TY  - JOUR
AU  - Vitorović-Todorović, Maja D.
AU  - Cvijetić, Ilija
AU  - Zloh, Mire
AU  - Perdih, Andrej
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4979
AB  - Recently, we designed and synthesized a subnanomolar, reversible, dual-binding site acetylcholinesterase (AChE) inhibitor which consists of the tacrine and aroylacrylic acid phenylamide moieties, mutually linked by eight methylene units. To further investigate the process of the molecular recognition between the AChE and its inhibitor, we performed six unconstrained molecular dynamics (MD) simulations, where the compound in three possible protonation states was placed inside binding sites of two available AChE crystal structures. In all six MD trajectories, the ligand generally occupied similar space inside the AChE active site, but the pattern of the interactions between the ligand functional groups and the amino acid residues was significantly different and highly dependent upon the crystal structure used to generate initial systems for simulation. The greatest differences were observed between the trajectories obtained with different AChE crystal structures used as starting target conformations. In some trajectories, several unusual positions and dynamic behavior of the tacrine moiety were observed. Therefore, this study provides important structure-based data useful in further optimization of the reversible, dual binding AChE inhibitors, and also emphasizes the importance of the starting crystal structure used for dynamics as well as the protonation state of the reversible inhibitors.Communicated by Ramaswamy H. Sarma
PB  - Taylor & Francis
T2  - Journal of Biomolecular Structure and Dynamics
T1  - Molecular recognition of acetylcholinesterase and its subnanomolar reversible inhibitor: a molecular simulations study
VL  - 40
IS  - 4
SP  - 1671
EP  - 1691
DO  - 10.1080/07391102.2020.1831960
ER  - 

@article{
author = "Vitorović-Todorović, Maja D. and Cvijetić, Ilija and Zloh, Mire and Perdih, Andrej",
year = "2022",
abstract = "Recently, we designed and synthesized a subnanomolar, reversible, dual-binding site acetylcholinesterase (AChE) inhibitor which consists of the tacrine and aroylacrylic acid phenylamide moieties, mutually linked by eight methylene units. To further investigate the process of the molecular recognition between the AChE and its inhibitor, we performed six unconstrained molecular dynamics (MD) simulations, where the compound in three possible protonation states was placed inside binding sites of two available AChE crystal structures. In all six MD trajectories, the ligand generally occupied similar space inside the AChE active site, but the pattern of the interactions between the ligand functional groups and the amino acid residues was significantly different and highly dependent upon the crystal structure used to generate initial systems for simulation. The greatest differences were observed between the trajectories obtained with different AChE crystal structures used as starting target conformations. In some trajectories, several unusual positions and dynamic behavior of the tacrine moiety were observed. Therefore, this study provides important structure-based data useful in further optimization of the reversible, dual binding AChE inhibitors, and also emphasizes the importance of the starting crystal structure used for dynamics as well as the protonation state of the reversible inhibitors.Communicated by Ramaswamy H. Sarma",
publisher = "Taylor & Francis",
journal = "Journal of Biomolecular Structure and Dynamics",
title = "Molecular recognition of acetylcholinesterase and its subnanomolar reversible inhibitor: a molecular simulations study",
volume = "40",
number = "4",
pages = "1671-1691",
doi = "10.1080/07391102.2020.1831960"
}

Vitorović-Todorović, M. D., Cvijetić, I., Zloh, M.,& Perdih, A.. (2022). Molecular recognition of acetylcholinesterase and its subnanomolar reversible inhibitor: a molecular simulations study. in Journal of Biomolecular Structure and Dynamics
Taylor & Francis., 40(4), 1671-1691.
https://doi.org/10.1080/07391102.2020.1831960

Vitorović-Todorović MD, Cvijetić I, Zloh M, Perdih A. Molecular recognition of acetylcholinesterase and its subnanomolar reversible inhibitor: a molecular simulations study. in Journal of Biomolecular Structure and Dynamics. 2022;40(4):1671-1691.
doi:10.1080/07391102.2020.1831960 .

Vitorović-Todorović, Maja D., Cvijetić, Ilija, Zloh, Mire, Perdih, Andrej, "Molecular recognition of acetylcholinesterase and its subnanomolar reversible inhibitor: a molecular simulations study" in Journal of Biomolecular Structure and Dynamics, 40, no. 4 (2022):1671-1691,
https://doi.org/10.1080/07391102.2020.1831960 . .

TY  - DATA
AU  - Vitorović-Todorović, Maja D.
AU  - Cvijetić, Ilija
AU  - Zloh, Mire
AU  - Perdih, Andrej
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/4980
AB  - Recently, we designed and synthesized a subnanomolar, reversible, dual-binding site acetylcholinesterase (AChE) inhibitor which consists of the tacrine and aroylacrylic acid phenylamide moieties, mutually linked by eight methylene units. To further investigate the process of the molecular recognition between the AChE and its inhibitor, we performed six unconstrained molecular dynamics (MD) simulations, where the compound in three possible protonation states was placed inside binding sites of two available AChE crystal structures. In all six MD trajectories, the ligand generally occupied similar space inside the AChE active site, but the pattern of the interactions between the ligand functional groups and the amino acid residues was significantly different and highly dependent upon the crystal structure used to generate initial systems for simulation. The greatest differences were observed between the trajectories obtained with different AChE crystal structures used as starting target conformations. In some trajectories, several unusual positions and dynamic behavior of the tacrine moiety were observed. Therefore, this study provides important structure-based data useful in further optimization of the reversible, dual binding AChE inhibitors, and also emphasizes the importance of the starting crystal structure used for dynamics as well as the protonation state of the reversible inhibitors.
PB  - Taylor & Francis
T2  - Journal of Biomolecular Structure and Dynamics
T1  - Supplementary data for the article: Vitorović-Todorović, M.; Cvijetić, I.; Zloh, M.; Perdih, A. Molecular Recognition of Acetylcholinesterase and Its Subnanomolar Reversible Inhibitor: A Molecular Simulations Study. Journal of Biomolecular Structure and Dynamics 2022, 40 (4), 1671–1691. https://doi.org/10.1080/07391102.2020.1831960.
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4980
ER  - 

@misc{
author = "Vitorović-Todorović, Maja D. and Cvijetić, Ilija and Zloh, Mire and Perdih, Andrej",
year = "2022",
abstract = "Recently, we designed and synthesized a subnanomolar, reversible, dual-binding site acetylcholinesterase (AChE) inhibitor which consists of the tacrine and aroylacrylic acid phenylamide moieties, mutually linked by eight methylene units. To further investigate the process of the molecular recognition between the AChE and its inhibitor, we performed six unconstrained molecular dynamics (MD) simulations, where the compound in three possible protonation states was placed inside binding sites of two available AChE crystal structures. In all six MD trajectories, the ligand generally occupied similar space inside the AChE active site, but the pattern of the interactions between the ligand functional groups and the amino acid residues was significantly different and highly dependent upon the crystal structure used to generate initial systems for simulation. The greatest differences were observed between the trajectories obtained with different AChE crystal structures used as starting target conformations. In some trajectories, several unusual positions and dynamic behavior of the tacrine moiety were observed. Therefore, this study provides important structure-based data useful in further optimization of the reversible, dual binding AChE inhibitors, and also emphasizes the importance of the starting crystal structure used for dynamics as well as the protonation state of the reversible inhibitors.",
publisher = "Taylor & Francis",
journal = "Journal of Biomolecular Structure and Dynamics",
title = "Supplementary data for the article: Vitorović-Todorović, M.; Cvijetić, I.; Zloh, M.; Perdih, A. Molecular Recognition of Acetylcholinesterase and Its Subnanomolar Reversible Inhibitor: A Molecular Simulations Study. Journal of Biomolecular Structure and Dynamics 2022, 40 (4), 1671–1691. https://doi.org/10.1080/07391102.2020.1831960.",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4980"
}

Vitorović-Todorović, M. D., Cvijetić, I., Zloh, M.,& Perdih, A.. (2022). Supplementary data for the article: Vitorović-Todorović, M.; Cvijetić, I.; Zloh, M.; Perdih, A. Molecular Recognition of Acetylcholinesterase and Its Subnanomolar Reversible Inhibitor: A Molecular Simulations Study. Journal of Biomolecular Structure and Dynamics 2022, 40 (4), 1671–1691. https://doi.org/10.1080/07391102.2020.1831960.. in Journal of Biomolecular Structure and Dynamics
Taylor & Francis..
https://hdl.handle.net/21.15107/rcub_cherry_4980

Vitorović-Todorović MD, Cvijetić I, Zloh M, Perdih A. Supplementary data for the article: Vitorović-Todorović, M.; Cvijetić, I.; Zloh, M.; Perdih, A. Molecular Recognition of Acetylcholinesterase and Its Subnanomolar Reversible Inhibitor: A Molecular Simulations Study. Journal of Biomolecular Structure and Dynamics 2022, 40 (4), 1671–1691. https://doi.org/10.1080/07391102.2020.1831960.. in Journal of Biomolecular Structure and Dynamics. 2022;.
https://hdl.handle.net/21.15107/rcub_cherry_4980 .

Vitorović-Todorović, Maja D., Cvijetić, Ilija, Zloh, Mire, Perdih, Andrej, "Supplementary data for the article: Vitorović-Todorović, M.; Cvijetić, I.; Zloh, M.; Perdih, A. Molecular Recognition of Acetylcholinesterase and Its Subnanomolar Reversible Inhibitor: A Molecular Simulations Study. Journal of Biomolecular Structure and Dynamics 2022, 40 (4), 1671–1691. https://doi.org/10.1080/07391102.2020.1831960." in Journal of Biomolecular Structure and Dynamics (2022),
https://hdl.handle.net/21.15107/rcub_cherry_4980 .

TY  - JOUR
AU  - Cvijetić, Ilija
AU  - Bigović, Miljan
AU  - Ristivojević, Petar
AU  - Vitorović-Todorović, Maja D.
AU  - Zloh, Mire
AU  - Milojković-Opsenica, Dušanka
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4534
AB  - Humulones and iso-humulones are potent natural antioxidants found in beer. In this study, density functional theory (DFT) method was applied for elucidating the structure-antioxidant activity relationship and molecular mechanism of antioxidant activity of eight bioactive humulones previously identified in different beer samples: isoxanthohumol, (R)- and (S)-adhumulone, cis- and trans-iso-adhumulone, cis- and trans-iso-n-humulone, and desdimethyl-octahydro-iso-cohumulone. The calculated bond dissociation enthalpies (BDEs) suggest that desdimethyl-octahydro-iso-cohumulone was the most potent compound with BDEs 5.1 and 23.9 kJ/mol lower compared to the values for resveratrol in gas phase and water, respectively. The enolic –OH is the most reactive site for hydrogen atom transfer (HAT). The presence of β-keto group with respect to enolic –OH diminishes the HAT potency via the formation of a strong intramolecular hydrogen bond. Another common antioxidant mechanism, single electron transfer followed by proton transfer (SET-PT), is only feasible for isoxanthohumol. The results of this study indicate a strong correlation between the increased antioxidant activity of beer products and the higher content of reduced iso-α-acids.
PB  - Springer
T2  - Structural Chemistry
T1  - DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer
VL  - 32
SP  - 2051
EP  - 2059
DO  - 10.1007/s11224-021-01780-4
ER  - 

@article{
author = "Cvijetić, Ilija and Bigović, Miljan and Ristivojević, Petar and Vitorović-Todorović, Maja D. and Zloh, Mire and Milojković-Opsenica, Dušanka",
year = "2021",
abstract = "Humulones and iso-humulones are potent natural antioxidants found in beer. In this study, density functional theory (DFT) method was applied for elucidating the structure-antioxidant activity relationship and molecular mechanism of antioxidant activity of eight bioactive humulones previously identified in different beer samples: isoxanthohumol, (R)- and (S)-adhumulone, cis- and trans-iso-adhumulone, cis- and trans-iso-n-humulone, and desdimethyl-octahydro-iso-cohumulone. The calculated bond dissociation enthalpies (BDEs) suggest that desdimethyl-octahydro-iso-cohumulone was the most potent compound with BDEs 5.1 and 23.9 kJ/mol lower compared to the values for resveratrol in gas phase and water, respectively. The enolic –OH is the most reactive site for hydrogen atom transfer (HAT). The presence of β-keto group with respect to enolic –OH diminishes the HAT potency via the formation of a strong intramolecular hydrogen bond. Another common antioxidant mechanism, single electron transfer followed by proton transfer (SET-PT), is only feasible for isoxanthohumol. The results of this study indicate a strong correlation between the increased antioxidant activity of beer products and the higher content of reduced iso-α-acids.",
publisher = "Springer",
journal = "Structural Chemistry",
title = "DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer",
volume = "32",
pages = "2051-2059",
doi = "10.1007/s11224-021-01780-4"
}

Cvijetić, I., Bigović, M., Ristivojević, P., Vitorović-Todorović, M. D., Zloh, M.,& Milojković-Opsenica, D.. (2021). DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer. in Structural Chemistry
Springer., 32, 2051-2059.
https://doi.org/10.1007/s11224-021-01780-4

Cvijetić I, Bigović M, Ristivojević P, Vitorović-Todorović MD, Zloh M, Milojković-Opsenica D. DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer. in Structural Chemistry. 2021;32:2051-2059.
doi:10.1007/s11224-021-01780-4 .

Cvijetić, Ilija, Bigović, Miljan, Ristivojević, Petar, Vitorović-Todorović, Maja D., Zloh, Mire, Milojković-Opsenica, Dušanka, "DFT study of the radical scavenging activity of isoxanthohumol, humulones (α-acids), and iso-α-acids from beer" in Structural Chemistry, 32 (2021):2051-2059,
https://doi.org/10.1007/s11224-021-01780-4 . .

TY  - JOUR
AU  - Erić, Slavica
AU  - Cvijetić, Ilija
AU  - Zloh, Mire
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4603
AB  - Metabolism of sulfur (sulfur assimilation pathway, SAP) is one of the key pathways for the pathogenesis and survival of persistant bacteria, such as Mycobacterium tuberculosis (Mtb), in the latent period. Adenosine 5'-phosphosulfate reductase (APSR) is an important enzyme involved in the SAP, absent from the human body, so it might represent a valid target for development of new antituberculosis drugs. This work aimed to develop 3D-QSAR model based on the crystal structure of APSR from Pseudomonas aeruginosa, which shows high degree of homology with APSR from Mtb, in complex with its substrate, adenosine 5'-phosphosulfate (APS). 3D-QSAR model was built from a set of 16 nucleotide analogues of APS using alignment-independent descriptors derived from molecular interaction fields (MIF). The model improves the understanding of the key characteristics of molecules necessary for the interaction with target, and enables the rational design of novel small molecule inhibitors of Mtb APSR.
AB  - Метаболизам  сумпора (пут асимилације  сумпора, SAP) један је од кључних путева  за  патогенезу  и  преживљавање  Mycobacterium  tuberculosis  (Mtb)  у  латентном  периоду.  Аденозин  5'-фосфосфат  редуктаза  (APSR)  је  значајан  ензим  који  је  укључен  у  SAP,  не  налази се у људском организму и може бити валиднo циљно место за развој нових анти- туберкулотика.  Циљ  овог  рада  је  развој  3D-QSAR  модела  који  се  заснива  на  кристалној  структури APSR из Pseudomonas aeruginosa, који има висок степен хомологије са APSR из  Mtb, у комплексу са супстратом, аденозин 5'-фосфoсулфатом (APS). 3D-QSAR модел је  постављен коришћењем сета 16 нуклеотидних аналога APS применом дескриптора неза- висних од полазних тачака, изведених из поља молекуларних интеракција (MIF). Модел  служи  за  боље  разумевање  кључних  карактеристика  молекула  неопходних  за  интерак- цију са циљним местом, у сврху рационалног дизајнирања малих молекула, инхибитора  APSR из Mtb.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - 3D-QSAR study of adenosine 5'-phosphosulfate (APS) analouges as ligands for APS reductase
VL  - 86
IS  - 6
SP  - 561
EP  - 570
DO  - 10.2298/JSC201128015E
ER  - 

@article{
author = "Erić, Slavica and Cvijetić, Ilija and Zloh, Mire",
year = "2021",
abstract = "Metabolism of sulfur (sulfur assimilation pathway, SAP) is one of the key pathways for the pathogenesis and survival of persistant bacteria, such as Mycobacterium tuberculosis (Mtb), in the latent period. Adenosine 5'-phosphosulfate reductase (APSR) is an important enzyme involved in the SAP, absent from the human body, so it might represent a valid target for development of new antituberculosis drugs. This work aimed to develop 3D-QSAR model based on the crystal structure of APSR from Pseudomonas aeruginosa, which shows high degree of homology with APSR from Mtb, in complex with its substrate, adenosine 5'-phosphosulfate (APS). 3D-QSAR model was built from a set of 16 nucleotide analogues of APS using alignment-independent descriptors derived from molecular interaction fields (MIF). The model improves the understanding of the key characteristics of molecules necessary for the interaction with target, and enables the rational design of novel small molecule inhibitors of Mtb APSR., Метаболизам  сумпора (пут асимилације  сумпора, SAP) један је од кључних путева  за  патогенезу  и  преживљавање  Mycobacterium  tuberculosis  (Mtb)  у  латентном  периоду.  Аденозин  5'-фосфосфат  редуктаза  (APSR)  је  значајан  ензим  који  је  укључен  у  SAP,  не  налази се у људском организму и може бити валиднo циљно место за развој нових анти- туберкулотика.  Циљ  овог  рада  је  развој  3D-QSAR  модела  који  се  заснива  на  кристалној  структури APSR из Pseudomonas aeruginosa, који има висок степен хомологије са APSR из  Mtb, у комплексу са супстратом, аденозин 5'-фосфoсулфатом (APS). 3D-QSAR модел је  постављен коришћењем сета 16 нуклеотидних аналога APS применом дескриптора неза- висних од полазних тачака, изведених из поља молекуларних интеракција (MIF). Модел  служи  за  боље  разумевање  кључних  карактеристика  молекула  неопходних  за  интерак- цију са циљним местом, у сврху рационалног дизајнирања малих молекула, инхибитора  APSR из Mtb.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "3D-QSAR study of adenosine 5'-phosphosulfate (APS) analouges as ligands for APS reductase",
volume = "86",
number = "6",
pages = "561-570",
doi = "10.2298/JSC201128015E"
}

Erić, S., Cvijetić, I.,& Zloh, M.. (2021). 3D-QSAR study of adenosine 5'-phosphosulfate (APS) analouges as ligands for APS reductase. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 86(6), 561-570.
https://doi.org/10.2298/JSC201128015E

Erić S, Cvijetić I, Zloh M. 3D-QSAR study of adenosine 5'-phosphosulfate (APS) analouges as ligands for APS reductase. in Journal of the Serbian Chemical Society. 2021;86(6):561-570.
doi:10.2298/JSC201128015E .

Erić, Slavica, Cvijetić, Ilija, Zloh, Mire, "3D-QSAR study of adenosine 5'-phosphosulfate (APS) analouges as ligands for APS reductase" in Journal of the Serbian Chemical Society, 86, no. 6 (2021):561-570,
https://doi.org/10.2298/JSC201128015E . .

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  - JOUR
AU  - Drakulić, Branko J.
AU  - Stavri, Michael
AU  - Gibbons, Simon
AU  - Žižak, Željko S.
AU  - Verbić, Tatjana
AU  - Jiranic, Ivan O.
AU  - Zloh, Mire
PY  - 2009
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1037
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - ChemMedChem
T1  - Aryldiketo Acids Have Antibacterial Activity Against MDR Staphylococcus aureus Strains: Structural Insights Based on Similarity and Molecular Interaction Fields
VL  - 4
IS  - 12
SP  - 1971
EP  - 1975
DO  - 10.1002/cmdc.200900273
ER  - 

@article{
author = "Drakulić, Branko J. and Stavri, Michael and Gibbons, Simon and Žižak, Željko S. and Verbić, Tatjana and Jiranic, Ivan O. and Zloh, Mire",
year = "2009",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "ChemMedChem",
title = "Aryldiketo Acids Have Antibacterial Activity Against MDR Staphylococcus aureus Strains: Structural Insights Based on Similarity and Molecular Interaction Fields",
volume = "4",
number = "12",
pages = "1971-1975",
doi = "10.1002/cmdc.200900273"
}

Drakulić, B. J., Stavri, M., Gibbons, S., Žižak, Ž. S., Verbić, T., Jiranic, I. O.,& Zloh, M.. (2009). Aryldiketo Acids Have Antibacterial Activity Against MDR Staphylococcus aureus Strains: Structural Insights Based on Similarity and Molecular Interaction Fields. in ChemMedChem
Wiley-V C H Verlag Gmbh, Weinheim., 4(12), 1971-1975.
https://doi.org/10.1002/cmdc.200900273

Drakulić BJ, Stavri M, Gibbons S, Žižak ŽS, Verbić T, Jiranic IO, Zloh M. Aryldiketo Acids Have Antibacterial Activity Against MDR Staphylococcus aureus Strains: Structural Insights Based on Similarity and Molecular Interaction Fields. in ChemMedChem. 2009;4(12):1971-1975.
doi:10.1002/cmdc.200900273 .

Drakulić, Branko J., Stavri, Michael, Gibbons, Simon, Žižak, Željko S., Verbić, Tatjana, Jiranic, Ivan O., Zloh, Mire, "Aryldiketo Acids Have Antibacterial Activity Against MDR Staphylococcus aureus Strains: Structural Insights Based on Similarity and Molecular Interaction Fields" in ChemMedChem, 4, no. 12 (2009):1971-1975,
https://doi.org/10.1002/cmdc.200900273 . .

TY  - JOUR
AU  - Verbić, Tatjana
AU  - Drakulić, Branko J.
AU  - Zloh, Mire
AU  - Juranić, Ivan O.
PY  - 2008
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/595
AB  - Butanoic moiety of 4-aryl-2,4-dioxobutanoic acids is involved in interactions with metal ions within HIV-1 integrase active site. Sixteen congeneric 4-phenyl-2,4-dioxobutanoic acid derivatives with different substitution on the phenyl ring were prepared. Effects of substitution were studied by spectrometric methods (NMR, MS, UV/VIS) and linear free energy relationships. Better metal complexation ability of meta-alkyl substituted compounds, was observed. This observation might have pharmacological implications.
PB  - Bentham Science Publ Ltd, Sharjah
T2  - Letters in Organic Chemistry
T1  - The Effect of Phenyl Substituents on C-13 NMR Shifts and Metal Ions Binding to 4-Phenyl-2,4-Dioxobutanoic Acid Derivatives
VL  - 5
IS  - 8
SP  - 692
EP  - 699
DO  - 10.2174/157017808786857589
ER  - 

@article{
author = "Verbić, Tatjana and Drakulić, Branko J. and Zloh, Mire and Juranić, Ivan O.",
year = "2008",
abstract = "Butanoic moiety of 4-aryl-2,4-dioxobutanoic acids is involved in interactions with metal ions within HIV-1 integrase active site. Sixteen congeneric 4-phenyl-2,4-dioxobutanoic acid derivatives with different substitution on the phenyl ring were prepared. Effects of substitution were studied by spectrometric methods (NMR, MS, UV/VIS) and linear free energy relationships. Better metal complexation ability of meta-alkyl substituted compounds, was observed. This observation might have pharmacological implications.",
publisher = "Bentham Science Publ Ltd, Sharjah",
journal = "Letters in Organic Chemistry",
title = "The Effect of Phenyl Substituents on C-13 NMR Shifts and Metal Ions Binding to 4-Phenyl-2,4-Dioxobutanoic Acid Derivatives",
volume = "5",
number = "8",
pages = "692-699",
doi = "10.2174/157017808786857589"
}

Verbić, T., Drakulić, B. J., Zloh, M.,& Juranić, I. O.. (2008). The Effect of Phenyl Substituents on C-13 NMR Shifts and Metal Ions Binding to 4-Phenyl-2,4-Dioxobutanoic Acid Derivatives. in Letters in Organic Chemistry
Bentham Science Publ Ltd, Sharjah., 5(8), 692-699.
https://doi.org/10.2174/157017808786857589

Verbić T, Drakulić BJ, Zloh M, Juranić IO. The Effect of Phenyl Substituents on C-13 NMR Shifts and Metal Ions Binding to 4-Phenyl-2,4-Dioxobutanoic Acid Derivatives. in Letters in Organic Chemistry. 2008;5(8):692-699.
doi:10.2174/157017808786857589 .

Verbić, Tatjana, Drakulić, Branko J., Zloh, Mire, Juranić, Ivan O., "The Effect of Phenyl Substituents on C-13 NMR Shifts and Metal Ions Binding to 4-Phenyl-2,4-Dioxobutanoic Acid Derivatives" in Letters in Organic Chemistry, 5, no. 8 (2008):692-699,
https://doi.org/10.2174/157017808786857589 . .

TY  - JOUR
AU  - Verbić, Tatjana
AU  - Drakulić, Branko J.
AU  - Zloh, Mire
AU  - Pecelj, Jovana R.
AU  - Popović, Gordana V.
AU  - Juranić, Ivan O.
PY  - 2007
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/902
AB  - The protolytic equilibria of 13 4-aryl-2,4-dioxobutanoic acids (ADKs) were spectrophotometrically studied in aqueous solutions in the pH range 1-9 at 25 +/- 1 degrees C and an ionic strength of 0.1 mol 1(-1) (NaCl), with the exception of the 4-OH-derivative which was also potentiometrically studied in the pH range 7-10 at 25 +/- 1 degrees C and an ionic strength of 0.1 mol 1(-1) (NaCl). In solution, the compounds simultaneously exist in one diketo and two enolic forms; therefore, the determined acidity constants (pK(al) 1.87-2.29. pK(a2) 6.63-8.13 and pK(a3)(4-OH-) 9.52) represent system macro constants. The H-1-NMR spectrum of the parent compound (4-phenyl-2,4-dioxobutanoic acid) (25 degrees C, pD 5.0) proved the existence of all tautomeric forms. Using the extended Hammett relation, the determined pK(a) values were correlated with literature sigma values. The predicted pK(a) values were in fair accordance with the experimentally observed ones. Molecular, monoanionic and dianionic forms of the parent compound were optimized by the semi-empirical molecular orbital PM6 method using the implicit water solvation model (COSMO). The obtained geometries were used to explain the quality of the LEER models.
AB  - Protolitičke ravnoteže 13 jedinjenja iz klase 4-aril-2,4-dioksobutanskih kiselina (ADK) spektrofotometrijski su proučavane u vodenim rastvorima u pH intervalu 1-9 pri temperaturi 25±1 °C i jonskoj jačini rastvora 0.1 mol l-1 (NaCl), sa izuzetkom 4-OH-derivata koji je proučavan i potenciometrijski u pH intervalu 7-10 pri istim uslovima. Kako ADK u vodenom rastvoru podležu keto-enolnoj tautomeriji i istovremeno postoje u diketo i dva enolna oblika, to određene kiselinske konstante (pKa1 1.87-2.29, pKa2 6.63-8.13 i pKa3(4-OH-) 9.52) predstavljaju makro konstante za dati sistem. 1H-NMR spektar osnovne supstance (4-fenil-2,4-dioksobutanska kiselina) (25 °C, pD 5.0) potvrđuje prisustvo svih tautomernih oblika. Upotrebom proširene Hametove korelacije, određene pKa vrednosti korelisane su sa literaturnim σ vrednostima. Predviđene pKa vrednosti dobro se slažu sa eksperimentalno dobijenim. Molekulski, monoanjonski i dianjonski oblici osnovne supstance su optimizovani semiempirijskom molekulsko-orbitalnom PM6 metodom sa implicitnim modelom solvatacije u vodi (COSMO). Dobijene geometrije su upotrebljene za objašnjenje kvaliteta LFER modela.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - An LFER study of the protolytic equililbria of 4-aryl-2,4-dioxolbutanoic acids in aqueous solutions
T1  - Linearne korelacije slobodne energije (LFER) protolitičkih ravnoteža 4-aril-2,4-dioksobutanskih kiselina u vodenim rastvorima
VL  - 72
IS  - 12
SP  - 1201
EP  - 1216
DO  - 10.2298/JSC0712201V
ER  - 

@article{
author = "Verbić, Tatjana and Drakulić, Branko J. and Zloh, Mire and Pecelj, Jovana R. and Popović, Gordana V. and Juranić, Ivan O.",
year = "2007",
abstract = "The protolytic equilibria of 13 4-aryl-2,4-dioxobutanoic acids (ADKs) were spectrophotometrically studied in aqueous solutions in the pH range 1-9 at 25 +/- 1 degrees C and an ionic strength of 0.1 mol 1(-1) (NaCl), with the exception of the 4-OH-derivative which was also potentiometrically studied in the pH range 7-10 at 25 +/- 1 degrees C and an ionic strength of 0.1 mol 1(-1) (NaCl). In solution, the compounds simultaneously exist in one diketo and two enolic forms; therefore, the determined acidity constants (pK(al) 1.87-2.29. pK(a2) 6.63-8.13 and pK(a3)(4-OH-) 9.52) represent system macro constants. The H-1-NMR spectrum of the parent compound (4-phenyl-2,4-dioxobutanoic acid) (25 degrees C, pD 5.0) proved the existence of all tautomeric forms. Using the extended Hammett relation, the determined pK(a) values were correlated with literature sigma values. The predicted pK(a) values were in fair accordance with the experimentally observed ones. Molecular, monoanionic and dianionic forms of the parent compound were optimized by the semi-empirical molecular orbital PM6 method using the implicit water solvation model (COSMO). The obtained geometries were used to explain the quality of the LEER models., Protolitičke ravnoteže 13 jedinjenja iz klase 4-aril-2,4-dioksobutanskih kiselina (ADK) spektrofotometrijski su proučavane u vodenim rastvorima u pH intervalu 1-9 pri temperaturi 25±1 °C i jonskoj jačini rastvora 0.1 mol l-1 (NaCl), sa izuzetkom 4-OH-derivata koji je proučavan i potenciometrijski u pH intervalu 7-10 pri istim uslovima. Kako ADK u vodenom rastvoru podležu keto-enolnoj tautomeriji i istovremeno postoje u diketo i dva enolna oblika, to određene kiselinske konstante (pKa1 1.87-2.29, pKa2 6.63-8.13 i pKa3(4-OH-) 9.52) predstavljaju makro konstante za dati sistem. 1H-NMR spektar osnovne supstance (4-fenil-2,4-dioksobutanska kiselina) (25 °C, pD 5.0) potvrđuje prisustvo svih tautomernih oblika. Upotrebom proširene Hametove korelacije, određene pKa vrednosti korelisane su sa literaturnim σ vrednostima. Predviđene pKa vrednosti dobro se slažu sa eksperimentalno dobijenim. Molekulski, monoanjonski i dianjonski oblici osnovne supstance su optimizovani semiempirijskom molekulsko-orbitalnom PM6 metodom sa implicitnim modelom solvatacije u vodi (COSMO). Dobijene geometrije su upotrebljene za objašnjenje kvaliteta LFER modela.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "An LFER study of the protolytic equililbria of 4-aryl-2,4-dioxolbutanoic acids in aqueous solutions, Linearne korelacije slobodne energije (LFER) protolitičkih ravnoteža 4-aril-2,4-dioksobutanskih kiselina u vodenim rastvorima",
volume = "72",
number = "12",
pages = "1201-1216",
doi = "10.2298/JSC0712201V"
}

Verbić, T., Drakulić, B. J., Zloh, M., Pecelj, J. R., Popović, G. V.,& Juranić, I. O.. (2007). An LFER study of the protolytic equililbria of 4-aryl-2,4-dioxolbutanoic acids in aqueous solutions. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 72(12), 1201-1216.
https://doi.org/10.2298/JSC0712201V

Verbić T, Drakulić BJ, Zloh M, Pecelj JR, Popović GV, Juranić IO. An LFER study of the protolytic equililbria of 4-aryl-2,4-dioxolbutanoic acids in aqueous solutions. in Journal of the Serbian Chemical Society. 2007;72(12):1201-1216.
doi:10.2298/JSC0712201V .

Verbić, Tatjana, Drakulić, Branko J., Zloh, Mire, Pecelj, Jovana R., Popović, Gordana V., Juranić, Ivan O., "An LFER study of the protolytic equililbria of 4-aryl-2,4-dioxolbutanoic acids in aqueous solutions" in Journal of the Serbian Chemical Society, 72, no. 12 (2007):1201-1216,
https://doi.org/10.2298/JSC0712201V . .