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

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

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

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

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

TY  - JOUR
AU  - Ostojić, Bojana
AU  - Stankovic, Branislav
AU  - Đorđević, Dragana
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1592
AB  - There is little information available on methyl derivatives of anthracene and their interaction with the enzymes of bacterial consortia that could be found in petroleum sludge. In this study a theoretical investigation of all dimethylanthracenes (DMA) isomers and their relation to biodegradation are presented. Equilibrium geometries, ionization potentials (IP), electronic affinities (EA), dipole moments and electronic dipole polarizabilities of DMA isomers calculated by Density Functional Theory (DFT) methods are reported. The calculated IP and EA values vary little along the series of isomers. The polarizability values ([alpha], Delta alpha, and alpha(yy)) increase on passing from meso,meso- and alpha,meso- to beta,beta-DMA isomers. The computed polarizability values of DMAs can be used as predictors in determining differences in biodegradation rates of DMAs. The summation over Raman activity Sigma A(Raman) over 3N-6 vibrational modes is sensitive to the position of the methyl substituent. The Sigma A(Raman) values of 1-methylanthracene (MA), 2-MA, 2,9-DMA and 9,10-DMA are consistent with observed mutagenic activities in Salmonella Typhimurium strains TA98 and TA100.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Chemosphere
T1  - Theoretical study of the molecular properties of dimethylanthracenes as properties for the prediction of their biodegradation and mutagenicity
VL  - 111
SP  - 144
EP  - 150
DO  - 10.1016/j.chemosphere.2014.03.067
ER  - 

@article{
author = "Ostojić, Bojana and Stankovic, Branislav and Đorđević, Dragana",
year = "2014",
abstract = "There is little information available on methyl derivatives of anthracene and their interaction with the enzymes of bacterial consortia that could be found in petroleum sludge. In this study a theoretical investigation of all dimethylanthracenes (DMA) isomers and their relation to biodegradation are presented. Equilibrium geometries, ionization potentials (IP), electronic affinities (EA), dipole moments and electronic dipole polarizabilities of DMA isomers calculated by Density Functional Theory (DFT) methods are reported. The calculated IP and EA values vary little along the series of isomers. The polarizability values ([alpha], Delta alpha, and alpha(yy)) increase on passing from meso,meso- and alpha,meso- to beta,beta-DMA isomers. The computed polarizability values of DMAs can be used as predictors in determining differences in biodegradation rates of DMAs. The summation over Raman activity Sigma A(Raman) over 3N-6 vibrational modes is sensitive to the position of the methyl substituent. The Sigma A(Raman) values of 1-methylanthracene (MA), 2-MA, 2,9-DMA and 9,10-DMA are consistent with observed mutagenic activities in Salmonella Typhimurium strains TA98 and TA100.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Chemosphere",
title = "Theoretical study of the molecular properties of dimethylanthracenes as properties for the prediction of their biodegradation and mutagenicity",
volume = "111",
pages = "144-150",
doi = "10.1016/j.chemosphere.2014.03.067"
}

Ostojić, B., Stankovic, B.,& Đorđević, D.. (2014). Theoretical study of the molecular properties of dimethylanthracenes as properties for the prediction of their biodegradation and mutagenicity. in Chemosphere
Oxford : Pergamon-Elsevier Science Ltd., 111, 144-150.
https://doi.org/10.1016/j.chemosphere.2014.03.067

Ostojić B, Stankovic B, Đorđević D. Theoretical study of the molecular properties of dimethylanthracenes as properties for the prediction of their biodegradation and mutagenicity. in Chemosphere. 2014;111:144-150.
doi:10.1016/j.chemosphere.2014.03.067 .

Ostojić, Bojana, Stankovic, Branislav, Đorđević, Dragana, "Theoretical study of the molecular properties of dimethylanthracenes as properties for the prediction of their biodegradation and mutagenicity" in Chemosphere, 111 (2014):144-150,
https://doi.org/10.1016/j.chemosphere.2014.03.067 . .

TY  - JOUR
AU  - Ostojić, Bojana
AU  - Stankovic, Branislav
AU  - Đorđević, Dragana
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1515
AB  - The mutagenic activity of five mono-substituted nitrobenzanthrones (NBA) has been determined in the Ames assay (Takamura-Enya et al., 2006). In the present study, a theoretical investigation of the electronic properties of all mono-substituted NBA isomers and their relation to mutagenic activity are presented. Equilibrium geometries, vertical ionization potentials (VIP), vertical electron affinities (VEA), relative energies, dipole moments and electronic dipole polarizabilities, and the IR and Raman spectra of NBA isomers calculated by Density Functional Theory (DFT) methods are presented. The position of the nitro group affects the spectral features of the IR and Raman spectra of the NBA isomers. The results show that a good linear relationship exists between the summation of Raman activities (Sigma A(Raman)) over all the 3N-6 vibrational modes and the mutagenic activity of the NBA isomers in Salmonella typhimurium strains. The spectroscopic results suggest that the unknown mutagenic activities of 4-NBA, 5-NBA, 6NBA, 8-NBA and 10-NBA are predicted to follow the order 4-NBA > 10-NBA > 5-NBA > 8-NBA >6-NBA.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Chemosphere
T1  - The molecular properties of nitrobenzanthrone isomers and their mutagenic activities
VL  - 104
SP  - 228
EP  - 236
DO  - 10.1016/j.chemosphere.2013.11.057
ER  - 

@article{
author = "Ostojić, Bojana and Stankovic, Branislav and Đorđević, Dragana",
year = "2014",
abstract = "The mutagenic activity of five mono-substituted nitrobenzanthrones (NBA) has been determined in the Ames assay (Takamura-Enya et al., 2006). In the present study, a theoretical investigation of the electronic properties of all mono-substituted NBA isomers and their relation to mutagenic activity are presented. Equilibrium geometries, vertical ionization potentials (VIP), vertical electron affinities (VEA), relative energies, dipole moments and electronic dipole polarizabilities, and the IR and Raman spectra of NBA isomers calculated by Density Functional Theory (DFT) methods are presented. The position of the nitro group affects the spectral features of the IR and Raman spectra of the NBA isomers. The results show that a good linear relationship exists between the summation of Raman activities (Sigma A(Raman)) over all the 3N-6 vibrational modes and the mutagenic activity of the NBA isomers in Salmonella typhimurium strains. The spectroscopic results suggest that the unknown mutagenic activities of 4-NBA, 5-NBA, 6NBA, 8-NBA and 10-NBA are predicted to follow the order 4-NBA > 10-NBA > 5-NBA > 8-NBA >6-NBA.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Chemosphere",
title = "The molecular properties of nitrobenzanthrone isomers and their mutagenic activities",
volume = "104",
pages = "228-236",
doi = "10.1016/j.chemosphere.2013.11.057"
}

Ostojić, B., Stankovic, B.,& Đorđević, D.. (2014). The molecular properties of nitrobenzanthrone isomers and their mutagenic activities. in Chemosphere
Oxford : Pergamon-Elsevier Science Ltd., 104, 228-236.
https://doi.org/10.1016/j.chemosphere.2013.11.057

Ostojić B, Stankovic B, Đorđević D. The molecular properties of nitrobenzanthrone isomers and their mutagenic activities. in Chemosphere. 2014;104:228-236.
doi:10.1016/j.chemosphere.2013.11.057 .

Ostojić, Bojana, Stankovic, Branislav, Đorđević, Dragana, "The molecular properties of nitrobenzanthrone isomers and their mutagenic activities" in Chemosphere, 104 (2014):228-236,
https://doi.org/10.1016/j.chemosphere.2013.11.057 . .

TY  - JOUR
AU  - Ostojić, Bojana
AU  - Stankovic, Branislav
AU  - Đorđević, Dragana
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1487
AB  - There is little information on methylated anthracenes which are constituents of diesel fuel. In this paper, a theoretical investigation of some molecular properties of methyl-anthracenes (MAs), 1-MA and 2-MA, and all dimethylanthracene isomers (DMAs), 1,2-DMA, 1,3-DMA, 1,4-DMA, 1,5-DMA, 1,6-DMA, 1,7-DMA, 1,8-DMA, 1,9-DMA, 1,10-DMA, 2,3-DMA, 2,6-DMA, 2,7-DMA, 2,9-DMA, 2,10-DMA, and 9,10-DMA, are presented. The aromaticity indices, based on nucleus-independent chemical shifts (NICS), indicate the aromatic character of methylated anthracenes. The lowest frequencies associated with the out-of-plane deformations of the anthracene (ANTH) aromatic system decrease in the order ANTH > MAs > DMAs. They are related to an increase in conformational non-rigidity of the aromatic system in these molecules, and indicate that they can change their conformation easily through intermolecular interactions, such as interactions with the enzymes of bacteria that catalyze the dioxygenation of these molecules.
PB  - Parlar Scientific Publications
T2  - Fresenius Environmental Bulletin
T1  - Aromaticity and conformational deformability of some environmental pollutants - methylated anthracenes
VL  - 23
IS  - 12
SP  - 3036
EP  - 3040
UR  - https://hdl.handle.net/21.15107/rcub_cer_1487
ER  - 

@article{
author = "Ostojić, Bojana and Stankovic, Branislav and Đorđević, Dragana",
year = "2014",
abstract = "There is little information on methylated anthracenes which are constituents of diesel fuel. In this paper, a theoretical investigation of some molecular properties of methyl-anthracenes (MAs), 1-MA and 2-MA, and all dimethylanthracene isomers (DMAs), 1,2-DMA, 1,3-DMA, 1,4-DMA, 1,5-DMA, 1,6-DMA, 1,7-DMA, 1,8-DMA, 1,9-DMA, 1,10-DMA, 2,3-DMA, 2,6-DMA, 2,7-DMA, 2,9-DMA, 2,10-DMA, and 9,10-DMA, are presented. The aromaticity indices, based on nucleus-independent chemical shifts (NICS), indicate the aromatic character of methylated anthracenes. The lowest frequencies associated with the out-of-plane deformations of the anthracene (ANTH) aromatic system decrease in the order ANTH > MAs > DMAs. They are related to an increase in conformational non-rigidity of the aromatic system in these molecules, and indicate that they can change their conformation easily through intermolecular interactions, such as interactions with the enzymes of bacteria that catalyze the dioxygenation of these molecules.",
publisher = "Parlar Scientific Publications",
journal = "Fresenius Environmental Bulletin",
title = "Aromaticity and conformational deformability of some environmental pollutants - methylated anthracenes",
volume = "23",
number = "12",
pages = "3036-3040",
url = "https://hdl.handle.net/21.15107/rcub_cer_1487"
}

Ostojić, B., Stankovic, B.,& Đorđević, D.. (2014). Aromaticity and conformational deformability of some environmental pollutants - methylated anthracenes. in Fresenius Environmental Bulletin
Parlar Scientific Publications., 23(12), 3036-3040.
https://hdl.handle.net/21.15107/rcub_cer_1487

Ostojić B, Stankovic B, Đorđević D. Aromaticity and conformational deformability of some environmental pollutants - methylated anthracenes. in Fresenius Environmental Bulletin. 2014;23(12):3036-3040.
https://hdl.handle.net/21.15107/rcub_cer_1487 .

Ostojić, Bojana, Stankovic, Branislav, Đorđević, Dragana, "Aromaticity and conformational deformability of some environmental pollutants - methylated anthracenes" in Fresenius Environmental Bulletin, 23, no. 12 (2014):3036-3040,
https://hdl.handle.net/21.15107/rcub_cer_1487 .

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

TY  - JOUR
AU  - Grozdanović, Milica
AU  - Drakulić, Branko
AU  - Gavrović-Jankulović, Marija
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2714
AB  - Background: Actinidin, a protease from kiwifruit, belongs to the C1 family of cysteine proteases. Cysteine proteases were found to be involved in many disease states and are valid therapeutic targets. Actinidin has a wide pH activity range and wide substrate specificity, which makes it a good model system for studying enzyme-substrate interactions. Methods: The influence of inhibitor (E-64) binding on the conformation of actinidin was examined by 2D PAGE, circular dichroism (CD) spectroscopy, hydrophobic ligand binding assay, and molecular dynamics simulations. Results: Significant differences were observed in electrophoretic mobility of proteolytically active and E-64-inhibited actinidin. CD spectrometry and hydrophobic ligand binding assay revealed a difference in conformation between active and inhibited actinidin. Molecular dynamics simulations showed that a loop defined by amino-acid residues 88-104 had greater conformational mobility in the inhibited enzyme than in the active one. During MD simulations, the covalently bound inhibitor was found to change its conformation from extended to folded, with the guanidino moiety approaching the carboxylate. Conclusions: Conformational mobility of actinidin changes upon binding of the inhibitor, leading to a sequence of events that enables water and ions to protrude into a newly formed cavity of the inhibited enzyme. Drastic conformational mobility of E-64, a common inhibitor of cysteine proteases found in many crystal structures stored in PDB, was also observed. General significance: The analysis of structural changes which occur upon binding of an inhibitor to a cysteine protease provides a valuable starting point for the future design of therapeutic agents. (c) 2013 Elsevier B.V. All rights reserved.
PB  - Elsevier
T2  - Biochimica et Biophysica Acta: General Subjects
T1  - Conformational mobility of active and E-64-inhibited actinidin
VL  - 1830
IS  - 10
SP  - 4790
EP  - 4799
DO  - 10.1016/j.bbagen.2013.06.015
ER  - 

@article{
author = "Grozdanović, Milica and Drakulić, Branko and Gavrović-Jankulović, Marija",
year = "2013",
abstract = "Background: Actinidin, a protease from kiwifruit, belongs to the C1 family of cysteine proteases. Cysteine proteases were found to be involved in many disease states and are valid therapeutic targets. Actinidin has a wide pH activity range and wide substrate specificity, which makes it a good model system for studying enzyme-substrate interactions. Methods: The influence of inhibitor (E-64) binding on the conformation of actinidin was examined by 2D PAGE, circular dichroism (CD) spectroscopy, hydrophobic ligand binding assay, and molecular dynamics simulations. Results: Significant differences were observed in electrophoretic mobility of proteolytically active and E-64-inhibited actinidin. CD spectrometry and hydrophobic ligand binding assay revealed a difference in conformation between active and inhibited actinidin. Molecular dynamics simulations showed that a loop defined by amino-acid residues 88-104 had greater conformational mobility in the inhibited enzyme than in the active one. During MD simulations, the covalently bound inhibitor was found to change its conformation from extended to folded, with the guanidino moiety approaching the carboxylate. Conclusions: Conformational mobility of actinidin changes upon binding of the inhibitor, leading to a sequence of events that enables water and ions to protrude into a newly formed cavity of the inhibited enzyme. Drastic conformational mobility of E-64, a common inhibitor of cysteine proteases found in many crystal structures stored in PDB, was also observed. General significance: The analysis of structural changes which occur upon binding of an inhibitor to a cysteine protease provides a valuable starting point for the future design of therapeutic agents. (c) 2013 Elsevier B.V. All rights reserved.",
publisher = "Elsevier",
journal = "Biochimica et Biophysica Acta: General Subjects",
title = "Conformational mobility of active and E-64-inhibited actinidin",
volume = "1830",
number = "10",
pages = "4790-4799",
doi = "10.1016/j.bbagen.2013.06.015"
}

Grozdanović, M., Drakulić, B.,& Gavrović-Jankulović, M.. (2013). Conformational mobility of active and E-64-inhibited actinidin. in Biochimica et Biophysica Acta: General Subjects
Elsevier., 1830(10), 4790-4799.
https://doi.org/10.1016/j.bbagen.2013.06.015

Grozdanović M, Drakulić B, Gavrović-Jankulović M. Conformational mobility of active and E-64-inhibited actinidin. in Biochimica et Biophysica Acta: General Subjects. 2013;1830(10):4790-4799.
doi:10.1016/j.bbagen.2013.06.015 .

Grozdanović, Milica, Drakulić, Branko, Gavrović-Jankulović, Marija, "Conformational mobility of active and E-64-inhibited actinidin" in Biochimica et Biophysica Acta: General Subjects, 1830, no. 10 (2013):4790-4799,
https://doi.org/10.1016/j.bbagen.2013.06.015 . .

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

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

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

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

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

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

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

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

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

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

TY  - JOUR
AU  - Tasić, Gordana
AU  - Ranđelović, Jelena
AU  - Vusurović, Nikola
AU  - Maslak, Veselin
AU  - Husinec, Suren
AU  - Savić, Vladimir
PY  - 2013
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1586
UR  - http://farfar.pharmacy.bg.ac.rs/handle/123456789/1924
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3504
AB  - Intramolecular Pd-catalysed cyclisation reactions for the preparation of bicyclic compounds have been studied as a model system towards the synthesis of corialstonine and corialstonidine. Significant differences in reactivity have been observed for the cyclic allyl alcohols possessing O-protected and free OH functionalities. Cyclisation via the intramolecular Heck reaction, for both derivatives, proved to be highly regioselective and while the O-protected compound favoured the exo mode of cyclisation, the unprotected alcohol preferred the endo cyclisation pathway. Brief computational studies were carried out in order to obtain further insight into these processes.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron Letters
T1  - A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations
VL  - 54
IS  - 18
SP  - 2243
EP  - 2246
DO  - 10.1016/j.tetlet.2013.02.068
ER  - 

@article{
author = "Tasić, Gordana and Ranđelović, Jelena and Vusurović, Nikola and Maslak, Veselin and Husinec, Suren and Savić, Vladimir",
year = "2013",
abstract = "Intramolecular Pd-catalysed cyclisation reactions for the preparation of bicyclic compounds have been studied as a model system towards the synthesis of corialstonine and corialstonidine. Significant differences in reactivity have been observed for the cyclic allyl alcohols possessing O-protected and free OH functionalities. Cyclisation via the intramolecular Heck reaction, for both derivatives, proved to be highly regioselective and while the O-protected compound favoured the exo mode of cyclisation, the unprotected alcohol preferred the endo cyclisation pathway. Brief computational studies were carried out in order to obtain further insight into these processes.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron Letters",
title = "A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations",
volume = "54",
number = "18",
pages = "2243-2246",
doi = "10.1016/j.tetlet.2013.02.068"
}

Tasić, G., Ranđelović, J., Vusurović, N., Maslak, V., Husinec, S.,& Savić, V.. (2013). A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations. in Tetrahedron Letters
Oxford : Pergamon-Elsevier Science Ltd., 54(18), 2243-2246.
https://doi.org/10.1016/j.tetlet.2013.02.068

Tasić G, Ranđelović J, Vusurović N, Maslak V, Husinec S, Savić V. A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations. in Tetrahedron Letters. 2013;54(18):2243-2246.
doi:10.1016/j.tetlet.2013.02.068 .

Tasić, Gordana, Ranđelović, Jelena, Vusurović, Nikola, Maslak, Veselin, Husinec, Suren, Savić, Vladimir, "A highly regioselective, protecting group controlled, synthesis of bicyclic compounds via Pd-catalysed intramolecular cyclisations" in Tetrahedron Letters, 54, no. 18 (2013):2243-2246,
https://doi.org/10.1016/j.tetlet.2013.02.068 . .

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

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

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

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

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

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

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

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

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

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