Artículos de revistas
Evaluation Of Photodynamic Activity Of Porphyrins For Use In Photodynamic Therapy Through Tryptophan Photo-oxidation [avaliação Da Atividade Fotodinâmica De Porfirinas Para Uso Em Terapia Fotodinâmica Através Da Fotoxidação De Triptofano]
Registro en:
Ecletica Quimica. , v. 32, n. 1, p. 7 - 14, 2007.
1004670
2-s2.0-34250318525
Autor
Ribeiro J.N.
Jorge R.A.
Da Silva A.R.
Flores A.V.
Ronchi L.M.
Tedesco A.C.
Institución
Resumen
In this work an investigation of the photodynamic efficiency of octaethylporphyrin (OEP), vanadyl octaethylporphyrin (VOOEP), and meso-tetramesitylporphyrin (m-TMP) was done. This study was performed by the determination of photoxidation rate constants (k f) of the tryptophan amino acid (Trp). The mechanism involved in the photoxidation of Trp was also studied using sodium azide (singlet oxygen scavenger) and deuterium oxide. The values of k f/10 -4s -1 for Trp photoxidation demonstrated that OEP (2.80 ± 0.05) is more efficient than m-TMP (1.62 ± 0.07) and VOOEP (0.81 ± 0.08). The values of k f were reduced by the presence of sodium azide and increased by deuterium oxide indicating that singlet oxygen is responsible by OEP, VOOEP, and m-TMP photoactivity. These results indicated that differences in the photodynamic activity between porphyrins could be associated with differences in their molecular structures. The presence of vanadyl group (V=O) interferes clearly in the photodynamic activity of OEP causing a considerable reduction in its efficiency. 32 1 7 14 E.S. Nyman, P.H. Hynninen, J. Photoch. Photobio. B 73 (2004) 28Dickson, E.F.G., Goyan, R.L., Pottier, R.H., (2003) Cell. Mol. Biol, 48, p. 939 I.J. Mac Donald, T.J. Doughert, J. Porphy. Phthalocya. 5(2) (2001) 105Calin, M.A., Parasca, S.V., (2006) J. Optoelectro. Adv. Mat, 8 (3), p. 1173 Y.N. Konan, R. Gurny, E. Allemann, J. Photoch. Photobio. B 66 (2002)106S. Michels, S.U. Schmidt-Erfurth, Invest. Ophth. Vis. Sci. 44 (2003)-2154Simplicio, F.I., Maionchi, F., Hioka, N., (2002) Quím. Nova, 25, p. 801 Via, L.V., Magno, S.M., (2001) Curr. Med. Chem, 8, p. 1405 Ostler, R.B., Scully, A.D., Taylor, A.G., Gould, I.R., Smith, T.A., Waite, A., Phillips, D., (2000) Photochem. Photobiol, 71, p. 397 Gorman, A., Killoran, J., O'Shea, C., Kenna, T., Gallagher, W.M., O'Shea, D.F., (2004) J. Am. Chem. Soc, 126, p. 10619 Oleinick, N.L., Morris, R.L., Belichenko, I., (2002) Photochem. Photobiol. Sci, 1, p. 1 Van Nostrum, C.F., (2004) Adv. Drug Deliver. Rev, 56, p. 9 Bonnett, R., (1995) Chem. Soc. Rev, 24, p. 19 M. Ochsner, J. Photoch. Photobio. B. 39 (1997) 1Sibata, C.H., Colussi, V.C., Oleinick, N.L., Kinsella, T.J., (2000) Braz. J. Med. Biol. Res, 33, p. 880 Ribeiro, J.N., Flores, A.V., Mesquita, R., Nicola, J.H., Nicola, E.M., (2004) Physicae, 5 (2), p. 31 S.P. Songca, B. Mbatha, J. Pharm. Pharmacol. 52 (2000) 1361E. Zenkevich, E. Sagun, V. Knyukshto, S.P. Shulga, A. Mironov, O. Efremova, R. Bonnett, S.P. Songca, M. Kassem, J. Photoch. Photobio. B 33 (1996) 171Howe, L., Zhang, J.Z., (1998) Photochem. Photobiol, 67, p. 90 Grossweiner, L.I., Patel, A.S., Grossweiner, J.B., (1982) Photochem. Photobiol, 36, p. 159 J.N. Ribeiro, A.R. Silva, R.A. Jorge, J. Bras. Patol. Med. Lab. 40(6) (2004) 385Lai, J.C., Lo, P.C., Ng, D.K.P., Ko, W.H., Leung, S.C.H., Fung, K.P., Fong, W.P., Cancer Biol (2006) Therapy, 5 (4), p. 413 Stavropoulos, N.E., Kim, A., Nseyo, U.U., Tsimaris, I., Chung, T.D., Miller, T.A., Redlak, M., Skalkos, D., (2006) Photochem. Photobiol. B-Biol, 84 (1), p. 64 Kessel, D., (1999) Photodynamic therapy of neoplasic disease, , CRC Press, London K. Berg, H. Anhot, J. Moan, A. Ronnestad, C. Rimington, J. Photoch. Photobio. B 20 (1993) 37André Romero da Silva, Dissertação de mestrado Análise das Propriedades Fotossensibilizantes do In(III)-mesotetrafenilporfirina para uso em Terapia Fotodinâmica, Instituto de Química, UNICAMP, 2003]Falk, J.E., (1964) Porphyrins and Metalloporphyrins, 2, pp. 72-93. , Elsevier 1st Edition p Karns, G.A., Gallagher, W.A., Elliott, W.B., (1979) Bioorg. Chem, 8, p. 69 Rotomskis, R., Bagdonas, S., Streckyte, G., (1996) J. Photochem. Photobiol. B, 33, p. 61 Schmidt, R., (1989) J. Am. Chem. Soc, 111, p. 6983 Sconfienza, C., Vorst, A.V., Jori, G., (1979) Photochem. Photobiol, 31, p. 351 Inoue, K., Matsuura, T., Saito, I., (1982) Bull. Chem. Soc. Jpn, 55, p. 2959 Machado, A.E.H., (2000) Quím. Nova, 23 (2), p. 237