Syntheses of new chlorin derivatives containing maleimide functional group and their photodynamic activity evaluation

Bioorg Med Chem Lett. 2015 Oct 1;25(19):4078-81. doi: 10.1016/j.bmcl.2015.08.036. Epub 2015 Aug 18.

Abstract

Nine new chlorin derivatives containing maleimide functional group and amino acid residue with chlorin e6 scaffold (compounds 1-6) or pheophorbide a scaffold (compounds 7-9) were synthesised from chlorophyll a. The all nine derivatives demonstrated increased photo cytotoxic activity in HepG2 cell (IC50 3.2-20.5 μM) comparing with chlorin e6 and its trimethyl ester. Their photo cytotoxicities were approximately dependent on their abilities to produce singlet oxygen ((1)O2) in the cells.

Keywords: Chlorin derivatives; Chlorin e6; Photo cytotoxic activity; Singlet oxygen.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Hep G2 Cells
  • Humans
  • Maleimides / chemistry*
  • Maleimides / pharmacology*
  • Molecular Conformation
  • Photosensitizing Agents / chemical synthesis
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / pharmacology*
  • Porphyrins / chemistry*
  • Porphyrins / pharmacology*
  • Structure-Activity Relationship

Substances

  • Maleimides
  • Photosensitizing Agents
  • Porphyrins
  • maleimide
  • chlorin