TY  - JOUR
AU  - Penjišević, Jelena
AU  - Andrić, Deana
AU  - Šukalović, Vladimir
AU  - Roglić, Goran
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3661
AB  - A total of 14 novel arylpiperazines were synthesized, and pharmaco-logically evaluated by measuring their affinities towards the D2 dopamine receptor (DRD2) in a [3H]spiperone competition assay. All the herein described compounds consist of a benzimidazole moiety connected to N-(2-methoxyphenyl)piperazine via linkers of various lengths. Molecular docking analysis and molecular dynamics simulations were performed on the DRD2–arylpiperazine complexes with the objective of exploring the receptor–ligand interactions and properties of the receptor binding site. The recently published crystal structure of DRD2 was used throughout this study. The major finding is that high affinity arylpiperazines must interact with both the orthosteric binding site and the extended binding pocket of DRD2 and therefore should contain a linker of 5 or 6 methylene groups long.
PB  - Beograd : Srpsko hemijsko društvo
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor
VL  - 84
IS  - 9
SP  - 925
EP  - 934
DO  - 10.2298/JSC181029104P
ER  - 

@article{
author = "Penjišević, Jelena and Andrić, Deana and Šukalović, Vladimir and Roglić, Goran and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2019",
abstract = "A total of 14 novel arylpiperazines were synthesized, and pharmaco-logically evaluated by measuring their affinities towards the D2 dopamine receptor (DRD2) in a [3H]spiperone competition assay. All the herein described compounds consist of a benzimidazole moiety connected to N-(2-methoxyphenyl)piperazine via linkers of various lengths. Molecular docking analysis and molecular dynamics simulations were performed on the DRD2–arylpiperazine complexes with the objective of exploring the receptor–ligand interactions and properties of the receptor binding site. The recently published crystal structure of DRD2 was used throughout this study. The major finding is that high affinity arylpiperazines must interact with both the orthosteric binding site and the extended binding pocket of DRD2 and therefore should contain a linker of 5 or 6 methylene groups long.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor",
volume = "84",
number = "9",
pages = "925-934",
doi = "10.2298/JSC181029104P"
}

Penjišević, J., Andrić, D., Šukalović, V., Roglić, G., Šoškić, V.,& Kostić-Rajačić, S.. (2019). Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor. in Journal of the Serbian Chemical Society
Beograd : Srpsko hemijsko društvo., 84(9), 925-934.
https://doi.org/10.2298/JSC181029104P

Penjišević J, Andrić D, Šukalović V, Roglić G, Šoškić V, Kostić-Rajačić S. Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor. in Journal of the Serbian Chemical Society. 2019;84(9):925-934.
doi:10.2298/JSC181029104P .

Penjišević, Jelena, Andrić, Deana, Šukalović, Vladimir, Roglić, Goran, Šoškić, Vukić, Kostić-Rajačić, Slađana, "Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor" in Journal of the Serbian Chemical Society, 84, no. 9 (2019):925-934,
https://doi.org/10.2298/JSC181029104P . .

TY  - JOUR
AU  - Kostić-Rajačić, Slađana
AU  - Schwall, Gerhard
AU  - Penjišević, Jelena
AU  - Andrić, Deana
AU  - Šukalović, Vladimir
AU  - Šoškić, Vukić
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2167
AB  - Affinity chromatography was used to identify potential cellular targets that are responsible for neuroprotective activity of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides. Active and inactive representatives of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides bearing an extended linker were synthesized and immobilized on an agarose-based matrix. This was followed by the identification of specifically bound proteins isolated out of the whole rat brain extract. Inducible flavoprotein NAD(P)H:quinone oxidoreductase (NQO1) was identified as candidates for cellular targets.
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Identification of NQO1 and ferrochelatase as interaction partners for neuroprotective N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides
VL  - 92
IS  - 1
SP  - 1393
EP  - 1397
DO  - 10.1111/cbdd.13193
ER  - 

@article{
author = "Kostić-Rajačić, Slađana and Schwall, Gerhard and Penjišević, Jelena and Andrić, Deana and Šukalović, Vladimir and Šoškić, Vukić",
year = "2018",
abstract = "Affinity chromatography was used to identify potential cellular targets that are responsible for neuroprotective activity of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides. Active and inactive representatives of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides bearing an extended linker were synthesized and immobilized on an agarose-based matrix. This was followed by the identification of specifically bound proteins isolated out of the whole rat brain extract. Inducible flavoprotein NAD(P)H:quinone oxidoreductase (NQO1) was identified as candidates for cellular targets.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Identification of NQO1 and ferrochelatase as interaction partners for neuroprotective N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides",
volume = "92",
number = "1",
pages = "1393-1397",
doi = "10.1111/cbdd.13193"
}

Kostić-Rajačić, S., Schwall, G., Penjišević, J., Andrić, D., Šukalović, V.,& Šoškić, V.. (2018). Identification of NQO1 and ferrochelatase as interaction partners for neuroprotective N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides. in Chemical Biology and Drug Design
Wiley, Hoboken., 92(1), 1393-1397.
https://doi.org/10.1111/cbdd.13193

Kostić-Rajačić S, Schwall G, Penjišević J, Andrić D, Šukalović V, Šoškić V. Identification of NQO1 and ferrochelatase as interaction partners for neuroprotective N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides. in Chemical Biology and Drug Design. 2018;92(1):1393-1397.
doi:10.1111/cbdd.13193 .

Kostić-Rajačić, Slađana, Schwall, Gerhard, Penjišević, Jelena, Andrić, Deana, Šukalović, Vladimir, Šoškić, Vukić, "Identification of NQO1 and ferrochelatase as interaction partners for neuroprotective N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides" in Chemical Biology and Drug Design, 92, no. 1 (2018):1393-1397,
https://doi.org/10.1111/cbdd.13193 . .

TY  - JOUR
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Novaković, Irena T.
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1937
AB  - A series of sixteen novel substituted piperidines and (2-methoxyphenyl)piperazines were synthesized, starting from the key intermediates 1-(2-methoxyphenyl)-4-(piperidin-4-yl)piperazine and 1-(2-methoxyphenyl)-4-[(piperidin-4-yl)methyl] piperazine. Biological evaluation of the synthesized compounds was illustrated by seven compounds, of which 1-(2-methoxyphenyl)-4-{[1-(2-nitrobenzyl) piperidin-4-yl] methyl} piperazine had the highest affinity for the dopamine D-2 receptor. For all seven selected compounds, docking analysis was performed in order to establish their structure-to-activity relationship.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines
VL  - 81
IS  - 4
SP  - 347
EP  - 356
DO  - 10.2298/JSC151021097P
ER  - 

@article{
author = "Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Novaković, Irena T. and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2016",
abstract = "A series of sixteen novel substituted piperidines and (2-methoxyphenyl)piperazines were synthesized, starting from the key intermediates 1-(2-methoxyphenyl)-4-(piperidin-4-yl)piperazine and 1-(2-methoxyphenyl)-4-[(piperidin-4-yl)methyl] piperazine. Biological evaluation of the synthesized compounds was illustrated by seven compounds, of which 1-(2-methoxyphenyl)-4-{[1-(2-nitrobenzyl) piperidin-4-yl] methyl} piperazine had the highest affinity for the dopamine D-2 receptor. For all seven selected compounds, docking analysis was performed in order to establish their structure-to-activity relationship.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines",
volume = "81",
number = "4",
pages = "347-356",
doi = "10.2298/JSC151021097P"
}

Penjišević, J., Šukalović, V., Andrić, D., Roglić, G., Novaković, I. T., Šoškić, V.,& Kostić-Rajačić, S.. (2016). Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 81(4), 347-356.
https://doi.org/10.2298/JSC151021097P

Penjišević J, Šukalović V, Andrić D, Roglić G, Novaković IT, Šoškić V, Kostić-Rajačić S. Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines. in Journal of the Serbian Chemical Society. 2016;81(4):347-356.
doi:10.2298/JSC151021097P .

Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Novaković, Irena T., Šoškić, Vukić, Kostić-Rajačić, Slađana, "Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines" in Journal of the Serbian Chemical Society, 81, no. 4 (2016):347-356,
https://doi.org/10.2298/JSC151021097P . .

TY  - JOUR
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2286
AB  - Sixteen new 1-(2-methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines were synthesized to be used as probes for mapping the dopamine D-2 receptor (D(2)DAR) arylpiperazine binding site. All compounds were evaluated for their affinity toward D(2)DAR in an in vitro competitive displacement assay. The most active one was 1-(2-methoxyphenyl)-4-{[1-(3-nitrophenethyl)piperidin-4-yl]methyl}piperazine (25) with an affinity of K-i = 54 nM. Docking analysis was conducted on all herein described compounds, whereas molecular dynamic simulation was performed on ligand 25 to establish its mode of interaction with D(2)DAR. Two possible docking orientations are proposed; the one with a salt bridge between the piperidine moiety and Asp114 of D(2)DAR is more stable.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands
VL  - 349
IS  - 8
SP  - 614
EP  - 626
DO  - 10.1002/ardp.201600081
ER  - 

@article{
author = "Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2016",
abstract = "Sixteen new 1-(2-methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines were synthesized to be used as probes for mapping the dopamine D-2 receptor (D(2)DAR) arylpiperazine binding site. All compounds were evaluated for their affinity toward D(2)DAR in an in vitro competitive displacement assay. The most active one was 1-(2-methoxyphenyl)-4-{[1-(3-nitrophenethyl)piperidin-4-yl]methyl}piperazine (25) with an affinity of K-i = 54 nM. Docking analysis was conducted on all herein described compounds, whereas molecular dynamic simulation was performed on ligand 25 to establish its mode of interaction with D(2)DAR. Two possible docking orientations are proposed; the one with a salt bridge between the piperidine moiety and Asp114 of D(2)DAR is more stable.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands",
volume = "349",
number = "8",
pages = "614-626",
doi = "10.1002/ardp.201600081"
}

Penjišević, J., Šukalović, V., Andrić, D., Roglić, G., Šoškić, V.,& Kostić-Rajačić, S.. (2016). Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim., 349(8), 614-626.
https://doi.org/10.1002/ardp.201600081

Penjišević J, Šukalović V, Andrić D, Roglić G, Šoškić V, Kostić-Rajačić S. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands. in Archiv der Pharmazie. 2016;349(8):614-626.
doi:10.1002/ardp.201600081 .

Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Šoškić, Vukić, Kostić-Rajačić, Slađana, "Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands" in Archiv der Pharmazie, 349, no. 8 (2016):614-626,
https://doi.org/10.1002/ardp.201600081 . .

TY  - DATA
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Novaković, Irena T.
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3630
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Novaković, I. T.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological Evaluation and Docking Analysis of Substituted Piperidines and (2-Methoxyphenyl)Piperazines. Journal of the Serbian Chemical Society 2016, 81 (4), 347–356. https://doi.org/10.2298/JSC151021097P
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3630
ER  - 

@misc{
author = "Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Novaković, Irena T. and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2016",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Novaković, I. T.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological Evaluation and Docking Analysis of Substituted Piperidines and (2-Methoxyphenyl)Piperazines. Journal of the Serbian Chemical Society 2016, 81 (4), 347–356. https://doi.org/10.2298/JSC151021097P",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3630"
}

Penjišević, J., Šukalović, V., Andrić, D., Roglić, G., Novaković, I. T., Šoškić, V.,& Kostić-Rajačić, S.. (2016). Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Novaković, I. T.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological Evaluation and Docking Analysis of Substituted Piperidines and (2-Methoxyphenyl)Piperazines. Journal of the Serbian Chemical Society 2016, 81 (4), 347–356. https://doi.org/10.2298/JSC151021097P. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade..
https://hdl.handle.net/21.15107/rcub_cherry_3630

Penjišević J, Šukalović V, Andrić D, Roglić G, Novaković IT, Šoškić V, Kostić-Rajačić S. Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Novaković, I. T.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological Evaluation and Docking Analysis of Substituted Piperidines and (2-Methoxyphenyl)Piperazines. Journal of the Serbian Chemical Society 2016, 81 (4), 347–356. https://doi.org/10.2298/JSC151021097P. in Journal of the Serbian Chemical Society. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3630 .

Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Novaković, Irena T., Šoškić, Vukić, Kostić-Rajačić, Slađana, "Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Novaković, I. T.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological Evaluation and Docking Analysis of Substituted Piperidines and (2-Methoxyphenyl)Piperazines. Journal of the Serbian Chemical Society 2016, 81 (4), 347–356. https://doi.org/10.2298/JSC151021097P" in Journal of the Serbian Chemical Society (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3630 .

TY  - DATA
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3631
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-Phenethylpiperidin-4-Yl)Piperazines and 1-(2-Methoxyphenyl)-4-[(1-Phenethylpiperidin-4-Yl)Methyl]Piperazines as Dopaminergic Ligands. Archiv der Pharmazie 2016, 614–626. https://doi.org/10.1002/ardp.201600081
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3631
ER  - 

@misc{
author = "Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2016",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-Phenethylpiperidin-4-Yl)Piperazines and 1-(2-Methoxyphenyl)-4-[(1-Phenethylpiperidin-4-Yl)Methyl]Piperazines as Dopaminergic Ligands. Archiv der Pharmazie 2016, 614–626. https://doi.org/10.1002/ardp.201600081",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3631"
}

Penjišević, J., Šukalović, V., Andrić, D., Roglić, G., Šoškić, V.,& Kostić-Rajačić, S.. (2016). Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-Phenethylpiperidin-4-Yl)Piperazines and 1-(2-Methoxyphenyl)-4-[(1-Phenethylpiperidin-4-Yl)Methyl]Piperazines as Dopaminergic Ligands. Archiv der Pharmazie 2016, 614–626. https://doi.org/10.1002/ardp.201600081. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim..
https://hdl.handle.net/21.15107/rcub_cherry_3631

Penjišević J, Šukalović V, Andrić D, Roglić G, Šoškić V, Kostić-Rajačić S. Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-Phenethylpiperidin-4-Yl)Piperazines and 1-(2-Methoxyphenyl)-4-[(1-Phenethylpiperidin-4-Yl)Methyl]Piperazines as Dopaminergic Ligands. Archiv der Pharmazie 2016, 614–626. https://doi.org/10.1002/ardp.201600081. in Archiv der Pharmazie. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3631 .

Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Šoškić, Vukić, Kostić-Rajačić, Slađana, "Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-Phenethylpiperidin-4-Yl)Piperazines and 1-(2-Methoxyphenyl)-4-[(1-Phenethylpiperidin-4-Yl)Methyl]Piperazines as Dopaminergic Ligands. Archiv der Pharmazie 2016, 614–626. https://doi.org/10.1002/ardp.201600081" in Archiv der Pharmazie (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3631 .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Šoškić, Vukić
AU  - Ignjatović, Đurđica
AU  - Andrić, Deana
AU  - Penjišević, Jelena
AU  - Kostić-Rajačić, Slađana
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1646
AB  - The dopaminergic receptor system has been the focus for the development of new pharmacotherapeutic agents targeting a number of central nervous system related disorders, such as drug addiction, schizophrenia, depression, and Parkinson's disease, to name just a few. To date, the crystal structure for the human D2 receptor is not known, despite its vital function and importance as a therapeutic target. Herein, a recent advancement in the determination of key receptor ligand interactions for the available arylpiperazine-like ligands, using a D2 receptor model based on the crystal structure of the D3 receptor is presented. To determine key interactions responsible for high dopaminergic activity, computer-docking analysis was used together with experimental data. A total of 4 dopaminergic ligands showing moderate to high affinity were tested and the obtained results rationalized using ligand structures docked into the proposed D2 receptor model.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Investigation of key interactions between the second extracellular loop of the dopamine D2 receptor and several hydroxy-N-{[2-(4-phenylpiperazin-1-yl)ethyl]phenyl}nicotinamides
VL  - 79
IS  - 12
SP  - 1461
EP  - 1467
DO  - 10.2298/JSC140423070S
ER  - 

@article{
author = "Šukalović, Vladimir and Šoškić, Vukić and Ignjatović, Đurđica and Andrić, Deana and Penjišević, Jelena and Kostić-Rajačić, Slađana",
year = "2014",
abstract = "The dopaminergic receptor system has been the focus for the development of new pharmacotherapeutic agents targeting a number of central nervous system related disorders, such as drug addiction, schizophrenia, depression, and Parkinson's disease, to name just a few. To date, the crystal structure for the human D2 receptor is not known, despite its vital function and importance as a therapeutic target. Herein, a recent advancement in the determination of key receptor ligand interactions for the available arylpiperazine-like ligands, using a D2 receptor model based on the crystal structure of the D3 receptor is presented. To determine key interactions responsible for high dopaminergic activity, computer-docking analysis was used together with experimental data. A total of 4 dopaminergic ligands showing moderate to high affinity were tested and the obtained results rationalized using ligand structures docked into the proposed D2 receptor model.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Investigation of key interactions between the second extracellular loop of the dopamine D2 receptor and several hydroxy-N-{[2-(4-phenylpiperazin-1-yl)ethyl]phenyl}nicotinamides",
volume = "79",
number = "12",
pages = "1461-1467",
doi = "10.2298/JSC140423070S"
}

Šukalović, V., Šoškić, V., Ignjatović, Đ., Andrić, D., Penjišević, J.,& Kostić-Rajačić, S.. (2014). Investigation of key interactions between the second extracellular loop of the dopamine D2 receptor and several hydroxy-N-{[2-(4-phenylpiperazin-1-yl)ethyl]phenyl}nicotinamides. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 79(12), 1461-1467.
https://doi.org/10.2298/JSC140423070S

Šukalović V, Šoškić V, Ignjatović Đ, Andrić D, Penjišević J, Kostić-Rajačić S. Investigation of key interactions between the second extracellular loop of the dopamine D2 receptor and several hydroxy-N-{[2-(4-phenylpiperazin-1-yl)ethyl]phenyl}nicotinamides. in Journal of the Serbian Chemical Society. 2014;79(12):1461-1467.
doi:10.2298/JSC140423070S .

Šukalović, Vladimir, Šoškić, Vukić, Ignjatović, Đurđica, Andrić, Deana, Penjišević, Jelena, Kostić-Rajačić, Slađana, "Investigation of key interactions between the second extracellular loop of the dopamine D2 receptor and several hydroxy-N-{[2-(4-phenylpiperazin-1-yl)ethyl]phenyl}nicotinamides" in Journal of the Serbian Chemical Society, 79, no. 12 (2014):1461-1467,
https://doi.org/10.2298/JSC140423070S . .

TY  - JOUR
AU  - Stanojević, Marija
AU  - Trifković, Jelena
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
AU  - Tešić, Živoslav Lj.
AU  - Milojković-Opsenica, Dušanka
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1796
AB  - The chromatographic behavior of arylureas and arylacetamides derivatives with observed biological activity toward dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors were examined by high-performance thin-layer chromatography in order to determine their lipophilicity and to correlate their structure and retention. The binary water-dimethyl sulfoxid mobile phases and RP-18 silica as stationary phase were used in order to determine chromatographic descriptors R-M(0), b, and C-0, as a measure of the lipophilicity of tested compounds. Based on the respective retention, the lipophilicity of the investigated compounds was discussed. Principal component analysis followed by partial least squares was used to select variables that best describe the behavior of the investigated compounds in the chromatographic system and to quantify their influences. The models reveal the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities and the size and the shape of the molecule, pointing out on that way the possible separation mechanism in the studied chromatographic systems.
PB  - Taylor & Francis Inc, Philadelphia
T2  - Journal of Liquid Chromatography and Related Technologies
T1  - Assessment of Lipophilicity of Some Biologically Active Arylpiperazines by Rptlc and Multivariate Analysis
VL  - 37
IS  - 20
SP  - 2814
EP  - 2828
DO  - 10.1080/10826076.2014.907112
ER  - 

@article{
author = "Stanojević, Marija and Trifković, Jelena and Kostić-Rajačić, Slađana and Šoškić, Vukić and Tešić, Živoslav Lj. and Milojković-Opsenica, Dušanka",
year = "2014",
abstract = "The chromatographic behavior of arylureas and arylacetamides derivatives with observed biological activity toward dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors were examined by high-performance thin-layer chromatography in order to determine their lipophilicity and to correlate their structure and retention. The binary water-dimethyl sulfoxid mobile phases and RP-18 silica as stationary phase were used in order to determine chromatographic descriptors R-M(0), b, and C-0, as a measure of the lipophilicity of tested compounds. Based on the respective retention, the lipophilicity of the investigated compounds was discussed. Principal component analysis followed by partial least squares was used to select variables that best describe the behavior of the investigated compounds in the chromatographic system and to quantify their influences. The models reveal the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities and the size and the shape of the molecule, pointing out on that way the possible separation mechanism in the studied chromatographic systems.",
publisher = "Taylor & Francis Inc, Philadelphia",
journal = "Journal of Liquid Chromatography and Related Technologies",
title = "Assessment of Lipophilicity of Some Biologically Active Arylpiperazines by Rptlc and Multivariate Analysis",
volume = "37",
number = "20",
pages = "2814-2828",
doi = "10.1080/10826076.2014.907112"
}

Stanojević, M., Trifković, J., Kostić-Rajačić, S., Šoškić, V., Tešić, Ž. Lj.,& Milojković-Opsenica, D.. (2014). Assessment of Lipophilicity of Some Biologically Active Arylpiperazines by Rptlc and Multivariate Analysis. in Journal of Liquid Chromatography and Related Technologies
Taylor & Francis Inc, Philadelphia., 37(20), 2814-2828.
https://doi.org/10.1080/10826076.2014.907112

Stanojević M, Trifković J, Kostić-Rajačić S, Šoškić V, Tešić ŽL, Milojković-Opsenica D. Assessment of Lipophilicity of Some Biologically Active Arylpiperazines by Rptlc and Multivariate Analysis. in Journal of Liquid Chromatography and Related Technologies. 2014;37(20):2814-2828.
doi:10.1080/10826076.2014.907112 .

Stanojević, Marija, Trifković, Jelena, Kostić-Rajačić, Slađana, Šoškić, Vukić, Tešić, Živoslav Lj., Milojković-Opsenica, Dušanka, "Assessment of Lipophilicity of Some Biologically Active Arylpiperazines by Rptlc and Multivariate Analysis" in Journal of Liquid Chromatography and Related Technologies, 37, no. 20 (2014):2814-2828,
https://doi.org/10.1080/10826076.2014.907112 . .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Bogdan, Anca Elena
AU  - Tovilović, Gordana
AU  - Ignjatović, Đurđica
AU  - Andrić, Deana
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1413
AB  - The ratio of affinities toward the dopamine D-2 and the 5-hydroxytryptamine 5-HT1A receptors is one of the important parameters that determine the efficiency of antipsychotic drugs. Here, we present the synthesis of ortho-, meta-, and para-N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides and their structure-activity relationship studies on dopamine D-2 and 5-hydroxytryptamine 5-HT1A receptors. It was shown that the biological activity of the described ligands strongly depends on their topology as well as on the nature of the heteroaryl group in the head of the molecules. Docking simulations together with conformational analysis revealed a rational explanation for the ligands' behavior. The molecular model of receptor-ligand interactions described herein provided us with a tool for the rational design of new compounds with a favorable D-2/5-HT1A profile.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling
VL  - 346
IS  - 10
SP  - 708
EP  - 717
DO  - 10.1002/ardp.201300189
ER  - 

@article{
author = "Šukalović, Vladimir and Bogdan, Anca Elena and Tovilović, Gordana and Ignjatović, Đurđica and Andrić, Deana and Kostić-Rajačić, Slađana and Šoškić, Vukić",
year = "2013",
abstract = "The ratio of affinities toward the dopamine D-2 and the 5-hydroxytryptamine 5-HT1A receptors is one of the important parameters that determine the efficiency of antipsychotic drugs. Here, we present the synthesis of ortho-, meta-, and para-N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides and their structure-activity relationship studies on dopamine D-2 and 5-hydroxytryptamine 5-HT1A receptors. It was shown that the biological activity of the described ligands strongly depends on their topology as well as on the nature of the heteroaryl group in the head of the molecules. Docking simulations together with conformational analysis revealed a rational explanation for the ligands' behavior. The molecular model of receptor-ligand interactions described herein provided us with a tool for the rational design of new compounds with a favorable D-2/5-HT1A profile.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling",
volume = "346",
number = "10",
pages = "708-717",
doi = "10.1002/ardp.201300189"
}

Šukalović, V., Bogdan, A. E., Tovilović, G., Ignjatović, Đ., Andrić, D., Kostić-Rajačić, S.,& Šoškić, V.. (2013). N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim., 346(10), 708-717.
https://doi.org/10.1002/ardp.201300189

Šukalović V, Bogdan AE, Tovilović G, Ignjatović Đ, Andrić D, Kostić-Rajačić S, Šoškić V. N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. in Archiv der Pharmazie. 2013;346(10):708-717.
doi:10.1002/ardp.201300189 .

Šukalović, Vladimir, Bogdan, Anca Elena, Tovilović, Gordana, Ignjatović, Đurđica, Andrić, Deana, Kostić-Rajačić, Slađana, Šoškić, Vukić, "N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling" in Archiv der Pharmazie, 346, no. 10 (2013):708-717,
https://doi.org/10.1002/ardp.201300189 . .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Šoškić, Vukić
AU  - Senćanski, Milan
AU  - Andrić, Deana
AU  - Kostić-Rajačić, Slađana
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1617
AB  - Interest in structure-based G-protein-coupled receptor (GPCR) ligand discovery is huge, given that almost 30 % of all approved drugs belong to this category of active compounds. The GPCR family includes the dopamine receptor subtype D2 (D2DR), but unfortunately-as is true of most GPCRs-no experimental structures are available for these receptors. In this publication, we present the molecular model of D2DR based on the previously published crystal structure of the dopamine D3 receptor (D3DR). A molecular modeling study using homology modeling and docking simulation provided a rational explanation for the behavior of the arylpiperazine ligand. The observed binding modes and receptor-ligand interactions provided us with fresh clues about how to optimize selectivity for D2DR receptors.
PB  - Springer, New York
T2  - Journal of Molecular Modeling
T1  - Determination of key receptor-ligand interactions of dopaminergic arylpiperazines and the dopamine D2 receptor homology model
VL  - 19
IS  - 4
SP  - 1751
EP  - 1762
DO  - 10.1007/s00894-012-1731-6
ER  - 

@article{
author = "Šukalović, Vladimir and Šoškić, Vukić and Senćanski, Milan and Andrić, Deana and Kostić-Rajačić, Slađana",
year = "2013",
abstract = "Interest in structure-based G-protein-coupled receptor (GPCR) ligand discovery is huge, given that almost 30 % of all approved drugs belong to this category of active compounds. The GPCR family includes the dopamine receptor subtype D2 (D2DR), but unfortunately-as is true of most GPCRs-no experimental structures are available for these receptors. In this publication, we present the molecular model of D2DR based on the previously published crystal structure of the dopamine D3 receptor (D3DR). A molecular modeling study using homology modeling and docking simulation provided a rational explanation for the behavior of the arylpiperazine ligand. The observed binding modes and receptor-ligand interactions provided us with fresh clues about how to optimize selectivity for D2DR receptors.",
publisher = "Springer, New York",
journal = "Journal of Molecular Modeling",
title = "Determination of key receptor-ligand interactions of dopaminergic arylpiperazines and the dopamine D2 receptor homology model",
volume = "19",
number = "4",
pages = "1751-1762",
doi = "10.1007/s00894-012-1731-6"
}

Šukalović, V., Šoškić, V., Senćanski, M., Andrić, D.,& Kostić-Rajačić, S.. (2013). Determination of key receptor-ligand interactions of dopaminergic arylpiperazines and the dopamine D2 receptor homology model. in Journal of Molecular Modeling
Springer, New York., 19(4), 1751-1762.
https://doi.org/10.1007/s00894-012-1731-6

Šukalović V, Šoškić V, Senćanski M, Andrić D, Kostić-Rajačić S. Determination of key receptor-ligand interactions of dopaminergic arylpiperazines and the dopamine D2 receptor homology model. in Journal of Molecular Modeling. 2013;19(4):1751-1762.
doi:10.1007/s00894-012-1731-6 .

Šukalović, Vladimir, Šoškić, Vukić, Senćanski, Milan, Andrić, Deana, Kostić-Rajačić, Slađana, "Determination of key receptor-ligand interactions of dopaminergic arylpiperazines and the dopamine D2 receptor homology model" in Journal of Molecular Modeling, 19, no. 4 (2013):1751-1762,
https://doi.org/10.1007/s00894-012-1731-6 . .

TY  - DATA
AU  - Šukalović, Vladimir
AU  - Šoškić, Vukić
AU  - Senćanski, Milan
AU  - Andrić, Deana
AU  - Kostić-Rajačić, Slađana
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3483
PB  - Springer, New York
T2  - Journal of Molecular Modeling
T1  - Supplementary data for article: Šukalović, V.; Šoškić, V.; Senčanski, M.; Andrić, D.; Kostić-Rajačić, S. Determination of Key Receptor-Ligand Interactions of Dopaminergic Arylpiperazines and the Dopamine D2 Receptor Homology Model. Journal of Molecular Modeling 2013, 19 (4), 1751–1762. https://doi.org/10.1007/s00894-012-1731-6
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3483
ER  - 

@misc{
author = "Šukalović, Vladimir and Šoškić, Vukić and Senćanski, Milan and Andrić, Deana and Kostić-Rajačić, Slađana",
year = "2013",
publisher = "Springer, New York",
journal = "Journal of Molecular Modeling",
title = "Supplementary data for article: Šukalović, V.; Šoškić, V.; Senčanski, M.; Andrić, D.; Kostić-Rajačić, S. Determination of Key Receptor-Ligand Interactions of Dopaminergic Arylpiperazines and the Dopamine D2 Receptor Homology Model. Journal of Molecular Modeling 2013, 19 (4), 1751–1762. https://doi.org/10.1007/s00894-012-1731-6",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3483"
}

Šukalović, V., Šoškić, V., Senćanski, M., Andrić, D.,& Kostić-Rajačić, S.. (2013). Supplementary data for article: Šukalović, V.; Šoškić, V.; Senčanski, M.; Andrić, D.; Kostić-Rajačić, S. Determination of Key Receptor-Ligand Interactions of Dopaminergic Arylpiperazines and the Dopamine D2 Receptor Homology Model. Journal of Molecular Modeling 2013, 19 (4), 1751–1762. https://doi.org/10.1007/s00894-012-1731-6. in Journal of Molecular Modeling
Springer, New York..
https://hdl.handle.net/21.15107/rcub_cherry_3483

Šukalović V, Šoškić V, Senćanski M, Andrić D, Kostić-Rajačić S. Supplementary data for article: Šukalović, V.; Šoškić, V.; Senčanski, M.; Andrić, D.; Kostić-Rajačić, S. Determination of Key Receptor-Ligand Interactions of Dopaminergic Arylpiperazines and the Dopamine D2 Receptor Homology Model. Journal of Molecular Modeling 2013, 19 (4), 1751–1762. https://doi.org/10.1007/s00894-012-1731-6. in Journal of Molecular Modeling. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3483 .

Šukalović, Vladimir, Šoškić, Vukić, Senćanski, Milan, Andrić, Deana, Kostić-Rajačić, Slađana, "Supplementary data for article: Šukalović, V.; Šoškić, V.; Senčanski, M.; Andrić, D.; Kostić-Rajačić, S. Determination of Key Receptor-Ligand Interactions of Dopaminergic Arylpiperazines and the Dopamine D2 Receptor Homology Model. Journal of Molecular Modeling 2013, 19 (4), 1751–1762. https://doi.org/10.1007/s00894-012-1731-6" in Journal of Molecular Modeling (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3483 .

TY  - DATA
AU  - Šukalović, Vladimir
AU  - Bogdan, Anca Elena
AU  - Tovilović, Gordana
AU  - Ignjatović, Đurđica
AU  - Andrić, Deana
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3511
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - Supplementary data for article: Šukalović, V.; Bogdan, A. E.; Tovilovic, G.; Ignjatovic, D.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V. N-{[2-(4-Phenyl-Piperazin-1-Yl)-Ethyl]-Phenyl}-Arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. Archiv der Pharmazie 2013, 346 (10), 708–717. https://doi.org/10.1002/ardp.201300189
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3511
ER  - 

@misc{
author = "Šukalović, Vladimir and Bogdan, Anca Elena and Tovilović, Gordana and Ignjatović, Đurđica and Andrić, Deana and Kostić-Rajačić, Slađana and Šoškić, Vukić",
year = "2013",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "Supplementary data for article: Šukalović, V.; Bogdan, A. E.; Tovilovic, G.; Ignjatovic, D.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V. N-{[2-(4-Phenyl-Piperazin-1-Yl)-Ethyl]-Phenyl}-Arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. Archiv der Pharmazie 2013, 346 (10), 708–717. https://doi.org/10.1002/ardp.201300189",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3511"
}

Šukalović, V., Bogdan, A. E., Tovilović, G., Ignjatović, Đ., Andrić, D., Kostić-Rajačić, S.,& Šoškić, V.. (2013). Supplementary data for article: Šukalović, V.; Bogdan, A. E.; Tovilovic, G.; Ignjatovic, D.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V. N-{[2-(4-Phenyl-Piperazin-1-Yl)-Ethyl]-Phenyl}-Arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. Archiv der Pharmazie 2013, 346 (10), 708–717. https://doi.org/10.1002/ardp.201300189. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim..
https://hdl.handle.net/21.15107/rcub_cherry_3511

Šukalović V, Bogdan AE, Tovilović G, Ignjatović Đ, Andrić D, Kostić-Rajačić S, Šoškić V. Supplementary data for article: Šukalović, V.; Bogdan, A. E.; Tovilovic, G.; Ignjatovic, D.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V. N-{[2-(4-Phenyl-Piperazin-1-Yl)-Ethyl]-Phenyl}-Arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. Archiv der Pharmazie 2013, 346 (10), 708–717. https://doi.org/10.1002/ardp.201300189. in Archiv der Pharmazie. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3511 .

Šukalović, Vladimir, Bogdan, Anca Elena, Tovilović, Gordana, Ignjatović, Đurđica, Andrić, Deana, Kostić-Rajačić, Slađana, Šoškić, Vukić, "Supplementary data for article: Šukalović, V.; Bogdan, A. E.; Tovilovic, G.; Ignjatovic, D.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V. N-{[2-(4-Phenyl-Piperazin-1-Yl)-Ethyl]-Phenyl}-Arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. Archiv der Pharmazie 2013, 346 (10), 708–717. https://doi.org/10.1002/ardp.201300189" in Archiv der Pharmazie (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3511 .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Šoškić, Vukić
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Kostić-Rajačić, Slađana
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1273
AB  - Second extracellular loop (ec12) of the dopamine (DA) D2 receptor is an essential part of the binding pocket of dopaminergic ligands. To form a part of the ligand-binding surface, it has to fold down into the transmembrane domain of the DA receptor. The current study describes the modeling of the D2 DA receptor ec12 and its interactions with arylpiperazine ligands. In order to model the D2 DA receptor ec12, several arylpiperazine ligands were used to propose a pharmacophore model. D2 DA receptor ec12 model was built using Accelrys Discovery Studio. To test the proposed model, docking analysis was performed and key amino acid residues were determined. The proposed receptor ligand interactions were rationalized and compared with measured binding affinities. It is shown that D2 DA receptor ec12 significantly participates in the formation of the receptor ligand complex through aromatic, hydrophobic and polar interaction. Considering them would benefit molecular modeling of G-protein-coupled receptors (GPCRs) and facilitate the design of novel active compounds.
AB  - Druga ekstracelularna petlja dopaminskog D2 receptora je esencijalni deo vezivnog mesta receptora. Da bi se definisala gornja strana vezivnog mesta, ona mora da se savije nadole, i orijentiše ka transmembranskom domenu receptora. U ovom radu opisan je proces modelovanja druge ekstracelularne petlje dopaminskog D2 receptora i njene interakcije sa arilpiperazinskim ligandima. Za modelovanje je korišćen Accelrys Discovery Studio paket programa. Predloženi model je testiran doking analizom literaturno dostupnih liganada i poređenjem dobijenih rezultata sa njihovim afinitetom vezivanja za D2 receptor. Određeni su amino-kiselinski ostaci koji stupaju u interakcije sa ligandima. Ključne interakcije su definisane i upoređene sa afinitetima liganada prema receptoru kako bi se predloženim modelom objasnile razlike u eksperimentalnim rezultatima. Naša istraživanja su pokazala da druga ekstracelularna petlja dopaminskog D2 receptora može stupati u različite interakcije sa arilpiperazinskim ligandima koje između ostalih uključuju hidrofobne, aromatične interakcije ali i vodnonične veze. Ova saznanja, u kombinaciji sa predloženim modelom D2 receptora, koji uključuje ekstracelularne petlje, mogu biti od velike koristi prilikom budućeg dizajna novih dopaminergičkih liganada.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Modeling key interactions between the second extracellular loop of the dopamine D2 receptor and arylpiperazine ligands
T1  - Modelovanje ključnih interakcija između druge ekstracelularne petlje dopaminskog D2 receptora i arilpiperazina kao liganada
VL  - 77
IS  - 3
SP  - 259
EP  - 277
DO  - 10.2298/JSC111028212S
ER  - 

@article{
author = "Šukalović, Vladimir and Šoškić, Vukić and Andrić, Deana and Roglić, Goran and Kostić-Rajačić, Slađana",
year = "2012",
abstract = "Second extracellular loop (ec12) of the dopamine (DA) D2 receptor is an essential part of the binding pocket of dopaminergic ligands. To form a part of the ligand-binding surface, it has to fold down into the transmembrane domain of the DA receptor. The current study describes the modeling of the D2 DA receptor ec12 and its interactions with arylpiperazine ligands. In order to model the D2 DA receptor ec12, several arylpiperazine ligands were used to propose a pharmacophore model. D2 DA receptor ec12 model was built using Accelrys Discovery Studio. To test the proposed model, docking analysis was performed and key amino acid residues were determined. The proposed receptor ligand interactions were rationalized and compared with measured binding affinities. It is shown that D2 DA receptor ec12 significantly participates in the formation of the receptor ligand complex through aromatic, hydrophobic and polar interaction. Considering them would benefit molecular modeling of G-protein-coupled receptors (GPCRs) and facilitate the design of novel active compounds., Druga ekstracelularna petlja dopaminskog D2 receptora je esencijalni deo vezivnog mesta receptora. Da bi se definisala gornja strana vezivnog mesta, ona mora da se savije nadole, i orijentiše ka transmembranskom domenu receptora. U ovom radu opisan je proces modelovanja druge ekstracelularne petlje dopaminskog D2 receptora i njene interakcije sa arilpiperazinskim ligandima. Za modelovanje je korišćen Accelrys Discovery Studio paket programa. Predloženi model je testiran doking analizom literaturno dostupnih liganada i poređenjem dobijenih rezultata sa njihovim afinitetom vezivanja za D2 receptor. Određeni su amino-kiselinski ostaci koji stupaju u interakcije sa ligandima. Ključne interakcije su definisane i upoređene sa afinitetima liganada prema receptoru kako bi se predloženim modelom objasnile razlike u eksperimentalnim rezultatima. Naša istraživanja su pokazala da druga ekstracelularna petlja dopaminskog D2 receptora može stupati u različite interakcije sa arilpiperazinskim ligandima koje između ostalih uključuju hidrofobne, aromatične interakcije ali i vodnonične veze. Ova saznanja, u kombinaciji sa predloženim modelom D2 receptora, koji uključuje ekstracelularne petlje, mogu biti od velike koristi prilikom budućeg dizajna novih dopaminergičkih liganada.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Modeling key interactions between the second extracellular loop of the dopamine D2 receptor and arylpiperazine ligands, Modelovanje ključnih interakcija između druge ekstracelularne petlje dopaminskog D2 receptora i arilpiperazina kao liganada",
volume = "77",
number = "3",
pages = "259-277",
doi = "10.2298/JSC111028212S"
}

Šukalović, V., Šoškić, V., Andrić, D., Roglić, G.,& Kostić-Rajačić, S.. (2012). Modeling key interactions between the second extracellular loop of the dopamine D2 receptor and arylpiperazine ligands. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 77(3), 259-277.
https://doi.org/10.2298/JSC111028212S

Šukalović V, Šoškić V, Andrić D, Roglić G, Kostić-Rajačić S. Modeling key interactions between the second extracellular loop of the dopamine D2 receptor and arylpiperazine ligands. in Journal of the Serbian Chemical Society. 2012;77(3):259-277.
doi:10.2298/JSC111028212S .

Šukalović, Vladimir, Šoškić, Vukić, Andrić, Deana, Roglić, Goran, Kostić-Rajačić, Slađana, "Modeling key interactions between the second extracellular loop of the dopamine D2 receptor and arylpiperazine ligands" in Journal of the Serbian Chemical Society, 77, no. 3 (2012):259-277,
https://doi.org/10.2298/JSC111028212S . .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Ignjatović, Đurđica
AU  - Tovilović, Gordana
AU  - Andrić, Deana
AU  - Shakib, Kaveh
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1302
AB  - It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors. (C) 2012 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic and Medicinal Chemistry Letters
T1  - Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors
VL  - 22
IS  - 12
SP  - 3967
EP  - 3972
DO  - 10.1016/j.bmcl.2012.04.098
ER  - 

@article{
author = "Šukalović, Vladimir and Ignjatović, Đurđica and Tovilović, Gordana and Andrić, Deana and Shakib, Kaveh and Kostić-Rajačić, Slađana and Šoškić, Vukić",
year = "2012",
abstract = "It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors. (C) 2012 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry Letters",
title = "Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors",
volume = "22",
number = "12",
pages = "3967-3972",
doi = "10.1016/j.bmcl.2012.04.098"
}

Šukalović, V., Ignjatović, Đ., Tovilović, G., Andrić, D., Shakib, K., Kostić-Rajačić, S.,& Šoškić, V.. (2012). Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors. in Bioorganic and Medicinal Chemistry Letters
Pergamon-Elsevier Science Ltd, Oxford., 22(12), 3967-3972.
https://doi.org/10.1016/j.bmcl.2012.04.098

Šukalović V, Ignjatović Đ, Tovilović G, Andrić D, Shakib K, Kostić-Rajačić S, Šoškić V. Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors. in Bioorganic and Medicinal Chemistry Letters. 2012;22(12):3967-3972.
doi:10.1016/j.bmcl.2012.04.098 .

Šukalović, Vladimir, Ignjatović, Đurđica, Tovilović, Gordana, Andrić, Deana, Shakib, Kaveh, Kostić-Rajačić, Slađana, Šoškić, Vukić, "Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors" in Bioorganic and Medicinal Chemistry Letters, 22, no. 12 (2012):3967-3972,
https://doi.org/10.1016/j.bmcl.2012.04.098 . .

TY  - JOUR
AU  - Senćanski, Milan
AU  - Šukalović, Vladimir
AU  - Došen-Mićović, Ljiljana
AU  - Šoškić, Vukić
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Kostić-Rajačić, Slađana
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1567
AB  - Molecular modelling studies were undertaken in order to identify key interactions of selected ligands with alpha(1A) adrenergic receptor, responsible for their binding and presumably receptor activation. The previously made model of alpha(1A) adrenergic receptor was optimized by molecular dynamics and different arylpiperazine ligands were docked. The results show a high correlation to the experimentally determined binding affinities. Ligand orientations and its interactions with specific amino acid residues in the binding site explain trends in its structure-activity relationship. The key interactions for those trends are mainly aromatic, which are suggested by the calculation of their ESP surfaces.
PB  - Inst Materials Physics, Bucharest
T2  - Digest Journal of Nanomaterials and Biostructures
T1  - Modeling Interactions of Alpha(1a) Adrenergic Receptor and Different Arylpiperazine Ligands
VL  - 7
IS  - 4
SP  - 1767
EP  - 1777
UR  - https://hdl.handle.net/21.15107/rcub_cherry_1567
ER  - 

@article{
author = "Senćanski, Milan and Šukalović, Vladimir and Došen-Mićović, Ljiljana and Šoškić, Vukić and Andrić, Deana and Roglić, Goran and Kostić-Rajačić, Slađana",
year = "2012",
abstract = "Molecular modelling studies were undertaken in order to identify key interactions of selected ligands with alpha(1A) adrenergic receptor, responsible for their binding and presumably receptor activation. The previously made model of alpha(1A) adrenergic receptor was optimized by molecular dynamics and different arylpiperazine ligands were docked. The results show a high correlation to the experimentally determined binding affinities. Ligand orientations and its interactions with specific amino acid residues in the binding site explain trends in its structure-activity relationship. The key interactions for those trends are mainly aromatic, which are suggested by the calculation of their ESP surfaces.",
publisher = "Inst Materials Physics, Bucharest",
journal = "Digest Journal of Nanomaterials and Biostructures",
title = "Modeling Interactions of Alpha(1a) Adrenergic Receptor and Different Arylpiperazine Ligands",
volume = "7",
number = "4",
pages = "1767-1777",
url = "https://hdl.handle.net/21.15107/rcub_cherry_1567"
}

Senćanski, M., Šukalović, V., Došen-Mićović, L., Šoškić, V., Andrić, D., Roglić, G.,& Kostić-Rajačić, S.. (2012). Modeling Interactions of Alpha(1a) Adrenergic Receptor and Different Arylpiperazine Ligands. in Digest Journal of Nanomaterials and Biostructures
Inst Materials Physics, Bucharest., 7(4), 1767-1777.
https://hdl.handle.net/21.15107/rcub_cherry_1567

Senćanski M, Šukalović V, Došen-Mićović L, Šoškić V, Andrić D, Roglić G, Kostić-Rajačić S. Modeling Interactions of Alpha(1a) Adrenergic Receptor and Different Arylpiperazine Ligands. in Digest Journal of Nanomaterials and Biostructures. 2012;7(4):1767-1777.
https://hdl.handle.net/21.15107/rcub_cherry_1567 .

Senćanski, Milan, Šukalović, Vladimir, Došen-Mićović, Ljiljana, Šoškić, Vukić, Andrić, Deana, Roglić, Goran, Kostić-Rajačić, Slađana, "Modeling Interactions of Alpha(1a) Adrenergic Receptor and Different Arylpiperazine Ligands" in Digest Journal of Nanomaterials and Biostructures, 7, no. 4 (2012):1767-1777,
https://hdl.handle.net/21.15107/rcub_cherry_1567 .

TY  - JOUR
AU  - Sencanski, M.V.
AU  - Šukalović, Vladimir
AU  - Došen-Mićović, Ljiljana
AU  - Šoškić, Vukić
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Kostić-Rajačić, Slađana
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/112
AB  - Molecular modelling studies were undertaken in order to identify key interactions of selected ligands with α1A adrenergic receptor, responsible for their binding and presumably receptor activation. The previously made model of α1A adrenergic receptor was optimized by molecular dynamics and different arylpiperazine ligands were docked. The results show a high correlation to the experimentally determined binding affinities. Ligand orientations and its interactions with specific amino acid residues in the binding site explain trends in its structure-activity relationship. The key interactions for those trends are mainly aromatic, which are suggested by the calculation of their ESP surfaces.
T2  - Digest Journal of Nanomaterials and Biostructures
T1  - Modeling interactions of α1a adrenergic receptor and different arylpiperazine ligands
VL  - 7
IS  - 4
SP  - 1761
EP  - 1777
UR  - https://hdl.handle.net/21.15107/rcub_cherry_112
ER  - 

@article{
author = "Sencanski, M.V. and Šukalović, Vladimir and Došen-Mićović, Ljiljana and Šoškić, Vukić and Andrić, Deana and Roglić, Goran and Kostić-Rajačić, Slađana",
year = "2012",
abstract = "Molecular modelling studies were undertaken in order to identify key interactions of selected ligands with α1A adrenergic receptor, responsible for their binding and presumably receptor activation. The previously made model of α1A adrenergic receptor was optimized by molecular dynamics and different arylpiperazine ligands were docked. The results show a high correlation to the experimentally determined binding affinities. Ligand orientations and its interactions with specific amino acid residues in the binding site explain trends in its structure-activity relationship. The key interactions for those trends are mainly aromatic, which are suggested by the calculation of their ESP surfaces.",
journal = "Digest Journal of Nanomaterials and Biostructures",
title = "Modeling interactions of α1a adrenergic receptor and different arylpiperazine ligands",
volume = "7",
number = "4",
pages = "1761-1777",
url = "https://hdl.handle.net/21.15107/rcub_cherry_112"
}

Sencanski, M.V., Šukalović, V., Došen-Mićović, L., Šoškić, V., Andrić, D., Roglić, G.,& Kostić-Rajačić, S.. (2012). Modeling interactions of α1a adrenergic receptor and different arylpiperazine ligands. in Digest Journal of Nanomaterials and Biostructures, 7(4), 1761-1777.
https://hdl.handle.net/21.15107/rcub_cherry_112

Sencanski M, Šukalović V, Došen-Mićović L, Šoškić V, Andrić D, Roglić G, Kostić-Rajačić S. Modeling interactions of α1a adrenergic receptor and different arylpiperazine ligands. in Digest Journal of Nanomaterials and Biostructures. 2012;7(4):1761-1777.
https://hdl.handle.net/21.15107/rcub_cherry_112 .

Sencanski, M.V., Šukalović, Vladimir, Došen-Mićović, Ljiljana, Šoškić, Vukić, Andrić, Deana, Roglić, Goran, Kostić-Rajačić, Slađana, "Modeling interactions of α1a adrenergic receptor and different arylpiperazine ligands" in Digest Journal of Nanomaterials and Biostructures, 7, no. 4 (2012):1761-1777,
https://hdl.handle.net/21.15107/rcub_cherry_112 .

TY  - JOUR
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Šukalović, Vladimir
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2008
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/969
AB  - In this publication we are describing synthesis, binding properties, and receptor docking of 4-halo-6-[2-(4-arylpiperazin-1-yl)ethyl]-1H-benzimidazoles, a new compounds with potential antipsychotics properties. Affinity towards the dopamine D(1)-like and D(2)-like, and serotonin 5-HT(1A) receptors was evaluated using the radioligand binding assays. All compounds tested had affinity for the D(2)-like and 5-HT(1A) receptors, but were inactive towards the D(1)-like receptor. Halogenated 6-[2-(4-arylpiperazin-1-yl)ethyl]-1H-benzimidazoles showed higher affinity compared to their nonhalogenated congeners. In silico docking analysis of selected ligands was performed in order to explain the results of binding assays. Our analysis suggests that stabilizing interactions between the halogen atom at the benzimidazole ring and the Ser-122 of the D(2)-like and Trp-358 of the 5-HT(1A) receptor. Energy contributions for these interactions were calculated using the ab initio method. (c) 2007 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, binding properties and receptor docking of 4-halo-6-[2-(4-arylpiperazin-1-yl)ethyl]-1H-benzimidazoles, mixed ligands of D(2) and 5-HT(1A) receptors
VL  - 43
IS  - 8
SP  - 1696
EP  - 1705
DO  - 10.1016/j.ejmech.2007.09.027
ER  - 

@article{
author = "Andrić, Deana and Roglić, Goran and Šukalović, Vladimir and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2008",
abstract = "In this publication we are describing synthesis, binding properties, and receptor docking of 4-halo-6-[2-(4-arylpiperazin-1-yl)ethyl]-1H-benzimidazoles, a new compounds with potential antipsychotics properties. Affinity towards the dopamine D(1)-like and D(2)-like, and serotonin 5-HT(1A) receptors was evaluated using the radioligand binding assays. All compounds tested had affinity for the D(2)-like and 5-HT(1A) receptors, but were inactive towards the D(1)-like receptor. Halogenated 6-[2-(4-arylpiperazin-1-yl)ethyl]-1H-benzimidazoles showed higher affinity compared to their nonhalogenated congeners. In silico docking analysis of selected ligands was performed in order to explain the results of binding assays. Our analysis suggests that stabilizing interactions between the halogen atom at the benzimidazole ring and the Ser-122 of the D(2)-like and Trp-358 of the 5-HT(1A) receptor. Energy contributions for these interactions were calculated using the ab initio method. (c) 2007 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, binding properties and receptor docking of 4-halo-6-[2-(4-arylpiperazin-1-yl)ethyl]-1H-benzimidazoles, mixed ligands of D(2) and 5-HT(1A) receptors",
volume = "43",
number = "8",
pages = "1696-1705",
doi = "10.1016/j.ejmech.2007.09.027"
}

Andrić, D., Roglić, G., Šukalović, V., Šoškić, V.,& Kostić-Rajačić, S.. (2008). Synthesis, binding properties and receptor docking of 4-halo-6-[2-(4-arylpiperazin-1-yl)ethyl]-1H-benzimidazoles, mixed ligands of D(2) and 5-HT(1A) receptors. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Paris., 43(8), 1696-1705.
https://doi.org/10.1016/j.ejmech.2007.09.027

Andrić D, Roglić G, Šukalović V, Šoškić V, Kostić-Rajačić S. Synthesis, binding properties and receptor docking of 4-halo-6-[2-(4-arylpiperazin-1-yl)ethyl]-1H-benzimidazoles, mixed ligands of D(2) and 5-HT(1A) receptors. in European Journal of Medicinal Chemistry. 2008;43(8):1696-1705.
doi:10.1016/j.ejmech.2007.09.027 .

Andrić, Deana, Roglić, Goran, Šukalović, Vladimir, Šoškić, Vukić, Kostić-Rajačić, Slađana, "Synthesis, binding properties and receptor docking of 4-halo-6-[2-(4-arylpiperazin-1-yl)ethyl]-1H-benzimidazoles, mixed ligands of D(2) and 5-HT(1A) receptors" in European Journal of Medicinal Chemistry, 43, no. 8 (2008):1696-1705,
https://doi.org/10.1016/j.ejmech.2007.09.027 . .

TY  - JOUR
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
AU  - Roglić, Goran
PY  - 2007
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/876
AB  - Clinical properties of atypical antipsychotics are based on their interaction with D-2 dopamine receptor and serotonin 5-HT1A and 5-HT2A receptors. As a part of our research program on new antipsychotics, we synthesized various derivatives of 1-cinnamyl-4-(2-methoxyphenyl)piperazines, and evaluated their affinities for D2, 5-HT1A, 5-HT2A, and adrenergic (a,) receptors using radioligand-binding assays. In addition, we performed docking analysis using models for the D2 and 5-HT1A receptors. All compounds exhibited low to moderate affinity to 5-HT1A and 5-HT2A receptors, high affinity to the D2 receptor and large variability in affinities for the alpha(1) receptor. Docking analysis indicated that the binding to D2 and 5-HT1A receptors is based on (i) interaction between protonated N1 of the piperazine ring and various aspartate residues, (ii) hydrogen bonds between various moieties of the ligand and the residues of threonine, serine, histidine or tryptophane, and (iii) edge-to-face interactions of the aromatic ring of the arylpiperazine moiety with phenylalanine or tyrosine residues. Docking data for the D2 receptor can account for the binding properties obtained in binding assays, suggesting that the model is reliable and robust. However, docking data for the 5-HT1A receptor cannot account for actual binding properties, suggesting that further refinement of the model is required.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - 1-cinnamyl-4-(2-methoxyphenyl)piperazines: Synthesis, binding properties, and docking to dopamine (D-2) and serotonin (5-HT1A) receptors
VL  - 340
IS  - 9
SP  - 456
EP  - 465
DO  - 10.1002/ardp.200700062
ER  - 

@article{
author = "Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Kostić-Rajačić, Slađana and Šoškić, Vukić and Roglić, Goran",
year = "2007",
abstract = "Clinical properties of atypical antipsychotics are based on their interaction with D-2 dopamine receptor and serotonin 5-HT1A and 5-HT2A receptors. As a part of our research program on new antipsychotics, we synthesized various derivatives of 1-cinnamyl-4-(2-methoxyphenyl)piperazines, and evaluated their affinities for D2, 5-HT1A, 5-HT2A, and adrenergic (a,) receptors using radioligand-binding assays. In addition, we performed docking analysis using models for the D2 and 5-HT1A receptors. All compounds exhibited low to moderate affinity to 5-HT1A and 5-HT2A receptors, high affinity to the D2 receptor and large variability in affinities for the alpha(1) receptor. Docking analysis indicated that the binding to D2 and 5-HT1A receptors is based on (i) interaction between protonated N1 of the piperazine ring and various aspartate residues, (ii) hydrogen bonds between various moieties of the ligand and the residues of threonine, serine, histidine or tryptophane, and (iii) edge-to-face interactions of the aromatic ring of the arylpiperazine moiety with phenylalanine or tyrosine residues. Docking data for the D2 receptor can account for the binding properties obtained in binding assays, suggesting that the model is reliable and robust. However, docking data for the 5-HT1A receptor cannot account for actual binding properties, suggesting that further refinement of the model is required.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "1-cinnamyl-4-(2-methoxyphenyl)piperazines: Synthesis, binding properties, and docking to dopamine (D-2) and serotonin (5-HT1A) receptors",
volume = "340",
number = "9",
pages = "456-465",
doi = "10.1002/ardp.200700062"
}

Penjišević, J., Šukalović, V., Andrić, D., Kostić-Rajačić, S., Šoškić, V.,& Roglić, G.. (2007). 1-cinnamyl-4-(2-methoxyphenyl)piperazines: Synthesis, binding properties, and docking to dopamine (D-2) and serotonin (5-HT1A) receptors. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim., 340(9), 456-465.
https://doi.org/10.1002/ardp.200700062

Penjišević J, Šukalović V, Andrić D, Kostić-Rajačić S, Šoškić V, Roglić G. 1-cinnamyl-4-(2-methoxyphenyl)piperazines: Synthesis, binding properties, and docking to dopamine (D-2) and serotonin (5-HT1A) receptors. in Archiv der Pharmazie. 2007;340(9):456-465.
doi:10.1002/ardp.200700062 .

Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Kostić-Rajačić, Slađana, Šoškić, Vukić, Roglić, Goran, "1-cinnamyl-4-(2-methoxyphenyl)piperazines: Synthesis, binding properties, and docking to dopamine (D-2) and serotonin (5-HT1A) receptors" in Archiv der Pharmazie, 340, no. 9 (2007):456-465,
https://doi.org/10.1002/ardp.200700062 . .

TY  - JOUR
AU  - Andrić, Deana
AU  - Tovilović, Gordana
AU  - Roglić, Goran
AU  - Šoškić, Vukić
AU  - Tomic, Mirko
AU  - Kostić-Rajačić, Slađana
PY  - 2007
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/877
AB  - Eight new compounds with halogen atom introduced into the benzimidazole-2-thione dopaminergic pharmacophore of 5-[2-(4-arylpiperazin-1-yl)ethyl]-1,3-dihydro-2H-benzi -2-thiones with the arylpiperazine part of the molecule being selected according to known structure-affinity requirements, have been synthesized. All the new compounds were evaluated for the in vitro binding affinity at the dopamine (DA) D-1 and D-2 and serotonin 5-HT1A receptors by the competitive radioassays, performed on synaptosomal membranes prepared from fresh bovine caudate nuclei and hippocampi. All the new compounds were strong competitors for the binding of the radioligands to the D-2 and 5-HT1A receptors, with the most active of them having 34 and 170 time higher affinity than non-halogenated congeners in the D-2 DA receptor radioassays (compounds 9.1b and 9.2b, respectively). Divergently, these compounds were without significant affinities for the D-1 DA receptors.
AB  - Sintetisano je osam novih jedinjenja kod kojih je atom halogena uveden u benzimidazol-2-tionsku dopaminergičku farmakoforu 5-[2-(4-arilpiperazin-1-il)etil]-1,3-dihidro-2N-benzimidazol-2-tiona sa arilpiperazinskim delom molekula izabranim shodno pozna- tim zahtevima o odnosu strukture i reaktivnosti. Za sva novosintetisana jedinjenja je određen afinitet vezivanja za dopaminske (D1 i D2) i 5-NT1A receptore u in vitro eksperimentima kompeticije sa radioligandima. Kao izvor dopaminskih i 5-NT1A receptora su korištene sinaptozomalne membrane izolovane iz goveđeg nukleusa kaudatusa i hipokampusa. Sva novosintetisana jedinjenja pokazala su se kao jaki kompetitori [3H]spiperona i [3H]8-OH-DPAT, od kojih najaktivnija (9.1b i 9.2b) poseduju 34 i 170 puta veći afinitet ka D2 DA receptorima od polaznih, nehalogenovanih jedinjenja. Sa druge strane, ova jedinjenja ne poseduju značajan afinitet ka D1 dopaminskim receptorima. .
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - 6-[2-(4-Arylpiperazin-1-yl)ethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation
T1  - 6-[2-(4-arilpiperazin-1-il)etil]-4-halo-1,3-dihidro-2h-benzimidazol-2-tioni - sinteza i farmakološko ispitivanje
VL  - 72
IS  - 8-9
SP  - 747
EP  - 755
DO  - 10.2298/JSC0709747A
ER  - 

@article{
author = "Andrić, Deana and Tovilović, Gordana and Roglić, Goran and Šoškić, Vukić and Tomic, Mirko and Kostić-Rajačić, Slađana",
year = "2007",
abstract = "Eight new compounds with halogen atom introduced into the benzimidazole-2-thione dopaminergic pharmacophore of 5-[2-(4-arylpiperazin-1-yl)ethyl]-1,3-dihydro-2H-benzi -2-thiones with the arylpiperazine part of the molecule being selected according to known structure-affinity requirements, have been synthesized. All the new compounds were evaluated for the in vitro binding affinity at the dopamine (DA) D-1 and D-2 and serotonin 5-HT1A receptors by the competitive radioassays, performed on synaptosomal membranes prepared from fresh bovine caudate nuclei and hippocampi. All the new compounds were strong competitors for the binding of the radioligands to the D-2 and 5-HT1A receptors, with the most active of them having 34 and 170 time higher affinity than non-halogenated congeners in the D-2 DA receptor radioassays (compounds 9.1b and 9.2b, respectively). Divergently, these compounds were without significant affinities for the D-1 DA receptors., Sintetisano je osam novih jedinjenja kod kojih je atom halogena uveden u benzimidazol-2-tionsku dopaminergičku farmakoforu 5-[2-(4-arilpiperazin-1-il)etil]-1,3-dihidro-2N-benzimidazol-2-tiona sa arilpiperazinskim delom molekula izabranim shodno pozna- tim zahtevima o odnosu strukture i reaktivnosti. Za sva novosintetisana jedinjenja je određen afinitet vezivanja za dopaminske (D1 i D2) i 5-NT1A receptore u in vitro eksperimentima kompeticije sa radioligandima. Kao izvor dopaminskih i 5-NT1A receptora su korištene sinaptozomalne membrane izolovane iz goveđeg nukleusa kaudatusa i hipokampusa. Sva novosintetisana jedinjenja pokazala su se kao jaki kompetitori [3H]spiperona i [3H]8-OH-DPAT, od kojih najaktivnija (9.1b i 9.2b) poseduju 34 i 170 puta veći afinitet ka D2 DA receptorima od polaznih, nehalogenovanih jedinjenja. Sa druge strane, ova jedinjenja ne poseduju značajan afinitet ka D1 dopaminskim receptorima. .",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "6-[2-(4-Arylpiperazin-1-yl)ethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation, 6-[2-(4-arilpiperazin-1-il)etil]-4-halo-1,3-dihidro-2h-benzimidazol-2-tioni - sinteza i farmakološko ispitivanje",
volume = "72",
number = "8-9",
pages = "747-755",
doi = "10.2298/JSC0709747A"
}

Andrić, D., Tovilović, G., Roglić, G., Šoškić, V., Tomic, M.,& Kostić-Rajačić, S.. (2007). 6-[2-(4-Arylpiperazin-1-yl)ethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 72(8-9), 747-755.
https://doi.org/10.2298/JSC0709747A

Andrić D, Tovilović G, Roglić G, Šoškić V, Tomic M, Kostić-Rajačić S. 6-[2-(4-Arylpiperazin-1-yl)ethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation. in Journal of the Serbian Chemical Society. 2007;72(8-9):747-755.
doi:10.2298/JSC0709747A .

Andrić, Deana, Tovilović, Gordana, Roglić, Goran, Šoškić, Vukić, Tomic, Mirko, Kostić-Rajačić, Slađana, "6-[2-(4-Arylpiperazin-1-yl)ethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation" in Journal of the Serbian Chemical Society, 72, no. 8-9 (2007):747-755,
https://doi.org/10.2298/JSC0709747A . .

TY  - JOUR
AU  - Andrić, Deana
AU  - Tovilović, Gordana
AU  - Roglić, Goran
AU  - Vasković, Đurđica
AU  - Šoškić, Vukić
AU  - Tomic, Mirko
AU  - Kostić-Rajačić, Slađana
PY  - 2007
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/845
AB  - Six newly synthesized heterocyclic (2-nitroplienyl)piperazines. with a specific structure of the heteroaryl group, which mimics the catechol moiety of dopamine (benzimidazoles and substituted benzimidazoles), were evaluated for their binding affinity to rat dopamine (DA), serotonin (5-HT) and alpha I receptors. All compounds with a benzimidazole group had a 5-HT2A/D-2 receptors binding ratio characteristic for atypical neuroleptics ( gt  1, pK(i) values). Compound 7e, 4-bromo-6-{2-[4-(2-nitrophenyl)piperazin-1-yl]etliyl}-1H-benziniidazole, expressed higher affinities for all receptor classes than clozapine. Also, it exhibited the best characteristic for atypical neuroleptics and presents a compound with the best profile for further in vivo investigations.
AB  - Sintetisano je šest heterocikličnih (2-nitrofenil)piperazina sa specifičnom heteroaril grupom, koja podražava kateholsku grupu dopamina (benzimidazoli i supstituisani benzimidazoli), i ispitan je njihov afinitet ka dopaminskim, serotoninskim i _1 receptorima. Sva jedinjenja sa benzimidazolskim grupama su pokazala 5-HT 1A/D2 odnos vezivanja karakterističan za atipične neuroleptike ( gt 1, pK i vrednosti). Jedinjenje 7c, 4-bromo-6-{2-_4-(2-nitrofenil)piperazin-1-il_etil}-1H-benzimidazol, pokazalo je izraženiji afinitet ka svim klasama receptora u poređenju sa klozapinom i takođe predstavlja jedinjenje sa najboljim karakteristikama za dalja in vivo istraživanja.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives
T1  - Sinteza i farmakološko ispitivanje novih derivata N-(2-nitrofenil) piperazina
VL  - 72
IS  - 5
SP  - 429
EP  - 435
DO  - 10.2298/JSC0705429A
ER  - 

@article{
author = "Andrić, Deana and Tovilović, Gordana and Roglić, Goran and Vasković, Đurđica and Šoškić, Vukić and Tomic, Mirko and Kostić-Rajačić, Slađana",
year = "2007",
abstract = "Six newly synthesized heterocyclic (2-nitroplienyl)piperazines. with a specific structure of the heteroaryl group, which mimics the catechol moiety of dopamine (benzimidazoles and substituted benzimidazoles), were evaluated for their binding affinity to rat dopamine (DA), serotonin (5-HT) and alpha I receptors. All compounds with a benzimidazole group had a 5-HT2A/D-2 receptors binding ratio characteristic for atypical neuroleptics ( gt  1, pK(i) values). Compound 7e, 4-bromo-6-{2-[4-(2-nitrophenyl)piperazin-1-yl]etliyl}-1H-benziniidazole, expressed higher affinities for all receptor classes than clozapine. Also, it exhibited the best characteristic for atypical neuroleptics and presents a compound with the best profile for further in vivo investigations., Sintetisano je šest heterocikličnih (2-nitrofenil)piperazina sa specifičnom heteroaril grupom, koja podražava kateholsku grupu dopamina (benzimidazoli i supstituisani benzimidazoli), i ispitan je njihov afinitet ka dopaminskim, serotoninskim i _1 receptorima. Sva jedinjenja sa benzimidazolskim grupama su pokazala 5-HT 1A/D2 odnos vezivanja karakterističan za atipične neuroleptike ( gt 1, pK i vrednosti). Jedinjenje 7c, 4-bromo-6-{2-_4-(2-nitrofenil)piperazin-1-il_etil}-1H-benzimidazol, pokazalo je izraženiji afinitet ka svim klasama receptora u poređenju sa klozapinom i takođe predstavlja jedinjenje sa najboljim karakteristikama za dalja in vivo istraživanja.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives, Sinteza i farmakološko ispitivanje novih derivata N-(2-nitrofenil) piperazina",
volume = "72",
number = "5",
pages = "429-435",
doi = "10.2298/JSC0705429A"
}

Andrić, D., Tovilović, G., Roglić, G., Vasković, Đ., Šoškić, V., Tomic, M.,& Kostić-Rajačić, S.. (2007). Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 72(5), 429-435.
https://doi.org/10.2298/JSC0705429A

Andrić D, Tovilović G, Roglić G, Vasković Đ, Šoškić V, Tomic M, Kostić-Rajačić S. Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives. in Journal of the Serbian Chemical Society. 2007;72(5):429-435.
doi:10.2298/JSC0705429A .

Andrić, Deana, Tovilović, Gordana, Roglić, Goran, Vasković, Đurđica, Šoškić, Vukić, Tomic, Mirko, Kostić-Rajačić, Slađana, "Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives" in Journal of the Serbian Chemical Society, 72, no. 5 (2007):429-435,
https://doi.org/10.2298/JSC0705429A . .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Zlatović, Mario
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2005
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/690
AB  - The docking of several 1-benzyl-4-arylpiperazines to the dopamine receptor (DAR) D-2 was examined. The results demonstrated that the interaction of protonated NI of the piperazine ring with Asp 86 (III.32) and edge-to-face interactions of the aromatic ring of the arylpiperazine part of the ligand with Phe 178 (VI.44), Trp 182 (VI.48) and Tyr 216 (VII.58) of the receptor, represent the major stabilizing forces. Besides, the hydrogen bond acceptor group in position 2 of the phenylpiperazine aromatic ring could build one more hydrogen bond with Trp 182 (VI.48). Bulky substituents; in position 4 were not tolerated due to the unfavorable sterical interaction with Phe 178 (VI.44). Substituents in position 2 and 3 were found to be sterically well tolerated. Introduction of electron attractive -NO2 group in position 3 of arylpiperazines decreased, while electron donors (-OMe) and the second aromatic ring (naphthyl) increased the binding affinity comparing to that of the phenylpiperazine 1. This can be explained in terms of favoured edge-to-face interactions in ligands with a high negative electrostatic surface potential (ESP) in the centre of aromatic residue of arylpiperazines. Thus, besides the salt bridges and hydrogen bonds, edge-to-face interactions significantly contribute to arylpiperazine ligands to form complexes with the DAR D-2. Phe 178 (VI.44), Trp 182 (VI.48) and Tyr 216 (VII.58) can be considered as a part of the ancillary DAR D-2 pocket preserved in most G protein-coupled receptors of the A class and obviously, the arylpiperazine structural motif represents one of the privileged structures that bind to this pocket.
PB  - Ecv-Editio Cantor Verlag Medizin Naturwissenschaften, Aulendorf
T2  - Arzneimittel-forschung = Drug Research
T1  - Interaction of arylpiperazines with the dopamine receptor D-2 binding site
VL  - 55
IS  - 3
SP  - 145
EP  - 152
UR  - https://hdl.handle.net/21.15107/rcub_cherry_690
ER  - 

@article{
author = "Šukalović, Vladimir and Zlatović, Mario and Andrić, Deana and Roglić, Goran and Kostić-Rajačić, Slađana and Šoškić, Vukić",
year = "2005",
abstract = "The docking of several 1-benzyl-4-arylpiperazines to the dopamine receptor (DAR) D-2 was examined. The results demonstrated that the interaction of protonated NI of the piperazine ring with Asp 86 (III.32) and edge-to-face interactions of the aromatic ring of the arylpiperazine part of the ligand with Phe 178 (VI.44), Trp 182 (VI.48) and Tyr 216 (VII.58) of the receptor, represent the major stabilizing forces. Besides, the hydrogen bond acceptor group in position 2 of the phenylpiperazine aromatic ring could build one more hydrogen bond with Trp 182 (VI.48). Bulky substituents; in position 4 were not tolerated due to the unfavorable sterical interaction with Phe 178 (VI.44). Substituents in position 2 and 3 were found to be sterically well tolerated. Introduction of electron attractive -NO2 group in position 3 of arylpiperazines decreased, while electron donors (-OMe) and the second aromatic ring (naphthyl) increased the binding affinity comparing to that of the phenylpiperazine 1. This can be explained in terms of favoured edge-to-face interactions in ligands with a high negative electrostatic surface potential (ESP) in the centre of aromatic residue of arylpiperazines. Thus, besides the salt bridges and hydrogen bonds, edge-to-face interactions significantly contribute to arylpiperazine ligands to form complexes with the DAR D-2. Phe 178 (VI.44), Trp 182 (VI.48) and Tyr 216 (VII.58) can be considered as a part of the ancillary DAR D-2 pocket preserved in most G protein-coupled receptors of the A class and obviously, the arylpiperazine structural motif represents one of the privileged structures that bind to this pocket.",
publisher = "Ecv-Editio Cantor Verlag Medizin Naturwissenschaften, Aulendorf",
journal = "Arzneimittel-forschung = Drug Research",
title = "Interaction of arylpiperazines with the dopamine receptor D-2 binding site",
volume = "55",
number = "3",
pages = "145-152",
url = "https://hdl.handle.net/21.15107/rcub_cherry_690"
}

Šukalović, V., Zlatović, M., Andrić, D., Roglić, G., Kostić-Rajačić, S.,& Šoškić, V.. (2005). Interaction of arylpiperazines with the dopamine receptor D-2 binding site. in Arzneimittel-forschung = Drug Research
Ecv-Editio Cantor Verlag Medizin Naturwissenschaften, Aulendorf., 55(3), 145-152.
https://hdl.handle.net/21.15107/rcub_cherry_690

Šukalović V, Zlatović M, Andrić D, Roglić G, Kostić-Rajačić S, Šoškić V. Interaction of arylpiperazines with the dopamine receptor D-2 binding site. in Arzneimittel-forschung = Drug Research. 2005;55(3):145-152.
https://hdl.handle.net/21.15107/rcub_cherry_690 .

Šukalović, Vladimir, Zlatović, Mario, Andrić, Deana, Roglić, Goran, Kostić-Rajačić, Slađana, Šoškić, Vukić, "Interaction of arylpiperazines with the dopamine receptor D-2 binding site" in Arzneimittel-forschung = Drug Research, 55, no. 3 (2005):145-152,
https://hdl.handle.net/21.15107/rcub_cherry_690 .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Kostić-Rajačić, Slađana
AU  - Schrattenholz, A
AU  - Šoškić, Vukić
PY  - 2005
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/715
AB  - 5-[3-(4-Arylpiperazin-1-yl)propyl]-1H-benzimidazoles and 5-[2-(4-aryipiperazin-1-yl)ethoxy]-1H-benzimidazoles were synthesized and their affinity for the D-1, D-2 and 5-HT1A, receptors examined. They expressed a rather high affinity for the D-2 doparnine receptor. The main features of ligand-D-2 receptor interactions revealed by docking analyses were: salt bridge between piperazine ring protonated N-1 and Asp 86, hydrogen bonds of ligand bezimidazole part with Ser 141, Ser 122 and His 189, edge-to-face interactions of arylpiperazine aromatic ring with Phe 178, Tyr 216 and Trp 182 and hydrogen bond between ethereal oxygen in ethylenoxy ligands and hydrogen of Phe 185 or Trp 115. The most active 5-{2-[4-(2-methoxyphenyl)-piperazin-1-yl]ethoxy}-1,3-di hydro-2H-benzimidazole-2-thione (27) has a maximal number of attractive interactions. A satisfactory correlation between docking of the compounds into the D-2 receptor and competition binding results was observed. (c) 2005 Elsevier SAS. All rights reserved.
PB  - Editions Scientifiques Medicales Elsevier, Paris
T2  - European Journal of Medicinal Chemistry
T1  - Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs
VL  - 40
IS  - 5
SP  - 481
EP  - 493
DO  - 10.1016/j.ejmech.2004.10.006
ER  - 

@article{
author = "Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Kostić-Rajačić, Slađana and Schrattenholz, A and Šoškić, Vukić",
year = "2005",
abstract = "5-[3-(4-Arylpiperazin-1-yl)propyl]-1H-benzimidazoles and 5-[2-(4-aryipiperazin-1-yl)ethoxy]-1H-benzimidazoles were synthesized and their affinity for the D-1, D-2 and 5-HT1A, receptors examined. They expressed a rather high affinity for the D-2 doparnine receptor. The main features of ligand-D-2 receptor interactions revealed by docking analyses were: salt bridge between piperazine ring protonated N-1 and Asp 86, hydrogen bonds of ligand bezimidazole part with Ser 141, Ser 122 and His 189, edge-to-face interactions of arylpiperazine aromatic ring with Phe 178, Tyr 216 and Trp 182 and hydrogen bond between ethereal oxygen in ethylenoxy ligands and hydrogen of Phe 185 or Trp 115. The most active 5-{2-[4-(2-methoxyphenyl)-piperazin-1-yl]ethoxy}-1,3-di hydro-2H-benzimidazole-2-thione (27) has a maximal number of attractive interactions. A satisfactory correlation between docking of the compounds into the D-2 receptor and competition binding results was observed. (c) 2005 Elsevier SAS. All rights reserved.",
publisher = "Editions Scientifiques Medicales Elsevier, Paris",
journal = "European Journal of Medicinal Chemistry",
title = "Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs",
volume = "40",
number = "5",
pages = "481-493",
doi = "10.1016/j.ejmech.2004.10.006"
}

Šukalović, V., Andrić, D., Roglić, G., Kostić-Rajačić, S., Schrattenholz, A.,& Šoškić, V.. (2005). Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs. in European Journal of Medicinal Chemistry
Editions Scientifiques Medicales Elsevier, Paris., 40(5), 481-493.
https://doi.org/10.1016/j.ejmech.2004.10.006

Šukalović V, Andrić D, Roglić G, Kostić-Rajačić S, Schrattenholz A, Šoškić V. Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs. in European Journal of Medicinal Chemistry. 2005;40(5):481-493.
doi:10.1016/j.ejmech.2004.10.006 .

Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Kostić-Rajačić, Slađana, Schrattenholz, A, Šoškić, Vukić, "Synthesis, dopamine D-2 receptor binding studies and docking analysis of 5-[3-(4-arylpiperazin-1-yl)propyl]-1H-benzimidazole, 5-[2-(4-arylpiperazin-1-yl)ethoxy]-1H-benzimidazole and their analogs" in European Journal of Medicinal Chemistry, 40, no. 5 (2005):481-493,
https://doi.org/10.1016/j.ejmech.2004.10.006 . .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2004
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/648
AB  - We examined the effects of the electron density distribution (electrostatic surface potential; ESP) of several new benzimidazole-type ligands on their binding affinity for the D-1 and D-2 dopamine receptors (DAR). Receptors were prepared from synaptosomal membranes of bovine caudate nuclei. [H-3]SCH 23390 and [H-3]spiperone were used as specific radiolabels for the D-1 and D-2 receptors, respectively. The ESP of these compounds was calculated using Gaussian 98 W software. Calculations performed with known dopaminergic ligands showed that the electron density charge in the aromatic ring of these compounds favors a higher binding affinity for the D-2 DAR. This was confirmed by the synthesis of halogenated analogues of several known dopaminergic ligands. Halogenation resulted in an increase in the positive charge of the aromatic part of the molecule. None of the newly synthesized compounds was efficient in displacing [3H]SCH 23390 from the D-1 DAR. The introduction of chlorine into the molecule led to a higher binding affinity for the D-2 DAR of the new ligands in comparison to both parent compounds and brominated ligands. This difference probably originates from the difference in the sizes of chlorine and bromine atoms, which could influence the interaction of a ligand with the receptor binding site. However, among the new ligands with bromine as a substituent, two compounds (8b and 10b) expressed a higher binding affinity and two of them (9b and 11b) a lower binding affinity for the D-2 DAR, when compared to unsubstituted parent compounds. These results indicate that the electrostatic surface potential of a ligand is an important factor in its interaction with the D-2 DAR and that this should be taken into account during design and synthesis of dopaminergic compounds.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - Electrostatic surface potential calculation on several new halogenated benzimidazole-like dopaminergic ligands
VL  - 337
IS  - 7
SP  - 376
EP  - 382
DO  - 10.1002/ardp.200300846
ER  - 

@article{
author = "Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Kostić-Rajačić, Slađana and Šoškić, Vukić",
year = "2004",
abstract = "We examined the effects of the electron density distribution (electrostatic surface potential; ESP) of several new benzimidazole-type ligands on their binding affinity for the D-1 and D-2 dopamine receptors (DAR). Receptors were prepared from synaptosomal membranes of bovine caudate nuclei. [H-3]SCH 23390 and [H-3]spiperone were used as specific radiolabels for the D-1 and D-2 receptors, respectively. The ESP of these compounds was calculated using Gaussian 98 W software. Calculations performed with known dopaminergic ligands showed that the electron density charge in the aromatic ring of these compounds favors a higher binding affinity for the D-2 DAR. This was confirmed by the synthesis of halogenated analogues of several known dopaminergic ligands. Halogenation resulted in an increase in the positive charge of the aromatic part of the molecule. None of the newly synthesized compounds was efficient in displacing [3H]SCH 23390 from the D-1 DAR. The introduction of chlorine into the molecule led to a higher binding affinity for the D-2 DAR of the new ligands in comparison to both parent compounds and brominated ligands. This difference probably originates from the difference in the sizes of chlorine and bromine atoms, which could influence the interaction of a ligand with the receptor binding site. However, among the new ligands with bromine as a substituent, two compounds (8b and 10b) expressed a higher binding affinity and two of them (9b and 11b) a lower binding affinity for the D-2 DAR, when compared to unsubstituted parent compounds. These results indicate that the electrostatic surface potential of a ligand is an important factor in its interaction with the D-2 DAR and that this should be taken into account during design and synthesis of dopaminergic compounds.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "Electrostatic surface potential calculation on several new halogenated benzimidazole-like dopaminergic ligands",
volume = "337",
number = "7",
pages = "376-382",
doi = "10.1002/ardp.200300846"
}

Šukalović, V., Andrić, D., Roglić, G., Kostić-Rajačić, S.,& Šoškić, V.. (2004). Electrostatic surface potential calculation on several new halogenated benzimidazole-like dopaminergic ligands. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim., 337(7), 376-382.
https://doi.org/10.1002/ardp.200300846

Šukalović V, Andrić D, Roglić G, Kostić-Rajačić S, Šoškić V. Electrostatic surface potential calculation on several new halogenated benzimidazole-like dopaminergic ligands. in Archiv der Pharmazie. 2004;337(7):376-382.
doi:10.1002/ardp.200300846 .

Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Kostić-Rajačić, Slađana, Šoškić, Vukić, "Electrostatic surface potential calculation on several new halogenated benzimidazole-like dopaminergic ligands" in Archiv der Pharmazie, 337, no. 7 (2004):376-382,
https://doi.org/10.1002/ardp.200300846 . .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Zlatović, Mario
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2004
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/663
AB  - Docking of several 1-{2-[5-(1H-benzimidazole-2-thione)]ethyl}-4- and 1-benzylarylpiperazines to the D-2 dopamine receptor (DAR) was examined. The binding pocket of the D-2 DAR defined according to Teeter and DuRand [1] was extended using the Insight II software. It was found that (i) the interaction of the protonated N1 of the piperazine ring with Asp86, (ii) the hydrogen bond formation between the benzimidazole part of the ligand and Ser141, as well as Ser122, and (iii) the edge-to-face interactions of the aromatic ring or arylpiperazine part of the ligand with Phe178, Tyr216 and Trpl 82 of the receptor represent the mayor stabilizing forces. Besides, the hydrogen bond acceptor group in position 2 of the phenylpiperazine aromatic ring could form one more hydrogen bond with Trp182. Bulky substituents in position 4 are not tolerated, due to the unfavorable sterical interaction with Phe178. Substituents in positions 2 and 3 are sterically well tolerated. Electron-attractive groups (F, Cl, CF3, and NO2) decreased, while electron donors (-OMe) and the second aromatic ring (naphthyl) increased the binding affinity, as compared to that of the parent compound 1. This can be explained by strong edge-to-face interactions of negative electrostatic surface potential (ESP) in the center of aromatic residues of the ligand with positive-ESP protons in the aromatic residues of the receptor. Thus, besides the salt bridges and hydrogen bonds, edge-to-face interactions significantly contribute to arylpiperazine ligands forming complexes with the D-2 DAR.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - Modeling of the D-2 dopamine receptor arylpiperazine binding site for 1-{2-[5-(1H-benzimidazoIe-2-thione)]ethyl}-4-arylpiperazines
VL  - 337
IS  - 9
SP  - 502
EP  - 512
DO  - 10.1002/ardp.200400901
ER  - 

@article{
author = "Šukalović, Vladimir and Zlatović, Mario and Andrić, Deana and Roglić, Goran and Kostić-Rajačić, Slađana and Šoškić, Vukić",
year = "2004",
abstract = "Docking of several 1-{2-[5-(1H-benzimidazole-2-thione)]ethyl}-4- and 1-benzylarylpiperazines to the D-2 dopamine receptor (DAR) was examined. The binding pocket of the D-2 DAR defined according to Teeter and DuRand [1] was extended using the Insight II software. It was found that (i) the interaction of the protonated N1 of the piperazine ring with Asp86, (ii) the hydrogen bond formation between the benzimidazole part of the ligand and Ser141, as well as Ser122, and (iii) the edge-to-face interactions of the aromatic ring or arylpiperazine part of the ligand with Phe178, Tyr216 and Trpl 82 of the receptor represent the mayor stabilizing forces. Besides, the hydrogen bond acceptor group in position 2 of the phenylpiperazine aromatic ring could form one more hydrogen bond with Trp182. Bulky substituents in position 4 are not tolerated, due to the unfavorable sterical interaction with Phe178. Substituents in positions 2 and 3 are sterically well tolerated. Electron-attractive groups (F, Cl, CF3, and NO2) decreased, while electron donors (-OMe) and the second aromatic ring (naphthyl) increased the binding affinity, as compared to that of the parent compound 1. This can be explained by strong edge-to-face interactions of negative electrostatic surface potential (ESP) in the center of aromatic residues of the ligand with positive-ESP protons in the aromatic residues of the receptor. Thus, besides the salt bridges and hydrogen bonds, edge-to-face interactions significantly contribute to arylpiperazine ligands forming complexes with the D-2 DAR.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "Modeling of the D-2 dopamine receptor arylpiperazine binding site for 1-{2-[5-(1H-benzimidazoIe-2-thione)]ethyl}-4-arylpiperazines",
volume = "337",
number = "9",
pages = "502-512",
doi = "10.1002/ardp.200400901"
}

Šukalović, V., Zlatović, M., Andrić, D., Roglić, G., Kostić-Rajačić, S.,& Šoškić, V.. (2004). Modeling of the D-2 dopamine receptor arylpiperazine binding site for 1-{2-[5-(1H-benzimidazoIe-2-thione)]ethyl}-4-arylpiperazines. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim., 337(9), 502-512.
https://doi.org/10.1002/ardp.200400901

Šukalović V, Zlatović M, Andrić D, Roglić G, Kostić-Rajačić S, Šoškić V. Modeling of the D-2 dopamine receptor arylpiperazine binding site for 1-{2-[5-(1H-benzimidazoIe-2-thione)]ethyl}-4-arylpiperazines. in Archiv der Pharmazie. 2004;337(9):502-512.
doi:10.1002/ardp.200400901 .

Šukalović, Vladimir, Zlatović, Mario, Andrić, Deana, Roglić, Goran, Kostić-Rajačić, Slađana, Šoškić, Vukić, "Modeling of the D-2 dopamine receptor arylpiperazine binding site for 1-{2-[5-(1H-benzimidazoIe-2-thione)]ethyl}-4-arylpiperazines" in Archiv der Pharmazie, 337, no. 9 (2004):502-512,
https://doi.org/10.1002/ardp.200400901 . .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Roglić, Goran
AU  - Husinec, S
AU  - Kostić-Rajačić, Slađana
AU  - Andrić, Deana
AU  - Šoškić, Vukić
PY  - 2003
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/521
AB  - Several tertiary 2-phenylethyl, 2-(1-naphthyl)ethyl and 2-(2-naphthyl)ethyl amines were synthesized and their binding affinities for dopamine D(1), D(2) and serotonin 5-HT(1A) receptors evaluated in radioligand binding assays. All compounds were inactive in D(1) dopamine radioligand binding assay. The 2-(1-naphthyl)ethyl analogues expressed a low but significant binding affinity for the D(2) and moderate one for the 5-HT(1A) receptor subtypes. Most of the remaining compounds expressed binding affinity at the 5-HT(1A) receptor subtype but were inactive in D(2) receptor binding assay. Based on these results and considering the chemical characteristics of the compounds synthesized and evaluated for dopaminergic and serotonergic activity throughout the present study it can be concluded that hydrophobic type of interaction (stacking or edge-to-face) plays a significant role in the formation of receptor-ligand complexes of 2-(1-naphthyl)ethyl amines. This structural motive can be applied to design and synthesize new, more potent dopaminergic/serotonergic ligands by slight chemical modifications.
PB  - Wiley-Blackwell, Malden
T2  - Archiv der Pharmazie
T1  - D(2) dopaminergic and 5-HT(1A) serotonergic activity of 2-(1-naphthyl)ethyl- and 2-(2-naphthyl)ethyl amines
VL  - 336
IS  - 11
SP  - 514
EP  - 522
DO  - 10.1002/ardp.200300776
ER  - 

@article{
author = "Šukalović, Vladimir and Roglić, Goran and Husinec, S and Kostić-Rajačić, Slađana and Andrić, Deana and Šoškić, Vukić",
year = "2003",
abstract = "Several tertiary 2-phenylethyl, 2-(1-naphthyl)ethyl and 2-(2-naphthyl)ethyl amines were synthesized and their binding affinities for dopamine D(1), D(2) and serotonin 5-HT(1A) receptors evaluated in radioligand binding assays. All compounds were inactive in D(1) dopamine radioligand binding assay. The 2-(1-naphthyl)ethyl analogues expressed a low but significant binding affinity for the D(2) and moderate one for the 5-HT(1A) receptor subtypes. Most of the remaining compounds expressed binding affinity at the 5-HT(1A) receptor subtype but were inactive in D(2) receptor binding assay. Based on these results and considering the chemical characteristics of the compounds synthesized and evaluated for dopaminergic and serotonergic activity throughout the present study it can be concluded that hydrophobic type of interaction (stacking or edge-to-face) plays a significant role in the formation of receptor-ligand complexes of 2-(1-naphthyl)ethyl amines. This structural motive can be applied to design and synthesize new, more potent dopaminergic/serotonergic ligands by slight chemical modifications.",
publisher = "Wiley-Blackwell, Malden",
journal = "Archiv der Pharmazie",
title = "D(2) dopaminergic and 5-HT(1A) serotonergic activity of 2-(1-naphthyl)ethyl- and 2-(2-naphthyl)ethyl amines",
volume = "336",
number = "11",
pages = "514-522",
doi = "10.1002/ardp.200300776"
}

Šukalović, V., Roglić, G., Husinec, S., Kostić-Rajačić, S., Andrić, D.,& Šoškić, V.. (2003). D(2) dopaminergic and 5-HT(1A) serotonergic activity of 2-(1-naphthyl)ethyl- and 2-(2-naphthyl)ethyl amines. in Archiv der Pharmazie
Wiley-Blackwell, Malden., 336(11), 514-522.
https://doi.org/10.1002/ardp.200300776

Šukalović V, Roglić G, Husinec S, Kostić-Rajačić S, Andrić D, Šoškić V. D(2) dopaminergic and 5-HT(1A) serotonergic activity of 2-(1-naphthyl)ethyl- and 2-(2-naphthyl)ethyl amines. in Archiv der Pharmazie. 2003;336(11):514-522.
doi:10.1002/ardp.200300776 .

Šukalović, Vladimir, Roglić, Goran, Husinec, S, Kostić-Rajačić, Slađana, Andrić, Deana, Šoškić, Vukić, "D(2) dopaminergic and 5-HT(1A) serotonergic activity of 2-(1-naphthyl)ethyl- and 2-(2-naphthyl)ethyl amines" in Archiv der Pharmazie, 336, no. 11 (2003):514-522,
https://doi.org/10.1002/ardp.200300776 . .