title: Synthesis and cytotoxicity of 2,3-enopyranosyl C-linked conjugates of genistein.
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 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.
authors.affiliation: Department of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, Poland. wieslaw.szeja@adres.pl.
authors.forename: Wieslaw
authors.initials: W
authors.lastname: Szeja
authors.affiliation: Pharmaceutical Research Institute, Rydygiera 8, 01-793 Warsaw, Poland. g.grynkiewicz@ifarm.eu.
authors.forename: Grzegorz
authors.initials: G
authors.lastname: Grynkiewicz
authors.affiliation: Department of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, Poland. tadeusz.bieg@polsl.pl.
authors.forename: Tadeusz
authors.initials: T
authors.lastname: Bieg
authors.affiliation: Department of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, Poland. piotr.swierk@polsl.pl.
authors.forename: Piotr
authors.initials: P
authors.lastname: Swierk
authors.affiliation: Department of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, Poland. anna.byczek@polsl.pl.
authors.forename: Anna
authors.initials: A
authors.lastname: Byczek
authors.affiliation: Department of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, Poland. katarzyna.papaj@polsl.pl.
authors.forename: Katarzyna
authors.initials: K
authors.lastname: Papaj
authors.affiliation: Department of Chemistry, Biochemistry and Biotechnology, Silesian Technical University, Krzywoustego 8, 44-100 Gliwice, Poland. radoslaw_kitel@o2.pl.
authors.forename: Radosław
authors.initials: R
authors.lastname: Kitel
authors.affiliation: Maria Sklodowska-Curie Memorial Cancer Center & Institute of Oncology, Branch Gliwice, Wybrzeze AK 15, 44-100 Gliwice, Poland. arusin@io.gliwice.pl.
authors.forename: Aleksandra
authors.initials: A
authors.lastname: Rusin
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry*; D002453:Cell Cycle / Q000187:drug effects; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects; D019833:Genistein / Q000737:chemistry* / Q000494:pharmacology*; D006031:Glycosylation; D045325:HCT116 Cells; D006801:Humans; D015394:Molecular Structure; D000644:Quaternary Ammonium Compounds / Q000737:chemistry
chemical_list: D000970:Antineoplastic Agents; D000644:Quaternary Ammonium Compounds; C009405:tetrabutylammonium; D019833:Genistein