title: Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells.
abstract: 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]phthalocyaninatozinc(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-alpha-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 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).
authors.affiliation: Instituto de Química y Fisicoquímica Biológicas (UBA-CONICET), Facultad de Farmacia y Bioquímica, Junín 956, 1113 Buenos Aires, Argentina.
authors.forename: Julieta
authors.initials: J
authors.lastname: Marino
authors.forename: María C
authors.initials: MC
authors.lastname: García Vior
authors.forename: Lelia E
authors.initials: LE
authors.lastname: Dicelio
authors.forename: Leonor P
authors.initials: LP
authors.lastname: Roguin
authors.forename: Josefina
authors.initials: J
authors.lastname: Awruch
mesh_terms: D017209:Apoptosis / Q000187:drug effects / Q000528:radiation effects; D001692:Biological Transport; D049109:Cell Proliferation / Q000187:drug effects / Q000528:radiation effects; D006801:Humans; D007211:Indoles / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D042541:Intracellular Space / Q000378:metabolism; D054833:Isoindoles; D007624:KB Cells; D009303:Nasopharyngeal Neoplasms / Q000473:pathology*; D055668:Photochemical Processes; D010778:Photochemotherapy; D012995:Solubility; D014867:Water / Q000737:chemistry*
chemical_list: D007211:Indoles; D054833:Isoindoles; D014867:Water; C013647:phthalocyanine