A New Family of Homoleptic Copper Complexes of Curcuminoids: Synthesis, Characterization and Biological Properties

Molecules. 2019 Mar 5;24(5):910. doi: 10.3390/molecules24050910.

Abstract

We report herein the synthesis and crystal structures of five new homoleptic copper complexes of curcuminoids. The scarcity of reports of homoleptic complex structures of curcuminoids is attributed to the lack of crystallinity of such derivatives, and therefore, their characterization by single crystal X-ray diffraction is rare. The ligand design suppressing the phenolic interaction by esterification or etherification has afforded a significant increase in the number of known crystal structures of homoleptic metal complexes of curcuminoids revealing more favorable crystallinity. The crystal structures of the present new copper complexes show four-fold coordination with a square planar geometry. Two polymorphs were found for DiBncOC-Cu when crystallized from DMF. The characterization of these new complexes was carried out using infrared radiation (IR), nuclear magnetic resonance (NMR), electron paramagnetic resonance (EPR), and single crystal X-ray diffraction (SCXRD) and the antioxidant and cytotoxic activity of the obtained complexes was evaluated.

Keywords: antioxidant activity; crystal structure; curcuminoids; homoleptic copper complexes.

MeSH terms

  • Animals
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology
  • Cell Line, Tumor
  • Coordination Complexes / chemical synthesis
  • Coordination Complexes / chemistry*
  • Coordination Complexes / pharmacology
  • Copper / chemistry*
  • Dose-Response Relationship, Drug
  • Ligands
  • Lipid Peroxidation / drug effects
  • Male
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Rats
  • Spectrum Analysis

Substances

  • Antioxidants
  • Coordination Complexes
  • Ligands
  • Copper