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Antiproliferative activity of novel synthetic genistein glycoside derivatives

Jadwiga R. Zawisza-Puchałka 1Wiesław Szeja 1Aleksandra Rusin 2Zdzisław Krawczyk 2

1. Silesian University of Technology, Department of Organic Chem., Bioorganic Chem. and Biotechnol., Krzywoustego 4, Gliwice 44-100, Poland
2. Maria Sklodowska-Curie Memorial Cancer Center and Institute of Oncology, Gliwice 44-100, Poland

Abstract
Genistein, a naturally occurring soy isoflavonoid, displays antitumor, antioxidant and antiinflammatory properties. It inhibits the activity of topoisomerases and several protein-tyrosine kinases. Genistein is capable of binding to the estrogen receptor. These activities, along with low toxicity, make genistein an important candidate for experimental anticancer therapy, as well as new lead-compound for anticancer drug design [1].
The principal aim of this study was the synthesis of glycoconjugates, which are the drug candidates in antitumor therapy research program. The sugar part is connected to isoflavonoid ring system through a carbonic chain. Our thesis is that the structure modification of glycoconjugates should enhance the bioavailability of these compounds. Therefore, we decided to carry out reactions of glycals with glycosyl acceptors - derivatives of genistein, and we obtained glycoconjugates with high α –stereoselectivity [2].

This new class of substances was shown to possess anticancer activity. Cytotoxic activity of genistein glycoconjugates was evaluated against the model cell lines. Active derivatives were processed for subsequent in vitro toxicity test. For each active derivative IC50 values were obtained. It was found, that all new compounds inhibit proliferation of various cancer cells.

Acknowledgementα
Research studies part-financed by the European Union within the European Regional Development Fund (POIG. 01.01.02-14-102/09).

References
[1] Aleksandra Rusin, Zdzisław Krawczyk, Grzegorz Grynkiewicz, Jadwiga Zawisza-Puchałka, Wiesław Szeja, „Synthetic derivatives of genistein, properties and possible applications” (sent to Acta Biochimica Polonica)
[2] Polish Patent Application P384578

 

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Related papers

Presentation: Poster at VII Multidyscyplinarna Konferencja Nauki o Leku, by Jadwiga R. Zawisza-Puchałka
See On-line Journal of VII Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2010-03-14 19:05
Revised:   2010-04-01 10:24