Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells

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 a...

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Autores principales: Marino, J., García Vior, M.C., Dicelio, L.E., Roguin, L.P., Awruch, J.
Formato: JOUR
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Acceso en línea:http://hdl.handle.net/20.500.12110/paper_02235234_v45_n9_p4129_Marino
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spelling todo:paper_02235234_v45_n9_p4129_Marino2023-10-03T15:11:14Z Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells Marino, J. García Vior, M.C. Dicelio, L.E. Roguin, L.P. Awruch, J. 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 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. Fil:Dicelio, L.E. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_02235234_v45_n9_p4129_Marino
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic 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
spellingShingle 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
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
topic_facet 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
description 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.
format JOUR
author Marino, J.
García Vior, M.C.
Dicelio, L.E.
Roguin, L.P.
Awruch, J.
author_facet Marino, J.
García Vior, M.C.
Dicelio, L.E.
Roguin, L.P.
Awruch, J.
author_sort Marino, J.
title Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells
title_short Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells
title_full Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells
title_fullStr Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells
title_full_unstemmed Photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx KB carcinoma cells
title_sort photodynamic effects of isosteric water-soluble phthalocyanines on human nasopharynx kb carcinoma cells
url http://hdl.handle.net/20.500.12110/paper_02235234_v45_n9_p4129_Marino
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AT garciaviormc photodynamiceffectsofisostericwatersolublephthalocyaninesonhumannasopharynxkbcarcinomacells
AT diceliole photodynamiceffectsofisostericwatersolublephthalocyaninesonhumannasopharynxkbcarcinomacells
AT roguinlp photodynamiceffectsofisostericwatersolublephthalocyaninesonhumannasopharynxkbcarcinomacells
AT awruchj photodynamiceffectsofisostericwatersolublephthalocyaninesonhumannasopharynxkbcarcinomacells
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