2D-and 3D-QSAR studies on 54 anti-tumor Rubiaceae-type cyclopeptides
Yan, He1,2; Pan, Xulin1; Tan, Ninghua1; Fan, Junting1,2; Zeng, Guangzhi1; Han, Hongjin1
2009-09-01
Source PublicationEUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume44Issue:9Pages:3425-3432
AbstractRA-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.
KeywordRubiaceae-type Cyclopeptides Hqsar Comfa Comsia Anti-tumor Activity
Subject AreaChemistry, Medicinal
DOI10.1016/j.ejmech.2009.02.005
Indexed BySCI
Language英语
WOS Research AreaPharmacology & Pharmacy
WOS SubjectChemistry, Medicinal
WOS IDWOS:000268744700007
Citation statistics
Cited Times:9[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/5072
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.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
Recommended Citation
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.
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