Study on Redox Properties and Cytotoxicity of Anthraquinone Derivatives to Understand Antitumor Active Anthracycline Substances

Chem Pharm Bull (Tokyo). 2019;67(7):717-720. doi: 10.1248/cpb.c19-00103.

Abstract

This study demonstrates the relation between the redox properties and cytotoxicity of anthraquinone derivatives with a hydroxyl and methoxy group. The redox behavior of the anthraquinone derivatives was initially observed via cyclic voltammetry and their characteristics were investigated using molecular orbital calculations. The cytotoxicity of the anthraquinone derivatives was then evaluated using human leukemia HL-60 and H2O2 resistant HP100 cells, and its correlation with the redox properties of these compounds was investigated. Therefore, it was suggested that the anthraquinone derivatives express cytotoxicity through H2O2 production, and that generation of the oxidized radical form influences their cytotoxicity.

Keywords: anthracycline antibiotic; anthraquinone derivative; cyclic voltammogram; cytotoxicity.

MeSH terms

  • Anthracyclines / chemistry*
  • Anthracyclines / pharmacology
  • Anthraquinones / chemistry*
  • Anthraquinones / pharmacology
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Cell Survival / drug effects
  • Electrochemical Techniques
  • HL-60 Cells
  • Humans
  • Hydrogen Peroxide / metabolism
  • Oxidation-Reduction
  • Quantum Theory

Substances

  • Anthracyclines
  • Anthraquinones
  • Antineoplastic Agents
  • Hydrogen Peroxide