Highly singlet oxygen generative water-soluble coumarin substituted zinc(II) phthalocyanine photosensitizers for photodynamic therapy

New tetra-non-peripherally and peripherally ethyl butyrate or butanoic acid and their sodium salts bearing coumarin substituted zinc(II) phthalocyanine complexes have been synthesized and characterized for the first time. Butanoic acid bearing coumarin substituted zinc(II) phthalocyanine complexes and their sodium salts show excellent solubility in aqueous solution. Photophysical and photochemical properties of these phthalocyanines were investigated. General trends are described for photodegradation, fluorescence and singlet oxygen quantum yields as well as fluorescence lifetimes of these compounds. The value of singlet oxygen quantum yields ranged from 0.65 to 0.93 in phosphate-buffered saline + Triton X-100 solution indicating that they can produce singlet oxygen in high efficiency. This study also presented the synthesized water soluble zinc(II) phthalocyanines strongly bind to bovine serum albumin.

In this work the synthesis and characterization of tetra-non-peripherally and peripherally ethyl butyrate or butanoic acid and their sodium salts bearing coumarin substituted zinc(II) phthalocyanine complexes are presented. Butanoic acid bearing coumarin substituted zinc(II) phthalocyanine complexes and their sodium salts are soluble in aqueous solution. The value of ΦΔ ranged from 0.65 to 0.93 in PBS + Triton X-100 solution indicating that they can produce singlet oxygen in high efficiency.Figure optionsDownload as PowerPoint slideHighlights
► Synthesis of water soluble coumarin substituted zinc(II) phthalocyanines.
► Photophysical and photochemical properties in DMF, PBS and PBS + Triton X-100 solutions.
► Bovine serum albumin (BSA) binding properties.
► Photodynamic therapy (PDT).