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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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 |
work_keys_str_mv |
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1807316625245863936 |