Artículos de revistas
Electrochemical Study Of Methyl 2- [p -nitrophenyl(hydroxy)methyl]acrylate
Registro en:
Journal Of The Electrochemical Society. , v. 154, n. 11, p. P121 - P129, 2007.
134651
10.1149/1.2773535
2-s2.0-34848840694
Autor
Goulart M.O.F.
De Souza A.A.
De Abreu F.C.
De Paula F.S.
Sales E.M.
Almeida W.P.
Buriez O.
Amatore C.
Institución
Resumen
Electrochemical experiments with methyl 2- [p -nitrophenyl(hydroxy)methyl] acrylate (1) were performed in protic (EtOH+phosphate buffer 1:9, 0.1 mol L-1, pH 6.9; EtOH+phosphate buffer+NaOH 1:9, 0.1 mol L-1 or 0.2 mol L-1, pH 9.4 and EtOH+ NaHCO3 +NaOH 2:8, 0.18 mol L-1, pH 9.6) and aprotic [dimethylformamide (DMF)+tetrabutylammonium perchlorate (TBAP), 0.1 mol L-1] media. The primary reduction behavior in aprotic medium was typical of nitroaromatics along with an additional wave related to the reduction of the acrylate function. Kinetic analysis carried out in aprotic and aqueous basic media pointed out to the high stability of the electrogenerated nitro radical anion, especially in DMF+TBAP. Reduced (GSH) and oxidized (GSSG) gluthatione in phosphate buffer influenced the reduction behavior of 1, due mainly to protonation effects. Direct reduction of 1, in the presence of GSH, led to a transient nitroso-GS adduct. In the presence of GSSG, hydrogen-bonding-associated GSSG-hydroxylamine was the main product. Electrochemical studies of 1, in the presence of oxygen, showed no chemical reactivity between O2 and 1 -. These electrochemical results help in the understanding of the anticancer activity of 1 that can be considered a bioreductive agent with a glutathione depleting function. © 2007 The Electrochemical Society. 154 11 P121 P129 Garret, M.D., Workman, P., (1999) Eur. J. Cancer, 35, p. 2010 Russo, A., Degraff, W., Friedman, N., Mitchell, J.B., (1986) Cancer Res., 46, p. 2845 Tew, K.D., (1994) Cancer Res., 54, p. 4313 Griffith, O.W., Meister, A., (1979) J. Biol. Chem., 254, p. 7558 Williamson, J.M., Boettcher, B., Meister, A., (1982) Proc. Natl. Acad. Sci. U.S.A., 79, p. 6246 Kirlin, W.G., Cai, J., Thompson, S.A., Diaz, D., Kavanagh, T.J., Jones, D.P., (1999) Free Radic Biol. Med., 27, p. 1208 Powis, G., Gasdaka, J.R., Baker, A., (1997) Adv. Pharmacol. (San Diego), 38, p. 329 Berube, L.R., Farah, S., McClelland, R.A., Rauth, A.M., (1992) Int. J. Radiat. Oncol., Biol., Phys., 22, p. 817 McCarthy, T.J., Hayes, E.P., Schwartz, C.S., Witz, G., (1994) Fundam. Appl. Toxicol., 22, p. 543 Kohn, L.K., Pavam, C.H., Veronese, D., Coelho, F., De Carvalho, J.E., Almeida, W.P., (2006) Eur. J. Med. Chem., 41, p. 738 Kundu, M.K., Sundar, N., Kumar, S.K., Bhat, S.V., Biswas, S., Valecha, N., (1999) Bioorg. Med. Chem. Lett., 9, p. 731 De Abreu, F.C., Ferraz, P.A.L., Goulart, M.O.F., (2002) J. Braz. Chem. Soc., 13, p. 19 Squella, J.A., Bollo, S., Núez-Vergara, L.J., (2005) Curr. Org. Chem., 9, p. 565. , 1385-2728 10.2174/1385272053544380 Da Julião, D.M.S., Ferreira, E.I., Ferreira, N.G., Serrano, S.H.P., (2006) Electrochim. Acta, 51, p. 5080 Tocher, J.H., Edwards, D.I., (1995) Biochem. Pharmacol., 50, p. 1367 Bollo, S., Gunckel, S., Nunez-Vergara, L.J., Chauviere, G., Squella, J.A., (2005) Electroanalysis, 17, p. 134 Coelho, F., Almeida, W.P., Mateus, C.R., Veronese, D., Lopes, E.C.S., Silveira, G.P.S., Rossi, R.C., Pavam, C.H., (2002) Tetrahedron, 58, p. 7437 Krezel, A., Bal, W., (2003) Org. Biomol. Chem., 1, p. 3885 Olmstead, M.L., Nicholson, R.S., (1969) Anal. Chem., 41, p. 862 Bard, A.J., Faulkner, R.L., (2000) Electrochemical Methods, Fundamentals and Applications, p. 240. , 2nd ed., Wiley and Sons, New York Carbajo, L., Bollo, S., Núez-Vergara, L.J., Campero, A., Squella, J.A., (2002) J. Electroanal. Chem., 531, p. 187 Lund, H., (2001) Organic Electrochemistry, p. 389. , 4th ed., H.Lund and O.Hammerich, Editors, Marcel Dekker, New York Grimshaw, J., (2001) Organic Electrochemistry: An Introduction and A Guide., pp. 411-434. , 3rd ed., H.Lund, and O.Hammerich, Editors, Marcel Dekker, New York Zuman, P., Fijalek, Z., Dumanovic, D., Suznjevic, D., (1992) Electroanalysis, 4, p. 783 Nicholson, R.S., Shain, I., (1964) Anal. Chem., 36, p. 706 McClelland, R.A., (1990) Selective Activation of Drugs by Redox Processes, p. 125. , G. E.Adams, A. Breccia, E. M.Fielden, and P.Wardman, Editors, Plenum Press, New York Wardman, P., (1986) Environ. Health Perspect., 64, p. 309 Aguilar-Martinez, M., MacÍas-Ruvalcaba, N.A., Bautista-Martínez, J.A., Gómez, M., González, F.J., González, I., (2004) Curr. Org. Chem., 8, p. 1721 Miller, C., Folkes, L.K., Mottley, C., Wardman, P., Mason, R.P., (2002) Arch. Biochem. Biophys., 397, p. 113 Eyer, P., (1979) Chem. Biol. Interact., 24, p. 227 Kazanis, S., McClelland, R., (1992) J. Am. Chem. Soc., 114, p. 3052 Clancy, R., Cederbaum, A.I., Stoyanovsky, D.A., (2001) J. Med. Chem., 44, p. 2035 Singh, R.J., Hogg, N., Joseph, I., Kalyanaraman, B., (1996) J. Biol. Chem., 271, p. 18596 Soul̀re, L., Sturm, J.-C., Núez-Vergara, L.J., Hoffmann, P., Ṕrí, J., (2001) Tetrahedron, 57, p. 7137 How, N., (2000) Free Radic Biol. Med., 28, p. 1478