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

Bioorganic & Medicinal Chemistry
Cheng-Ting ZiJiang-Miao Hu

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.

References

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Nov 17, 2004·Mini Reviews in Medicinal Chemistry·Steven J Miller
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Citations

Nov 30, 2018·Endocrine, Metabolic & Immune Disorders Drug Targets·Haroon KhanAtanas G Atanasov
Apr 4, 2018·Current Medicinal Chemistry·Haroon KhanAnupam Bishayee

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