Photosensitizing properties of a boronated phthalocyanine: studies at the molecular and cellular level

J Photochem Photobiol B. 2001 Nov 1;64(1):1-7. doi: 10.1016/s1011-1344(01)00184-1.

Abstract

A synthetic procedure has been developed for the preparation of a Zn-phthalocyanine peripherally substituted with a dodecaborane. The absorption spectrum of the derivative is typical of the phthalocyanine chromophore. Moreover, the boronated phthalocyanine exhibits a high photosensitizing efficiency against a model biological substrate, such as N-acetyl-L-tryptophanamide, and a singlet oxygen quantum yield of 0.53 in dimethylformamide. Even though the presence of the dodecaborane moiety appears to decrease the affinity of the phthalocyanine for HT-1080 transformed human fibroblasts, the boronated phthalocyanine causes an essentially complete loss of cell viability upon irradiation with 600-700 nm light under mild conditions (1 microM concentration, 5-min irradiation at 10 mW/cm(2)).

MeSH terms

  • Boron Compounds / chemistry*
  • Boron Compounds / pharmacology
  • Cell Line, Transformed
  • Cell Survival / drug effects
  • Dimethylformamide
  • Fibroblasts / drug effects
  • Humans
  • Indoles / chemistry*
  • Indoles / pharmacology
  • Light
  • Photosensitizing Agents / chemistry*
  • Photosensitizing Agents / pharmacology
  • Singlet Oxygen

Substances

  • Boron Compounds
  • Indoles
  • Photosensitizing Agents
  • Singlet Oxygen
  • Dimethylformamide
  • phthalocyanine