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题名: Synthesis and Anticancer Activity of Glucosylated Podophyllotoxin Derivatives Linked via 4 beta-Triazole Rings
作者: Zi, Cheng-Ting1, 2; Xu, Feng-Qing1; Li, Gen-Tao1; null(李艳)1; Ding, Zhong-Tao2; Zhou, Jun1; Jiang, Zi-Hua3; Hu, Jiang-Miao1
刊名: MOLECULES
出版日期: 2013-11-01
卷号: 18, 期号:11, 页码:13992-14012
关键词: podophyllotoxin ; 4 beta-triazole ring ; click chemistry ; anticancer activity
文章类型: Article
英文摘要: A series of 4 beta-triazole-linked glucose podophyllotoxin conjugates have been designed and synthesized by employing a click chemistry approach. All the compounds were evaluated for their anticancer activity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using MTT assays. Most of these triazole derivatives have good anticancer activity. Among them, compound 35 showed the highest potency against all five cancer cell lines tested, with IC50 values ranging from 0.59 to 2.90 mu M, which is significantly more active than the drug etoposide currently in clinical use. Structure-activity relationship analysis reveals that the acyl substitution on the glucose residue, the length of oligoethylene glycol linker, and the 4'-demethylation of podophyllotoxin scaffold can significantly affect the potency of the anticancer activity. Most notably, derivatives with a perbutyrylated glucose residue show much higher activity than their counterparts with either a free glucose or a peracetylated glucose residue.
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
关键词[WOS]: DNA TOPOISOMERASE-II ; ANTITUMOR AGENTS ; BIOLOGICAL EVALUATION ; GLUCOSE TRANSPORTERS ; INHIBITORS ; CANCER ; ACID ; 4'-DEMETHYL-EPIPODOPHYLLOTOXIN ; GLYCOSYLATION ; BIOSYNTHESIS
收录类别: SCI
语种: 英语
WOS记录号: WOS:000330311500058
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.kib.ac.cn/handle/151853/19221
Appears in Collections:植物化学与西部植物资源持续利用国家重点实验室_期刊论文

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作者单位: 1.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Peoples R China
2.Yunnan Univ, Key Lab Med Chem Nat Resource, Kunming 650091, Peoples R China
3.Lakehead Univ, Dept Chem, Thunder Bay, ON P7B 5E1, Canada
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