Autoxidation and MAO-mediated metabolism of dopamine as a potential cause of oxidative stress: Role of ferrous and ferric ions

Neurochemistry International

Volumn 45, Issue 1, 2004, Pages 103-116

  Hermida Ameijeiras, Álvaro ^a   Méndez Álvarez, Estefanía ^a   Sánchez Iglesias, Sofía ^a   Sanmartín Suárez, Carolina ^a   Soto Otero, Ramón ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

3,4 dihydroxyphenylacetic acid; Bovine serum albumin; BSA; Catechol O methyltransferase; COMT; DA; DOPAC; Dopamine; Homovanillic acid; HVA; Malonodialdehyde; MAO; MDA; Monoamine oxidase; SDS; Sodium dodecylsulfate; TBARS; Thiobarbituric acid reagent substances

Indexed keywords

AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME A; AMINE OXIDASE (FLAVIN CONTAINING) ISOENZYME B; ANTIOXIDANT; CARBONYL DERIVATIVE; DOPAMINE; FERRIC ION; FERROUS ION; HYDROGEN PEROXIDE; HYDROXYL RADICAL; MITOCHONDRIAL PROTEIN; MONOAMINE OXIDASE INHIBITOR; PARGYLINE; THIOBARBITURIC ACID DERIVATIVE; THIOL;

ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; AUTOOXIDATION; CONTROLLED STUDY; DOPAMINE METABOLISM; ENZYME ACTIVITY; ENZYME INHIBITION; FENTON REACTION; LIPID PEROXIDATION; MALE; MITOCHONDRION; NONHUMAN; OXIDATION KINETICS; OXIDATIVE STRESS; PRIORITY JOURNAL; RAT;

ANIMALS; CORPUS STRIATUM; DOPAMINE; FERRIC COMPOUNDS; FERROUS COMPOUNDS; HYDROGEN PEROXIDE; MALE; MITOCHONDRIA; MONOAMINE OXIDASE; OXIDANTS; OXIDATION-REDUCTION; OXIDATIVE STRESS; RATS; RATS, SPRAGUE-DAWLEY; THIOBARBITURIC ACID REACTIVE SUBSTANCES;

BOVINAE; GYMNOMYZA SAMOENSIS;

EID: 1842788061     PISSN: 01970186     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.neuint.2003.11.018     Document Type: Article

References (65)

1. Aikens J., Dix J.A. Perhydroxyl radical (HOO·) initiated lipid peroxidation. The role of fatty acid hydroperoxides. J. Biol. Chem. 266:1991;15091-15098.
2. Avdeef A., Sofen S.R., Bregante T.L., Raymond K.N. Coordination chemistry of microbial iron transport compounds. Part 9. Stability constants for catechol models of enterobactin. J. Am. Chem. Soc. 100:1978;5362-5370.
3. Ayala A., Cutler R.G. The utilization of 5-hydroxyl-2-amino valeric acid as a specific marker of oxidized arginine and proline residues in proteins. Free Radic. Biol. Med. 21:1996;65-80.
4. Ben-Shachar D., Zuk R., Glinka Y. Dopamine neurotoxicity: inhibition of mitochondrial respiration. J. Neurochem. 64:1995;718-723.
5. Bernheimer H., Birkmayer W., Hornykiewicz O., Jellinger K., Seitelberger F. Brain dopamine and the syndromes of Parkinson and Huntington - clinical, morphological and neurochemical correlations. J. Neurol. Sci. 29:1973;415-455.
6. Chakrabarti S., Naik A.A., Reddy G.R. Phenylhydrazine mediated degradation of bovine serum albumin and membrane proteins of human erythrocytes. Biochim. Biophys. Acta. 1028:1990;89-94.
7. Chakraborty H., Ray S.N., Chakrabarti S. Lipid peroxidation associated protein damage in rat brain crude synaptosomal fraction mediated by iron and ascorbate. Neurochem. Int. 39:2001;311-317.
8. Chiueh C.C., Miyake H., Peng M.T. Role of dopamine autoxidation, hydroxyl radical generation and calcium overload in underlying mechanisms involved in MTP-induced parkinsonism. Adv. Neurol. 60:1993;251-258.
9. Clark, J.B., 1993. Electrochemical assay. In: Eisenthal, R., Danson, M.J. (Eds.), Enzyme Assay: A Practical Approach. IRL Press, Oxford, pp. 181-190.
10. Cohen G. Monoamine oxidase and oxidative stress at dopaminergic synapse. J. Neural Transm. 32:1990;229-238.
11. Dean R.T., Fu S., Stocker R., Davies M.J. Biochemistry and pathology of radical-mediated protein oxidation. Biochem. J. 324:1997;1-18.
12. Dean R.T., Hunt J.V., Grant A.J., Yamamoto Y., Niki E. Free radical damage to proteins: the influence of the relative localization of radical generation, antioxidants, and target proteins. Free Radic. Biol. Med. 11:1991;161-168.
13. Dean R.T., Thomas S.M., Garner A. Free radical-mediated fragmentation of monoamine oxidase in the mitochondrial membrane. Roles for lipid radicals. Biochem. J. 240:1986;489-494.
14. Dostert P., Strolin Benedetti M., Frigerio E. Effect of L-DOPA, oxyferriscorbone, and ferrous iron on in vivo lipid peroxidation. J. Neural Transm. 84:1991;119-128.
15. Enoch W.S., Sarna T., Zecca L., Riley P.A., Swartz H.M. The roles of neuromelanin, binding of metal ions, and the oxidative cytotoxicity in the pathogenesis of Parkinson's disease: a hypothesis. J. Neural Transm. 7:1994;83-100.
16. Filloux F., Townsend J.J. Pre- and postsynaptic neurotoxic effects of dopamine demonstrated by intrastriatal injection. Exp. Neurol. 119:1993;79-88.
17. Fornstedt B. Role of catechol autoxidation in the degeneration of dopamine neurons. Acta Neurol. Scand. 129:1990;12-14.
18. Fornstedt B., Pileblad E., Carlsson A. In vivo autoxidation of dopamine in guinea pig striatum increases with age. J. Neurochem. 55:1990;655-659.
19. Fowler C.J., Callingham B.A., Mantel T.J., Tipton K.F. The effect of lipophilic compounds upon the activity of rat liver mitochondrial mono-oxidase-A and -B. Biochem. Pharmacol. 29:1980;1177-1183.
20. Fowler C.J., Mantel T.J., Tipton K.F. The nature of the inhibition of rat liver monoamine oxidase types A and B by the acetylenic inhibitors clorgyline, L-deprenyl and pargyline. Biochem. Pharmacol. 31:1982;3555-3561.
21. Fu S., Gebicki S., Jessup W., Gebicki J.M., Dean R.T. Biological fate of amino acid, peptide and protein hydroperoxides. Biochem. J. 311:1995;821-827.
22. Gebicki S., Gebicki J.M. Formation of peroxides in amino acids and proteins exposed to oxygen free radicals. Biochem. J. 289:1993;743-749.
23. Gerlach M., Xiao A.Y., Kuhn W., Lehnfeld R., Waldmeier P., Sontag K.H., Riederer P. The central catechol-O-methyltransferase inhibitor tolcapone increases striatal hydroxyl radical production in L-DOPA/carbidopa treated rats. J. Neural Transm. 108:2001;189-204.
24. Graham D.G. Oxidative pathway for catecholamines in the genesis of neuromelanin and cytotoxic quinones. Mol. Pharmacol. 14:1978;633-643.
25. Graham D.G., Tiffany S.M., Bell W.R., Gutknecht W.F. Autoxidation versus covalent binding of quinones as the mechanism of toxicity of dopamine, 6-hydroxydopamine, and related compounds toward C1300 neuroblastoma cells in vitro. Mol. Pharmacol. 14:1978;644-653.
26. Habeeb A.F.S.A. Reaction of protein sulfhydryl groups with Ellman's reagent. Methods Enzymol. 25:1972;457-464.
27. Halliwell, B., Gutteridge, J.M.C. (Eds.), 1999. Free Radicals in Biology and Medicine, third ed. Oxford University Press, Oxford.
28. Hastings T.G., Lewis D.A., Zigmond M.J. Role of oxidation in the neurotoxic effects of intrastriatal dopamine injections. Proc. Natl. Acad. Sci. U.S.A. 93:1996;1956-1961.
29. Kalir A., Sabbagh A., Youdim M.B. Selective acetylenic "suicide" and inhibitors of monoamine oxidase types A and B. Br. J. Pharmacol. 73:1981;55-64.
30. Konradi C., Riederer P., Youdim M.B.H. Hydrogen peroxide enhances the activity of monoamine oxidase type-B but not type-A: a pilot study. J. Neural Transm. 22:1986;61-73.
31. Langston J.W. Predicting Parkinson's disease. Neurology. 40(Suppl.):1990;70-74.
32. Lees A.J. On the behalf of the Parkinson's Disease Research Group of the United Kingdom, 1995 Comparison of the therapeutic effects and mortality data of levodopa and levodopa combined with selegiline in patients with early, mild Parkinson's disease. Br. Med. J. 311:1995;1602-1607.
33. Li C.-L., Werner P., Cohen G. Lipid peroxidation in brain: interactions of L-DOPA/dopamine with ascorbate and iron. Neurodegeneration. 4:1995;147-153.
34. Linert W., Herlinger E., Jameson R.F., Kienzl E., Jellinger K., Youdim M.B.H. Dopamine, 6-hydroxydopamine, iron, and dioxygen - their mutual interactions and possible implications in the development of Parkinson's disease. Biochim. Biophys. Acta. 1316:1996;160-168.
35. Linert W., Jameson G.N.L. Redox reactions of neurotransmitters possibly involved in the progression of Parkinson's disease. J. Inorg. Biochem. 79:2000;319-326.
36. Liu J., Mori A. Monoamine metabolism provides an antioxidant defense in the brain against oxidant- and free radical-induced damage. Arch. Biochem. Biophys. 302:1993;118-127.
37. Mann D.M.A., Yates P.O. Possible role of neuromelanin in the pathogenesis of Parkinson's disease. Mech. Age Dev. 21:1983;193-203.
38. Markwell M.A.K., Haas S.M., Bieber L.L., Tolbert N.E. A modification of the Lowry procedure to simplify protein determination in membrane and lipoprotein samples. Anal. Biochem. 87:1978;206-210.
39. McGeer P.L., McGeer E.G., Suzuki J.S. Aging and extrapyramidal function. Arch. Neurol. 34:1977;33-35.
40. Méndez-Álvarez E., Soto-Otero R., Hermida-Ameijeiras A., López-Martín M.E., Labandeira-García J.L. Effect of iron and manganese on hydroxyl radical production by 6-hydroxydopamine: mediation of antioxidants. Free Radic. Biol. Med. 31:2001;986-998.
41. Méndez-Álvarez E., Soto-Otero R., Sánchez-Sellero I., López-Rivadulla Lamas M. Inhibition of brain monoamine oxidase by adducts of 1,2,3,4-tetrahydroisoquinoline with components of cigarette smoke. Life Sci. 60:1997;1719-1727.
42. Michel P.P., Hefti F. Toxicity of 6-hydroxydopamine and dopamine for dopaminergic neurons in culture. J. Neurosci. Res. 26:1990;428-435.
43. Nappi A.J., Vass E. Comparative studies of enhanced iron-mediated production of hydroxyl radical by glutathione, cysteine, ascorbic acid, and selected catechols. Biochim. Biophys. Acta. 1336:1997;295-301.
44. Neuzil J., Stocker R. Bilirrubin attenuates radical-mediated damage to serum albumin. FEBS Lett. 331:1993;281-284.
45. Palkovits, M., Brownstein, M., 1989. Catecholamines in the central nervous system. In: Trendelenberg, U., Weiner, N. (Eds.), Catecholamines II. Springer, Berlin, pp. 1-26.
46. Pedrosa R., Soares-da-Silva P. Oxidative and non-oxidative mechanism of neuronal cell death and apoptosis by L-3,4-dihydroxyphenylalanine (L-DOPA) and dopamine. Br. J. Pharmacol. 137:2002;1305-1313.
47. Pryor, W.A., 1976. The role of free radical reactions in biological systems. In: Pryor, W.A. (Ed.), Free Radicals in Biology, vol. 1. Academic Press, New York, pp. 1-49.
48. Ravinovic A.D., Lewis D.A., Hastings T.G. Role of oxidative changes in the degeneration of dopamine terminals after injection of neurotoxic levels of dopamine. Neuroscience. 101:2000;67-76.
49. Raymond K.N., Isied S.S., Brown L.D., Fronczek F.R., Nibert J.H. Coordination isomers of biological iron transport compounds. Part VI. Models of the enterobactin coordination site. J. Am. Chem. Soc. 98:1976;1767-1774.
50. Reznick A.Z., Packer L. Oxidative damage to proteins: spectrophotometric method for carbonyl assay. Methods Enzymol. 233:1994;357-363.
51. Richter H.W., Waddell W.H. Mechanism of the oxidation of dopamine by the hydroxyl radical in aqueous solution. J. Am. Chem. Soc. 105:1983;5434-5440.
52. Schild L., Reinheckel T., Wiswedel I., Augustin W. Short-term impairment of energy production in isolated rat liver mitochondria by hypoxia/ reoxygenation: involvement of oxidative protein modification. Biochem. J. 328:1997;205-210.
53. Severson J.A., Marcusson J., Winblad B., Finch C.E. Age-correlated loss of dopaminergic binding sites in human basal ganglia. J. Neurochem. 39:1982;1623-1631.
54. Slivka A., Cohen G. Hydroxyl radical attack on dopamine. J. Biol. Chem. 260:1985;15466-15472.
55. Soto-Otero R., Méndez-Álvarez E., Hermida-Ameijeiras A., López-Real A.M., Labandeira-García J.L. Effects of (-)-nicotine and (-)-cotinine on 6-hydroxydopamine-induced oxidative stress and neurotoxicity: relevance for Parkinson's disease. Biochem. Pharmacol. 64:2002;125-135.
56. Soto-Otero R., Méndez-Álvarez E., Hermida-Ameijeiras A., Muñoz-Patiño A.M., Labandeira-García J.L. Autoxidation and neurotoxicity of 6-hydroxydopamine in the presence of some antioxidants: potential implication in relation to the pathogenesis of Parkinson's disease. J. Neurochem. 74:2000;1605-1612.
57. Spencer J.P.E., Jenner A., Butler J., Aruoma O.I., Dexter D.T., Jenner P., Halliwell B. Evaluation of the pro-oxidant and antioxidant actions of L-DOPA and dopamine in vitro: implications for Parkinson's disease. Free Radic. Res. 24:1996;95-105.
58. Svingen B.A., Buege J.A., O'Neal F.O., Aust S.D. The mechanism of NADPH-dependent lipid peroxidation. The propagation of lipid peroxidation. J. Biol. Chem. 254:1979;5892-5899.
59. Tanaka M., Sotomatsu A., Kanai H., Hirai S. Dopa and dopamine cause cultured neuronal death in the presence of iron. J. Neurol. Sci. 101:1991;198-203.
60. Thomas S.M., Gebicki J.M., Dean R.T. Radical initiated alpha-tocopherol depletion and lipid peroxidation in mitochondrial membranes. Biochim. Biophys. Acta. 1002:1989;189-197.
61. Thomas C.E., Huber E.W., Ohlweiler D.F. Hydroxyl and peroxyl radical trapping by monoamine oxidase-B inhibitors deprenyl and MLD 72,974A: implications for protection of biological substrates. Free Radic. Biol. Med. 22:1997;733-737.
62. + in vivo. Eur. J. Pharmacol. 243:1993;241-247.
63. Yen G.-C., Hsieh C.-L. Antioxidant effects of dopamine and related compounds. Biosci. Biotech. Biochem. 61:1997;1646-1649.
64. Zaleska M.M., Floyd R.A. Regional lipid peroxidation in rat brain in vitro: possible role of endogenous iron. Neurochem. Res. 10:1985;397-410.
65. Zhang F., Dryhurst G. Oxidation chemistry of dopamine: possible insights into the age-dependent loss of dopaminergic nigrostriatal neurons. Bioorg. Chem. 21:1993;392-410.