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.
Xiuhan Guo  1 ,  Liu Wang  1 ,  Shisheng Wang  2 ,  Yueqing Li  1 ,  Fan Zhang  1 ,  Bo Song  3 ,  Weijie Zhao  4
Affiliations
  • 1. School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, PR China.
  • 2. School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, PR China. Electronic address: [email protected].
  • 3. School of Chemistry, Dalian University of Technology, Dalian 116024, PR China.
  • 4. School of Pharmaceutical Science and Technology, State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, PR China. Electronic address: [email protected].
PMID: 26306981 DOI: 10.1016/j.bmcl.2015.08.036
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.