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Issue 15, 2012
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Gluconjugates of 8-hydroxyquinolines as potential anti-cancer prodrugs

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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.

Graphical abstract: Gluconjugates of 8-hydroxyquinolines as potential anti-cancer prodrugs

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Supplementary files

Article information


Submitted
07 Dec 2011
Accepted
13 Jan 2012
First published
22 Feb 2012

Dalton Trans., 2012,41, 4530-4535
Article type
Paper

Gluconjugates of 8-hydroxyquinolines as potential anti-cancer prodrugs

V. Oliveri, M. L. Giuffrida, G. Vecchio, C. Aiello and M. Viale, Dalton Trans., 2012, 41, 4530
DOI: 10.1039/C2DT12371A

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