Synthesis, dark and photoinduced cytotoxicity of a deuteroporphyrin IX derivative with two galactose fragments on the macrocycle periphery

Abstract

A deuteroporphyrin IX derivative with two D-galactose fragments with an ester bond between macrocycle and carbohydrate fragments was synthesized. The synthesis was done by esterifying both ester groups of deuteroporphyrin IX with diacetone-D-galactose using 2-chloro-1-methylpyridinium iodide (Mukayama reagent) followed by the removal of the isopropylidene protection of carbohydrate fragments by the action of aqueous trifluoroacetic acid to form the target derivative. The study of dark toxicity of the deuteroporphyrin IX derivative synthesized against HeLa cells allows us to conclude that galactose fragment introduction resulted in the cytotoxicity decrease as compared with the parent deuteroporphyrin IX but photoinduced cytotoxicity of the deuteroporphyrin IX derivative with two D-galactose fragments had increased in contrast to the deuteroporphyrin IX. It has been shown that oxidative stress due to ROS induction causes the photoinduced toxicity of the porphyrins studied.