO, Juranić Z. LC/DAD analysis of serum biogenic amines in patients with diabetes mellitus, chronic urticaria and Hashimoto's thyroiditis. in Immunology. 2012;137:673-673.
https://hdl.handle.net/21.15107/rcub_cherry_1535 .

Trifunović, Jelena, Jadranin, Milka, Damjanović, Ana, Rašković, Sanvila S., Djurovic, M. N., Draskovic, D., Pudar, G., Tešević, Vele, Juranić, Ivan O., Juranić, Z., "LC/DAD analysis of serum biogenic amines in patients with diabetes mellitus, chronic urticaria and Hashimoto's thyroiditis" in Immunology, 137 (2012):673-673,
https://hdl.handle.net/21.15107/rcub_cherry_1535 .

TY  - CONF
AU  - Trifunović, Jelena
AU  - Jadranin, Milka
AU  - Damjanović, Ana
AU  - Ristic, D.
AU  - Milanovic, N.
AU  - Tešević, Vele
AU  - Juranić, Ivan O.
AU  - Ristić, S.
AU  - Juranić, Z.
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1571
PB  - Elsevier Sci Ltd, Oxford
C3  - European Journal of Cancer / EJC
T1  - Serum Polyamines in Patients With Non-Hodgkin's Lymphoma
VL  - 48
DO  - 10.1016/S0959-8049(12)71111-5
ER  - 

@conference{
author = "Trifunović, Jelena and Jadranin, Milka and Damjanović, Ana and Ristic, D. and Milanovic, N. and Tešević, Vele and Juranić, Ivan O. and Ristić, S. and Juranić, Z.",
year = "2012",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "European Journal of Cancer / EJC",
title = "Serum Polyamines in Patients With Non-Hodgkin's Lymphoma",
volume = "48",
doi = "10.1016/S0959-8049(12)71111-5"
}

Trifunović, J., Jadranin, M., Damjanović, A., Ristic, D., Milanovic, N., Tešević, V., Juranić, I. O., Ristić, S.,& Juranić, Z.. (2012). Serum Polyamines in Patients With Non-Hodgkin's Lymphoma. in European Journal of Cancer / EJC
Elsevier Sci Ltd, Oxford., 48.
https://doi.org/10.1016/S0959-8049(12)71111-5

Trifunović J, Jadranin M, Damjanović A, Ristic D, Milanovic N, Tešević V, Juranić IO, Ristić S, Juranić Z. Serum Polyamines in Patients With Non-Hodgkin's Lymphoma. in European Journal of Cancer / EJC. 2012;48.
doi:10.1016/S0959-8049(12)71111-5 .

Trifunović, Jelena, Jadranin, Milka, Damjanović, Ana, Ristic, D., Milanovic, N., Tešević, Vele, Juranić, Ivan O., Ristić, S., Juranić, Z., "Serum Polyamines in Patients With Non-Hodgkin's Lymphoma" in European Journal of Cancer / EJC, 48 (2012),
https://doi.org/10.1016/S0959-8049(12)71111-5 . .

TY  - JOUR
AU  - Vitorović-Todorović, Maja D.
AU  - Cvijetić, Ilija
AU  - Juranić, Ivan O.
AU  - Drakulić, Branko J.
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1574
AB  - The 3D-QSAR analysis based on alignment independent descriptors (GRIND-2) was performed on the set of 110 structurally diverse, dual binding AChE reversible inhibitors. Three separate models were built, based on different conformations, generated following next criteria: (i) minimum energy conformations, (ii) conformation most similar to the co-crystalized ligand conformation, and (iii) docked conformation. We found that regardless on conformation used, all the three models had good statistic and predictivity. The models revealed the importance of protonated pyridine nitrogen of tacrine moiety for anti AChE activity, and recognized HBA and HBD interactions as highly important for the potency. This was revealed by the variables associated with protonated pyridinium nitrogen, and the two amino groups of the linker. MIFs calculated with the N1= (pyridinium nitrogen) and the DRY GRID probes in the AChE active site enabled us to establish the relationship between amino acid residues within AChE active site and the variables having high impact on models. External predictive power of the models was tested on the set of 40 AChE reversible inhibitors, most of them structurally different from the training set. Some of those compounds were tested on the different enzyme source. We found that external predictivity was highly sensitive on conformations used. Model based on docked conformations had superior predictive ability, emphasizing the need for the employment of conformations built by taking into account geometrical restrictions of AChE active site gorge. (C) 2012 Elsevier Inc. All rights reserved.
PB  - Elsevier Science Inc, New York
T2  - Journal of Molecular Graphics and Modelling
T1  - The 3D-QSAR study of 110 diverse, dual binding, acetylcholinesterase inhibitors based on alignment independent descriptors (GRIND-2). The effects of conformation on predictive power and interpretability of the models
VL  - 38
SP  - 194
EP  - 210
DO  - 10.1016/j.jmgm.2012.08.001
ER  - 

@article{
author = "Vitorović-Todorović, Maja D. and Cvijetić, Ilija and Juranić, Ivan O. and Drakulić, Branko J.",
year = "2012",
abstract = "The 3D-QSAR analysis based on alignment independent descriptors (GRIND-2) was performed on the set of 110 structurally diverse, dual binding AChE reversible inhibitors. Three separate models were built, based on different conformations, generated following next criteria: (i) minimum energy conformations, (ii) conformation most similar to the co-crystalized ligand conformation, and (iii) docked conformation. We found that regardless on conformation used, all the three models had good statistic and predictivity. The models revealed the importance of protonated pyridine nitrogen of tacrine moiety for anti AChE activity, and recognized HBA and HBD interactions as highly important for the potency. This was revealed by the variables associated with protonated pyridinium nitrogen, and the two amino groups of the linker. MIFs calculated with the N1= (pyridinium nitrogen) and the DRY GRID probes in the AChE active site enabled us to establish the relationship between amino acid residues within AChE active site and the variables having high impact on models. External predictive power of the models was tested on the set of 40 AChE reversible inhibitors, most of them structurally different from the training set. Some of those compounds were tested on the different enzyme source. We found that external predictivity was highly sensitive on conformations used. Model based on docked conformations had superior predictive ability, emphasizing the need for the employment of conformations built by taking into account geometrical restrictions of AChE active site gorge. (C) 2012 Elsevier Inc. All rights reserved.",
publisher = "Elsevier Science Inc, New York",
journal = "Journal of Molecular Graphics and Modelling",
title = "The 3D-QSAR study of 110 diverse, dual binding, acetylcholinesterase inhibitors based on alignment independent descriptors (GRIND-2). The effects of conformation on predictive power and interpretability of the models",
volume = "38",
pages = "194-210",
doi = "10.1016/j.jmgm.2012.08.001"
}

Vitorović-Todorović, M. D., Cvijetić, I., Juranić, I. O.,& Drakulić, B. J.. (2012). The 3D-QSAR study of 110 diverse, dual binding, acetylcholinesterase inhibitors based on alignment independent descriptors (GRIND-2). The effects of conformation on predictive power and interpretability of the models. in Journal of Molecular Graphics and Modelling
Elsevier Science Inc, New York., 38, 194-210.
https://doi.org/10.1016/j.jmgm.2012.08.001

Vitorović-Todorović MD, Cvijetić I, Juranić IO, Drakulić BJ. The 3D-QSAR study of 110 diverse, dual binding, acetylcholinesterase inhibitors based on alignment independent descriptors (GRIND-2). The effects of conformation on predictive power and interpretability of the models. in Journal of Molecular Graphics and Modelling. 2012;38:194-210.
doi:10.1016/j.jmgm.2012.08.001 .

Vitorović-Todorović, Maja D., Cvijetić, Ilija, Juranić, Ivan O., Drakulić, Branko J., "The 3D-QSAR study of 110 diverse, dual binding, acetylcholinesterase inhibitors based on alignment independent descriptors (GRIND-2). The effects of conformation on predictive power and interpretability of the models" in Journal of Molecular Graphics and Modelling, 38 (2012):194-210,
https://doi.org/10.1016/j.jmgm.2012.08.001 . .

TY  - JOUR
AU  - Gržetić, Ivan
AU  - Juranić, Ivan O.
AU  - Damjanović, Ljiljana
AU  - Popović, Ivanka
AU  - Ivančev-Tumbas, Ivana
AU  - Matović, Zoran
AU  - Anđelković, Tatjana
AU  - Diković, Ljubica
AU  - Antonijević, Milan
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/284
AB  - One of the results of the work on the TEMPUS project 'Modernisation of Post-Graduate Studies in Chemistry and Chemistry Related Programmes - MCHEM' are benchmark standards for chemistry and chemistry related subjects. The goal of this text was to make these standards available to Serbian community. Obtained text is a result of the consensus among participants of the project coming from educational institutions that are responsible for chemistry and it is based on already existing standards in Europe created by 'The Chemistry Quality Eurolabels®' and adopted by 'European Association for Chemical and Molecular Sciences' since 2003.
T2  - Hemijski pregled
T1  - Referentni obrazovni standardi za hemiju i srodne discipline
VL  - 53
IS  - 4
SP  - 100
EP  - 105
UR  - https://hdl.handle.net/21.15107/rcub_cherry_284
ER  - 

@article{
author = "Gržetić, Ivan and Juranić, Ivan O. and Damjanović, Ljiljana and Popović, Ivanka and Ivančev-Tumbas, Ivana and Matović, Zoran and Anđelković, Tatjana and Diković, Ljubica and Antonijević, Milan",
year = "2012",
abstract = "One of the results of the work on the TEMPUS project 'Modernisation of Post-Graduate Studies in Chemistry and Chemistry Related Programmes - MCHEM' are benchmark standards for chemistry and chemistry related subjects. The goal of this text was to make these standards available to Serbian community. Obtained text is a result of the consensus among participants of the project coming from educational institutions that are responsible for chemistry and it is based on already existing standards in Europe created by 'The Chemistry Quality Eurolabels®' and adopted by 'European Association for Chemical and Molecular Sciences' since 2003.",
journal = "Hemijski pregled",
title = "Referentni obrazovni standardi za hemiju i srodne discipline",
volume = "53",
number = "4",
pages = "100-105",
url = "https://hdl.handle.net/21.15107/rcub_cherry_284"
}

Gržetić, I., Juranić, I. O., Damjanović, L., Popović, I., Ivančev-Tumbas, I., Matović, Z., Anđelković, T., Diković, L.,& Antonijević, M.. (2012). Referentni obrazovni standardi za hemiju i srodne discipline. in Hemijski pregled, 53(4), 100-105.
https://hdl.handle.net/21.15107/rcub_cherry_284

Gržetić I, Juranić IO, Damjanović L, Popović I, Ivančev-Tumbas I, Matović Z, Anđelković T, Diković L, Antonijević M. Referentni obrazovni standardi za hemiju i srodne discipline. in Hemijski pregled. 2012;53(4):100-105.
https://hdl.handle.net/21.15107/rcub_cherry_284 .

Gržetić, Ivan, Juranić, Ivan O., Damjanović, Ljiljana, Popović, Ivanka, Ivančev-Tumbas, Ivana, Matović, Zoran, Anđelković, Tatjana, Diković, Ljubica, Antonijević, Milan, "Referentni obrazovni standardi za hemiju i srodne discipline" in Hemijski pregled, 53, no. 4 (2012):100-105,
https://hdl.handle.net/21.15107/rcub_cherry_284 .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Žižak, Željko S.
AU  - Stanojković, Tatjana
AU  - Juranić, Zorica D.
AU  - Terzić-Jovanović, Nataša
AU  - Opsenica, Igor
AU  - Opsenica, Dejan M.
AU  - Juranić, Ivan O.
AU  - Drakulić, Branko J.
PY  - 2010
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1120
AB  - An alignment-free 3D QSAR study on antiproliferative activity of the thirty-three 1,2,4,5-tetraoxane derivatives toward two human dedifferentiated cell lines was reported. GRIND methodology, where descriptors are derived from GRID molecular interaction fields (MIF), were used It was found that pharmacophoric pattern attributed to the most potent derivatives Include amido NH of the primary or secondary amide, and the acetoxy fragments at positions 7 and 12 of steroid core which are, along with the tetraoxane ring, common for all studied compounds. Independently, simple multiple regression model obtained by using the whole-molecular properties, confirmed that the hydrophobicity and the H-bond donor properties are the main parameters influencing potency of compounds toward human cervix carcinoma (HeLa) and human malignant melanoma (FemX) cell lines Corollary, similar structural motifs are found to be Important for the potency toward both examined cell lines. (C) 2010 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes
VL  - 45
IS  - 10
SP  - 4570
EP  - 4577
DO  - 10.1016/j.ejmech.2010.07.019
ER  - 

@article{
author = "Cvijetić, Ilija and Žižak, Željko S. and Stanojković, Tatjana and Juranić, Zorica D. and Terzić-Jovanović, Nataša and Opsenica, Igor and Opsenica, Dejan M. and Juranić, Ivan O. and Drakulić, Branko J.",
year = "2010",
abstract = "An alignment-free 3D QSAR study on antiproliferative activity of the thirty-three 1,2,4,5-tetraoxane derivatives toward two human dedifferentiated cell lines was reported. GRIND methodology, where descriptors are derived from GRID molecular interaction fields (MIF), were used It was found that pharmacophoric pattern attributed to the most potent derivatives Include amido NH of the primary or secondary amide, and the acetoxy fragments at positions 7 and 12 of steroid core which are, along with the tetraoxane ring, common for all studied compounds. Independently, simple multiple regression model obtained by using the whole-molecular properties, confirmed that the hydrophobicity and the H-bond donor properties are the main parameters influencing potency of compounds toward human cervix carcinoma (HeLa) and human malignant melanoma (FemX) cell lines Corollary, similar structural motifs are found to be Important for the potency toward both examined cell lines. (C) 2010 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes",
volume = "45",
number = "10",
pages = "4570-4577",
doi = "10.1016/j.ejmech.2010.07.019"
}

Cvijetić, I., Žižak, Ž. S., Stanojković, T., Juranić, Z. D., Terzić-Jovanović, N., Opsenica, I., Opsenica, D. M., Juranić, I. O.,& Drakulić, B. J.. (2010). An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 45(10), 4570-4577.
https://doi.org/10.1016/j.ejmech.2010.07.019

Cvijetić I, Žižak ŽS, Stanojković T, Juranić ZD, Terzić-Jovanović N, Opsenica I, Opsenica DM, Juranić IO, Drakulić BJ. An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes. in European Journal of Medicinal Chemistry. 2010;45(10):4570-4577.
doi:10.1016/j.ejmech.2010.07.019 .

Cvijetić, Ilija, Žižak, Željko S., Stanojković, Tatjana, Juranić, Zorica D., Terzić-Jovanović, Nataša, Opsenica, Igor, Opsenica, Dejan M., Juranić, Ivan O., Drakulić, Branko J., "An alignment independent 3D QSAR study of the antiproliferative activity of 1,2,4,5-tetraoxanes" in European Journal of Medicinal Chemistry, 45, no. 10 (2010):4570-4577,
https://doi.org/10.1016/j.ejmech.2010.07.019 . .

TY  - JOUR
AU  - Vitorović-Todorović, Maja D.
AU  - Juranić, Ivan O.
AU  - Mandić, Ljuba M.
AU  - Drakulić, Branko J.
PY  - 2010
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/875
AB  - Synthesis and anticholinesterase activity of 4-aryl-4-oxo-N-phenyl-2-aminylbutyramides, novel class of reversible, moderately potent cholinesterase inhibitors, are reported. Simple substituent variation on aroyl moiety changes anti-AChE activity for two orders of magnitude; also substitution and type of hetero(ali)cycle in position 2 of butanoic moiety govern AChE/BChE selectivity. The most potent compounds showed mixed-type inhibition, indicating their binding to free enzyme and enzyme-substrate complex. Alignment-independent 3D QSAR study on reported compounds, and compounds having similar potencies obtained from the literature, confirmed that alkyl substitution on aroyl moiety of molecules is requisite for inhibition activity. The presence of hydrophobic moiety at close distance from hydrogen bond acceptor has favorable influence on inhibition potency. Docking studies show that compounds probably bind in the middle of the AChE active site gorge, but are buried deeper inside BChE active site gorge, as a consequence of larger BChE gorge void. (C) 2009 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic and Medicinal Chemistry
T1  - 4-Aryl-4-oxo-N-phenyl-2-aminylbutyramides as acetyl- and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields
VL  - 18
IS  - 3
SP  - 1181
EP  - 1193
DO  - 10.1016/j.bmc.2009.12.042
ER  - 

@article{
author = "Vitorović-Todorović, Maja D. and Juranić, Ivan O. and Mandić, Ljuba M. and Drakulić, Branko J.",
year = "2010",
abstract = "Synthesis and anticholinesterase activity of 4-aryl-4-oxo-N-phenyl-2-aminylbutyramides, novel class of reversible, moderately potent cholinesterase inhibitors, are reported. Simple substituent variation on aroyl moiety changes anti-AChE activity for two orders of magnitude; also substitution and type of hetero(ali)cycle in position 2 of butanoic moiety govern AChE/BChE selectivity. The most potent compounds showed mixed-type inhibition, indicating their binding to free enzyme and enzyme-substrate complex. Alignment-independent 3D QSAR study on reported compounds, and compounds having similar potencies obtained from the literature, confirmed that alkyl substitution on aroyl moiety of molecules is requisite for inhibition activity. The presence of hydrophobic moiety at close distance from hydrogen bond acceptor has favorable influence on inhibition potency. Docking studies show that compounds probably bind in the middle of the AChE active site gorge, but are buried deeper inside BChE active site gorge, as a consequence of larger BChE gorge void. (C) 2009 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry",
title = "4-Aryl-4-oxo-N-phenyl-2-aminylbutyramides as acetyl- and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields",
volume = "18",
number = "3",
pages = "1181-1193",
doi = "10.1016/j.bmc.2009.12.042"
}

Vitorović-Todorović, M. D., Juranić, I. O., Mandić, L. M.,& Drakulić, B. J.. (2010). 4-Aryl-4-oxo-N-phenyl-2-aminylbutyramides as acetyl- and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields. in Bioorganic and Medicinal Chemistry
Pergamon-Elsevier Science Ltd, Oxford., 18(3), 1181-1193.
https://doi.org/10.1016/j.bmc.2009.12.042

Vitorović-Todorović MD, Juranić IO, Mandić LM, Drakulić BJ. 4-Aryl-4-oxo-N-phenyl-2-aminylbutyramides as acetyl- and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields. in Bioorganic and Medicinal Chemistry. 2010;18(3):1181-1193.
doi:10.1016/j.bmc.2009.12.042 .

Vitorović-Todorović, Maja D., Juranić, Ivan O., Mandić, Ljuba M., Drakulić, Branko J., "4-Aryl-4-oxo-N-phenyl-2-aminylbutyramides as acetyl- and butyrylcholinesterase inhibitors. Preparation, anticholinesterase activity, docking study, and 3D structure-activity relationship based on molecular interaction fields" in Bioorganic and Medicinal Chemistry, 18, no. 3 (2010):1181-1193,
https://doi.org/10.1016/j.bmc.2009.12.042 . .

TY  - JOUR
AU  - Vitnik, V. D.
AU  - Ivanović, Milovan
AU  - Vitnik, Z. J.
AU  - Dordevic, J. B.
AU  - Žižak, Željko S.
AU  - Juranic, Z. D.
AU  - Juranić, Ivan O.
PY  - 2009
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/616
AB  - Phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent result in the formation of alpha,beta-unsaturated carboxylic acids. The reaction was performed at room temperature for 24h. The corresponding conjugated acids were obtained from cyclic or aromatic ketones, whereas bromo acids were obtained from 4-oxo-piperidine-1-carboxylic acid ethyl ester (13) and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (14).
PB  - Taylor & Francis Inc, Philadelphia
T2  - Synthetic Communications
T1  - One-Step Conversion of Ketones to Conjugated Acids Using Bromoform
VL  - 39
IS  - 8
SP  - 1457
EP  - 1471
DO  - 10.1080/00397910802531955
ER  - 

@article{
author = "Vitnik, V. D. and Ivanović, Milovan and Vitnik, Z. J. and Dordevic, J. B. and Žižak, Željko S. and Juranic, Z. D. and Juranić, Ivan O.",
year = "2009",
abstract = "Phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent result in the formation of alpha,beta-unsaturated carboxylic acids. The reaction was performed at room temperature for 24h. The corresponding conjugated acids were obtained from cyclic or aromatic ketones, whereas bromo acids were obtained from 4-oxo-piperidine-1-carboxylic acid ethyl ester (13) and 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (14).",
publisher = "Taylor & Francis Inc, Philadelphia",
journal = "Synthetic Communications",
title = "One-Step Conversion of Ketones to Conjugated Acids Using Bromoform",
volume = "39",
number = "8",
pages = "1457-1471",
doi = "10.1080/00397910802531955"
}

Vitnik, V. D., Ivanović, M., Vitnik, Z. J., Dordevic, J. B., Žižak, Ž. S., Juranic, Z. D.,& Juranić, I. O.. (2009). One-Step Conversion of Ketones to Conjugated Acids Using Bromoform. in Synthetic Communications
Taylor & Francis Inc, Philadelphia., 39(8), 1457-1471.
https://doi.org/10.1080/00397910802531955

Vitnik VD, Ivanović M, Vitnik ZJ, Dordevic JB, Žižak ŽS, Juranic ZD, Juranić IO. One-Step Conversion of Ketones to Conjugated Acids Using Bromoform. in Synthetic Communications. 2009;39(8):1457-1471.
doi:10.1080/00397910802531955 .

Vitnik, V. D., Ivanović, Milovan, Vitnik, Z. J., Dordevic, J. B., Žižak, Željko S., Juranic, Z. D., Juranić, Ivan O., "One-Step Conversion of Ketones to Conjugated Acids Using Bromoform" in Synthetic Communications, 39, no. 8 (2009):1457-1471,
https://doi.org/10.1080/00397910802531955 . .

TY  - JOUR
AU  - Miodragović Đenana U.
AU  - Mitić, Dragana
AU  - Miodragović, Zoran
AU  - Bogdanović, Goran A.
AU  - Vitnik, Zeljko J.
AU  - Vitorovic, Maja D.
AU  - Radulovic, Milanka D.
AU  - Nastasijevic, Branislav J.
AU  - Juranić, Ivan O.
AU  - Anđelković, Katarina K.
PY  - 2008
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/914
AB  - For the first time, complexes of Zn(II), Cd(II) and Co(II) (1-3) with N-benzyloxycarbonylglycine have been synthesized and characterized. The complexes adopt tetrahedral, pentagonal-bipyramidal and octahedral geometry, respectively. The structure of the polymeric cadmium complex was resolved by single crystal X-ray analysis. The cadmium ion has a distorted pentagonal-bipyramidal coordination formed by two water molecules and two N-benzyloxycarbonylglycinato ligands (N-Boc) coordinated in different fashions, one as bidentate and the second connecting three cadmium atoms. In a rather complicated 2D supramolecular structure, the phenyl rings interact mutually exclusively by the CH center dot center dot center dot pi interactions. Investigation of the antimicrobial activity of the obtained complexes and N-benzyloxycarbonylglycine revealed that the ligand does not inhibit the growth of Candida albicans, whereas the newly synthesized complexes suppress the growth of this human fungal pathogen. (c) 2007 Elsevier B.V. All rights reserved.
PB  - Elsevier Science Sa, Lausanne
T2  - Inorganica Chimica Acta
T1  - Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine - X-ray crystal structure of the polymeric Cd(II) complex
VL  - 361
IS  - 1
SP  - 86
EP  - 94
DO  - 10.1016/j.ica.2007.06.041
ER  - 

@article{
author = "Miodragović Đenana U. and Mitić, Dragana and Miodragović, Zoran and Bogdanović, Goran A. and Vitnik, Zeljko J. and Vitorovic, Maja D. and Radulovic, Milanka D. and Nastasijevic, Branislav J. and Juranić, Ivan O. and Anđelković, Katarina K.",
year = "2008",
abstract = "For the first time, complexes of Zn(II), Cd(II) and Co(II) (1-3) with N-benzyloxycarbonylglycine have been synthesized and characterized. The complexes adopt tetrahedral, pentagonal-bipyramidal and octahedral geometry, respectively. The structure of the polymeric cadmium complex was resolved by single crystal X-ray analysis. The cadmium ion has a distorted pentagonal-bipyramidal coordination formed by two water molecules and two N-benzyloxycarbonylglycinato ligands (N-Boc) coordinated in different fashions, one as bidentate and the second connecting three cadmium atoms. In a rather complicated 2D supramolecular structure, the phenyl rings interact mutually exclusively by the CH center dot center dot center dot pi interactions. Investigation of the antimicrobial activity of the obtained complexes and N-benzyloxycarbonylglycine revealed that the ligand does not inhibit the growth of Candida albicans, whereas the newly synthesized complexes suppress the growth of this human fungal pathogen. (c) 2007 Elsevier B.V. All rights reserved.",
publisher = "Elsevier Science Sa, Lausanne",
journal = "Inorganica Chimica Acta",
title = "Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine - X-ray crystal structure of the polymeric Cd(II) complex",
volume = "361",
number = "1",
pages = "86-94",
doi = "10.1016/j.ica.2007.06.041"
}

Miodragović Đenana U., Mitić, D., Miodragović, Z., Bogdanović, G. A., Vitnik, Z. J., Vitorovic, M. D., Radulovic, M. D., Nastasijevic, B. J., Juranić, I. O.,& Anđelković, K. K.. (2008). Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine - X-ray crystal structure of the polymeric Cd(II) complex. in Inorganica Chimica Acta
Elsevier Science Sa, Lausanne., 361(1), 86-94.
https://doi.org/10.1016/j.ica.2007.06.041

Miodragović Đenana U., Mitić D, Miodragović Z, Bogdanović GA, Vitnik ZJ, Vitorovic MD, Radulovic MD, Nastasijevic BJ, Juranić IO, Anđelković KK. Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine - X-ray crystal structure of the polymeric Cd(II) complex. in Inorganica Chimica Acta. 2008;361(1):86-94.
doi:10.1016/j.ica.2007.06.041 .

Miodragović Đenana U., Mitić, Dragana, Miodragović, Zoran, Bogdanović, Goran A., Vitnik, Zeljko J., Vitorovic, Maja D., Radulovic, Milanka D., Nastasijevic, Branislav J., Juranić, Ivan O., Anđelković, Katarina K., "Syntheses, characterization and antimicrobial activity of the first complexes of Zn(II), Cd(II) and Co(II) with N-benzyloxycarbonylglycine - X-ray crystal structure of the polymeric Cd(II) complex" in Inorganica Chimica Acta, 361, no. 1 (2008):86-94,
https://doi.org/10.1016/j.ica.2007.06.041 . .