Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein

Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein

A series of glycoconjugates, derivatives of genistein containing a C-glycosylated carbohydrate moiety, were synthesized and their anticancer activity was tested in vitro in the human cell lines HCT 116 and DU 145. The target compounds 15–17 were synthesized by treating ω-bromoalkyl C-glycosides der...

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Bibliographic Details
Main Authors: Wieslaw Szeja, Grzegorz Grynkiewicz, Tadeusz Bieg, Piotr Swierk, Anna Byczek, Katarzyna Papaj, Radosław Kitel, Aleksandra Rusin
Format: Article
Language:English
Published: MDPI AG 2014-05-01
Series:Molecules
Subjects:
L-rhamnal
C-glycosylation
genistein conjugates
cell cycle
Online Access:http://www.mdpi.com/1420-3049/19/6/7072
Description
Summary:A series of glycoconjugates, derivatives of genistein containing a C-glycosylated carbohydrate moiety, were synthesized and their anticancer activity was tested in vitro in the human cell lines HCT 116 and DU 145. The target compounds 15–17 were synthesized by treating ω-bromoalkyl C-glycosides derived from L-rhamnal (1) with a tetrabutylammonium salt of genistein. The new, metabolically stable analogs of previously studied O-glycosidic genistein derivatives inhibited proliferation of cancer cell lines through inhibition of the cell cycle.
ISSN:1420-3049

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