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

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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
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
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/360
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