title: Gluconjugates of 8-hydroxyquinolines as potential anti-cancer prodrugs.
abstract: 8-Hydroxyquinolines are systems of great interest in the field of inorganic and bioinorganic chemistry. They are metal-binding compounds and are known to exhibit a variety of biological activities, such as antibacterial and anticancer activities. Among these systems, clioquinol has been the focus of a renewed interest in recent years. In this scenario, we synthesized and characterized the new clioquinol glucoconjugate, 5-chloro-7-iodo-8-quinolinyl-β-D-glucopyranoside in order to compare this system to that of clioquinol. We also synthesized, 8-quinolinyl-β-D-glucopyranoside, an 8-hydroxyquinoline glucoconjugate. The reason for the development of glucoconjugates is the glucose avidity, and the over-expression of glucose transporters in cancer cells. Here we demonstrate that glycoconjugates are cleaved in vitro by β-glucosidase and these systems exhibit antiproliferative activity against different tumor cell lines in the presence of copper(II) ions.
authors.affiliation: Dipartimento di Scienze Chimiche, University of Catania, Viale A. Doria 6, 95125 Catania, Italy.
authors.forename: Valentina
authors.initials: V
authors.lastname: Oliveri
authors.forename: Maria Laura
authors.initials: ML
authors.lastname: Giuffrida
authors.forename: Graziella
authors.initials: G
authors.lastname: Vecchio
authors.forename: Cinzia
authors.initials: C
authors.lastname: Aiello
authors.forename: Maurizio
authors.initials: M
authors.lastname: Viale
mesh_terms: D000970:Antineoplastic Agents / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D006001:Glycoconjugates / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D015125:Oxyquinoline / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D011355:Prodrugs / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D001617:beta-Glucosidase / Q000378:metabolism
chemical_list: D000970:Antineoplastic Agents; D006001:Glycoconjugates; D011355:Prodrugs; D015125:Oxyquinoline; D001617:beta-Glucosidase