Synthesis and comparative photodynamic properties of two isosteric alkyl substituted zinc(II) phthalocyanines

GABRIELA A. GAUNA; JULIETA MARINO; MARÍA C. GARCÍA VIOR; LEONOR P. ROGUIN; JOSEFINA AWRUCH

EUROPEAN JOURNAL OF MEDICAL CHEMISTRY

ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER

Lugar: Paris; Año: 2011 vol. 46 p. 5532 - 5539

0223-5234

The synthesis and photophysical parameters of two novel isosteric cationic zinc(II) phthalocyanines: 2,9(10),16(17),23(24)-tetrakis[(N-butyl-N-methylammoniumethylsulfanyl]phthalocyaninatozinc(II) tetraiodide (6) and 2,9(10),16(17),23(24)-tetrakis[(N-dibutyl-N-methylammonium)ethoxy]phthalocyaninatozinc(II) tetraiodide (7) were investigated. Maximum absorption values were 686.5 nm and 678 nm for 6 and 7, respectively, whereas singletmolecular oxygen generationwas 0.42 and 0.67, respectively. The photodynamic effect and the cellular uptake of both phthalocyanines were evaluated on human nasopharynx KB carcinoma cells. After light exposure, phthalocyanine 6 showed a higher cytotoxic activity than 7. In addition, a higher intracellular uptake of 6 and a preferential localization within lysosomeswere demonstrated. The production of a greater amount of reactive oxygen species after phthalocyanine 6 irradiationwould be responsible for its potent phototoxic action on KB cells.