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Molecules 2013, 18(11), 13992-14012; doi:10.3390/molecules181113992

Synthesis and Anticancer Activity of Glucosylated Podophyllotoxin Derivatives Linked via 4β-Triazole Rings

State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China
Key Laboratory of Medicinal Chemistry for Natural Resource, Yunnan University, Kunming 650091, China
Department of Chemistry, Lakehead University, 955 Oliver Road, Thunder Bay, ON P7B 5E1, Canada
Author to whom correspondence should be addressed.
Received: 16 September 2013 / Revised: 4 November 2013 / Accepted: 5 November 2013 / Published: 13 November 2013
(This article belongs to the Section Medicinal Chemistry)
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A series of 4β-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 μM, 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.
Keywords: podophyllotoxin; 4β-triazole ring; click chemistry; anticancer activity podophyllotoxin; 4β-triazole ring; click chemistry; anticancer activity

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Zi, C.-T.; Xu, F.-Q.; Li, G.-T.; Li, Y.; Ding, Z.-T.; Zhou, J.; Jiang, Z.-H.; Hu, J.-M. Synthesis and Anticancer Activity of Glucosylated Podophyllotoxin Derivatives Linked via 4β-Triazole Rings. Molecules 2013, 18, 13992-14012.

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