Actas de congresos
Electrochemical Study Of Methyl 2-[p-nitrophenyi(hydroxy)methyl]acrylate, An Anticancer Drug, In The Presence Of Gsh And Dsdna
Registro en:
9781604233803
Ecs Transactions. , v. 3, n. 29, p. 137 - 146, 2007.
19385862
10.1149/1.2753298
2-s2.0-44849118824
Autor
Goulart M.O.F.
De Souza A.A.
Sales E.M.
De Abreu F.C.
De Paula F.S.
Almeida W.P.
Institución
Resumen
Electrochemical experiments (CV, DPV, SWV, CPE) 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 and EtOH + phosphate buffer: 1:9, 0.1 mol L1, pH 9.4) and aprotic (DMF + TBAP, 0.1 mol L-1) media. The reduction behaviours were typical of nitroaromatics, with an additional wave, in aprotic medium, related to the reduction of the olefin. Electrolysis, in protic media, furnished a reduced dimer. The incubation of 1 into a dsDNA biosensor revealed, that, after reduction of the nitroaromatic function, diagnostic oxidation peaks of the nucleobases were observed, indicative of interaction between them. GSH influenced the reduction behaviour of 1. Direct reduction of 1, in phosphate buffer, pH 9.38, to a stable nitroso/GSH adduct is facilitated. These electrochemical results help in the understanding of the anticancer activity of 1 that can be considered a hypoxia targeted bioreductive agent with a glutathione depleting function. copyright The Electrochemical Society. 3 29 137 146 Rauf, S., Gooding, J.J., Akhtar, K., Ghauri, M.A., Rahman, M., Anwar, M.A., Khalid, A.M., (2005) J. Pharm. Biomed. Anal, 37, p. 205 Russo, A., Degraff, W., Friedman, N., Mitchell, J.B., (1986) Cancer Res, 46, p. 2845 Tew, K.D., (1994) Cancer Res, 54, p. 4313 Berube, L.R., Farah, S., McClelland, R.A., Rauth, A.M., (1992) Int. J. Radiat. Oncol. Biol. Phys, 22, p. 817 Griffith, O.W., Meister, A., (1979) J. Biol. Chem, 254, p. 7558 Williamson, J.M., Boettcher, B., Meister, A., (1982) Proc. Natl. Acad. Sci. USA, 79, p. 6246 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 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., Núñez-Vergara, L.J., (2005) Current Org. Chem, 9, p. 565 Julião, M.D.D.S., Ferreira, E.I., Ferreira, N.G., Serrano, S.H.P., (2006) Electrochim. Acta, 51, p. 5080 A. M. O. Brett, M.O.F. Goulart and F.C. de Abreu, Biosens. Bioelectron., 17, 913 (2002)Brett, A.M.O., Serrano, S.H.P.J., Piedade, A.P., (1999) Comprehensive Chemical Kinetics, 37, pp. 91-119. , R. G. Compton and H. G. Hancock, Editors, Elsevier: Amsterdam Coelho, F., Almeida, W.P., Mateus, C.R., Veronese, D., Lopes, E.C.S., Silvira, G.P.S., Rossi, R.C., Pavam, C.H., (2002) Tetrahedron, 58, p. 7437 Lund, H., Cathodic Reduction of Nitro and Related Compounds (2001) Organic Electrochemistry, p. 389. , 4th Ed, H. Lund and O. Hammerich, Editors, p, Marcel Dekker, New York 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, p, Plenum Press, New York Tocher, J.H., Edwards, D.I., (1995) Biochem. Pharmacol, 50, p. 1367