Cys34 adducts of reactive oxygen species in human serum albumin

Chemical Research in Toxicology

Volumn 25, Issue 8, 2012, Pages 1633-1642

  Grigoryan, Hasmik ^a   Li, He ^a   Iavarone, Anthony T ^b   Williams, Evan R ^a,b   Rappaport, Stephen M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE; GLUTAMINE; HUMAN SERUM ALBUMIN; HYDROGEN; OXYGEN; REACTIVE OXYGEN METABOLITE; SULFINAMIDE; SULFINIC ACID DERIVATIVE; SULFONIC ACID DERIVATIVE;

ACCURACY; ARTICLE; CHEMICAL COMPOSITION; CHRONIC DISEASE; CONTROLLED STUDY; DIGESTION; HUMAN; LIQUID CHROMATOGRAPHY; MOLECULAR BIOLOGY; MOLECULAR DYNAMICS; MOLECULAR MODEL; OXIDATION KINETICS; PROTEIN MODIFICATION; TANDEM MASS SPECTROMETRY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYSTEINE; HUMANS; OXIDATION-REDUCTION; PEPTIDES; REACTIVE OXYGEN SPECIES; SERUM ALBUMIN; SULFENIC ACIDS; SULFINIC ACIDS; SULFONIC ACIDS; TANDEM MASS SPECTROMETRY; TRYPSIN;

EID: 84865211972     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx300096a     Document Type: Article

References (20)

1. Dalle-Donne, I., Rossi, R., Colombo, R., Giustarini, D., and Milzani, A. (2006) Biomarkers of oxidative damage in human disease Clin. Chem. 52, 601-623
2. Halliwell, B. and Whiteman, M. (2004) Measuring reactive species and oxidative damage in vivo and in cell culture: how should you do it and what do the results mean? Br. J. Pharmacol. 142, 231-255 (Pubitemid 38746160)
3. Aldini, G., Vistoli, G., Regazzoni, L., Gamberoni, L., Facino, R. M., Yamaguchi, S., Uchida, K., and Carini, M. (2008) Albumin is the main nucleophilic target of human plasma: a protective role against pro-atherogenic electrophilic reactive carbonyl species? Chem. Res. Toxicol. 21, 824-835 (Pubitemid 351644560)
4. Bourdon, E. and Blache, D. (2001) The importance of proteins in defense against oxidation Antioxid. Redox Signaling 3, 293-311 (Pubitemid 32473344)
5. Stewart, A. J., Blindauer, C. A., Berezenko, S., Sleep, D., Tooth, D., and Sadler, P. J. (2005) Role of Tyr84 in controlling the reactivity of Cys34 of human albumin FEBS J. 272, 353-362
6. Carballal, S., Alvarez, B., Turell, L., Botti, H., Freeman, B. A., and Radi, R. (2007) Sulfenic acid in human serum albumin Amino Acids 32, 543-551 (Pubitemid 46790936)
7. Turell, L., Botti, H., Carballal, S., Ferrer-Sueta, G., Souza, J. M., Duran, R., Freeman, B. A., Radi, R., and Alvarez, B. (2008) Reactivity of sulfenic acid in human serum albumin Biochemistry 47, 358-367
8. Aldini, G., Gamberoni, L., Orioli, M., Beretta, G., Regazzoni, L., Maffei Facino, R., and Carini, M. (2006) Mass spectrometric characterization of covalent modification of human serum albumin by 4-hydroxy-trans-2-nonenal J. Mass Spectrom. 41, 1149-1161 (Pubitemid 44454168)
9. Finch, J. W., Crouch, R. K., Knapp, D. R., and Schey, K. L. (1993) Mass spectrometric identification of modifications to human serum albumin treated with hydrogen peroxide Arch. Biochem. Biophys. 305, 595-599 (Pubitemid 23282951)
10. Li, H., Grigoryan, H., Funk, W. E., Lu, S. S., Rose, S., Williams, E. R., and Rappaport, S. M. (2011) Profiling Cys34 adducts of human serum albumin by fixed-step selected reaction monitoring Mol. Cell Proteomics 10, M110 004606
11. Jacob, C., Holme, A. L., and Fry, F. H. (2004) The sulfinic acid switch in proteins Org. Biomol. Chem. 2, 1953-1956
12. Lin, Y. S., McKelvey, W., Waidyanatha, S., and Rappaport, S. M. (2006) Variability of albumin adducts of 1,4-benzoquinone, a toxic metabolite of benzene, in human volunteers Biomarkers 11, 14-27 (Pubitemid 43250549)
13. Funk, W. E., Li, H., Iavarone, A. T., Williams, E. R., Riby, J., and Rappaport, S. M. (2010) Enrichment of cysteinyl adducts of human serum albumin Anal. Biochem. 400, 61-68
14. Shetty, V., Spellman, D. S., and Neubert, T. A. (2007) Characterization by tandem mass spectrometry of stable cysteine sulfenic acid in a cysteine switch peptide of matrix metalloproteinases J. Am. Soc. Mass Spectrom. 18, 1544-1551 (Pubitemid 47089005)
15. Shetty, V. and Neubert, T. A. (2009) Characterization of novel oxidation products of cysteine in an active site motif peptide of PTP1B J. Am. Soc. Mass Spectrom. 20, 1540-1548
16. Fu, X., Mueller, D. M., and Heinecke, J. W. (2002) Generation of intramolecular and intermolecular sulfenamides, sulfinamides, and sulfonamides by hypochlorous acid: a potential pathway for oxidative cross-linking of low-density lipoprotein by myeloperoxidase Biochemistry 41, 1293-1301 (Pubitemid 34083782)
17. Salmeen, A., Andersen, J. N., Myers, M. P., Meng, T. C., Hinks, J. A., Tonks, N. K., and Barford, D. (2003) Redox regulation of protein tyrosine phosphatase 1B involves a sulphenyl-amide intermediate Nature 423, 769-773 (Pubitemid 36735701)
18. Turell, L., Botti, H., Carballal, S., Radi, R., and Alvarez, B. (2009) Sulfenic acid - a key intermediate in albumin thiol oxidation J. Chromatogr., B 877, 3384-3392
19. Roche, M., Rondeau, P., Singh, N. R., Tarnus, E., and Bourdon, E. (2008) The antioxidant properties of serum albumin FEBS Lett. 582, 1783-1787
20. Oettl, K. and Stauber, R. E. (2007) Physiological and pathological changes in the redox state of human serum albumin critically influence its binding properties Br. J. Pharmacol. 151, 580-590 (Pubitemid 47016287)