Artículo

Estamos trabajando para incorporar este artículo al repositorio
Consulte el artículo en la página del editor
Consulte la política de Acceso Abierto del editor

Abstract:

Lipophilic tetrakis-(1-adamantylsulfanyl)phthalocyaninatozinc(II) was incorporated into two different nanoemulsion formulations with the former emulsion containing isopropyl myristate and Tween 80® and the latter glycerol monocaprylocaprate and Tween 80®. A two- to three-fold increase in water solubility was observed for the zinc phthalocyanine when incorporated into the nanoemulsions in comparison with that observed for water-DMSO (98:2). Morphological evaluation confirmed the formation of thermodynamically stable nanoemulsions in the nanosize range. The zinc phthalocyanine incorporated into the nanoemulsions was photo-stable over the irradiation times studied and both formulations displayed excellent singlet oxygen generation ability with high values of quantum yield of singlet oxygen production of up to 0.58. In addition, the viscosity of the nanoemulsions ranged from 30.2 to 323.9 cP. The foregoing formulations are considered to be strong candidates for parenteral administration of the zinc phthalocyanine in photodynamic therapy clinical trials. © 2011 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:A comparative study of a novel lipophilic phthalocyanine incorporated into nanoemulsion formulations: Photophysics, size, solubility and thermodynamic stability
Autor:García Vior, M.C.; Monteagudo, E.; Dicelio, L.E.; Awruch, J.
Filiación:Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina
Departamento de Tecnología Farmacéutica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, 1113 Buenos Aires, Argentina
INQUIMAE, Departamento de Química Inorgánica, Analítica y Química Física, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, 1428 Buenos Aires, Argentina
Palabras clave:Nanoemulsions; Photodynamic therapy; Singlet oxygen; Solubility; Thermodynamic stability; Zinc(II) phthalocyanines; Clinical trial; Comparative studies; Isopropyl myristate; Nano-emulsions; Nano-size; Nanoemulsion; Parenteral administration; Photophysics; Singlet oxygen; Singlet oxygen generation; Singlet oxygen production; Tetrakis; Thermodynamically stable; Tween 80; Water solubilities; Zinc phthalocyanines; Emulsification; Gas generators; Glycerol; Oxygen; Photodynamic therapy; Plasmons; Quantum yield; Solubility; Thermodynamic stability; Zinc; Zinc compounds; Nitrogen compounds
Año:2011
Volumen:91
Número:2
Página de inicio:208
Página de fin:214
DOI: http://dx.doi.org/10.1016/j.dyepig.2011.03.011
Título revista:Dyes and Pigments
Título revista abreviado:Dyes Pigm.
ISSN:01437208
CODEN:DYPID
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_01437208_v91_n2_p208_GarciaVior

Referencias:

  • MacDonald, I.J., Dougherty, T.J., Basic principles of photodynamic therapy (2001) Journal of Porphyrins and Phthalocyanines, 5 (2), pp. 105-129. , DOI 10.1002/jpp.328
  • Rodriguez, M.E., Moran, F., Bonansea, A., Monetti, M., Fernandez, D.A., Strassert, C.A., Rivarola, V., Dicelio, L.E., 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 (2003) Photochemical and Photobiological Sciences, 2 (10), pp. 988-994. , DOI 10.1039/b303428n
  • Rodriguez, M.E., Fernández, D.A., Awruch, J., Braslavsky, S., Dicelio, L.E., Effect of aggregation of a cationic phthalocyanine in micelles and in the presence of human serum albumin (2006) J Porphyr Phthalocyanines, 10, pp. 33-42
  • Master, A.M., Rodriguez, M.E., Kenney, M.E., Oleinick, N.L., Gupta, A.S., Delivery of the photosensitizer Pc 4 in PEG-PCL micelles for in vitro PDT studies (2010) J Pharm Sci, 99, pp. 2386-2398
  • Konan, Y.N., Gurny, R., Allemann, E., State of the art in the delivery of photosensitizers for photodynamic therapy (2002) Journal of Photochemistry and Photobiology B: Biology, 66 (2), pp. 89-106. , DOI 10.1016/S1011-1344(01)00267-6, PII S1011134401002676
  • Van Nostrum, C.F., Polymeric micelles to deliver photosensitizers for photodynamic therapy (2004) Advanced Drug Delivery Reviews, 56 (1), pp. 9-16. , DOI 10.1016/j.addr.2003.07.013
  • Derycke, A.S.L., De Witte, P.A.M., Liposomes for photodynamic therapy (2004) Advanced Drug Delivery Reviews, 56 (1), pp. 17-30. , DOI 10.1016/j.addr.2003.07.014
  • Torchilin, V.P., Multifunctional nanocarriers (2006) Advanced Drug Delivery Reviews, 58 (14), pp. 1532-1555. , DOI 10.1016/j.addr.2006.09.009, PII S0169409X06001785, Particulate Nanomedicines
  • Chatterjee, D.K., Fong, L.S., Zhang, Y., Nanoparticles in photodynamic therapy: An emerging paradigm (2008) Adv Drug Deliv Rev, 60, pp. 1627-1637
  • Eccleston, M.J., Microemulsions (1994) Encyclopedia of Pharmaceutical Technology, 9, pp. 375-421
  • Lawrence, M.J., Rees, G.D., Microemulsion-based media as novel drug delivery system (2000) Adv Drug Deliv Rev, 45, pp. 89-121
  • García Vior, M.C., Dicelio, L.E., Awruch, J., Synthesis and properties of phthalocyanine zinc(II) complexes replaced with oxygen and sulfur adamantane moieties (2009) Dyes Pigm, 83, pp. 375-380
  • Fernandez, D.A., Awruch, J., Dicelio, L.E., Photophysical and aggregation studies of t-butyl-substituted Zn phthalocyanines (1996) Photochemistry and Photobiology, 63 (6), pp. 784-792
  • Bouchemal, K., Briancon, S., Perrier, E., Fessi, H., Nano-emulsion formulation using spontaneous emulsification: Solvent, oil and surfactant optimisation (2004) International Journal of Pharmaceutics, 280 (1-2), pp. 241-251. , DOI 10.1016/j.ijpharm.2004.05.016, PII S0378517304003072
  • Glisoni, R.J., Chiappetta, D., Finkielsztein, L.M., Moglioni, A.G., Sosnik, A., Self-aggregation behaviour of novel thiosemicarbazone drug candidates with potential antiviral activity (2010) New J Chem, 34, pp. 2047-2058
  • Wilkinson, F., Herman, 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
  • Kraljic, I., El Mohsni, S., A new method for the detection of singlet oxygen in aqueous solutions (1978) Photochem Photobiol, 28, pp. 577-581
  • Schnurpfeil, G., Sobbi, A.K., Spiller, W., Kliesch, H., Wohrle, D., Photo-oxidative stability and its correlation with semi-empirical MO calculations of various tetraazaporphyrin derivatives in solution (1997) Journal of Porphyrins and Phthalocyanines, 1 (2), pp. 159-167
  • Shafiq, S., Shakeel, F., Talegaonkar, S., Ahmad, F.J., Khar, R.K., Ali, M., Development and bioavailability assessment of ramipril nanoemulsion formulation (2007) European Journal of Pharmaceutics and Biopharmaceutics, 66 (2), pp. 227-243. , DOI 10.1016/j.ejpb.2006.10.014, PII S0939641106002839
  • Pouton, C.W., Formulation of poorly water-soluble drugs for oral administration: Physicochemical and physiological issues and the lipid formulation classification system (2006) European Journal of Pharmaceutical Sciences, 29 (3-4 SPEC. ISS.), pp. 278-287. , DOI 10.1016/j.ejps.2006.04.016, PII S0928098706001151
  • Kale, A., Patravale, V., Development and evaluation of lorazepam microemulsions for parenteral delivery (2008) AAPS PharmSciTech, 9, pp. 966-971
  • Palamakula, A., Khan, M.A., Evaluation of cytotoxicity of oils used in coenzyme Q10 Self-Emulsifying Drug Delivery Systems (SEDDS) (2004) International Journal of Pharmaceutics, 273 (1-2), pp. 63-73. , DOI 10.1016/j.ijpharm.2003.12.010, PII S0378517303007002
  • Porter, C.J.H., Pouton, C.W., Cuine, J.F., Charman, W.N., Enhancing intestinal drug solubilization using lipid-based delivery systems (2008) Adv Drug Deliv Rev, 60, pp. 673-691
  • Tagne, J.-B., Kakumanu, S., Ortiz, D., Shea, T., Nicolosi, R.J., A nanoemulsion formulation of tamoxifen increases its efficacy in a breast cancer cell line (2008) Molecular Pharmaceutics, 5 (2), pp. 280-286. , DOI 10.1021/mp700091j
  • Charman, S.A., Charman, W.N., Rogge, M.C., Wilson, T.D., Dutko, F.J., Pouton, C.W., Self-emulsifying drug delivery systems: Formulation and biopharmaceutic evaluation of an investigational lipophilic compound (1992) Pharm Res, 9, pp. 87-93
  • Tall, B., Yalkowski, S.H., Enhanced intestinal absorption of cyclosporine in rats through the reduction of emulsion droplet size (1989) Pharm Res, 6, pp. 40-43
  • Boonme, P., Krauel, K., Graf, A., Rades, T., Junyaprasert, V.B., Characterization of microemulsion structures in the pseudoternary phase diagram of isopropyl palmitate/water/Brij 97:1-butanol (2006) AAPS PharmSciTech, 7, p. 45
  • Weiwei, Z., Aihua, Y., Weihong, W., Ruiqian, D., Jun, W., Guangxi, Z., Formulation design of microemulsion for dermal delivery of penciclovir (2006) Int J Pharm, 360, pp. 184-190
  • Rumie Vittar, N.B., Prucca, C.G., Strassert, C., Awruch, J., Rivarola, V.A., Cellular inactivation and antitumor efficacy of a new zinc phthalocyanine with potential use in photodynamic therapy (2008) Int J Biochem Cell Biol, 40, pp. 2192-2205
  • Strassert, C.A., Bilmes, G.M., Awruch, J., Dicelio, L.E., Comparative photophysical investigation of oxygen and sulfur as covalent linkers on octaalkylamino substituted zinc(II) phthalocyanines (2008) Photochemical and Photobiological Sciences, 7 (6), pp. 738-747. , DOI 10.1039/b802709a
  • Minnes, R., Weitman, H., You, Y., Detty, M.R., Ehrenberg, B., Dithiaporphyrin derivatives as photosensitizers in membranes and cells (2008) J Phys Chem B, 112, pp. 3268-3276
  • Diz, V.E., Gauna, G.A., Strassert, C.A., Awruch, J., Dicelio, L.E., Photophysical properties of microencapsulated photosensitizers (2010) J Porphyr Phthalocyanines, 14, pp. 278-283

Citas:

---------- APA ----------
García Vior, M.C., Monteagudo, E., Dicelio, L.E. & Awruch, J. (2011) . A comparative study of a novel lipophilic phthalocyanine incorporated into nanoemulsion formulations: Photophysics, size, solubility and thermodynamic stability. Dyes and Pigments, 91(2), 208-214.
http://dx.doi.org/10.1016/j.dyepig.2011.03.011
---------- CHICAGO ----------
García Vior, M.C., Monteagudo, E., Dicelio, L.E., Awruch, J. "A comparative study of a novel lipophilic phthalocyanine incorporated into nanoemulsion formulations: Photophysics, size, solubility and thermodynamic stability" . Dyes and Pigments 91, no. 2 (2011) : 208-214.
http://dx.doi.org/10.1016/j.dyepig.2011.03.011
---------- MLA ----------
García Vior, M.C., Monteagudo, E., Dicelio, L.E., Awruch, J. "A comparative study of a novel lipophilic phthalocyanine incorporated into nanoemulsion formulations: Photophysics, size, solubility and thermodynamic stability" . Dyes and Pigments, vol. 91, no. 2, 2011, pp. 208-214.
http://dx.doi.org/10.1016/j.dyepig.2011.03.011
---------- VANCOUVER ----------
García Vior, M.C., Monteagudo, E., Dicelio, L.E., Awruch, J. A comparative study of a novel lipophilic phthalocyanine incorporated into nanoemulsion formulations: Photophysics, size, solubility and thermodynamic stability. Dyes Pigm. 2011;91(2):208-214.
http://dx.doi.org/10.1016/j.dyepig.2011.03.011