Glycosylated copper(ii) ionophores as prodrugs for β-glucosidase activation in targeted cancer therapy

Valentina Oliveri, Maurizio Viale, Giulia Caron, Cinzia Aiello, Rosaria Gangemi, Graziella Vecchio

Research output: Contribution to journalArticle

Abstract

8-Hydroxyquinoline derivatives are metal-binding compounds that have recently attracted interest as therapeutic agents for cancer therapy. In this scenario, we designed and synthesized three new glucoconjugates, 5,7-dichloro-8-quinolinyl-β-d-glucopyranoside, 5-chloro-8-quinolinyl- β-d-glucopyranoside and 2-methyl-8-quinolinyl-β-d-glucopyranoside and investigated their biological properties in comparison to the parent 8-hydroxyquinoline derivatives in the presence of Cu2+. In vitro data show that 2 out of 3 glycosylated compounds possess a pharmacologically- relevant antiproliferative activity against tumor cells, similar to that of their parent compounds; this activity is associated with a relevant triggering of apoptosis. The pharmacological profile of the glucoconjugates depends on the cellular enzymatic β-glucosidase activity, as demonstrated by the inhibition of antiproliferative activity in the presence of the 2,5-dideoxy-2,5-imino-d-mannitol.

Original languageEnglish
Pages (from-to)2023-2034
Number of pages12
JournalDalton Transactions
Volume42
Issue number6
DOIs
Publication statusPublished - Feb 14 2013

ASJC Scopus subject areas

  • Inorganic Chemistry

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