Abstract
The alkoxy and peroxy radicals formed in the degradation of hydroperoxides brought about by transition metal ions in acidic media can convert substrates with suitably low oxidation potentials, such as N,N-diethyl-para-phenylendiamine, to the corresponding radical cations. The possibility that these reactions are used in the evaluation of oxidative stress in human beings is discussed.
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References
B. Maillard, K.U. Ingold, and J.C. Scaiano, J. Am. Chem. Soc., 105, 5095 (1983).
B. Halliwell and J.M.C. Gutteridge, Biochem. J., 219, 1 (1984).
T.F. Slater, Biochem. J., 222, 1 (1984).
B. Halliwell and J.M.C. Gutteridge, Molec. Aspect Med., 8, 89 (1985).
A. Singh, G.W. Koroll and R.B. Cundall, Rad. Phys. Chem., 19, 137 (1982).
H. Sies, Angew. Chem. Int. Ed. Engl., 25, 1058 (1986).
K.J.A. Davies and A.L. Goldberg, J. Biol. Chem., 262, 8220 (1987).
P.J. Boon, P.M. Cullis, M.C.R. Symons and B.W. Wren, J. Chem. Soc., Perkin Trans. 2, 1393 (1984).
P.M. Cullis, G.D.D. Jones, and M.C.R. Symons, Nature, 330, 773 (1987).
J.M.C. Gutteridge, Free Rad. Res. Commun., 19, 141 (1993).
A.C. Bowling and M.F. Beal, Life Sciences, 56, 1151 (1994).
B. Haliwell, The Lancet, 344, 721 (1994).
N.A. Porter, Acc. Chem. Res., 19, 262 (1986).
J.A. Howard and K.U. Ingold, J. Am. Chem. Soc., 90, 1056 (1968).
J.A. Howard and K.U. Ingold, J. Am. Chem. Soc., 90, 1058 (1968).
C.A. Rice-Evans, A.T. Diplock and M.C.R. Symons, in R.H. Burdon and P.H. van Knippenberg, (Ed.s), Techniques in Free Radical Research. Laboratory Techniques in Biochemistry and Molecular Biology, Vol. 22, Elsevier, Amsterdam, 1991.
D. Swern Peroxides, in J.F. Stoddart, (Ed.), Comprehensive Organic Chemistry Vol. 1, Pergamon Press, Oxford, 1979.
R. Hiatt, K.C. Irwin, and C.W. Gould, J. Org. Chem., 33, 1430 (1968).
P.J. O’Brien, Can. J. Biochem., 47, 485 (1969).
G. Merényi, L. Lind, and L. Engman, J. Chem. Soc., Perkin Trans. 2, 2551 (1994).
P.J. Elving and A.F. Krivis, Anal. Chem., 30, 1645 (1958).
P.J. Elving and A.F. Krivis, Anal. Chem., 30, 1648 (1958).
A. Zweig, J.E. Lancaster, M.T. Neglia, and W.H. Jura, J. Am. Chem. Soc., 86, 4130 (1964).
L. Michaelis, M.P. Schubert, and S. Granick, J. Am. Chem. Soc., 61, 1981 (1939).
M.T. Melchior and A.H. Maki, J. Chem. Phys., 34, 471 (1961); J.R. Bolton, A. Carrington, and A.D. McLachlan, Mol. Phys., 5, 31 (1962); S.F. Nelsen in H. Fischer and K.-H. Hellwege, (Ed.s), Magnetic Properties of Free Radicals: Organic Cation Radicals and Polyradicals, Landolt-Börnstein: Numerical Data and Functional Relationships in Science and Technology. New Series Vol.9, Part d2, Springer-Verlag, Heidelberg, 1980.
G. Grampp and G. Stiegler, Zeit. Phys. Chem. Neue Folge, 141 S, 185 (1984).
A. Zweig, J.E. Lancaster, M.T. Neglia, and W.H. Jura, J. Am. Chem. Soc. 86, 4130 (1964); R. Hand, M. Melicharsk, D.I. Scoggins, R. Stotz, A.K. Carpenter, and R.F. Nelson, Collect. Czech. Chem. Commun., 36, 842 (1971).
L.H. Piette, P. Ludwig, and R.N. Adams, Anal. Chem., 34, 916 (1962).
G. Petterson, Acta. Chem. Scand., 22, 3063 (1968).
C. Störle and P. Eyer, Chem.-Biol. Interactions, 78, 321 (1991).
C. Störle, K. Stettmeier, and P. Eyer, Free Rad. Res. Commun., 17, 133 (1992).
G. Curzon, Biochem. J., 103, 289 (1967).
C. Störle and P. Eyer, Chem.-Biol. Interactions, 83, 271 (1992).
T. Sekiguchi and Y. Nosoh, Arch. Biochem. Biophys., 138, 319 (1970).
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Alberti, A., Bolognini, L., Macciantelli, D. et al. The radical cation of N,N-diethyl-para-phenylendiamine: A possible indicator of oxidative stress in biological samples. Res Chem Intermed 26, 253–267 (2000). https://doi.org/10.1163/156856700X00769
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DOI: https://doi.org/10.1163/156856700X00769