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1-Cinnamyl-4-(2-methoxyphenyl)piperazines: Synthesis, binding properties, and docking to dopamine (D2) and serotonin (5-HT1A) receptors

Authorized Users Only
2007
Authors
Penjišević, Jelena
Šukalović, Vladimir
Andrić, Deana
Kostić Rajačić, Slađana
Šoškić, Vukić
Roglić, Goran
Article (Published version)
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Abstract
Clinical properties of atypical antipsychotics are based on their interaction with D2 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 (α1) 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-HT 2A receptors, high affinity to the D2 receptor and large variability in affinities for the α1 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 interaction...s of the aromatic ring of the arylpiperazine moiety with phenylalanine or tyrosine residues. Docking data for the D 2 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.

Keywords:
5-HT2A receptor / Dopamine D2 receptor / Piperazines / Serotonin 5-HT1A
Source:
Archiv der Pharmazie, 2007, 340, 9, 456-465
Publisher:
  • Wiley-V C H Verlag Gmbh, Weinheim
Funding / projects:
  • Sinteza i karakterizacija biološki aktivnih supstanci i kompjuterska simulacija bioloških sistema (RS-142009)

DOI: 10.1002/ardp.200700062

ISSN: 0365-6233

PubMed: 17763374

WoS: 000249747700002

Scopus: 2-s2.0-34748901387
[ Google Scholar ]
32
27
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/360
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
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://cer.ihtm.bg.ac.rs/handle/123456789/360
AB  - Clinical properties of atypical antipsychotics are based on their interaction with D2 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 (α1) 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-HT 2A receptors, high affinity to the D2 receptor and large variability in affinities for the α1 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 D 2 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 (D2) 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 D2 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 (α1) 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-HT 2A receptors, high affinity to the D2 receptor and large variability in affinities for the α1 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 D 2 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 (D2) 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 (D2) 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 (D2) 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 (D2) and serotonin (5-HT1A) receptors" in Archiv der Pharmazie, 340, no. 9 (2007):456-465,
https://doi.org/10.1002/ardp.200700062 . .

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