Peroxidative reactions of diversozymes

FASEB Journal

Volumn 10, Issue 4, 1996, Pages 428-434

  Coon, Minor J ^a   Vaz, Alfin D N ^a   Bestervelt, Lorelle L ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

inactivation of P450 by trans 4 hydroxynonenal; P450 cytochromes; peroxidative deformylation of aldehydes; reductive cleavage of lipid hydroperoxides

Indexed keywords

4 HYDROXYNONENAL; ALDEHYDE; ALKENE; CYTOCHROME P450; FORMIC ACID; 4-HYDROXY-2-NONENAL; LIPID PEROXIDE; PEROXIDE;

AROMATIZATION; ELECTRON TRANSPORT; ENZYME INACTIVATION; HUMAN; HYDROXYLATION; LIPID PEROXIDATION; NONHUMAN; PRIORITY JOURNAL; REDUCTION; REVIEW; ANIMAL; METABOLISM; OXIDATION REDUCTION REACTION; PHYSIOLOGY;

ALDEHYDES; ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; LIPID PEROXIDATION; LIPID PEROXIDES; OXIDATION-REDUCTION; PEROXIDES;

EID: 0030098181     PISSN: 08926638     EISSN: None     Source Type: Journal    
DOI: 10.1096/fasebj.10.4.8647341     Document Type: Review

References (42)

1. Coon, M. J., Ding, X., Pernecky, S. J., and Vaz, A. D. N. (1992) Cytochrome P450: progress and predictions. FASEB J. 6, 669-673
2. Porter, T. D., and Coon, M. J. (1991) Cytochrome P-450. Multiplicity of isoforms, substrates, and catalytic and regulatory mechanisms. J. Biol. Chem. 266, 13469-13472
3. Blake, R. C., II, and Coon, M. J. (1981) On the mechanism of action of cytochrome P-450. Evaluation of homolytic and heterolytic mechanisms of oxygen-oxygen bond cleavage during substrate hydroxylation by peroxides. J. Biol. Chem. 256, 12127-12133
4. Nordblom, G. D., White, R. E., and Coon, M. J. (1976) Studies on hydroperoxide-dependent substrate hydroxylation by purified liver microsomal cytochrome P-450. Arch. Biochem. Biophys. 175, 524-533
5. Vaz, A. D. N., and Coon, M. J. (1987) Hydrocarbon formation in the reductive cleavage of hydroperoxides by cytochrome P-450. Proc. Natl. Acad. Sci. USA 84, 1172-1176
6. Hochstein, P., and Ernster, L. (1963) ADP-activated lipid peroxidation coupled to the TPNH oxidase system of microsomes. Biochem. Biophys. Res. Commun. 12, 388-394
7. Ekström, G., and Ingelman-Sundberg, M. (1984) Cytochrome P450-dependent lipid peroxidation in reconstituted membrane vesicles. Biochem. Pharmacol. 33, 2521-2523
8. Vaz, A. D. N., Roberts, E. S., and Coon, M. J. (1990) Reductive Β-seission of the hydroperoxides of fatty acids and xenobioties: Role of alcohol-inducible cytochrome P-450. Proc. Natl. Acad. Sci. USA 87, 5499-5503
9. Ekström, G., and Ingelman-Sundberg, M. (1989) Rat liver microsomal NADPH-supported oxidase activity and lipid peroxidation dependent on ethanol-inducible cytochrome P-450 (P-450IIE1). Biochem. Pharmacol. 38, 1313-1319
10. Esterbauer, H., and Zollner, H. (1989) Methods for determination of aldehydic lipid peroxidation products. Free Radical Biol. Med. 7, 197-203
11. Winkler, P., Lindner, W., Esterbauer, H., Schauenstein, E., Schaur, R. J., and Khoschsorur, G. A (1984) Detection of 4-hydroxynonenal as a product of lipid peroxidation in native Ehrlich ascites tumor cells. Biochim. Biophys. Acta 796, 232-237
12. Winkler, P., Schaur, R. J., and Schauenstein, E. (1984) Selective promotion of ferrous ion-dependent lipid peroxidation in Ehrlich ascites tumor cells by histidine as compared with other amino acids. Biochim. Biophys. Acta 796, 226-231
13. Schauenstein, E., and Esterhauer, H. (1978) Formation and properties of reactive aldehydes. CIBA Found. Symp. 67, 225-244
14. Esterbauer, H., Zollner, H., and Lang, J. (1985) Metabolism of the lipid peroxidation product 4-hydroxynonenal by isolated hepatoeytes and by liver cytosolic fractions. Biochem. J. 228, 363-373
15. Uchida, K., and Stadtman, E. R. (1992) Selective cleavage of thioether linkage in proteins modified with 4-hydroxynonenal. Proc. Natl. Acad. Sci. USA 89, 5611-5615
16. Uchida, K., and Stadtman, E. R. (1992) Modification of histidine residues in proteins by reaction with 4-hydroxynonenal. Proc. Natl. Acad. Sci. USA 89, 4544-4548
17. Szweda, L. I., Uchida, K., Tsai, L., and Stadtman, E. R. (1993) Inactivation of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal. J. Biol. Chem. 268, 3342-3347
18. Friguet, B., Stadtman, E. R., and Szweda, L. I. (1994) Modification of glucose-6-phosphate dehydrogenase by 4-hydroxy-2-nonenal. J. Biol. Chem. 269, 21639-21643
19. Uchida, K., and Stadtman, E. R. (1993) Covalent attachment of 4-hydroxynonenal to glyeeraldehyde-3-phosphate dehydrogenase. J. Biol. Chem. 268, 6388-6393
20. Bestervelt, L. L., Vaz, A. D. N., and Coon, M. J. (1995) Inactivation of ethanol-inducible cytochrome P450 and other microsomal P450 isozymes by trans-4-hydroxy-2-nonenal, a major product of membrane lipid peroxidation. Proc. Natl. Acad. Sci. USA 92, 3764-3768
21. Benedetti, A., Comporti, M., and Esterbauer, H. (1980) Identification of 4-hydroxynonenal as a eytotoxic product originating from the peroxidation of liver microsomal lipids. Biochim. Biophys. Acta 620, 281-296
22. 2-terminal region and expressed in Escherichia coli. Arch. Biochem. Biophys 318, 446-456
23. Esterbauer, H., Schaur, R. J., and Zollner, H. (1991) Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radical Biol. Med. 11, 81-128
24. Kamimura, S., Gaal, K., Britton, R. S., Bacon, B. R., Triadafilopoulos, G., and Tsukamoto, H. (1992) Increased 4-hydroxynonenal levels in experimental alcoholic liver disease: Association of lipid peroxidation with liver fibrogenesis. Hepatology 16, 448-453
25. Sagai, M., and Ichinose, T. (1980) Age-related changes in lipid peroxidation as measured by ethane, ethylene, butane and pentane in respired gases of rats. Life Sci. 27, 731-738
26. Kato, R., and Takanaka, A. (1968) Effect of phenobarbital on electron transport system, oxidation and reduction of drugs in liver microsomes of rats of different age. J. Biochcm. (Tokyo) 63, 406-408
27. Schmucker, D. L., and Wang, R. K. (1981) Effects of aging and phenobaibital on the rat liver microsomal drug-metabolizing system. Mech. Aging Dev. 15, 189-202
28. Sutter, M. A., Wood, W. G., Williamson, L. S., Strong, R., Pickham, K., and Richardson, A. (1985) Comparison of the hepatic mixed function oxidase system of young, adult, and old non-human primates (Macaca nemestrina). Biochem. Pharmacol. 34, 2983-2987
29. Chiang, J. Y. L., DiLella, A. G., and Steggles, A W. (1983) Effect of inducers and aging on rabbit liver microsomal drug-metabolizing enzymes. Mol. Pharmacol. 23, 244-251
30. Schmucker, D. L. (1985) Aging and drug disposition: An update. Pharmacol. Rev. 37, 133-148
31. Birnbaum, L. S (1993) Changes in cytochrome P450 in senescence. In Cytochrome P-450, Handbook of Experimental Pharmacology (Schenkman, J. B., and Greim, H., eds) Vol. 105, pp. 477-492, Springer, New York
32. Akhtar, M., Calder, M. R., Corina, D. L., and Wright, J. N. (1982) Mechanistic studies on C-19 demethylation in oestrogen biosynthesis. Biochem. J. 201, 569-580
33. Stevenson, D. E., Wright, J. N., and Akhtar, M. (1988) Mechanistic consideration of P-450 dependent enzymic reactions: Studies on oestriol biosynthesis. J. Chem. Soc. Perkin Trans. I. 1, 2043-2052
34. Cole, P. A., Bean, J. M., and Robinson, C. H. (1990) Conversion of a 3-desoxysteroid to 3-desoxyestrogen by human placental aromatase. Proc. Natl. Acad. Sci. USA 87, 2999-3003
35. Yoshida, Y., Aoyama, Y., Sonoda, Y., and Sato, Y. (1990) Consideration of the mechanism of C-C bond cleavage by lanosterol 14-demethylase (cytochrome P-450/14DM). In Proceedings of the VIIIth International Symposium on Microsomes and Drug Oxidations, (Ingelman-Sundberg, M., Gustafsson, J.-A., and Orrenius, S., eds) p. 118, Karolinska Institute, Stockholm
36. Fischer, R. T., Trzakos, J. M., Magolda, R. L., Ko, S. S., Brosz, C. S., and Larsen, B. (1991) Lanosterol 14α-methyl demethylase. Isolation and characterization of the third metabolically generated oxidative demethylation intermediate. J. Biol. Chem. 266 6124-6132
37. IIIPFP(Cl) PhIO and cytochrome P-450cam: A model study on aromatase cytochrome P450 reaction. J. Am. Chem. Soc. 111, 410-411
38. Vaz, A. D N., Roberts, E. S., and Coon, M. J. (1991) Olefin formation in the oxidative deformylation of aldehydes by cytochrome P-450. Mechanistic implications for catalysis by oxygen-derived peroxide. J. Am. Chem. Soc. 113, 5886-5887
39. Roberts, E. S., Vaz, A. D. N., and Coon, M. J. (1991) Catalysis by cytochrome P-450 of an oxidative reaction in xenobiotic aldehyde metabolism: Deformylation with olefin formation. Proc. Natl. Acad. Sci. USA 88, 8963-8966
40. Vaz, A. D. N., Kessell, K. J., and Coon, M. J. (1994) Aromatization of a bicyclic steroid analog, 3-oxodecalin-4-ene-10-carboxaldehyde, by liver microsomal cytochrome P450 2B4. Biochemistry 33, 13651-13661
41. G-hydroxy-L-arginine by nitric oxide synthase. Biochemistry 34, 1930-1941
42. 2. Proc. Natl. Acad. Sci USA 91, 10000-10004