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

JULIETA MARINO; MARÍA C. GARCÍA VIOR; LELIA E. DICELIO; LEONOR P. ROGUIN; JOSEFINA AWRUCH

EUROPEAN JOURNAL OF MEDICAL CHEMISTRY

ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER

Lugar: Paris; Año: 2010 vol. 45 p. 4129 - 4139

0223-5234

The photodynamic activity of water-soluble cationic zinc(II) phthalocyanines using human nasopharynxcarcinoma (KB cells) was investigated. A sulfur-linked cationic dye, named: 2,9(10),16(17),23(24)-tetrakis[(2-trimethylammonium)ethylsulfanyl]phthalocyaninatozinc(II) tetraioidide (13) is the most active offour sensitizer assays and shows a singlet oxygen quantum yield of 0.58 and a higher bathochromic shiftof 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)ethoxy]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 concentrationandlight dose-dependent manner. After photodynamic treatment, compound 13 induced an apoptoticresponse e as indicated by morphological cell changes e an increase in the activity of caspase-3 and thecleavage of poly-ADP-ribose-polymerase substrate (PARP)