Synthesis and Anticancer Activity of 4β-Triazole-podophyllotoxin Glycosides

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• 作者：Cheng-Ting Zi ; Gen-Tao Li ; Yan Li ; Jun Zhou…
• 关键词：Podophyllotoxin ; 4β ; Triazole ; podophyllotoxin ; Glycosides ; Click reaction ; Anticancer ; Synthesis
• 刊名：Natural Products and Bioprospecting
• 出版年：2015
• 出版时间：April 2015
• 年：2015
• 卷：5
• 期：2
• 页码：83-90
• 全文大小：685 KB
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• 作者单位：Cheng-Ting Zi (1) (2)
  Gen-Tao Li (1)
  Yan Li (1)
  Jun Zhou (1)
  Zhong-Tao Ding (2)
  Zi-Hua Jiang (3)
  Jiang-Miao Hu (1)
  
  1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, China
  2. Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, 650091, China
  3. Department of Chemistry, Lakehead University, 955 Oliver Road, Thunder Bay, ON, P7B 5E1, Canada
  
• 刊物主题：Plant Biochemistry; Bioorganic Chemistry; Medicinal Chemistry; Pharmacology/Toxicology; Plant Sciences; Food Science;
• 出版者：Springer Berlin Heidelberg
• ISSN：2192-2209

文摘

A series of novel 4β-triazole-podophyllotoxin glycosides were synthesized by utilizing the Click reaction. Evaluation of cytotoxicity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using MTT assay shows that most of these compounds show weak cytotoxicity. It was observed that compound 16 shows the highest activity with IC₅₀ values ranging from 2.85 to 7.28?μM, which is more potent than the control drugs etoposide and cisplatin against four of five cancer cell lines tested. Compound 16 is characterized with an α-d-galactosyl residue directly linked to the triazole ring and a 4-OH group on the E ring of the podophyllotoxin scaffold. HPLC investigation of representative compound indicates that incorporation of a sugar moiety seems to improve the chemical stability of the podophyllotoxin scaffold.