Synthesis and Optical Properties of Fluorine-Containing Phthalocyanine Conjugated with Glucofuranose and its Application to Photo-Dynamic Therapy

A novel fluorinated phthalocyanine 1a with four glucofuranoses at its peripheral positions was designed as a photosensitizer for photodynamic therapy of cancer. The target fluorinated phthalocyanine/glucofuranose conjugate 1a was synthesized by tetramerization of corresponding glucofuranose-attached fluorinated phthalonitrile 4 in the presence of zinc (II) acetate when heated. The optical and chemical properties of the target conjugate 1a were investigated by UV/Vis spectra, fluorescence, HPLC, MALDI-TOF MS, and partition coefficients. The biological (PDT) property of 1a was also examined via an in vitro assay using HT-1080 cells after exposure to light. All the properties of 1a were compared to the acetal analogue 2a and non-fluorinated counterparts 1b and 2b. Of note, the perfluorinated conjugate 1a showed a more efficient photo-dynamic effect than its non-fluorinated analogue 1b and their acetal analogues 2a,b in the in vitro cell assay.