Pyrrolization and antioxidant function of proteins following oxidative stress

Chemical Research in Toxicology

Volumn 14, Issue 5, 2001, Pages 582-588

  Hidalgo, Francisco J ^a   Alaiz, Manuel ^a   Zamora, Rosario ^a  

^a INSTITUTO DE LA GRASA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

4 DIMETHYLAMINOBENZALDEHYDE; ASCORBIC ACID; EPOXIDE; PYRROLE; SERUM ALBUMIN; THIOBARBITURIC ACID;

AMINO ACID ANALYSIS; ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CAPILLARY ELECTROPHORESIS; CONTROLLED STUDY; LIPID PEROXIDATION; MICROSOME; NONHUMAN; OXIDATION; OXIDATIVE STRESS; TROUT;

ANIMALS; ANTIOXIDANTS; ELECTROPHORESIS, CAPILLARY; LIPID PEROXIDATION; MICROSOMES; MUSCLES; NORLEUCINE; OXIDATIVE STRESS; PROTEINS; PYRROLES; REACTIVE OXYGEN SPECIES; SERUM ALBUMIN, BOVINE; THIOBARBITURIC ACID REACTIVE SUBSTANCES; TROUT;

ANIMALIA; BOVINAE; SALMONIDAE;

EID: 0034996584     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx000215m     Document Type: Article

References (30)

1. Halliwell, B., and Gutteridge, J. M. (1999) Free Radicals in Biology and Medicine, 3rd ed., Oxford, U.K.
2. Ogino, T., Packer, L., and Traber, M. C. (1999) Oxidant stress and host oxidant defense mechanisms. In Nutritional Oncology (Heber, D., Blackburn, G. L., and Go, V. L. W., Eds.) pp 253-275, Academic Press, San Diego, CA.
3. Keyse, S. M., Ed. (2000) Stress Response. Methods and Protocols, Humana Press, Totowa, NJ.
4. Rice-Evans, C., and Bruckdorfer, K. R., Eds. (1995) Oxidative Stress, Lipoproteins and Cardiovascular Dysfunction, Portland Press, London, U.K.
5. Scandalios, J. G., Ed. (1997) Oxidative Stress and the Molecular Biology of Antioxidant Defenses, Cold Spring Harbor Lab., Plainview, NY.
6. Özben, T., Ed. (1998) Free Radicals, Oxidative Stress, and Antioxidants: Pathological and Physiological Significance, Plenum Press, New York.
7. Zamora, R., Alaiz, M., and Hidalgo, F. J. (1997) Feed-back inhibition of oxidative stress by oxidized lipid/amino acid reaction products. Biochemistry 36, 15765-15771.
8. Kotani, K., Maekawa, M., Kanno, T., Kondo, A., Toda, N., and Manabe, M. (1994) Distribution of immunoreactive malondialdehyde-modified low-density lipoprotein in human serum. Biochim. Biophys. Acta 1215, 121-125.
9. Hidalgo, F. J., and Zamora, R. (2000) Modification of bovine serum albumin structure following reaction with 4,5(E)-epoxy-2(E)-heptenal. Chem. Res. Toxicol. 13, 501-508.
10. Xu, G., Liu, Y., Kansal, M. M., and Sayre, L. M. (1999) Rapid cross-linking of proteins by 4-ketoaldehydes and 4-hydroxy-2-alkenals does not arise from the lysine-derived monoalkylpyrroles. Chem. Res. Toxicol. 12, 855-861.
11. Salomon, R. G., Kaur, K., Podrez, E., Hoff, H. F., Krushinsky, A. V., and Sayre, L. M. (2000) HNE-derived 2-pentylpyrroles are generated during oxidation of LDL, are more prevalent in blood plasma from patients with renal disease or atherosclerosis, and are present in atherosclerotic plaques. Chem. Res. Toxicol. 13, 557-564.
12. Hidalgo, F. J., and Zamora, R. (1995) In vitro production of long chain pyrrole fatty esters from carbonyl-amine reactions. J. Lipid Res. 36, 725-735.
13. Zamora, R., and Hidalgo, F. J. (1995) Linoleic acid oxidation in the presence of amino compounds produces pyrroles by carbonyl amine reactions. Biochim. Biophys. Acta 1258, 319-327.
14. Salomon, R. G., Subbanagounder, G., O'Neil, J., Kaur, K., Smith, M. A., Hoff, H. F., Perry, G., and Monnier, V. M. (1997) Levuglandin E2-protein adducts in human plasma and vasculature. Chem. Res. Toxicol. 10, 536-545.
15. Peters, T., Jr. (1996) All About Albumin. Biochemistry, Genetics and Medical Applications, pp 238-239, Academic Press, San Diego, CA.
16. Das, D. K., and Maulik, N. (1994) Antioxidant effectiveness in ischemia-reperfusion tissue injury. Methods Enzymol. 233, 601-610.
17. Deigner, H. P., Friedrich, E., Sinn, H., and Dresel, H. A. (1992) Scavenging of lipid peroxidation products from oxidizing LDL by albumin alters the plasma half-life of a fraction of oxidized LDL particles. Free Radical Res. Commun. 16, 239-246.
18. Brown, J. R. (1977) Structure and evolution of serum albumin. In Albumin Structure, Biosynthesis, Function (Peters, T., and Sjoholm, I., Eds.) Vol. 50, pp 1-10, Pergamon Press, New York.
19. Zamora, R., and Hidalgo, F. J. (1994) Modification of lysine amino groups by the lipid peroxidation product 4,5(E)-epoxy-2(E)-heptenal. Lipids 29, 243-249.
20. Hidalgo, F. J., and Zamora, R. (1993) Fluorescent pyrrole products from carbonyl-amine reactions. J. Biol. Chem. 268, 16190-16197.
21. Zamora, R., Navarro, J. L., and Hidalgo, F. J. (1995) Determination of lysine modification product ε-N-pyrrolylnorleucine in hydrolyzed proteins and trout muscle microsomes by micellar electrokinetic capillary chromatography. Lipids 30, 477-483.
22. Parkin, K. L., and Hultin, H. O. (1982) Fish muscle microsomes catalyze the conversion of trimethylamine oxide to dimethylamine and formaldehyde. FEBS Lett. 139, 61-64.
23. De Luca, H. F. (1972) Methods for preparation and study of tissues and enzymes. In Manometric and Biochemical Techniques (Umbreit, W. W., Burris, R. H., and Stauffer, J. F., Eds.) pp 133-147, Burgess Publishing, Minneapolis, MN.
24. Bradford, M. M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72, 248-254.
25. Hidalgo, F. J., Alaiz, M., and Zamora, R. (1998) A spectrophotometric method for the determination of proteins damaged by oxidized lipids. Anal. Biochem. 262, 129-136.
26. Kosugi, H., Kojima, T., and Kikugawa, K. (1989) Thiobarbituric acid-reactive substances from peroxidized lipids. Lipids 24, 873-881.
27. Alaiz, M., Navarro, J. L., Giron, J., and Vioque, E. (1992) Amino acid analysis by high-performance liquid chromatography after derivatization with diethyl ethoxymethylene malonate. J. Chromatogr. 591, 181-186.
28. Snedecor, G. W., and Cochran, W. G. (1980) Statistical Methods, 7th ed., Iowa State University Press, Ames, Iowa.
29. Zamora, R., Alaiz, M., and Hidalgo, F. J. (1999) Modification of histidine residues by 4,5-epoxy-2-alkenals. Chem. Res. Toxicol. 12, 654-660.
30. Levine, R. L., Mosoni, L., Berlett, B. S., and Stadtman, E. R. (1996) Methionine residues as endogenous antioxidants in proteins. Proc. Natl. Acad. Sci. U.S.A. 93, 15036-15040.