A comparative study of the photophysical and phototoxic properties of octakis(decyloxy)phthalocyaninato zinc(II), incorporated in a hydrophilic polymer, in liposomes and in non-ionic micelles

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Factors such as charge, aggregation and lipophilicity influence photosensitiser localisation. The lipophilic octasubstituted sensitiser 2,3,9,10,16,17,23,24-octakis(decyloxy)phthalocyaninato zinc(II) was incorporated into liposomes of dimyristoyl-L-α-phosphatidylcholine (DMPC), non-ionic micelles of...

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Autor principal: Rodriguez, M.E
Otros Autores: Morán, F., Bonansea, A., Monetti, M., Fernández, D.A, Strassert, C.A, Rivarola, V., Awruch, J., Dicelio, L.E
Formato: Capítulo de libro
Lenguaje:Inglés
Publicado: 2003
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Acceso en línea:Registro en Scopus
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024 7 |2 scopus  |a 2-s2.0-0642275173 
024 7 |2 cas  |a dimyristoylphosphatidylcholine, 13699-48-4, 18194-24-6; polysorbate 80, 8050-83-7, 9005-65-6; Dimyristoylphosphatidylcholine, 13699-48-4; Liposomes; Micelles; Organometallic Compounds; Photosensitizing Agents; Polymers 
040 |a Scopus  |b spa  |c AR-BaUEN  |d AR-BaUEN 
030 |a PPSHC 
100 1 |a Rodriguez, M.E. 
245 1 2 |a A comparative study of the photophysical and phototoxic properties of octakis(decyloxy)phthalocyaninato zinc(II), incorporated in a hydrophilic polymer, in liposomes and in non-ionic micelles 
260 |c 2003 
270 1 0 |m Rodriguez, M.E.; Departamento de Quimica Inorgánica, Analitica y Quimica Fisica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
506 |2 openaire  |e Política editorial 
504 |a Rodriguez, M.E., Awruch, J., Dicelio, L.E., Photophysical properties of Zn(II) phthalocyaninates incorporated into liposomes (2002) J. Porphyrins Phthalocyanines, 6, pp. 122-129 
504 |a Morgan, J., Oseroff, A.R., Mitochondria-based photodynamic anti-cancer therapy (2001) Adv. Drug Delivery Rev., 49, pp. 71-86 
504 |a Ometto, C., Fabris, C., Milanesi, C., Jori, G., Cook, M.J., Russell, D.A., Tumour-localising and photosensitising properties of a novel zinc(II) octadecylphthalocyanine (1996) Br. J. Cancer, 74, pp. 1891-1899 
504 |a Kongshaung, M., Cheng, L.S., Moan, J., Rimington, C., Interaction of Cremophor-EL with human plasma (1991) Int. J. Biochem., 4, pp. 473-478 
504 |a McKean, D.L., Pesce, A.J., Koo, W., Analysis of polysorbate and its polyethoxylated metabolite (1987) Anal. Biochem., 161, pp. 348-351 
504 |a Mayhew, E., Vaughan, L.A., Panus, A., Murray, M., Henderson, B.W., Lipid-associated methylpheophorbide-a (hexyl-ether) as a photodynamic agent in tumor-bearing mice (1993) Photochem. Photobiol., 58, pp. 845-851 
504 |a Wan, L.S.C., Lee, P.F.S., CMC of polysorbates (1974) J. Pharm. Sci., 63, pp. 136-137 
504 |a Farhadieh, B., Determination of CMC and partial specific volume of polysorbates 20, 60, and 80 from densities of their aqueous solutions (1973) J. Pharm. Sci., 62, pp. 1685-1688 
504 |a Konan, Y.N., Gurny, R., Allémann, E., State of the art in the delivery of photosensitizers for photodynamic therapy (2002) J. Photochem. Photobiol., B, 66, pp. 89-106 
504 |a Reddi, E., Role of delivery vehicles for photosensitizers in the photodynamic therapy of tumours (1997) J. Photochem. Phobiol., B, 37, pp. 189-195 
504 |a Cook, M.J., Chambrier, I., Cracknell, S.J., Mayes, D.A., Russell, D.A., Octa-alkyl zinc phthalocyanines: Potential photosensitizers for use in the photodynamic therapy of cancer (1995) Photochem. Photobiol., 62, pp. 542-545 
504 |a Lagorio, M.G., Dicelio, L.E., San Román, E., Visible and near-IR spectroscopic and photochemical characterization of substituted metallophthalocyanines (1993) J. Photochem. Photobiol., A, 72, pp. 153-161 
504 |a Fernández, D.A., Dicelio, L.E., Awruch, J., Synthesis of two new N-alkyl substituted phthalocyanines (1995) J. Heterocycl. Chem., 32, pp. 519-522 
504 |a Kasuga, K., Mihara, T., Nakao, T., Takahashi, K., Electrical conductivity of octakisdecyloxyphthalocyaninato-copper(II) (1991) Inorg. Chim. Acta, 189, pp. 11-12 
504 |a Ohta, K., Jacquemin, L., Sirlin, C., Bosio, L., Simon, J., Influence of the nature of the side chains of the mesomorphic properties of octasubstituted phthalocyanines derivatives. Annelydes. XXIX (1988) New J. Chem., 12, pp. 751-754 
504 |a Hauschel, B., Jung, R., Hanack, M., Synthesis and Diels-Alder reactions of some new (phthalocyanine)nickel complexes (1999) Eur. J. Inorg. Chem., pp. 693-703. , and references therein 
504 |a Olson, F., Hunt, C.A., Szoka, F.C., Vail, W.J., Papahadjopoulos, D., Preparation of liposomes of defined size distribution by extrusion through polycarbonate membranes (1979) Biochim. Biophys. Acta, 557, pp. 9-23 
504 |a Nayar, R., Hope, M.J., Cullis, P.R., Generation of large unilamellar vesicles from long-chain saturated phosphatidylcholines by extrusion technique (1989) Biochim. Biophys. Acta, 986, pp. 200-206 
504 |a Bensasson, R., Land, E.J., A general method for measuring triplet-triplet extinction coefficients, singlet-triplet intersystem crossing efficiencies, and related parameters (1978) Photochem. Photobiol. Rev., 3, pp. 163-191 
504 |a Jacques, P., Braun, A.M., Laser flash photolysis of phthalocyanines in solution and microemulsion (1981) Helv. Chim. Acta, 64, pp. 1800-1805 
504 |a Fernández, D.A., Awruch, J., Dicelio, L.E., Photophysical and aggregation studies of t-butyl substituted Zn phthalocyanines (1996) Photochem. Photobiol., 63, pp. 784-792 
504 |a Wilkinson, F., Helman, W.P., Rose, A.D., Rate constant for the decay and reactions of the lowest electronically excited singlet state of molecular oxygen in solution. An expanded and revised compilation (1995) J. Phys. Chem. Ref. Data, 24, pp. 663-1021 
504 |a Angeli, N.G., Lagorio, M.G., San Román, E., Dicelio, L.E., Meso-substituted cationic porphyrins of biological interest. Photophysical and physicochemical properties in solution and bound to liposomes (2000) Photochem. Photobiol., 72, pp. 49-56 
504 |a Alvarez, M.G., Lapenna, M., Yslas, E.I., Rivarola, V., Durantini, E.N., Photodamiging effects of porphyrin in human carcinoma cell line (2000) Chem. Educator, 5, pp. 24-26 
504 |a Merlin, J., Azzi, S., Lignon, D., Ramacci, C., Zeghari, N., Guillemin, F., MTT assays allow quick and reliable measurement of the response of human tumour cells to photodynamic therapy (1992) Eur. J. Cancer, Part A, 28, pp. 1452-1458 
504 |a Fukuda, H., Casas, A., Chueke, F., Paredes, S., Battle, A., Photodynamic action of endogenously synthesized porphyrins from aminolevulinic acid, using a new model for assaying the effectiveness of tumoral cell killing (1993) Int. J. Biochem., 25, pp. 1395-1398 
504 |a Fernández, D.A., Awruch, J., Dicelio, L.E., Synthesis and Photophysical properties of a new cationic water-soluble Zn phthalocyanine (1997) J. Photochem. Photobiol., B, 41, pp. 227-232 
504 |a Scurlock, R.D., Ogilby, P.R., Effect of solvent on the rate constant for the radiative deactivation of singlet molecular oxygen (O21Δ8) (1987) J. Phys. Chem., 91, pp. 4599-4602 
504 |a Milanesio, M.E., Alvarez, M.G., Yslas, E.I., Borsarelli, C.D., Silber, J.J., Rivarola, V., Durantini, E.N., Photodynamic studies of metallo 5,10,15,20-tetrakis(4-methoxyphenyl) porphyrin: Photochemical characterization and biological consequences in a human carcinoma cell line (2001) Photochem. Photobiol., 74, pp. 14-21 
504 |a Fabris, C., Ometto, C., Milanessi, C., Jori, G., Cook, M.J., Russell, D.A., Tumour-localizing and tumour-photosensitizing properties of zinc(II) octapentyl-phthalocyanine (1992) J. Photochem. Photobiol., B, 39, pp. 270-284 
520 3 |a Factors such as charge, aggregation and lipophilicity influence photosensitiser localisation. The lipophilic octasubstituted sensitiser 2,3,9,10,16,17,23,24-octakis(decyloxy)phthalocyaninato zinc(II) was incorporated into liposomes of dimyristoyl-L-α-phosphatidylcholine (DMPC), non-ionic micelles of Tween 80 and the hydrosoluble polymer Solutol® HS 15 in order to investigate how these different environments affect the photophysical properties and phototoxicity of the photosensitiser. Fluorescence quantum yields and singlet molecular oxygen generation are enhanced in the presence of Solutol® HS 15. Phototoxicities were calculated by employing a concentration of 10-7 M of the dye against the Hcp-2 cell line, which showed a viability of 53 and 30% in DMPC and Solutol® HS 15, respectively. After 24 h of photodynamic therapy with 15 min irradiation, apoptotic and necrotic cells were observed. © The Royal Society of Chemistry and Owner Societies 2003.  |l eng 
593 |a Departamento de Quimica Inorgánica, Analitica y Quimica Fisica, Universidad de Buenos Aires, Ciudad Universitaria, 1428 Buenos Aires, Argentina 
593 |a Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina 
593 |a Departamento de Biologiá Molecular, Universidad Nacional de Rio Cuarto, Ruta 8 Km 601, 5800 Rio Cuarto, Córdoba, Argentina 
690 1 0 |a 2,3,9,10,16,17,23,24 OCTAKIS(DECYLOXY)PHTHALOCYANINATO ZINC 
690 1 0 |a DIMYRISTOYLPHOSPHATIDYLCHOLINE 
690 1 0 |a LIPOSOME 
690 1 0 |a PHOTOSENSITIZING AGENT 
690 1 0 |a POLYMER 
690 1 0 |a POLYSORBATE 80 
690 1 0 |a SINGLET OXYGEN 
690 1 0 |a SOLUTOL HS 15 
690 1 0 |a UNCLASSIFIED DRUG 
690 1 0 |a ZINC DERIVATIVE 
690 1 0 |a DIMYRISTOYLPHOSPHATIDYLCHOLINE 
690 1 0 |a LIPOSOME 
690 1 0 |a ORGANOMETALLIC COMPOUND 
690 1 0 |a PHOTOSENSITIZING AGENT 
690 1 0 |a POLYMER 
690 1 0 |a APOPTOSIS 
690 1 0 |a ARTICLE 
690 1 0 |a CELL DEATH 
690 1 0 |a CELL VIABILITY 
690 1 0 |a CONTROLLED STUDY 
690 1 0 |a DRUG MECHANISM 
690 1 0 |a DRUG STRUCTURE 
690 1 0 |a HEP 2 CELL 
690 1 0 |a HUMAN 
690 1 0 |a HUMAN CELL 
690 1 0 |a IRRADIATION 
690 1 0 |a LIPOPHILICITY 
690 1 0 |a MICELLE 
690 1 0 |a PHOTODYNAMIC THERAPY 
690 1 0 |a PHOTOTOXICITY 
690 1 0 |a PRIORITY JOURNAL 
690 1 0 |a BIOLOGY 
690 1 0 |a CELL LINE 
690 1 0 |a CELL SURVIVAL 
690 1 0 |a CHEMISTRY 
690 1 0 |a COMPARATIVE STUDY 
690 1 0 |a DRUG EFFECT 
690 1 0 |a PHOTOCHEMISTRY 
690 1 0 |a PHOTOCHEMOTHERAPY 
690 1 0 |a APOPTOSIS 
690 1 0 |a CELL LINE 
690 1 0 |a CELL SURVIVAL 
690 1 0 |a DIMYRISTOYLPHOSPHATIDYLCHOLINE 
690 1 0 |a HUMANS 
690 1 0 |a LIPOSOMES 
690 1 0 |a MICELLES 
690 1 0 |a ORGANOMETALLIC COMPOUNDS 
690 1 0 |a PHOTOBIOLOGY 
690 1 0 |a PHOTOCHEMISTRY 
690 1 0 |a PHOTOCHEMOTHERAPY 
690 1 0 |a PHOTOSENSITIZING AGENTS 
690 1 0 |a POLYMERS 
650 1 7 |2 spines  |a NECROSIS 
650 1 7 |2 spines  |a NECROSIS 
700 1 |a Morán, F. 
700 1 |a Bonansea, A. 
700 1 |a Monetti, M. 
700 1 |a Fernández, D.A. 
700 1 |a Strassert, C.A. 
700 1 |a Rivarola, V. 
700 1 |a Awruch, J. 
700 1 |a Dicelio, L.E. 
773 0 |d 2003  |g v. 2  |h pp. 988-994  |k n. 10  |p Photochem. Photobiol. Sci.  |x 1474905X  |t Photochemical and Photobiological Sciences 
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856 4 0 |u https://doi.org/10.1039/b303428n  |y DOI 
856 4 0 |u https://hdl.handle.net/20.500.12110/paper_1474905X_v2_n10_p988_Rodriguez  |y Handle 
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