Synthesis and Anticancer Activity of Glucosylated Podophyllotoxin Derivatives Linked via 4 beta-Triazole Rings
Zi, Cheng-Ting1,2; Xu, Feng-Qing1; Li, Gen-Tao1; Li, Yan1; Ding, Zhong-Tao2; Zhou, Jun1; Jiang, Zi-Hua3; Hu, Jiang-Miao1
2013-11-01
Source PublicationMOLECULES
Volume18Issue:11Pages:13992-14012
AbstractA 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.
KeywordPodophyllotoxin 4 Beta-triazole Ring Click Chemistry Anticancer Activity
Indexed BySCI
Language英语
WOS Research AreaChemistry
WOS SubjectChemistry, Organic
WOS IDWOS:000330311500058
Citation statistics
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/19221
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 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
Recommended Citation
GB/T 7714
Zi, Cheng-Ting,Xu, Feng-Qing,Li, Gen-Tao,et al. Synthesis and Anticancer Activity of Glucosylated Podophyllotoxin Derivatives Linked via 4 beta-Triazole Rings[J]. MOLECULES,2013,18(11):13992-14012.
APA Zi, Cheng-Ting.,Xu, Feng-Qing.,Li, Gen-Tao.,Li, Yan.,Ding, Zhong-Tao.,...&Hu, Jiang-Miao.(2013).Synthesis and Anticancer Activity of Glucosylated Podophyllotoxin Derivatives Linked via 4 beta-Triazole Rings.MOLECULES,18(11),13992-14012.
MLA Zi, Cheng-Ting,et al."Synthesis and Anticancer Activity of Glucosylated Podophyllotoxin Derivatives Linked via 4 beta-Triazole Rings".MOLECULES 18.11(2013):13992-14012.
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