2D-and 3D-QSAR studies on 54 anti-tumor Rubiaceae-type cyclopeptides

CORC > 昆明植物研究所 > 中国科学院昆明植物研究所 > 植物化学与西部植物资源持续利用国家重点实验室

	2D-and 3D-QSAR studies on 54 anti-tumor Rubiaceae-type cyclopeptides
	Yan, He 1,2; Pan, Xulin 1; Tan, Ninghua 1; Fan, Junting 1,2; Zeng, Guangzhi 1; Han, Hongjin 1
刊名	EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
	2009-09-01
卷号	44 期号:9 页码:3425-3432
关键词	Rubiaceae-type cyclopeptides HQSAR CoMFA CoMSIA Anti-tumor activity
英文摘要	RA-VII, a bicyclic hexapeptide isolated from the roots of Rubia cordifolia, Rubia akane belongs to Rubiaceae-type cyclopeptides (RAS) and has attracted much attention for its potent anti-tumor activity and its bicyclic structure incorporating the isodityrosine moiety. In this work, hologram quantitative structure-activity relationship (HQSAR), comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA) methods were employed to develop 2D- and 3D-QSAR models for 54 anti-tumor RAS. The LOO cross-validated q(2) values of HQSAR, CoMFA and CoMSIA models are 0.701, 0.510 and 0.613, respectively. The predictive ability of these models was validated by the test set including 7 RAS, and the predicted IC(50) values were in good agreement with the experimental IC50 values. HQSAR result showed that chirality descriptor plays an important role in anti-tumor activity of RAS and OMe at R(1) and R(2) is necessary for increasing their activity. CoMFA and CoMSIA results demonstrated that small bulky and electropositive side chains at R(3) Position and hydrophobic groups at R(7) and R(8) positions will increase their activity, and intra-molecular hydrogen bonds between residues 1 and 4 are necessary to maintain the pharmacophoric conformation of RAS. These results may be helpful in designing novel and potential anti-tumor RAS. (C) 2009 Elsevier Masson SAS. All rights reserved.
学科主题	Chemistry, Medicinal
类目[WOS]	Chemistry, Medicinal
研究领域[WOS]	Pharmacology & Pharmacy
关键词[WOS]	AKANE RA DERIVATIVES ; CYCLIC HEXAPEPTIDES ; VII ; PREDICTION ; INHIBITORS ; BINDING ; ANALOGS ; COMFA ; FIELD
收录类别	SCI
语种	英语
WOS记录号	WOS:000268744700007
公开日期	2012-04-05
内容类型	期刊论文
源URL	[http://ir.kib.ac.cn/handle/151853/5072]
专题	昆明植物研究所_植物化学与西部植物资源持续利用国家重点实验室
作者单位	1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources W China, Kunming 650204, Yunnan, Peoples R China 2.Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
推荐引用方式 GB/T 7714	Yan, He,Pan, Xulin,Tan, Ninghua,et al. 2D-and 3D-QSAR studies on 54 anti-tumor Rubiaceae-type cyclopeptides[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2009,44(9):3425-3432.
APA	Yan, He,Pan, Xulin,Tan, Ninghua,Fan, Junting,Zeng, Guangzhi,&Han, Hongjin.(2009).2D-and 3D-QSAR studies on 54 anti-tumor Rubiaceae-type cyclopeptides.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,44(9),3425-3432.
MLA	Yan, He,et al."2D-and 3D-QSAR studies on 54 anti-tumor Rubiaceae-type cyclopeptides".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 44.9(2009):3425-3432.