Metal phthalocyanine as photosensitizer for photodynamic therapy (PDT) -: Preparation, characterization and anticancer activities of an amphiphilic phthalocyanine ZnPcS2P2

A series of sulfonated (S) phthalimidomethyl (P) zinc phthalocyanines (Pc) was synthesized in a reaction, in which both kinds of substituents were introduced to ZnPc simultaneously. The products were separated by HPLC. The five different fractions obtained were further purified by a membrane separation method, and then characterized by UV/Vis, IR, element analysis and the abilities to generate singlet oxygen upon irradiation by light as well as a preliminary determination of in vitro antitumor activities. The results show that one of the five separating parts with formula of ZnPcS2P2 exhibited rather good PDT activity. The compound was further characterized by NMR, MS and thermal analysis. Studies on in vivo antitumor activities of ZnPcS2P2 as photosensitizer show that its inhibitory rate was up to 89.8% and 90.8% for S-180 and U-14 solid tumors transplanted in mice respectively when the dosage of drug was 2 mg/kg and the dosage of laser light with 670 nm wavelength was 72 J/cm(2). Several structural factors influenced on the PDT activities were discussed.