Oxidative Modification of Cytochrome c by Hydrogen Peroxide |
Kim, Nam Hoon
(Department of Genetic Engineering, Cheongju University)
Jeong, Moon Sik (Department of Genetic Engineering, Cheongju University) Choi, Soo Young (Department of Biomedical Science, Division of Life Sciences, Hallym University) Kang, Jung Hoon (Department of Genetic Engineering, Cheongju University) |
1 | Cadenas, E., Boveris, A., and Chance, B. (1980) Low-level chemiluminescence of hydroperoxide - supplemented cytochrome c. Biochem. J. 187, 131−140 |
2 | Davies, K. J. (1986) Intracellular proteolytic systems may function as secondary antioxidant defenses: a hypothesis. J. Free Radic. Biol. Med. 2, 155−173 DOI ScienceOn |
3 | Dumont, M. E., Corin, A. F., and Campbell, G. A. (1994) Noncovalent binding of heme induces a compact apocytochrome c structure. Biochemistry 33, 7368−7378 |
4 | Giulivi, C. and Davies, K. J. (1993) Dityrosine and tyrosine oxidation products are endogenous markers for the selective proteolysis of oxidatively modified red blood cell hemoglobin by (the 19 S) proteasome. J. Biol. Chem. 268, 8752−8759 |
5 | Radi, R., Thomson, L., Rubbo, H., and Prodanov, E. (1991) cytochrome c-catalyzed oxidation of organic molecules by hydrogen peroxide. Arch. Biochem. Biophys. 288, 112−117 DOI ScienceOn |
6 | Stadtman, E. R. (1993) Oxidation of free amino acids and amino acid residues in proteins by radiolysis and by metal-catalyzed reactions. Annu. Rev. Biochem. 62, 797−821 DOI ScienceOn |
7 | Wang, X. and Pielak, G. J. (1999) Equilibrium thermodynamics of a physiologically-relevant heme-protein complex. Biochemistry 38, 16876−16881 DOI ScienceOn |
8 | Banci, L., Bertini, I., Cavallaro, G., and Luchinat, C. (2002) Chemical shift-based constraints for solution structure determination of paramagnetic low-spin heme proteins with bis-His and His-CN axial ligands: the cases of oxidized cytochrome b(5) and Met80Ala cyano- cytochrome c. J. Biol. Inorg. Chem. 7, 416−426 DOI ScienceOn |
9 | Kato, Y., Kitamoto, N., Kawai, Y., and Osawa, T. (2001) The hydrogen peroxide/copper ion system, but not other metalcatalyzed oxidation systems, produces protein-bound dityrosine. Free Radic. Biol. Med. 31, 624−632 DOI ScienceOn |
10 | Pennathur, S., Jackson-Lewis, V., Przedborski, S., and Heinecke, J. W. (1999) Mass spectrometric quantification of 3-nitrotyrosine, ortho-tyrosine, and o,o′-dityrosine in brain tissue of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated mice, a model of oxidative stress in Parkinson's disease. J. Biol. Chem. 274, 34621−34628 DOI ScienceOn |
11 | Smith, P. K., Krohn, R. I., Hermanson. G. T., Mallia, A. K., Gartner, F. H., et al. (1985) Measurement of protein using bicinchoninic acid. Anal. Biochem. 150, 76−85 |
12 | Lawrence, A., Jones, C. M., Wardman, P., and Burkitt, M. J. (2003) Evidence for the role of a peroxidase compound Itype intermediate in the oxidation of glutathione, NADH, ascorbate, and dichlorofluorescin by cytochrome c/. Implications for oxidative stress during apoptosis. J. Biol. Chem. 278, 29410−29419 DOI ScienceOn |
13 | Moore, G. R. and Pettigrew, G. W. (1990) cytochrome c: Evolutionary, Structure, and Physicochemical Aspects, Springer- Verlag, Berlin |
14 | Radi, R., Sims, S., Cassina, A., and Turrens, J. F. (1993) Roles of catalase and cytochrome c in hydroperoxide-dependent lipid peroxidation and chemiluminescence in rat heart and kidney mitochondria. Free Radic. Biol. Med. 15, 653−659 DOI ScienceOn |
15 | Berlett, B. S. and Stadtman, E. R. (1997) Protein oxidation in aging, disease, and oxidative stress. J. Biol. Chem. 272, 20313− 20316 |
16 | Deshmukh, M. and Johnson, E. M., Jr. (1998) Evidence of a novel event during neuronal death: development of competence- to-die in response to cytoplasmic cytochrome c. Neuron 21, 695−705 DOI ScienceOn |
17 | Dumont, M. E., Cardillo, T. S., Hayes, M. K., and Sherman, F. (1991) Role of cytochrome c heme lyase in mitochondrial import and accumulation of cytochrome c in Saccharomyces cerevisiae. Mol. Cell. Biol. 11, 5487−5496 |
18 | Halliwell, B. and Gutteridge, J. M. (1981) Formation of thiobarbituric- acid-reactive substance from deoxyribose in the presence of iron salts: the role of superoxide and hydroxyl radicals. FEBS Lett. 128, 347−352 DOI ScienceOn |
19 | Sagripanti, J. L. and Kraemer, K. H. (1989) Site-specific oxidative DNA damage at polyguanosines produced by copper plus hydrogen peroxide. J. Biol. Chem. 264, 1729−1734 |
20 | Heinecke, J. W., Li, W., Daehnke, H. L. 3rd, and Goldstein, J. A. (1993) Dityrosine, a specific marker of oxidation, is synthesized by the myeloperoxidase-hydrogen peroxide system of human neutrophils and macrophages. J. Biol. Chem. 268, 4069−4077 |
21 | Zweier, J. L., Kuppusamy, P., Williams, R., Rayburn, B. K., Smith, D., et al. (1989) Measurement and characterization of postischemic free radical generation in the isolated perfused heart. J. Biol. Chem. 264, 18890−18895 |
22 | Imlay, J. A., Chin, S. M., and Linn, S. (1988) Toxic DNA damage by hydrogen peroxide through the Fenton reaction in vivo and in vitro. Science 240, 640−642 |
23 | Millett, F. and Scott, R. (1996) In cytochrome c, A Multidisciplinary Approach, Mauk, A. G. and Scott, R. A. (eds.), pp. 475−487, University Science Books, Sausalito, CA |
24 | Pelletier, H. and Kraut, J. (1992) Crystal structure of a complex between electron transfer partners, cytochrome c peroxidase and cytochrome c. Science 258, 1748−1755 |
25 | Hashimoto, M., Takeda, A., Hsu, L. J., Takenouchi, T., and Masliah, E. (1999) Role of cytochrome c as a stimulator of alpha-synuclein aggregation in Lewy body disease. J. Biol. Chem. 274, 28849−28852 DOI |
26 | Huggins, T. G., Wells-Knecht, M. C., Detorie, N. A., Baynes, J. W., and Thorpe, S. R. (1993) Formation of o-tyrosine and dityrosine in proteins during radiolytic and metal-catalyzed oxidation. J. Biol. Chem. 268, 12341−12347 |
27 | Hugli, T. E. and Moore, S. (1972) Determination of the tryptophan content of proteins by ion exchange chromatography of alkaline hydrolysates. J. Biol. Chem. 247, 2828−2834 |
28 | Li, P., Nijhawan, D., Budihardjo, I., Srinivasula, S. M., Ahmad, M., et al. (1997) cytochrome c and dATP-dependent formation of Apaf-1/caspase-9 complex initiates an apoptotic protease cascade. Cell 91, 479−489 DOI ScienceOn |
29 | Zou, H., Li, Y., Liu, X., and Wang, X. (1999) An APAF-1- cytochrome c multimeric complex is a functional apoptosome that activates procaspase-9. J. Biol. Chem. 274, 11549−11556 DOI ScienceOn |
30 | Chen, Y. R., Deterding, L. J., Sturgeon, B. E., Tomer, K. B., and Mason, R. P. (2002) Protein oxidation of cytochrome c by reactive halogen species enhances its peroxidase activity. J. Biol. Chem. 277, 29781−29791 |
31 | Pieroni, L., Khalil, L., Charlotte, F., Poynard, T., Piton, A., et al. (2001) Comparison of bathophenanthroline sulfonate and ferene as chromogens in colorimetric measurement of low hepatic iron concentration. Clin. Chem. 47, 2059−2061 |
32 | Laemmli, U. K. (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227, 680−685 |
33 | O'Connell, M. J. and Peters, T. J. (1987) Ferritin and haemosiderin in free radical generation, lipid peroxidation and protein damage. Chem. Phys. Lipids 45, 241−249 |
34 | Towbin, H., Staehelin, T., and Gordon, J. (1979) Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: procedure and some applications. Proc. Natl. Acad. Sci. USA 76, 4350−4354 |
35 | Barr, D. P., Gunther, M. R., Deterding, L. J., Tomer, K. B., and Mason, R. P. (1996) ESR spin-trapping of a protein-derived tyrosyl radical from the reaction of cytochrome c with hydrogen peroxide. J. Biol. Chem. 271, 15498−15503 DOI |
36 | Green, D. R. and Evan, G. I. (2002) A matter of life and death. Cancer Cell 1, 19−30 |
37 | Halliwell, B. and Gutteridge, J. M. C. (1999) Free Radicals in Biology and Medicine, Oxford Press, New York |
38 | Oliver, C. N., Levine, R. L., and Stadtman, E. R. (1987) A role of mixed-function oxidation reactions in the accumulation of altered enzyme forms during aging. J. Am. Geriatr. Soc. 35, 947−956 |
39 | Kim, C. S., Lee, C.-H., Lee, P. H., and Han, S. (2004) Inactivation of mitochondrial electron transport by photosensitization of a pheophorbide a derivative. Mol. Cells 17, 347−352 |
40 | Friedlander, R. M. (2003) Apoptosis and caspases in neurodegenerative diseases. N. Engl. J. Med. 348, 1365−1375 DOI ScienceOn |
41 | Liu, X., Kim, C. N., Yang, J., Jemmerson, R., and Wang, X. (1996) Induction of apoptotic program in cell-free extracts: requirement for dATP and cytochrome c. Cell 86, 147−157 DOI ScienceOn |
42 | Petrosillo, G., Ruggiero, F. M., Pistolese, M., and Paradies, G. (2001) Reactive oxygen species generated from the mitochondrial electron transport chain induce cytochrome c dissociation from beef-heart submitochondrial particles via cardiolipin peroxidation. Possible role in the apoptosis. FEBS Lett. 509, 435−438 DOI ScienceOn |
43 | Flaherty, J. T. and Weisfeldt, M. L. (1988) Reperfusion injury. Free Radic. Biol. Med. 5, 409−419 |
44 | Atwood, C. S., Perry, G., Zeng, H., Kato, Y., Jones, W. D., et al. (2004) Copper mediates dityrosine cross-linking of Alzheimer's amyloid-beta. Biochemistry 43, 560−568 DOI ScienceOn |
45 | Sagripanti, J. L., Swicord, M. L., and Davis, C. C. (1987) Microwave effects on plasmid DNA. Radiat. Res. 110, 219−231 |
46 | Levine, R. L., Williams, J. A., Stadtman, E. R., and Shacter, E. (1994) Carbonyl assays for determination of oxidatively modified proteins. Methods Enzymol. 233, 346−357 |