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N-苯基-4-吡唑并[1,5-b]哒嗪-3-基嘧啶-2-胺系列衍生物对糖原合成酶激酶-3的抑制模式:分子对接和三维定量构效关系分析

Inhibitory mode of N-phenyl-4-pyrazolo[1,5-b] pyridazin-3-ylpyrimidin-2-amine series derivatives against GSK-3: molecular docking and 3D-QSAR analyses.

作者信息

Xiao Jingfa, Guo Zongru, Guo Yanshen, Chu Fengming, Sun Piaoyang

机构信息

Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China and Jiangsu Hengrui Medicine Co., Ltd, Jiangsu, China.

出版信息

Protein Eng Des Sel. 2006 Feb;19(2):47-54. doi: 10.1093/protein/gzi074. Epub 2005 Dec 9.

Abstract

Glycogen synthase kinase 3 (GSK-3) inhibition is an important research topic because of its wide range of associated health implications. The interaction mode of a series of N-phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine compounds with human GSK-3 has been studied using molecular docking and 3D-QSAR approaches. In the 3D-QSAR studies, the molecular alignment and conformation determination are so important that they affect the success of a model. Flexible docking (AutoDock3.0.5) was used for the determination of 'active' conformation and molecular alignment. Comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were used to develop 3D-QSAR models of 80 N-phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amine compounds. The r(2) values were 0.870 and 0.861 for CoMFA and CoMSIA models, respectively. The predictive ability of these models was validated by 10 compounds of the test set. Mapping these models back to the topology of the active site of GSK-3 led to a better understanding of the vital N-phenyl-4-pyrazolo[1,5-b]pyridazin-3-ylpyrimidin-2-amines-GSK-3 interactions. The results demonstrate that combination of ligand-based and receptor-based modeling is a powerful approach to build 3D-QSAR models. The interaction mode from this study may be helpful for the design of a novel inhibitor and guide the selection of candidate sites for further experimental studies on site-directed mutagenesis.

摘要

糖原合酶激酶3(GSK-3)抑制是一个重要的研究课题,因为它与广泛的健康问题相关。使用分子对接和3D-QSAR方法研究了一系列N-苯基-4-吡唑并[1,5-b]哒嗪-3-基嘧啶-2-胺化合物与人GSK-3的相互作用模式。在3D-QSAR研究中,分子排列和构象确定非常重要,因为它们会影响模型的成功。使用柔性对接(AutoDock3.0.5)来确定“活性”构象和分子排列。采用比较分子场分析(CoMFA)和比较分子相似性指数分析(CoMSIA)来建立80种N-苯基-4-吡唑并[1,5-b]哒嗪-3-基嘧啶-2-胺化合物的3D-QSAR模型。CoMFA和CoMSIA模型的r(2)值分别为0.870和0.861。通过测试集中的10种化合物验证了这些模型的预测能力。将这些模型映射回GSK-3活性位点的拓扑结构,有助于更好地理解关键的N-苯基-4-吡唑并[1,5-b]哒嗪-3-基嘧啶-2-胺与GSK-3的相互作用。结果表明,基于配体和基于受体的建模相结合是构建3D-QSAR模型的有力方法。本研究的相互作用模式可能有助于新型抑制剂的设计,并指导定点诱变进一步实验研究候选位点的选择。

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