A study of photochemically-generated protein radical spin adducts on bovine serum albumin: The detection of genuine spin trapping and artefactual, non radical addition in the same molecule

Redox Report

Volumn 3, Issue 4, 1997, Pages 225-231

  Silvester, J A ^a   Wei, X D ^c   Davies, M J ^b   Timmins, G S ^a,c  

^a UNIVERSITY OF YORK   (United Kingdom)

^b HEART RESEARCH INSTITUTE   (Australia)

^c DARTMOUTH MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; BOVINE SERUM ALBUMIN; CYSTEINE; PORPHYRIN;

ARTICLE; CHEMICAL MODIFICATION; PHOTOOXIDATION; PRIORITY JOURNAL; SPIN TRAPPING;

BOVINAE;

EID: 0030668831     PISSN: 13510002     EISSN: None     Source Type: Journal    
DOI: 10.1080/13510002.1997.11747114     Document Type: Article

References (29)

1. Leeuwenburgh C, Rasmussen J E, Hsu F F, Mueller D M, Pennathur S, Heinecke J W. Mass spectrometric quantification of markers for protein oxidation by tyrosyl radical, copper, and hydroxyl radical in low density lipoprotein isolated from human atherosclerotic plaques. J Biol Chem 1997; 272: 3520-3526.
2. Thomas C E, Ohlweiler D F, Kalyanaraman B. Multiple mechanisms for inhibition of low-density-lipoprotein oxidation by novel cyclic nitrone spin traps. J Biol Chem 1994; 269: 28055-28061.
3. Maples K R, Jordan S J, Mason R P. In vivo rat hemoglobin thiyl free-radical formation following phenylhydrazine administration. Mol Pharmacol 1988, 33: 344-350.
4. Jiang J J, Liu K J, Jordan S J, Swartz H M, Mason R P. Detection of free-radical metabolite formation using in vivo EPR spectroscopy - evidence of rat hemoglobin thiyl radical formation. Arch Biochem Biophys 1996; 330: 266-270.
5. Dean R T, Gieseg S, Davies M J. Reactive species and their accumulation on radical-damaged proteins Trends Biochem Sci 1993, 18: 437-441.
6. Pacifici R E, Kono Y, Davies K J A. Hydrophobicity as the signal for selective degradation of hydroxyl radical-modified hemoglobin by the multicatalytic proteinase complex, proteasome. J Biol Chem 1993; 268: 15405-15411.
7. Davies M J, Fu S L, Dean R T. Protein hydroperoxides can give rise to reactive free-radicals. Biochem J 1995; 305: 643-649.
8. Grant A J, Jessup W, Dean R T. Accelerated endocytosis and incomplete catabolism of radical-damaged protein. Biochim Biophys Acta 1992; 1134: 203-209.
9. Cabiscol E, Levine R L. Carbonic anhydrase-III - oxidative modification in-vivo and loss of phosphatase-activity during aging. J Biol Chem 1995; 270: 14742-14747.
10. Grant A J, Jessup W, Dean R T. Inefficient degradation of oxidized regions of protein molecules. Free Radic Res Commun 1993; 18: 259-267.
11. Davies M J. Detection and identification of macromolecule-derived radicals by EPR spin-trapping. Res Chem Intermed 1993; 19: 669-679.
12. Gunther M R, Kelman D J, Corbett J T, Mason R P. Self peroxidation of metmyoglobin results in formation of an oxygen-reactive tryptophan-centered radical J Biol Chem 1995; 270: 16075-16081.
13. Moreau S, Davies M J, Mathieu C, Herouart D, Puppo A. Leghemoglobin-derived radicals - evidence for multiple protein-derived radicals and the initiation of peribacteroid membrane damage. J Biol Chem 1996; 271: 32557-32562.
14. Vasquezvivar J, Santos A M, Junqueira V B C, Augusto O. Peroxynitrite-mediated formation of free-radicals in human plasma - EPR detection of ascorbyl, albumin-thiyl and uric acid-derived free-radicals. Biochem J 1996; 314: 869-876.
15. Gatti R M, Radi R, Augusto O Peroxynitrite-mediated oxidation of albumin to the protein-thiyl free-radical. FEBS Letts 1994; 348: 287-290
16. Timmins G S, Davies M J. Conformational changes induced in bovine serum albumin by the photodynamic action of hematoporphyrin. J Photochem Photobiol B: Biol 1994; 24: 117-122.
17. Timmins G S, Davies M J. An EPR spin-trapping study of albumin protein radicals formed by the photodynamic action of hematoporphyrin. J Photochem Photobiol B: Biol 1993; 21: 167-173.
18. Silvester J A, Timmins G S, Davies M J. Detection of protein radicals formed by the photodynamic action of porphyrin sensitizers. Biochem Soc Trans 1995; 23: S 261
19. Davies M J, Gilbert B C, Haywood R M. Radical-induced damage to bovine serum albumin - role of the cysteine residue. Free Radic Res Commun 1993; 18: 353-367.
20. Altenbac C, Marti T, Khorana H G, Hubbell W L. Transmembrane protein structure - spin labeling of bacteriorhodopsin mutants. Science 1990; 248: 1088-1092.
21. Motley C, Mason R P. Nitroxide radical adducts in biology: chemistry, applications and pitfalls. In: Berliner L J, Reuben J, eds. Spin Labeling; Theory and Applications, Biological Magnetic Resonance Vol 8. New York: Plenum Press, 1989: 489-546.
22. Timmins G S, Barlow G K, Silvester J A, Wei X, Whitwood A C. Use of isotopically-labelled spin traps to determine definitively the presence or absence of non-radical addition artefacts in EPR spin trapping systems. Redox Report 1997; 2: 125-133.
23. Hu M-L. Measurement of protein thiol groups and glutathione in plasma. In: Packer L, ed. Methods in Enzymology Vol. 233. San Diego: Academic Press, 1994; 380-385.
24. Kaur H, Leung K H W, Perkins M J. A water-soluble, nitrosoaromatic spin-trap. J Chem Soc Chem Commun 1981; 142-143.
25. 2H isotopically-labelled derivative of the spin-trap 3,5-dibromo-4-nitrosobenzenesulphonic acid Redox Report 1996; 2: 407-410.
26. Pou S, Rosen G M, Wu Y X, Keana J F W. Synthesis of deuterium-containing and N-15-containing pyrroline-1-oxides - A spin trapping study. J Org Chem 1990; 55: 4438-4443.
27. Chang L S, Wen E Y, Hung J J, Chang CC. Energy-transfer from tryptophan residues of proteins to 8-Anilinonaphthalene-1-sulfonate. J Protein Chem 1994; 13: 635-640.
28. Johansson J S, Eckenhoff R G, Dutton P I. Binding of halothane to serum-albumin demonstrated using tryptophan fluorescence. Anesthesiology 1995; 83: 316-324.
29. Zuman P, Shah B. Addition, reduction and oxidation reactions of nitrosobenzene. Chem Rev 1994, 94: 1621-1641.