Click Glycosylation for the Synthesis of 1,2,3-Triazole-Linked Picropodophyllotoxin Glycoconjugates and Their Anticancer Activity
Zi, Cheng-Ting1; Yang, Liu2; Gao, Wei2; Li, Yan2; Zhou, Jun2; Ding, Zhong-Tao3; Hu, Jiang-Miao2; Jiang, Zi-Hua4
2017-07-21
Source PublicationCHEMISTRYSELECT
ISSN2365-6549
Volume2Issue:18Pages:5038-5044
AbstractCu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction was employed successfully to prepare a series 4 beta-triazole-linked picropodophyllotoxin glycoconjugates (25 - 34). Maltose residue, 1,6-beta-D-diglucose residue, and several triazole-linked disaccharide and trisaccharide residues were coupled to 4 beta-azido-podophyllotoxin derivatives through click glycosylation strategy. The initial click glycosylation products were treated with catalytic amount of NaOCH3 to facilitate global deacylation and epimerization at C-2 position to yield the cis-gamma-lactone moiety in the picropodophyllotoxin glycoconjugates. Most of these picropodophyllotoxin glycoconjugates show weak cytotoxicity (IC50 > 40 mu M) against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) as indicated by in vitro MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay. However, compound 27 that contains a 1,6-beta-D-di-glucose residue displays strong anticancer activity against all cancer cell lines tested, with IC50 values ranging from 0.67 to 7.41 mu M, which is significantly more potent than the control drug etoposide against four of the five cancer cells tested. Structure activity relationship analysis suggests that the 4'-O-methyl group on the E ring of podophyllotoxin scaffold is perhaps important for the anticancer activity of glycosylated picropodophyllotoxin derivatives with a cis-g-lactone moiety.
KeywordAnticancer Activity Cu(i)-catalyzed Click Reaction Glycoconjugates Picropodophyllotoxin Podophyllotoxin
Subject AreaChemistry, Multidisciplinary
DOI10.1002/slct.201700347
Indexed BySCI
Language英语
WOS IDWOS:000406674900009
Citation statistics
Cited Times:3[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.kib.ac.cn/handle/151853/54940
Collection植物化学与西部植物资源持续利用国家重点实验室
Affiliation1.Yunnan Agr Univ, Key Lab Pu Er Tea Sci, Minist Educ, Kunming 650201, Yunnan, Peoples R China
2.Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China
3.Yunnan Univ, Sch Chem Sci & Technol, Key Lab Med Chem Nat Resource, Minist Educ, Kunming 650091, Yunnan, Peoples R China
4.Lakehead Univ, Dept Chem, 955 Oliver Rd, Thunder Bay, ON P7B 5E1, Canada
Recommended Citation
GB/T 7714
Zi, Cheng-Ting,Yang, Liu,Gao, Wei,et al. Click Glycosylation for the Synthesis of 1,2,3-Triazole-Linked Picropodophyllotoxin Glycoconjugates and Their Anticancer Activity[J]. CHEMISTRYSELECT,2017,2(18):5038-5044.
APA Zi, Cheng-Ting.,Yang, Liu.,Gao, Wei.,Li, Yan.,Zhou, Jun.,...&Jiang, Zi-Hua.(2017).Click Glycosylation for the Synthesis of 1,2,3-Triazole-Linked Picropodophyllotoxin Glycoconjugates and Their Anticancer Activity.CHEMISTRYSELECT,2(18),5038-5044.
MLA Zi, Cheng-Ting,et al."Click Glycosylation for the Synthesis of 1,2,3-Triazole-Linked Picropodophyllotoxin Glycoconjugates and Their Anticancer Activity".CHEMISTRYSELECT 2.18(2017):5038-5044.
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