Comparative studies of protein modification mediated by fenton-like reactions of iron, hematin, and hemoglobin: Generation of different reactive oxidizing species

Journal of Biochemistry and Molecular Biology

Volumn 31, Issue 2, 1998, Pages 161-169

  Kim, Young Myeong ^a   Kim, Sung Soo ^a   Kang, Gu ^a   Yoo, Yeong Min ^a   Kim, Ki Mo ^a   Lee, Mi Eun ^a   Han, Jeong A ^a   Hong, Sun Joo ^a  

^a Kangwon National University   (South Korea)

Author keywords

Fenton reaction; Hemoglobin; Hydroxyl radical; Iron; Reactive oxygen species

Indexed keywords

EID: 0032361692     PISSN: 12258687     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (51)

1. Adams, P. A. and Berman, M. C. (1980) Kinetics and mechanism of the interaction between human serum albumin and monomeric haemin. Biochem. J. 191, 95-102.
2. Aft, R. L. and Mueller, G. C. (1984) Hemin-mediated oxidative degradation of proteins. J. Biol. Chem. 259, 301-305.
3. Beaven, G. H., Chen, S., D'Albis, A., and Gratzer, W. B. (1974) A spectroscopic study of the haemin-human serum albumin system. Eur. J. Biochem. 41, 539-546.
4. Bradshaw, R. A., Shearer, W. T., and Gurd, F. R. N. (1968) Sites of binding of copper(II) ion by peptide (1-24) of bovine serum albumin. J. Biol. Chem. 243, 3817-3825.
5. Buettner, G. R. (1987) Spin trapping: ESR parameters of spin adducts. Free Rad. Biol. Med. 3, 259-303.
6. Cederbaum, A. I., Dicker, E., Rubin, E., and Cohen, G. (1979) Effect of thiourea on microsomal oxidation of alcohols and associated microsomal functions. Biochemistry 18, 1187-1191.
7. Chance, B., Sies, H., and Boveris, A. (1979) Hydroperoxide metabolism in mammalian organs. Physiol. Rev. 59, 527-605.
8. Davies, K. J. A. (1987) Protein damage and degradation by oxygen radicals. I. General aspects. J. Biol. Chem. 262, 9895-9901.
9. Davies, K. J. A. and Delsignore, M. E. (1987) Protein damage and degradation by oxygen radicals. III. Modification of secondary and tertiary structure. J. Biol. Chem. 262, 9908-9913.
10. Davies, K. J. A., Delsignore, M. E., and Lin, S. W. (1987) Protein damage and degradation by oxygen radicals. II. Modification of amino acids. J. Biol. Chem. 262, 9902-9907.
11. Davies, K. J. A. and Goldberg, A. L. (1987) Oxygen radicals stimulate intracellular proteolysis and lipid peroxidation by independent mechanisms in erythrocytes. J. Biol. Chem. 262, 8220-8226.
12. Davies, M, J. (1990) Detection of myoglobin-derived radicals on reaction of metmyoglobin with hydrogen peroxide and other peroxidic compounds. Free rad. Res. Comm. 10, 361-370.
13. Finkelstein, E., Rosen, G. M., and Ranckman, E. J. (1980) Spin trapping. Kinetics of the superoxide and hydroxyl radicals with nitrones. J. Am. Chem. Soc. 102, 4994-4999.
14. Flitter, W. D. and Mason, R. P. (1990) The horseradish peroxidase catalysed oxidation of deoxyribose sugars. Free Rad. Res. Comm. 9, 297-302.
15. Forehand, J. R., Pabst, M. J., Phillips, W. A., and Johnston, R. B. Jr. (1989) Lipopolysaccharide priming of human neutrophils for an enhanced respiratory burst. Role of intracellular free calcium. J. Clin. Invest. 83, 74-83.
16. Fridovich, I. (1986) Biological effects of the superoxide radical. Arch. Biochem. Biophys. 247, 1-11.
17. Fucci, L., Oliver, C. N., Coon, M. J., and Stadtman, E. R. (1983) Inactivation of key metabolic enzymes by mixed-function oxidation reactions: possible implication in protein turnover and ageing. Proc. Natl. Acad. Sci. USA 80, 1521-1525.
18. Graf, E., Mahoney, J. R., Bryant, R. G., and Eaton, J. W. (1984) Iron-catalyzed hydroxyl radical formation. Stringent requirement for free iron coordination site. J. Biol. Chem. 259, 3620-3624.
19. Gutteridge, J. M. C. (1984) Reactivity of hydroxyl and hydroxyl-like radicals discriminated by release of thiobarbituric acid-reactive material from deoxy sugars, nucleosides and benzoate. Biochem. J. 224, 761-767.
20. Gutteridge, J. M. C. (1986) Iron promoters of the Fenton reaction and lipid peroxidation can be released from haemoglobin by peroxides. FEBS Lett. 201, 291-295.
21. Halliwell, B. (1978) Superoxide-dependent formation of hydroxyl radicals in the presence of iron chelates: is it a mechanism for hydroxyl radical production in biochemical systems? FEBS Lett. 92, 321-326.
22. Halliwell, B. and Gutteridge, J. M. C. (1986) Oxygen free radicals and iron in relation to biology and medicine: some problems and concepts. Arch. Biochem. Biophys. 246, 501-514.
23. Jackson, S. K., Stark, J. M., Rowlands, C. C., and Evans, J. C. (1989) Electron spin resonance detection of oxygen-centred radicals in murine macrophages stimulated with bacterial endotoxin. Free Rad. Biol. Med. 7, 165-170.
24. Kalyanaraman, B., Mottley, C., and Mason, R. P. (1983) A direct electron spin resonance and spin-trapping investigation of peroxyl free radical formation by hematin/hydroperoxide systems. J. Biol. Chem. 258, 3855-3858.
25. Kanner, J. and Harel, S. (1985) Initiation of membranal lipid peroxidation by activated metmyoglobin and methemoglobin. Arch. Biochem. Biophys. 237, 314-321.
26. Kim, E. H. and Sevanian, A. (1991) Hematin- and peroxide-catalyzed peroxidation of phospholipid liposomes. Arch. Biochem. Biophys. 288, 324-330.
27. Kim, Y. M., Jeong, S. H., Yamazaki, I., Piette, L. H., Han, S., and Hong, S. J. (1995) Decay studies of DMPO-spin adducts of free radicals produced by reactions of metmyoglobin and methemoglobin with hydrogen peroxide. Free Rad. Res. 22, 11-21.
28. Kim, Y. M., Yamazaki, I., and Piette, L. H. (1994) The effect of hemoglobin, hematin, and iron on neutrophil inactivation in superoxide generating systems. Arch. Biochem. Biophys. 309, 308-314.
29. Koga, S., Nakano, M., and Uehara, K. (1991) Mechanism for the generation of superoxide anion and singlet oxygen during heme compound-catalyzed linoleic acid hydroperoxide decomposition. Arch. Biochem. Biophys. 289, 223-229.
30. Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227, 680-685.
31. Levine, R. L. (1983) Oxidative modification of glutamine synthetase. II. Characterization of the ascorbate model system. J. Biol. Chem. 258, 11828-11833.
32. Levitzki, A. and Anbar, M. (1967) Modification of the radiolytic oxidation of ribonuclease induced by bound copper. J. Am. Chem. Soc. 89, 4185-1189.
33. Makino, R., Tanaka, T., Iizuka, T., Ishimura, Y., and Kanegasaki, S. (1986) Stoichiometric conversion of oxygen to superoxide anion during the respiratory burst in neutrophils. Direct evidence by a new method for measurement of superoxide anion with diacetyldeuteroheme-substituted horseradish peroxidase. J. Biol. Chem. 261, 11444-11447.
34. Meucci, E., Mordente, A., and Mortorana, G. (1991) Metal-catalyzed oxidation of human serum albumin: conformational and functional changes. Implications in protein aging. J. Biol. Chem. 266, 4692-1699.
35. Miki, H., Harrada, K., Yamazaki. I., Tamura, M., and Wadanabe, H. (1989) Electron spin resonance spectrum of Tyr-151 free radical formed in reactions of sperm whale metmyoglobin with ethyl hydroperoxide, and potassium irridate. Arch. Biochem. Biophys. 275, 354-362.
36. Nakamura, S. and Yamazaki, I. (1969) One-electron transfer reactions in biochemical systems. IV. A mixed mechanism in the reaction of milk xanthine oxidase with electron acceptors. Biochem. Biophys. Acta 189, 29-37.
37. Ortiz de Montellano, P. R. and Catalano, C. E. (1985) Epoxidation of styrene by hemoglobin and myoglobin. Transfer of oxidizing equivalents to the protein surface. J. Biol. Chem. 260, 9265-9271.
38. Prasad, M. R., Engelman, R. M., Jones, R. M. , and Das, D. K. (1989) Effects of oxyradicals on oxymyoglobin. Deoxygenation, haem removal and iron release. Biochem. J. 263, 731-736.
39. Pruett, T. L., Rotstein, O. D., Fiegel, V. D., Sorenson, J. J., Nelson, R. D., and Simmons, R. L. (1984) Mechanism of the adjuvant effect of hemoglobin in experimental peritonitis: VIII. A leukotoxin is produced by Escherichia coli metabolism in hemoglobin. Surg. 96, 375-383.
40. Puppo, A. and Halliwell, B. (1988) Formation of hydroxyl radicals from hydrogen peroxide in the presence of iron. Is haemoglobin a biological Fenton reagent? Biochem. J. 249, 185-190.
41. Sadrzadeh, S. M. H. and Eaton, J. W. (1988) Hemoglobin-mediated oxidant damage to the central nervous system requires endogenous ascorbate. J. Clin. Invest. 82, 1510-1515.
42. Sadrzadeh, S. M. H., Graf, E., Panter, S. S., Hallaway, P. E., and Eaton, J. W. (1984) Hemoglobin. A biologic Fenton reagent. J. Biol. Chem. 259, 14354-14356.
43. Schnessler, H. and Schilling, K. (1984) Oxygen effect in the radiolysis of proteins. Part 2. Bovine serum albumin. Int. J. Radiat. Biol. 45, 267-281.
44. Schulze-Osthoff, K., Bakker, A. C., Vanhaesebrock, B., Beyaert, R., Jacob, W. A., and Fiers, W. (1992) Cytotoxic activity of tumor necrosis factor is mediated by early damage of mitochondrial functions. Evidence for the involvement of mitochondrial radical generation. J. Biol. Chem. 267, 5317-5323.
45. Stadtman, E. R. and Berlett, B. S. (1991) Fenton chemistry. Amino acid oxidation. J. Biol. Chem. 266, 17201-17211.
46. Stadtman, E. R. and Oliver, C. N. (1991) Metal-catalyzed oxidation of proteins. Physiological consequences. J. Biol. Chem. 266, 2005-2008.
47. Ursini, F., Maiorino, M., Ferri, L., Valente, M., and Gregolin, C. (1981) Hydrogen peroxide and hematin in microsomal lipid peroxidation. J. Inorg. Biochem. 15, 163-169.
48. Winterbourn, C. C. (1991) Factors that influence the deoxyribose oxidation assay for Fenton reaction products. Free Rad. Biol. Med. 11, 353-360.
49. Wolff, S. P. and Dean, R. T. (1986) Fragmentation of proteins by free radicals and its effect on their susceptibility to enzymic hydrolysis. Biochem J. 234, 399-403 .
50. 2-reactive species in oxygen toxicity in biology. J. Biol. Chem. 265, 13589-13594.
51. Yamazaki. I. and Piette, L. H. (1991) EPR spin-trapping study on the oxidizing species formed in the reation of the ferrous ion with hydrogen peroxide. J. Am. Chem. Soc. 113, 7588-7593.