Synthesis and Photodynamic Activity of 5,10,15-Tris(p-chlorophenyl)-20-(2- hydroxy-3-methoxyphenyl)-21H,23H-porphyrin

Photodynamic therapy (PDT) is an effective option for the treatment of solid neoplastic tumors, as well as non-malignant diseases such as dermatological, ophthalmological and benign pathologies. PDT destroys cancer cells by photochemical generation of reactive oxygen species upon absorption of visible light by a photosensitizing agent (PS). Here, we describe the synthesis and characterization of the unsymmetrical A3B porphyrin 5,10,15-Tris(p-chlorophenyl)-20(2-hydroxy-3-methoxyphenyl)-21H,23H-porphyrin, which presents different groups at the meso positions, p-chlorophenyl and 2-hydroxy3-methoxyphenyl and is a novel target molecule in order to evaluate the synergistic effect of these hydrophobic and hydrophilic moieties distributed unsymmetrically on the porphyrin macrocycle. We demonstrated the in vitro cytotoxic effect of the synthesized porphyrin, by the WST-1 assay on a cultured human cervical adenocarcinoma cell line (HeLa ATCC: CCL-2), as well as the presence of apoptosis by T.U.N.E.L. assay. We compared the phototoxicity and intrinsic cytotoxicity of the PS and found a considerable difference in the IC50 between phototoxic activity (1.5 μM) and intrinsic cytotoxicity (7 μM). The results of the induction of apoptosis on HeLa cells treated with the unsymmetrical porphyrin at a final concentration of 80 μM showed 15% apoptotic cells, whereas the untreated HeLa cells had only 2.5% apoptotic cells.