Synthesis, separation and characterization of amphiphilic 2,10-di-sulfonato-18,26-di-phthalimidomethyl phthalocyanine zinc di-potassium salt by template reaction

An amphiphilic 2,10-di-sulfonato-18,26-di-phthalimidomethyl phthalocyanine zinc di-potassium salt (3) was synthesized by first direct condensation of hydrophilic precursor 4-sulfonic phthalic acid mono-potassium salt (1) with hydrophobic precursor 4-phthalimidomethyl phthalic acid (2). Then the condensed mixture was separated by reverse HPLC method and further purified by a membrane separation method. The composition of the title compound was characterized by elemental analysis, UV, 1H NMR, 13C NMR as well as TG and DTA, and its C4h-structure was identified according to the 1H NMR signal of submethyl protons of the phthalimidomethyl groups in the phthalocyanine ring, polarity and synthetic mechanism. In vivo antitumor activity of the title compound as photosensitizer showed that its inhibitory rate was up to 90.3%. This amphiphilic photosensitizer has a potential application in the photodynamic therapy of cancer.