Fully protected glycosylated zinc (II) phthalocyanine shows high uptake and photodynamic cytotoxicity in MCF-7 cancer cells

Kimani, Stanley; Shmigol, Tatiana; Hammond, Samantha; Phillips, James B.; Bruce, James I.; MacRobert, Alexander J.; Malakhov, Mikhail V. and Golding, Jon P. (2013). Fully protected glycosylated zinc (II) phthalocyanine shows high uptake and photodynamic cytotoxicity in MCF-7 cancer cells. Photochemistry and Photobiology, 89(1) pp. 139–149.

DOI: https://doi.org/10.1111/j.1751-1097.2012.01204.x

Abstract

Phthalocyanine photosensitizers are effective in anticancer photodynamic therapy (PDT) but suffer from limited solubility, limited cellular uptake, and limited selectivity for cancer cells. In order to improve these characteristics, we synthesized isopropylidene-protected and partially deprotected tetra β-glycosylated zinc (II) phthalocyanines and compared their uptake and accumulation kinetics, subcellular localization, in vitro photocytotoxicity, and reactive oxygen species generation to those of disulfonated aluminium phthalocyanine. In MCF-7 cancer cells, one of the compounds, Zinc phthalocyanine {4}, demonstrated ten-fold higher uptake, five-fold greater PDT-induced cellular reactive oxygen species concentration, and two-fold greater phototoxicity than equimolar (9 μM) disulfonated aluminium phthalocyanine. Thus, isopropylidene-protected β-glycosylation of phthalocyanines provides a simple method of improving the efficacy of photodynamic therapy.

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