Novel water soluble 7-oxy-4-(pyridine-3-yl) coumarin substituted phthalocyanines as potential photosensitizers for photodynamic therapy

Abstract

The new phthalonitriles (1 and 2) and zinc, indium, magnesium metalled tetrasubstituted phthalocyanines bearing 7-oxy-4-(pyridine-3-yl) coumarin substituents in the peripheral (1a-c)/non-peripheral (2a-c) positions were prepared for the develop novel water-soluble phthalocyanines. Newly synthesized phthalocyanines were turned into highly water-soluble quaternized ionic counterparts (1d-f, 2d-f). The effects of metal ions and substituents in the phthalocyanine ring on spectral, photochemical and photophysical properties of newly prepared phthalocyanines were examined of the non-ionic phthalocyanines (1a-c, 2a-c) in DMF and quaternized ionic phthalocyanines (1d-f, 2d-f) in both of DMF and water. Water-soluble peripheral substituted indium (III) (1e) and non-peripherally substituted zinc (II) (2d), indium (III) (2e) phthalocyanines showed good singlet oxygen formation that performed them as a highly promising photosensitizers for photodynamic therapies.