title: Synthesis and comparative photodynamic properties of two isosteric alkyl substituted zinc(II) phthalocyanines.
abstract: 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 singlet molecular oxygen generation was 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 lysosomes were demonstrated. The production of a greater amount of reactive oxygen species after phthalocyanine 6 irradiation would be responsible for its potent phototoxic action on KB cells.
authors.affiliation: Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina.
authors.forename: Gabriela A
authors.initials: GA
authors.lastname: Gauna
authors.forename: Julieta
authors.initials: J
authors.lastname: Marino
authors.forename: María C
authors.initials: MC
authors.lastname: García Vior
authors.forename: Leonor P
authors.initials: LP
authors.lastname: Roguin
authors.forename: Josefina
authors.initials: J
authors.lastname: Awruch
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D001692:Biological Transport; D060326:Chemistry Techniques, Synthetic; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D042541:Intracellular Space / Q000187:drug effects / Q000378:metabolism; D054833:Isoindoles; D007624:KB Cells; D009942:Organometallic Compounds / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D010778:Photochemotherapy; D017319:Photosensitizing Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D017382:Reactive Oxygen Species / Q000378:metabolism; D017967:Zinc Compounds
chemical_list: D000473:Alkanes; D007211:Indoles; D054833:Isoindoles; D009942:Organometallic Compounds; D017319:Photosensitizing Agents; D017382:Reactive Oxygen Species; D017967:Zinc Compounds; C052159:Zn(II)-phthalocyanine