MARINO Veronica Julieta
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
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.