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Synthesis of C3-Neoglycosides of digoxigenin and their anticancer activities.

Abstract：

:Cardiac glycosides exhibit significant anticancer effects and the glycosyl substitution at C3 position of digoxigenin is pivotal for their biological activity. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and explore more potent anticancer agents, a series of C3-O-neoglycosides and C3-MeON-neoglycosides of digoxigenin were synthesized by the Koenigs-Knorr and neoglycosylation method, respectively. In addition, digoxigenin bisdigitoxoside and monodigitoxoside were prepared from digoxin by sodium periodate (NaIO4) oxidation and 6-aminocaproic acid hydrolysis. The SAR analysis revealed that C3-O-neoglycosides of digoxigenin exhibited stronger cytotoxicity and induction of Nur77 expression of tumor cells than C3-MeON-neoglycosides. Also, 3β-O-glycosides exhibited stronger anticancer effects than 3α-O-glycosides. Among them, 3β-O-(β-l-fucopyranosyl)-digoxigenin (3i) showed the highest activity on induction of Nur77 expression and translocation from the nucleus to cytoplasm, leading to cancer cell apoptosis.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Li XS,Ren YC,Bao YZ,Liu J,Zhang XK,Zhang YW,Sun XL,Yao XS,Tang JS

doi

10.1016/j.ejmech.2017.12.086

subject

Has Abstract

pub_date

2018-02-10 00:00:00

pages

252-262

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(17)31117-0

journal_volume

145

pub_type

杂志文章

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