New cyclodextrin-bearing 8-hydroxyquinoline ligands as multifunctional molecules

Chemistry. 2013 Oct 4;19(41):13946-55. doi: 10.1002/chem.201300237. Epub 2013 Aug 22.

Abstract

Recent investigations have rekindled interest in 8-hydroxyquinolines as therapeutic agents for cancer, Alzheimer's disease, and other neurodegenerative disorders. Three new β-cyclodextrin conjugates of 8-hydroxyquinolines and their copper(II) and zinc(II) complexes have been synthesized and characterized spectroscopically. In addition to improving aqueous solubility, due to the presence of the cyclodextrin moiety, the hybrid systems have interesting characteristics including antioxidant activity, and their copper(II) complexes are efficient superoxide dismutase (SOD) mimics. The ligands and their copper(II) complexes show low cytotoxicity, attributed to the presence of the cyclodextrin moiety. These compounds have potential as therapeutic agents in diseases related both to metal dyshomeostasis and oxidative stress.

Keywords: antioxidants; chelating agents; copper; glycoconjugates; zinc.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemical synthesis*
  • Antioxidants / chemistry*
  • Antioxidants / metabolism
  • Chelating Agents / chemical synthesis*
  • Chelating Agents / chemistry*
  • Chelating Agents / metabolism
  • Coordination Complexes / chemical synthesis*
  • Coordination Complexes / chemistry*
  • Coordination Complexes / metabolism
  • Copper / chemistry
  • Cyclodextrins / chemistry*
  • Glycoconjugates / chemistry*
  • Ligands
  • Metals / chemistry*
  • Metals / therapeutic use
  • Oxidative Stress
  • Oxyquinoline / chemistry*
  • Solubility
  • Superoxide Dismutase / chemistry*
  • Superoxide Dismutase / metabolism
  • Superoxide Dismutase / therapeutic use
  • Zinc / chemistry

Substances

  • Antioxidants
  • Chelating Agents
  • Coordination Complexes
  • Cyclodextrins
  • Glycoconjugates
  • Ligands
  • Metals
  • Oxyquinoline
  • Copper
  • Superoxide Dismutase
  • Zinc