Gluconjugates of 8-hydroxyquinolines as potential anti-cancer prodrugs.

Oliveri V, Giuffrida ML, Vecchio G, Aiello C, Viale M.

Dalton Trans. 2012 Apr 21;41(15):4530-5.

Dipartimento di Scienze Chimiche, University of Catania, Viale A. Doria 6, 95125 Catania, Italy.

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-{Beta}-D-glucopyranoside in order to compare this system to that of clioquinol. We also synthesized, 8-quinolinyl-{Beta}-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 {Beta}-glucosidase and these systems exhibit antiproliferative activity against different tumor cell lines in the presence of copper(II) ions.

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