Synthesis of novel octa-cationic and non-ionic 1,2-ethanediamine substituted zinc (Ⅱ) phthalocyanines and their in vitro anti-cancer activity comparison

Novel tetra-substituted zinc phthalocyanines (Pcs) bearing 1,2-ethanediamine group and the quaternized derivatives were synthesized and characterized. The photophysical and cellular properties of these Pcs were investigated. The results indicated that the quaternized ionic effect can greatly improve the water-solubility of Pcs and reduce their aggregation degree in aqueous solution. Comparative studies with quaternized phthalocyanine and its unquaternized counterpart have also demonstrated that the quaternary action on the molecules significantly enhances the fluorescence quantum yields, fluorescence lifetimes, efficiency of singlet oxygen production and, thereby, the in vitro photodynamic therapy efficacy.

Graphical abstractA quaternized and two unqutaternized phthalocyanines have been synthesized; their pthotophysical and in vitro anti-cancer activity properties were studied and compared.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A novel ionic zinc phthalocyanine was synthesized. ► The ionic phthalocyanine has great photochemical and photophysical properties. ► The ionic phthalocyanine has high in vitro anti-cancer activity. ► The ionic phthalocyanine has potential to be used for PDT.