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Dalton Trans. 2012 Apr 21;41(15):4530-5. doi: 10.1039/c2dt12371a. Epub 2012 Feb 22.

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

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  • 1Dipartimento 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-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.

PMID:
22354329
[PubMed - indexed for MEDLINE]
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