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

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)).