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Journal of Chemistry
Volume 2013 (2013), Article ID 951392, 14 pages
http://dx.doi.org/10.1155/2013/951392
Research Article

C-Glycosidic Genistein Conjugates and Their Antiproliferative Activity

1Center for Translational Research and Molecular Biology of Cancer, Maria Sklodowska-Curie Memorial Cancer Center and Institute of Oncology, Wybrzeze AK 15, 44-100 Gliwice, Poland
2Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland
3Pharmaceutical Research Institute, Rydygiera 8, 01-793 Warsaw, Poland

Received 25 October 2012; Revised 22 March 2013; Accepted 2 April 2013

Academic Editor: Mehmet Emin Duru

Copyright © 2013 Aleksandra Rusin et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

This paper presents our attempt to investigate scopes and the limitations of olefin cross-metathesis (CM) reaction in the synthesis of complex C-glycosides of genistein and evaluation of their antiproliferative activities. Novel genistein glycoconjugates were synthesized with the utility of CM reaction initiated by first and second generation of Grubbs catalysts. The relative reactivity of utilized olefins, based on categories proposed by Grubbs, was estimated. In vitro experiments in cancer cell lines showed that the selected derivatives (3a and 3f) exhibited higher antiproliferative potential than the parent compound, genistein, and were able to block the cell cycle in the G2/M phase. The observed mechanism of action of C-glycosidic derivatives was similar to the activity of their O-glycosidic counterparts. These compounds were stable in culture medium. The obtained results show that our approach to genistein modification with application of cross-metathesis reaction allowed to obtain stable glycoconjugates with improved anticancer potential, compared to the parent isoflavone.