Catecholamines enhance dihydrolipoamide dehydrogenase inactivation by the copper fenton system. Enzyme protection by copper chelators

Free Radical Research

Volumn 24, Issue 4, 1996, Pages 311-322

  Gutierrez Correa, J ^a   Stoppani, A O M ^a,b  

^a School of Medicine   (Argentina)

^b UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Captopril; Catecholamines; Copper; Copper chelators; Hydrogen peroxide; Hydroxyl radicals; Lipoamide dehydrogenase; Oxidative damage; Thiol compounds

Indexed keywords

3,4 DIHYDROXYPHENYLACETIC ACID; ACETYLCYSTEINE; ADRENALIN; BENZOIC ACID; CAPTOPRIL; CATECHOL; CATECHOLAMINE; CHELATING AGENT; COPPER; DIHYDROLIPOAMIDE DEHYDROGENASE; DITHIOTHREITOL; DOPAMINE; HISTIDINE; HYDROGEN PEROXIDE; HYDROXYL RADICAL; LEVODOPA; NORADRENALIN; OXIDOPAMINE; TIOPRONIN; TRYPANOTHIONE;

ARTICLE; AUTOOXIDATION; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME BINDING; ENZYME DENATURATION; ENZYME INACTIVATION; HYDROXYLATION; OXIDATION; SCAVENGING SYSTEM;

EID: 0029995035     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.3109/10715769609088028     Document Type: Article

References (39)

1. J. Gutierrez Correa and A.O.M. Stoppani (1993) Inactivation of lipoamide dehydrogenase by cobalt(II) and iron(II) Fenton systems: effect of metal chelators, thiol compounds and adenine nucleotides. Free Radical Research Communications, 19, 303-314.
2. J. Gutierrez Correa and A.O.M. Stoppani (1995) Inactivation of heart lipoamide dehydrogenase by copper Fenton systems. Effect of thiol compounds and metal chelators. Free Radical Research, 22, 239-250.
3. G.S. Rao (1991) Release of 2-thiobarbituric acid reactive products from glutamate, deoxyuridine or DNA during autoxidation of dopamine in the presence of copper ions. Pharmacology and Toxicology, 69, 164-466.
4. T.P. Ryan, D.M. Milller and S.D. Aust (1993) The role of metals in the enzymatic and nonenzymatic oxidation of epinephrine. Journal of Biochemical Toxicology, 8, 33-39.
5. M.B. Mattammal, R. Strong, E. White and F.-F. Hsu (1994) Characterization of peroxidative oxidation products of dopamine by mass spectrometry. Journal of Chromatography B., 658, 21-30.
6. E. Herlinger, R.F. Jameson and W. Linert (1995) Spontaneous autoxidation of dopamine. Journal of Chemistry Society Perkin Transaction, 2, 259-263.
7. P.G. Noble, J.P. Antel and V.W. Yong (1994) Astrocytes and catalase prevent the toxicity of catecholamines to oligodendrocytes. Brain Research, 633, 83-90.
8. Y. Linderson, S. Baez and J. Segura-Aguilar (1994) The protective effect of superoxide dismutase and catalase against formation of reactive oxygen species during reduction of cyclized norepinephrine ortho-quinone by DT-diaphorase. Biochimica et Biophysica Acta, 1200, 197-204.
9. I.P.E. Spencer, A. Jenner, O.I. Aruoma, P.J. Evans, H. Kaur, D.T. Dexter, P. Jenner, A.J. Lees, D.C. Marsden and B. Halliwell (1994) Intense oxidative DNA damage promoted by L-DOPA and its metabolites. Implications for neurodegenerative disease. FEBS Letters, 353, 246-250.
10. A.N. Basma, E.J Morris, W.J. Nicklas and H.M. Geller (1995) L-DOPA cytotoxicity to PC12 cells in culture is via its autoxidation. Journal of Neurochemistry, 64, 825-832.
11. C.C. Chiueh, H. Miyake and M.-T. Peng (1993) Role of dopamine autoxidation, hydroxy 1 radical generation, and calcium overload in underlying mechanisms involved in MPTP-induced parkinsonism in, Advances in Neurology, Vol. 60, Raven Press, Ltd., New York, pp. 251-257.
12. S. Przedborski, V. Jackson-Lewis, U. Muthane, U. Jiang, M. Ferreira, A.B. Naini and S. Fahn (1993) Chronic levodopa administration alters cerebral mitochondrial respiratory chain activity. Annals of Neurology, 34, 715-723.
13. B. Pardo, M.A. Mena and J. Garcia de Yébenes (1995) L-DOPA inhibits complex IV of the electron transport chain in catecholamine-rich human neuroblastoma NB69 cells. Journal of Neurochemistry, 64, 576-582.
14. D. Ben-Shachar, R. Zuk and Y. Glinka (1995) Dopamine neurotoxicity: inhibition of mitochondrial respiration. Journal of Neurochemistry, 64, 718-723.
15. S.L. Jewett, L.J. Eddy and P. Hochstein (1989) Is the autoxidation of catecholamines involved in ischemia-reperfusion injury? Free Radical Biology and Medicine, 6, 185-188.
16. M. Chevion, Y. Jiang, R. Har-El, E. Berenshtein,G. Uretzky and N. Kitrossky (1993) Copper and iron are mobilized following myocardial ischemia: possible predictive criteria for tissue injury. Proceedings of the National Academy of Sciences of the United States of America, 90, 1102-1106.
17. •OH generation on myocardial ischemic injury by dialysis technique. American Journal of Physiology, 266, H903-H908.
18. J.M C. Gutteridge (1987) Ferrous-salt-promoted damage to deoxyribose and benzoate Biochemical Journal, 243, 709-714.
19. D.A. Rowley and B. Halliwell (1985) Formation of hydroxyl radicals from NADH and NADPH in the presence of copper salts. Journal of Inorganic Biochemistry, 23, 103-108.
20. M.A. Ondetti (1994) From peptides to peptidases: a chronicle of drug discovery. Annual Review of Pharmacology and Toxicology, 34, 1-16.
21. G. Sölen (1993) Radioprotective effect of N-acetylcysteine in vitro using the induction of DNA breaks and end-point. International Journal Radiation Biology, 64, 359-366.
22. A. Puppo, R. Cecchini, O.I. Aruoma, R. Bolli and B. Halliwell (1990) Scavenging of hypochlorous acid and of myoglobin-derived oxidants by the cardioprotective agent mercaptopropionylglycine. Free Radical Research Communications, 10, 371-381.
23. B. Scheer and G. Zimmer (1993) Dihydrolipoic acid prevents hypoxic/reoxygenation and peroxidative damage in rat heart mitochondria. Archives of Biochemistry and Biophysics, 302, 385-390.
24. Y.J. Suzuki, M. Tsuchiya and L. Packer (1993) Antioxidant activities of dihydrolipoic acid and its structural homologues. Free Radical Research Communications, 18, 115-122.
25. R.A. Løvstad (1987) Copper catalyzed oxidation of ascorbate (vitamin C). Inhibitory effect of catalase, superoxide dismutase, serum proteins (ceruloplasmin, albumin, apotransferrin) and amino acids. International Journal of Biochemistry, 19, 309-313.
26. R.C. Kukreja, K.E. Loesser, A.A. Kearns, S.A. Naseem and M.L. Hess (1993) Protective effects of histidine during ischemia-reperfusion in isolated perfused rat hearts. American Journal of Physiology, 264, H1370-H1381.
27. J.M.S. van Maanen, U.H. Verkerk, J. Broersen, M.V.M. Lafleur, J. de Vries, J. Retél and H.M. Pinedo (1988) Semi-quinone formation from the catechol and ortho-quinone metabolites of the antitumor agent VP-16-213. Free Radical Research Communications, 4, 371-384.
28. M.J. van der Merwe, K. Jenkins, E. Theron and B J. van der Walt (1993) Interaction of the di-catechols rooperol and nordihydroguaiaretic acid with oxidative systems in the human blood. Biochemical Pharmacology, 45, 303-311.
29. G. Cohen and R.E. Heikkila (1974) The generation of hydrogen peroxide, superoxide radical, and hydroxyl radical by 6-hydroxydopamine, dialuric acid, and related cytotoxic agents. Journal of Biological Chemistry, 249, 2447-2452.
30. R.G. Matthews and C.H. Williams (1974) Identification of the thiol residues involved in modifications of pig heart lipoamide dehydrogenase by cupric ion and by iodoacetamide. Biochimica et Biophysics Acta, 370, 39-48.
31. T. Ozawa, J. Ueda and A. Hanaki (1993) Copper(II)-albumin complex can activate hydrogen peroxide in the presence of biological reductants; first ESR evidence for the formation of hydroxyl radical. Biochemical and Molecular Biology International, 29, 247-253.
32. J.-I. Ueda, Y. Shimazu and T. Ozawa (1995) Reactions of copper(II)-oligopeptide complexes with hydrogen peroxide: effects of biological reductants. Free Radical Biology and Medicine, 18, 929-933.
33. E.P.W. Kable and P.G. Parsons (1988) Potency, selectivity and cell cycle dependence of catechols in human tumour cells in vitro, Biochemical Pharmacology, 37, 1711-1715.
34. V. Misik, I T. Mak, R.E. Stafford and W.B. Weglicki (1993) Reactions of captopril and epicaptopril with transition metal ions and hydroxyl radicals: an EPR spectroscopy study. Free Radical Biology and Medicine, 15, 611-619.
35. S.P. Andreoli (1993) Captopril scavenges hydrogen peroxide and reduces, but does not eliminate, oxidant-induced cell injury. American Journal of Physiology, 264, F120-F127.
36. K. Chopra, M. Singh, N. Kaul and N.K. Ganguly (1993) Oxygen free radicals and protective effect of captopril on myocardial infarct size. Archives internationales de Pharmacodynamic et de Thérapie, 322, 55-65.
37. J.-Z. Sun, H. Kaur, B. Halliwell, X.-Y. Li and R. Bolli (1993) Use of aromatic hydroxylation of phenylalanine to measure production of hydroxyl radicals after myocardial ischemia in vivo. Direct evidence for a pathogenetic role of the hydroxyl radical in myocardial stunning. Circulation Research, 73, 534-549.
38. M.L Mira, M.M. Silva, M.J. Queirzo and C.F. Manso (1993) Angiotensin converting enzyme inhibitors as oxygen free radicals scavengers. Free Radical Research Communications, 19, 173-181
39. J.D. Adams and I.N. Odunze (1991) Oxygen free radicals and Parkinson's disease. Free Radical Biology and Medicine, 10, 161-169.