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Molecules 2014, 19(6), 7072-7093; doi:10.3390/molecules19067072

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

1
Department of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, Poland
2
Pharmaceutical Research Institute, Rydygiera 8, 01-793 Warsaw, Poland
3
Maria Sklodowska-Curie Memorial Cancer Center & Institute of Oncology, Branch Gliwice, Wybrzeze AK 15, 44-100 Gliwice, Poland
*
Authors to whom correspondence should be addressed.
Received: 25 March 2014 / Revised: 23 May 2014 / Accepted: 23 May 2014 / Published: 30 May 2014
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Abstract

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 1517 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. View Full-Text
Keywords: L-rhamnal; C-glycosylation; genistein conjugates; cell cycle L-rhamnal; C-glycosylation; genistein conjugates; cell cycle
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MDPI and ACS Style

Szeja, W.; Grynkiewicz, G.; Bieg, T.; Swierk, P.; Byczek, A.; Papaj, K.; Kitel, R.; Rusin, A. Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein. Molecules 2014, 19, 7072-7093.

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