8-Hydroxyquinoline derivatives are metal-binding compounds that have recently awakened interest as therapeutic agents for cancer therapy. In this scenario, we designed and synthesized three new glucoconjugates, 5,7-dichloro-8-quinolinyl-â-D-glucopyranoside, 5-chloro-8-quinolinyl-â-D-glucopyranoside and 2-methyl-8-quinolinyl-â-D-glucopyranoside and investigated their biological 10 properties in comparison to the parent 8-hydroxyquinoline derivatives in the presence of Cu2+. In vitro data show that 2 out of 3 glycosilated 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 â-glucosidase activity, as demonstrated by the inhibition of antiproliferative activity in 15 the presence of the 2,5-dideoxy-2,5-imino-D-mannitol.

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

CARON, Giulia;
2013-01-01

Abstract

8-Hydroxyquinoline derivatives are metal-binding compounds that have recently awakened interest as therapeutic agents for cancer therapy. In this scenario, we designed and synthesized three new glucoconjugates, 5,7-dichloro-8-quinolinyl-â-D-glucopyranoside, 5-chloro-8-quinolinyl-â-D-glucopyranoside and 2-methyl-8-quinolinyl-â-D-glucopyranoside and investigated their biological 10 properties in comparison to the parent 8-hydroxyquinoline derivatives in the presence of Cu2+. In vitro data show that 2 out of 3 glycosilated 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 â-glucosidase activity, as demonstrated by the inhibition of antiproliferative activity in 15 the presence of the 2,5-dideoxy-2,5-imino-D-mannitol.
2013
42
6
2023
4203
Oliveri V.; Viale M.; Caron G.; Aiello C.; Gangemi R.; Vecchio G.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2318/125799
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