Issue 6, 2013

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

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.

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

Supplementary files

Article information

Article type
Paper
Submitted
11 Oct 2012
Accepted
02 Nov 2012
First published
06 Nov 2012

Dalton Trans., 2013,42, 2023-2034

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

V. Oliveri, M. Viale, G. Caron, C. Aiello, R. Gangemi and G. Vecchio, Dalton Trans., 2013, 42, 2023 DOI: 10.1039/C2DT32429F

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