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 language | English |
|---|---|
| Pages (from-to) | 2023-2034 |
| Number of pages | 12 |
| Journal | Dalton Transactions |
| Volume | 42 |
| Issue number | 6 |
| DOIs | |
| Publication status | Published - Feb 14 2013 |
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ASJC Scopus subject areas
- Inorganic Chemistry
Cite this
Glycosylated copper(ii) ionophores as prodrugs for β-glucosidase activation in targeted cancer therapy. / Oliveri, Valentina; Viale, Maurizio; Caron, Giulia; Aiello, Cinzia; Gangemi, Rosaria; Vecchio, Graziella.
In: Dalton Transactions, Vol. 42, No. 6, 14.02.2013, p. 2023-2034.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Glycosylated copper(ii) ionophores as prodrugs for β-glucosidase activation in targeted cancer therapy
AU - Oliveri, Valentina
AU - Viale, Maurizio
AU - Caron, Giulia
AU - Aiello, Cinzia
AU - Gangemi, Rosaria
AU - Vecchio, Graziella
PY - 2013/2/14
Y1 - 2013/2/14
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84872550607&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84872550607&partnerID=8YFLogxK
U2 - 10.1039/c2dt32429f
DO - 10.1039/c2dt32429f
M3 - Article
C2 - 23174818
AN - SCOPUS:84872550607
VL - 42
SP - 2023
EP - 2034
JO - Dalton Transactions
JF - Dalton Transactions
SN - 1477-9226
IS - 6
ER -