Gluconjugates of 8-hydroxyquinolines as potential anti-cancer prodrugs

Valentina Oliveri, Maria Laura Giuffrida, Graziella Vecchio, Cinzia Aiello, Maurizio Viale

Research output: Contribution to journalArticle

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.

Original languageEnglish
Pages (from-to)4530-4535
Number of pages6
JournalDalton Transactions
Volume41
Issue number15
DOIs
Publication statusPublished - Apr 21 2012

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ASJC Scopus subject areas

  • Inorganic Chemistry

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