The role of adrenochrome in stimulating the oxidation of catecholamines
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Adrenochrome, a stable oxidation product formed after oxidation of adrenaline, strongly stimulates oxygen uptake occurring during the autoxidation of adrenaline, other catecholamines and ascorbate. Oxygen consumed is converted to hydrogen peroxide suggesting the occurrence of a redox cycling process. The reduction of adrenochrome operated by adrenaline is accelerated by the exclusion of oxygen indicating that the oxidation of adrenaline occurs directly and superoxide anion does not necessarily mediate it. Oxygen consumption, observed in the catecholamine/adrenochrome and ascorbate/adrenochrome systems, is due to the autoxidation of leucoadrenochrome that, at variance with adrenaline, easily autoxidizes also at physiological pH. Therefore, in these systems, leucoadrenochrome appears to be the major determinant of the production of superoxide anion.
KeywordsAdrenaline Adrenochrome Aminochromes Ascorbate Catecholamine oxidation Redox cycling
diethylenetriamine pentaacetic acid
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- Ball, E.G. and Chen, T. (1933) Studies on oxidation-reduction. XX. Epinephrine and related compounds.J. Biol. Chem. 102, 691–719.Google Scholar
- Bindoli, A., Rigobello, M.P. and Galzigna, L. (1988) Production of reduced forms of oxygen by adrenochrome in the presence of ascorbate, microsomes and submitochondrial particles. In: Rice Evans, C. and Dormandy, T. (Eds.),Free Radicals: Chemistry, Pathology and Medicine (Richelieu Press, London), pp. 293–300.Google Scholar
- Cook, J.A., Wink, D.A., Blount, V., Krishna, M.C. and Hanbauer, I. (1996) Role of antioxidants in the nitric oxide-elicited inhibition of dopamine uptake in cultured mesencephalic neurons. Insight into potential mechanisms of nitric oxide-mediated neurotoxicity.Neurochem. Intern. 28, 609–617.CrossRefGoogle Scholar
- Ernster, L. (1987) DT-diaphorase: a historical review.Chemica Scripta 27A, 1–13.Google Scholar
- Falk, J.E. (1949) The formation of hydrogen carriers by haematin-catalyzed peroxidations. 2. Some reactions of adrenaline and adrenochrome.Biochem. J. 44, 369–373.Google Scholar
- Heacock, R.A. and Powell, W.S. (1973) Adrenochrome and related compounds. In: Ellis, G.P. and West, G.B. (Eds.),Progress in Medicinal Chemistry. Vol. 9 (North Holland, Amsterdam) pp. 275–339.Google Scholar
- Mukherjee, T. (1987) One-electron reduction of juglone (5-hydroxy-l,4-naphthoquinone): a pulse radiolysis study.Radiat. Phys. Chem. 29, 455–462.Google Scholar
- Vulpian, E.F.A. (1856) Notes sur quelques reactions propres a la substance des capsules surrenales.C.R. Acad. Sci. 43, 663–665.Google Scholar
- Wiesner, K. (1942) Polarographische Untersuchung des Adrenochroms.Biochem. Z. 313, 48–61.Google Scholar