Positional isomers of mannose-quinoline conjugates and their copper complexes: Exploring the biological activity

Valentina Oliveri, Federica Bentivegna, Leonardo Caputo, Laura Quintieri, Maurizio Viale, Irena Maric, Giovanni Lentini, Graziella Vecchio

Research output: Contribution to journalArticle

Abstract

8-Hydroxyquinolines show a wide range of pharmacological activities, and some are marketed as therapeutic agents. Despite the significant number of biologically active hydroxyquinolines proposed, there is a continued interest in the development of new active derivatives to overcome the drawbacks associated with their use. Herein, we report the synthesis and characterization of a set of positional isomers of hydroxyquinoline-mannose conjugates. Since in many cases the complexation ability of 8-hydroxyquinolines seems to be responsible for their pharmacological activities, we investigated the capacity of these systems to complex copper(ii) ions. We also examined diverse biological activities (antiproliferative, antimicrobial and antioxidant) of the new derivatives and their copper(ii) complex and compared them to those of their parent compounds and an analogous glucose-quinoline conjugate. All compounds show antioxidant activity that depends on the regioisomer. Moreover, specific isomers show significant antibacterial activity against P. aeruginosa and S. aureus. Furthermore only a regioisomer shows a pharmacologically relevant antiproliferative activity against human tumor cells, in the presence of copper(ii) ions.

Original languageEnglish
Pages (from-to)8882-8890
Number of pages9
JournalNew Journal of Chemistry
Volume42
Issue number11
DOIs
Publication statusPublished - Jan 1 2018

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Materials Chemistry

Fingerprint Dive into the research topics of 'Positional isomers of mannose-quinoline conjugates and their copper complexes: Exploring the biological activity'. Together they form a unique fingerprint.

  • Cite this

    Oliveri, V., Bentivegna, F., Caputo, L., Quintieri, L., Viale, M., Maric, I., Lentini, G., & Vecchio, G. (2018). Positional isomers of mannose-quinoline conjugates and their copper complexes: Exploring the biological activity. New Journal of Chemistry, 42(11), 8882-8890. https://doi.org/10.1039/c8nj00993g