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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-α-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). β-Sulfur-linked cationic aliphatic phthalocyanine 13 shows a ΦΔ = 0.58 and λmax = 686 nm, no dark cytotoxicity and triggers lysosomal-induced apoptosis after irradiation leading to 90% cell death. © 2010 Elsevier Masson SAS. All rights reserved.

Registro:

Documento: Artículo
Título:Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells
Autor:Marino, J.; García Vior, M.C.; Dicelio, L.E.; Roguin, L.P.; Awruch, J.
Filiación:Instituto de Química y Fisicoquímica Biológicas (UBA-CONICET), Facultad de Farmacia y Bioquímica, Junín 956, 1113 Buenos Aires, Argentina
Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina
INQUIMAE, Departamento de Química Inorgánica, Analítica y Química Física, Ciudad Universitaria, Pabellón II, 1428 Buenos Aires, Argentina
Palabras clave:Apoptosis; KB cells; Lysosomes; Photodynamic therapy; Phthalocyanines; Singlet oxygen; 1,8(11),15(18),22(25) tetrakis[(2 dimethylamino)ethoxy]phthalocyaninatozinc(II); 1,8(11),15(18),22(25) tetrakis[(2 dimethylamino)ethylsulfanyl]phthalocyaninatozinc(II); 1,8(11),15(18),22(25) tetrakis[(2 trimethylammonium)ethoxy]phthalocyaninatozinc(II) tetraioidide; 1,8(11),15(18),22(25) tetrakis[(2 trimethylammonium)ethylsulfanyl]phthalocyaninatozinc(II) tetraioidide; 2,9(10),16(17),23(24) tetrakis[(2 dimethylamino)ethoxy]phthalocyaninatozinc(II); 2,9(10),16(17),23(24) tetrakis[(2 dimethylamino)ethylsulfanyl]phthalocyaninatozinc(II); 2,9(10),16(17),23(24) tetrakis[(2 trimethylammonium)ethoxy]phthalocyaninatozinc(II) tetraioididey; 2,9(10),16(17),23(24) tetrakis[(2 trimethylammonium)ethylsulfanyl]phthalocyaninatozinc(II)tetraioidide; caspase 3; nicotinamide adenine dinucleotide adenosine diphosphate ribosyltransferase; oxygen; phthalocyanine derivative; sulfur; unclassified drug; apoptosis; article; cell strain KB; cell structure; controlled study; enzyme activity; human; human cell; lysosome; nasopharynx carcinoma; photodynamic therapy; protein cleavage
Año:2010
Volumen:45
Número:9
Página de inicio:4129
Página de fin:4139
DOI: http://dx.doi.org/10.1016/j.ejmech.2010.06.002
Título revista:European Journal of Medicinal Chemistry
Título revista abreviado:Eur. J. Med. Chem.
ISSN:02235234
CODEN:EJMCA
CAS:caspase 3, 169592-56-7; nicotinamide adenine dinucleotide adenosine diphosphate ribosyltransferase, 58319-92-9; oxygen, 7782-44-7; sulfur, 13981-57-2, 7704-34-9
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_02235234_v45_n9_p4129_Marino

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Citas:

---------- APA ----------
Marino, J., García Vior, M.C., Dicelio, L.E., Roguin, L.P. & Awruch, J. (2010) . Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells. European Journal of Medicinal Chemistry, 45(9), 4129-4139.
http://dx.doi.org/10.1016/j.ejmech.2010.06.002
---------- CHICAGO ----------
Marino, J., García Vior, M.C., Dicelio, L.E., Roguin, L.P., Awruch, J. "Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells" . European Journal of Medicinal Chemistry 45, no. 9 (2010) : 4129-4139.
http://dx.doi.org/10.1016/j.ejmech.2010.06.002
---------- MLA ----------
Marino, J., García Vior, M.C., Dicelio, L.E., Roguin, L.P., Awruch, J. "Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells" . European Journal of Medicinal Chemistry, vol. 45, no. 9, 2010, pp. 4129-4139.
http://dx.doi.org/10.1016/j.ejmech.2010.06.002
---------- VANCOUVER ----------
Marino, J., García Vior, M.C., Dicelio, L.E., Roguin, L.P., Awruch, J. Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells. Eur. J. Med. Chem. 2010;45(9):4129-4139.
http://dx.doi.org/10.1016/j.ejmech.2010.06.002