Bronowska A, Chilmonczyk Z, Leś A, Edvardsen O, Ostensen R, Sylte I
Department of Chemistry, University of Warsaw, Poland.
J Comput Aided Mol Des. 2001 Nov;15(11):1005-23. doi: 10.1023/a:1014856107486.
In the present study experimentally determined ligand selectivity of three methylated buspirone analogues (denoted as MM2, MM5 and P55) towards 5-HT1A and 5-HT2A serotonin receptors was theoretically investigated on a molecular level. The relationships between the ligand structure and 5-HT1A and 5-HT2A receptor affinities were studied and the results were found to be in agreement with the available site-directed mutagenesis and binding affinity data. Molecular dynamics (MD) simulations of ligand-receptor complexes were performed for each investigated analogue, docked twice into the central cavity of 5-HT1A/5-HT2A, each time in a different orientation. Present results were compared with our previous theoretical results, obtained for buspirone and its non-methylated analogues. It was found that due to the presence of the methyl group in the piperazine ring the ligand position alters and the structure of the ligand-receptor complex is modified. Further, the positions of derivatives with pyrimidinyl aromatic moiety and quinolinyl moiety are significantly different at the 5-HT2A receptor. Thus, methylation of such derivatives alters the 3D structures of ligand-receptor complexes in different ways. The ligand-induced changes of the receptor structures were also analysed. The obtained results suggest, that helical domains of both receptors have different dynamical behaviour. Moreover, both location and topography of putative binding sites for buspirone analogues are different at 5-HT1A and 5-HT2A receptors.
在本研究中,从分子水平对三种甲基化丁螺环酮类似物(分别记为MM2、MM5和P55)针对5-羟色胺1A(5-HT1A)和5-羟色胺2A(5-HT2A)血清素受体的实验测定配体选择性进行了理论研究。研究了配体结构与5-HT1A和5-HT2A受体亲和力之间的关系,结果发现与现有的定点诱变和结合亲和力数据一致。对每种研究的类似物进行了配体-受体复合物的分子动力学(MD)模拟,将其两次对接至5-HT1A/5-HT2A的中心腔,每次方向不同。将目前的结果与我们之前针对丁螺环酮及其非甲基化类似物获得的理论结果进行了比较。发现由于哌嗪环中存在甲基,配体位置发生改变,配体-受体复合物的结构也被修饰。此外,具有嘧啶基芳族部分和喹啉基部分的衍生物在5-HT2A受体处的位置显著不同。因此,此类衍生物的甲基化以不同方式改变了配体-受体复合物的三维结构。还分析了配体诱导的受体结构变化。所得结果表明,两种受体的螺旋结构域具有不同的动力学行为。此外,丁螺环酮类似物假定结合位点的位置和拓扑结构在5-HT1A和5-HT2A受体处均不同。