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Synthesis and antitumor activity of novel per-butyrylated glycosides of podophyllotoxin and its derivatives.

Abstract：

:A series of perbutyrylated glycosides of podophyllotoxin and its derivatives were synthesized and evaluated for their antitumor activity in vitro. Most of them exhibit cytotoxic activity against a panel of five human cancer cell lines (HL-60, SMMC-7721, A-549, MCF-7, SW480) using MTT assays. Among the synthesized compounds, epipodophyllotoxin α-d-galactopyranoside 8b, epipodophyllotoxin α-d-arabinopyranoside 8e, and podophyllotoxin β-d-glucopyranoside 11a show the highest potency of anticancer activity with their IC50 values ranging from 0.14 to 1.69μM. Structure activity relationship analysis indicates that the type of glycosidic linkage, the configuration at C-4 of the podophyllotoxin scaffold, and the substitution at 4'-position (OH vs OCH3) can all have significant effect on the potency of their anticancer activity. Several compounds are more active than the control drugs Etoposide and Cisplatin, suggesting their potential as anticancer agents for further development.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Zi CT,Yang D,Dong FW,Li GT,Li Y,Ding ZT,Zhou J,Jiang ZH,Hu JM

doi

10.1016/j.bmc.2015.02.021

subject

Has Abstract

pub_date

2015-04-01 00:00:00

pages

1437-46

issue

7

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(15)00115-7

journal_volume

23

pub_type

杂志文章

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