Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells

MARINO V.J.; GARCIA VIOR M.C.; DICELIO L.E.; ROGUIN, L. P; AWRUCH J

EUROPEAN JOURNAL OF MEDICAL CHEMISTRY

ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER

Año: 2010 vol. 45 p. 4129 - 4139

0223-5234

The photodynamic activity of water-soluble cationic zinc(II) phthalocyanines using human nasopharynx carcinoma (KB cells) was investigated. A sulfur-linked cationic dye, named: 2,9(10),16(17),23(24)-tetrakis[(2-trimethylammonium)ethylsulfanyl]phth-alocyaninatozinc(II) tetraioidide (13) is the most active of four sensitizer assays and shows a singlet oxygen quantum yield of 0.58 and a higher bathochromic shift of 10 nm for the Q-band as compared with the oxygen-linked cationic aliphatic phthalocyanine:  2,9(10),16(17),23(24)-tetrakis[(2-trimethylammonium)ethoxy]phthalocyaninatozinc(II) tetraioidide (11)  and the best photo-stability in water in comparison with their tetra-a-substituted counterparts 1,8(11),15(18),22(25)-tetrakis[(2-trimethylammonium)etho-xy]phthalocyaninatozinc(II) tetraioidide (12) and 1,8(11),15(18),22(25)-tetrakis[(2-trimethylammonium)ethylsulfanyl]phthalocyaninatozinc(II) tetraioidide (14). Phthalocyanine 13, partially localized in lysosomes, led to cell photoinactivation in a concentration and light dose-dependent manner. After photodynamic treatment, compound 13 induced an apoptotic response - as indicated by morphological cell changes - an increase in the activity of caspase-3 and the cleavage of Poly-ADP-Ribose-Polymerase substrate (PARP).