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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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

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spelling	doaj-73c89522c53a4f90a9b022dac9b5366f2020-11-24T20:41:57ZengMDPI AGMolecules1420-30492014-05-011967072709310.3390/molecules19067072molecules19067072Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of GenisteinWieslaw Szeja0Grzegorz Grynkiewicz1Tadeusz Bieg2Piotr Swierk3Anna Byczek4Katarzyna Papaj5Radosław Kitel6Aleksandra Rusin7Department of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, PolandPharmaceutical Research Institute, Rydygiera 8, 01-793 Warsaw, PolandDepartment of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, PolandDepartment of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, PolandDepartment of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, PolandDepartment of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, PolandDepartment of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, PolandMaria Sklodowska-Curie Memorial Cancer Center & Institute of Oncology, Branch Gliwice, Wybrzeze AK 15, 44-100 Gliwice, PolandA 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.http://www.mdpi.com/1420-3049/19/6/7072L-rhamnalC-glycosylationgenistein conjugatescell cycle
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Wieslaw Szeja Grzegorz Grynkiewicz Tadeusz Bieg Piotr Swierk Anna Byczek Katarzyna Papaj Radosław Kitel Aleksandra Rusin
spellingShingle	Wieslaw Szeja Grzegorz Grynkiewicz Tadeusz Bieg Piotr Swierk Anna Byczek Katarzyna Papaj Radosław Kitel Aleksandra Rusin Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein Molecules L-rhamnal C-glycosylation genistein conjugates cell cycle
author_facet	Wieslaw Szeja Grzegorz Grynkiewicz Tadeusz Bieg Piotr Swierk Anna Byczek Katarzyna Papaj Radosław Kitel Aleksandra Rusin
author_sort	Wieslaw Szeja
title	Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein
title_short	Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein
title_full	Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein
title_fullStr	Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein
title_full_unstemmed	Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein
title_sort	synthesis and cytotoxicity of 2,3-enopyranosyl c-linked conjugates of genistein
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2014-05-01
description	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.
topic	L-rhamnal C-glycosylation genistein conjugates cell cycle
url	http://www.mdpi.com/1420-3049/19/6/7072
work_keys_str_mv	AT wieslawszeja synthesisandcytotoxicityof23enopyranosylclinkedconjugatesofgenistein AT grzegorzgrynkiewicz synthesisandcytotoxicityof23enopyranosylclinkedconjugatesofgenistein AT tadeuszbieg synthesisandcytotoxicityof23enopyranosylclinkedconjugatesofgenistein AT piotrswierk synthesisandcytotoxicityof23enopyranosylclinkedconjugatesofgenistein AT annabyczek synthesisandcytotoxicityof23enopyranosylclinkedconjugatesofgenistein AT katarzynapapaj synthesisandcytotoxicityof23enopyranosylclinkedconjugatesofgenistein AT radosławkitel synthesisandcytotoxicityof23enopyranosylclinkedconjugatesofgenistein AT aleksandrarusin synthesisandcytotoxicityof23enopyranosylclinkedconjugatesofgenistein
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Synthesis and Cytotoxicity of 2,3-Enopyranosyl C-Linked Conjugates of Genistein

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