Gluconjugates of 8-hydroxyquinolines as potential anti-cancer prodrugs

Dalton Transactions : an International Journal of Inorganic Chemistry
Valentina OliveriMaurizio Viale

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.

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Citations

Oct 12, 2013·Drug Design, Development and Therapy·Veda PrachayasittikulVirapong Prachayasittikul
Dec 3, 2014·Journal of Inorganic Biochemistry·Valentina OliveriGraziella Vecchio
Oct 1, 2013·Chemical Science·Emilia C Calvaresi, Paul J Hergenrother
Feb 19, 2016·European Journal of Medicinal Chemistry·Gabriela Pastuch-GawołekRobert Musiol
Mar 19, 2016·Medicinal Research Reviews·Chin S KueHong B Lee
May 19, 2016·European Journal of Medicinal Chemistry·Valentina Oliveri, Graziella Vecchio
Mar 24, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Marian E Helsel, Katherine J Franz
May 28, 2014·Chemistry : a European Journal·Valentina OliveriGraziella Vecchio
Sep 17, 2013·Chemistry : a European Journal·Valentina OliveriJohn Spencer
Feb 29, 2020·Recent Patents on Anti-cancer Drug Discovery·Raheel KhanQ Ping Dou
Sep 22, 2017·Metallomics : Integrated Biometal Science·Valentina OliveriGraziella Vecchio
Nov 1, 2013·Chembiochem : a European Journal of Chemical Biology·Emilia C CalvaresiPaul J Hergenrother
Nov 24, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Valentina OliveriGraziella Vecchio
Nov 23, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Monika KrawczykPiotr Kurcok
Nov 26, 2020·Drug Design, Development and Therapy·Jing-Fang ShiZi-Hua Jiang
Jan 30, 2021·Bioorganic Chemistry·Rohini GuptaKamaldeep Paul
Mar 19, 2021·Chemical Society Reviews·Yufei XueNicolas Hans Voelcker
Jun 15, 2016·Journal of Inorganic Biochemistry·Valentina Oliveri, Graziella Vecchio
Jun 27, 2015·Journal of Inorganic Biochemistry·Valeria LanzaGraziella Vecchio

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