Characterization of 2,3,6,7,10,11-hexahydroxytriphenylene and its effects on cell viability in human cancer cell lines

Biochem Cell Biol. 2016 Apr;94(2):205-11. doi: 10.1139/bcb-2015-0093. Epub 2016 Jan 18.

Abstract

We synthesized 2,3,6,7,10,11-hexahydroxytriphenylene (HHTP), characterized it by electrochemistry, spectroelectrochemistry, and electron paramagnetic resonance techniques, and evaluated its cytotoxicity to human cancer cell lines. The results revealed that HHTP has accessible higher-oxidation states, especially the tris-semiquinone monoradical. This species is stable and is formed after being stored for months. HHTP exhibited cytotoxic effects on 5 human cancer cell lines, including glioma and lung cancer cells. The cytotoxic effect was evaluated based on the decrease in cell viability, increases in the percentage of cells with fragmented DNA, and elevated numbers of annexin V-PI-positive cells after HHTP treatment.

Keywords: cell viability; cytotoxicity; cytotoxicité; hexahydroxytriphenylene; hexahydroxytriphénylène; semiquinone; viabilité cellulaire.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Apoptosis / drug effects
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • Phenanthrenes / chemical synthesis
  • Phenanthrenes / chemistry
  • Phenanthrenes / pharmacology*
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • 2,3,6,7,10,11-hexahydroxytriphenylene
  • Phenanthrenes