Synthesis and characterization of six nonsymmetric A3B porphyrins with p-chlorophenyl as meso-substituent A or B and determination of their photodynamic activity

Photodynamic therapy is a promising alternative for cancer treatment of solid tumors through generation of reactive oxygen species mediated by light-activated photosensitizing agents. One of the most promising types of photosensitizers is tetrapyrrolic macrocyclic compounds, such as meso-substituted porphyrins. In the present study, the synthesis of nonsymmetric porphyrins A3B was accomplished, with p-chlorophenyl as B or A meso-substituent along with hydroxyl group, methoxyl group, or hydrogen atom as substituents of the phenyl in meso position and target molecules were designed in order to evaluate the synergistic effect of these hydrophobic and hydrophilic moieties unsymmetrically distributed. In vitro cytotoxic effect was demonstrated against human breast and cervix cancer cell lines (MCF-7 and HeLa cells, respectively). Terminal deoxynucleotidyl transferase dUTP nick end labeling assay and morphological studies were performed in order to elucidate part of the mechanism of cell damage for the most active compounds.