Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives
Zi, Cheng-Ting1,2; Yang, Dan2; Dong, Fa-Wu2; Li, Gen-Tao2; Li, Yan2; Ding, Zhong-Tao1; Zhou, Jun2; Jiang, Zi-Hua3; Hu, Jiang-Miao2; Jiang,ZH (reprint author),Yunnan Univ,Key Lab Med Chem Nat Resource,Kunming 650091,Peoples R China.; zjiang@lakeheadu.ca; hujiangmiao@mail.kib.ac.cn
2015-04-01
发表期刊BIOORGANIC & MEDICINAL CHEMISTRY
卷号23期号:7页码:1437-1446
摘要A series of perbutyrylated glycosides of podophyllotoxin and its derivatives were synthesized and evaluated for their antitumor activity in vitro. Most of them exhibit cytotoxic activity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using MTT assays. Among the synthesized compounds, epipodophyllotoxin alpha-D-galactopyranoside 8b, epipodophyllotoxin a-D-arabinopyranoside 8e, and podophyllotoxin beta-D-glucopyranoside 11a show the highest potency of anticancer activity with their IC50 values ranging from 0.14 to 1.69 mu M. Structure activity relationship analysis indicates that the type of glycosidic linkage, the configuration at C-4 of the podophyllotoxin scaffold, and the substitution at 4'-position (OH vs OCH3) can all have significant effect on the potency of their anticancer activity. Several compounds are more active than the control drugs Etoposide and Cisplatin, suggesting their potential as anticancer agents for further development. (C) 2015 Elsevier Ltd. All rights reserved.
关键词Podophyllotoxin Epipodophyllotoxin 4 '-demethylepipodophyllotoxin Butyrylated Glycosides Antitumor Cytotoxic Synthesis
资助信息Fund of State Key Laboratory of Phytochemistry and Plant Resource in West China [P2010-KF07]
收录类别SCI
语种英语
引用统计
文献类型期刊论文
条目标识符http://ir.kib.ac.cn/handle/151853/20630
专题植物化学与西部植物资源持续利用国家重点实验室
通讯作者Jiang,ZH (reprint author),Yunnan Univ,Key Lab Med Chem Nat Resource,Kunming 650091,Peoples R China.; zjiang@lakeheadu.ca; hujiangmiao@mail.kib.ac.cn
作者单位1.Yunnan Univ, Key Lab Med Chem Nat Resource, Kunming 650091, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
3.Lakehead Univ, Dept Chem, Thunder Bay, ON P7B 5E1, Canada
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Zi, Cheng-Ting,Yang, Dan,Dong, Fa-Wu,et al. Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives[J]. BIOORGANIC & MEDICINAL CHEMISTRY,2015,23(7):1437-1446.
APA Zi, Cheng-Ting.,Yang, Dan.,Dong, Fa-Wu.,Li, Gen-Tao.,Li, Yan.,...&hujiangmiao@mail.kib.ac.cn.(2015).Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives.BIOORGANIC & MEDICINAL CHEMISTRY,23(7),1437-1446.
MLA Zi, Cheng-Ting,et al."Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives".BIOORGANIC & MEDICINAL CHEMISTRY 23.7(2015):1437-1446.
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