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:

2,3,9,10,16,17,23,24-octakis[(N,N-dimethylaminoethylsulfanyl)]phthalocyaninatozinc (II) (S1) was used as a lipophilic photosensitizer to be encapsulated into biodegradable poly(d,l lactide-co-glycolide)-polyvinyl alcohol nanoparticles. The synthesis, size, and spectroscopic, photophysical, and magnetic properties of nanoparticles, were analyzed. A greater number of sonication cycles afforded smaller nanoparticles. The stabilization by means of polyvinyl alcohol of all the nanoparticles synthesized provided a negative charge to the systems in a wide pH range. The thermograms obtained by differential scanning calorimetry showed that the nanoparticles were stabilized by polyvinyl alcohol. The incorporation of magnetite nanoparticles was verified by FT-IR, magnetization measurements by means of hysteresis curves and potential Z. S1 retained its efficiency in generating singlet oxygen. The incorporation of magnetite into the nanoparticles showed an increase in singlet oxygen quantum yields due to the heavy atom effect. © 2015 Elsevier B.V. All rights reserved.

Registro:

Documento: Artículo
Título:Photophysics of an octasubstituted zinc(II) phthalocyanine incorporated into solid polymeric magnetic and non-magnetic PLGA-PVA nanoparticles
Autor:Diz, V.E.; Leyva, G.; Zysler, R.D.; Awruch, J.; Dicelio, L.E.
Filiación:INQUIMAE, Departamento de Química Inorgánica, Analítica y Química Física, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, Buenos Aires, 1428, Argentina
Instituto de Nanociencia y Nanotecnologia, Avenida General Paz 1499 San Martín, Comisión Nacional de Energia Atómica, Provincia de Buenos Aires, 1650, Argentina
Centro Atomico Bariloche, Río Negro, Bariloche, 8400, Argentina
Departamento de Química Orgánica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Junín 956, Buenos Aires, 1113, Argentina
INQUIMAE, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón II, Buenos Aires, 1428, Argentina
Palabras clave:Magnetite; Phthalocyanines; Poly(d,l lactide-co-glycolide)-polyvinyl alcohol; Singlet oxygen; Solid nanoparticles
Año:2016
Volumen:316
Página de inicio:44
Página de fin:51
DOI: http://dx.doi.org/10.1016/j.jphotochem.2015.10.018
Título revista:Journal of Photochemistry and Photobiology A: Chemistry
Título revista abreviado:J. Photochem. Photobiol. A Chem.
ISSN:10106030
CODEN:JPPCE
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_10106030_v316_n_p44_Diz

Referencias:

  • López Zeballos, N.C., García Vior, M.C., Awruch, J., Dicelio, L.E., An exhaustive study of a novel sulfur-linked adamantane tetrasubstituted zinc(II) phthalocyanine incorporated into liposomes (2012) J. Photochem. Photobiol. A, 235, pp. 7-13
  • Van Nostrum, C.F., Polymeric micelles to deliver photosensitizers for photodynamic therapy (2004) Adv. Drug Deliv. Rev., 56, pp. 9-16
  • 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 (2011) Dyes Pigm., 91, pp. 208-214
  • Gaspar Tosato, M., Orallo, D.E., Churio, M.S., Martín, A.A., Telléz Soto, C.A., Dicelio, L.E., Influence of mycosporine-like aminoacids and gadusol on the rheology and Raman spectroscopy of polymer geles (2014) Biorheology, 51, pp. 315-328
  • Lopez Zeballos, N.C., García Vior, M.C., Awruch, J., Dicelio, L.E., A comparative study of peripheral and non-peripheral zinc (II) phthalocyanines incorporated into mesoporous silica nanoparticles (2015) Dyes Pigm., 113, pp. 145-150
  • Daniel, M.C., Astruc, D., Gold Nanoparticles: Assembly, supramolecular chemistry, quantum-size-related properties, and applications toward biology, catalysis, and nanotechnology (2004) Chem. Rev., 104, pp. 293-346
  • Ye, F., Barrefelt, A., Asem, H., Abedi-Valugerdi, M., El-Serafi, I., Saghafian, M., Abu-Salah, K., Hassan, M., Biodegradable polymeric vesicles containing magnetic nanoparticles, quantum dots and anticancer drugs for drug delivery and imaging (2014) Biomaterials, 35, pp. 3885-3894
  • Zhang, Y., Chen, T., Targeting nanomaterials: Future drugs for cancer chemotherapy (2012) Int. J. Nanomed., 7, pp. 5283-5286
  • Lu, A.-H., Salabas, E.L., Schüth, F., Magnetic nanoparticles: Synthesis, protection, functionalization, and application (2007) Angew. Chem. Int. Ed., 46, pp. 1222-1244
  • Zhang, F., Jin, J., Zhong, X., Li, S., Niu, J., Li, R., Ma, J., Pd immobilized on amine-functionalized magnetite nanoparticles: A novel and highly active catalyst for hydrogenation and Heck reactions (2011) Green Chem., 13, pp. 1238-1243
  • Ranjbakhsh, E., Bordbar, A.K., Abbasi, M., Khosropour, A.R., Shams, E., Enhancement of stability and catalytic activity of immobilized lipase on silica-coated modified magnetite nanoparticles (2012) Chem. Eng. J., 179, pp. 272-276
  • Sosnovik, D.E., Nahrendorf, M., Weissleder, R., Magnetic nanoparticles for MR imaging: Agents, techniques and cardiovascular applications (2008) Basic Res. Cardiol., 103, pp. 122-130
  • Shenoy, D.B., Amiji, M.M., Poly (ethylene oxide)-modified poly-(caproloctone) nanoparticles for target delivery of tamoxifen in breast cancer (2005) Int. J. Pharm., 293, pp. 261-270
  • Konan, Y.N., Berton, M., Gurny, R., Allemann, E., Enhanced photodynamic activity of meso-tetra(4-hydroxyphenyl) porphyrin by incorporation into sub-200 nm nanoparticles (2003) Eur. J. Pharm. Sci., 18, pp. 241-249
  • Ricci-Junior, E., Marchetti, J.M., Zinc(II) phthalocyanine loaded PLGA nanoparticles for photodynamic therapy use (2006) Int. J. Pharm., 310, pp. 187-195
  • Essa, S., Rabanel, J.M., Hildgen, P., Effect of polyethylene glycol (PEG) chain organization on the physicochemical properties of poly(D, L-lactide) (PLA) based nanoparticles (2010) Eur. J. Pharm. Biopharm., 75, pp. 96-106
  • Chen, D., Tang, Q., Li, X., Zhou, X., Zang, J., Xue, W., Xiang, J., Guo, C., Biocompatibility of magnetic Fe3O4 nanoparticles and their cytotoxic effect on MCF-7 cells (2012) Int. J. Nanomed., 7, pp. 4973-4982
  • Mahmoudi, M., Sant, S., Wang, B., Laurent, S., Sen, T., Superparamagnetic iron oxide nanoparticles (SPIONs): Development, surface modification and applications in chemotherapy (2011) Adv. Drug Deliv. Rev., 63, pp. 24-46
  • Arora, W.S., Superparamagnetic iron oxide nanoparticles: Magnetic nanoplatforms as drug carriers (2012) Int. J. Nanomed., 7, pp. 3445-3471
  • Diz, V.E., Gauna, G.A., Strassert, C.A., Awruch, J., Dicelio, L.E., Photophysical properties of microencapsulated phthalocyanines (2010) J. Porphyrins Phthalocyanines, 14, pp. 278-283
  • Vargas, J.M., Zysler, R.D., Tayloring the size in colloidal iron oxide magnetic nanoparticles (2005) Nanotechnology, 16, pp. 1474-1476
  • Gürsoy, S., Cihan, A., Kocak, M.B., Bekaroglu, Ö., Synthesis of new metal-free and metal-containing phthalocyanines with tertiary or quaternary aminoethyl substituents (2001) Monatsh. Chem., 132, pp. 813-819
  • Pinto Reis, C., Neufeld, R.J., Ribeiro, A.J., Veiga, F., Nanoencapsulation II. Biomedical applications and current status of peptide and protein nanoparticulate delivery systems (2006) Nanomedicine, 2, pp. 53-65
  • Cu, Y., Saltzman, W.M., Controlled surface modification with poly(ethylene) glycol enhances diffusion of PLGA nanoparticles in human cervical mucus molecules (2008) Pharmaceutics, 6, pp. 173-181
  • Lagorio, M.G., Reflectance spectroscopy using wine bottle glass (1999) J. Chem. Educ., 76, pp. 1551-1554
  • Amore, S., Lagorio, M.G., Dicelio, L.E., San Roman, E., Photophysical properties of supported dyes. Quantum yield calculations in scattering media (2001) Prog. React. Kinet. Mech., 26, pp. 159-177
  • Rodriguez, M.E., Morán, F., Bonansea, A., Monetti, M., Fernández, D.A., Strassert, C.A., Rivarola, V., Dicelio, L.E., A comparative study of photophysical and phototoxic properties of a new octaalkyl zinc (II) phthalocyanine incorporated in an hydrophilic polymer, in liposomes and in non ionic micelles (2003) Photochem. Photobiol. Sci., 2, pp. 988-994
  • Alarcón, E., Edwards, A.M., Garcia Muñoz, A.M., Aspée, A., Borsarelli, C.D., Lissi, E.A., Photophysics and photochemistry of zinc phthalocyanine/bovine serum albumin adducts (2009) Photochem. Photobiol. Sci., 8, pp. 255-263
  • 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
  • Vandervoort, J., Yoncheva, K., Ludwig, A., Influence of the homogenisation procedure on the physicochemical properties of PLGA nanoparticles (2004) Chem. Pharm. Bull., 52, pp. 1273-1279
  • Roca, A.G., Preparación de nanopartículas nanomagnéticas uniformes y de alta cristalinidad para biomedicina (2009) Tesis Doctoral, , Departamento de Química Física, Instituto de Ciencia de Materiales de Madrid, CSIC, Universidad Complutense de Madrid España
  • Barrera, C., Herrera, A., Zayas, Y., Rinaldi, C., Surface modification of magnetite nanoparticles for biomedical applications (2009) J. Magn. Magn. Mater., 321, pp. 1397-1399
  • Hergt, R., Andra, A.W., D'Ambly, C.G., Hilger, I., Kaiser, W.A., Richter, U., Schmidt, H.G., Physical limits of hyperthermia using magnetite fine particles (1998) IEEE Trans. Magn., 34, pp. 374-375
  • 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) Photochem. Photobiol. Sci., 7, pp. 738-747
  • Rodríguez, 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. Porphyrins Phthalocyanines, 10, pp. 33-42

Citas:

---------- APA ----------
Diz, V.E., Leyva, G., Zysler, R.D., Awruch, J. & Dicelio, L.E. (2016) . Photophysics of an octasubstituted zinc(II) phthalocyanine incorporated into solid polymeric magnetic and non-magnetic PLGA-PVA nanoparticles. Journal of Photochemistry and Photobiology A: Chemistry, 316, 44-51.
http://dx.doi.org/10.1016/j.jphotochem.2015.10.018
---------- CHICAGO ----------
Diz, V.E., Leyva, G., Zysler, R.D., Awruch, J., Dicelio, L.E. "Photophysics of an octasubstituted zinc(II) phthalocyanine incorporated into solid polymeric magnetic and non-magnetic PLGA-PVA nanoparticles" . Journal of Photochemistry and Photobiology A: Chemistry 316 (2016) : 44-51.
http://dx.doi.org/10.1016/j.jphotochem.2015.10.018
---------- MLA ----------
Diz, V.E., Leyva, G., Zysler, R.D., Awruch, J., Dicelio, L.E. "Photophysics of an octasubstituted zinc(II) phthalocyanine incorporated into solid polymeric magnetic and non-magnetic PLGA-PVA nanoparticles" . Journal of Photochemistry and Photobiology A: Chemistry, vol. 316, 2016, pp. 44-51.
http://dx.doi.org/10.1016/j.jphotochem.2015.10.018
---------- VANCOUVER ----------
Diz, V.E., Leyva, G., Zysler, R.D., Awruch, J., Dicelio, L.E. Photophysics of an octasubstituted zinc(II) phthalocyanine incorporated into solid polymeric magnetic and non-magnetic PLGA-PVA nanoparticles. J. Photochem. Photobiol. A Chem. 2016;316:44-51.
http://dx.doi.org/10.1016/j.jphotochem.2015.10.018