A tandem MS precursor-ion scan approach to identify variable covalent modification of albumin Cys34: A new tool for studying vascular carbonylation

Journal of Mass Spectrometry

Volumn 43, Issue 11, 2008, Pages 1470-1481

  Aldini, Giancarlo ^a   Regazzoni, Luca ^a   Orioli, Marica ^a   Rimoldi, Isabella ^b   Facino, Roberto Maffei ^a   Carini, Marina ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b Dipartimento di Chimica Inorganica Metallorganica ed Analitica   (Italy)

Author keywords

Cys34; Human serum albumin; LC ESI MS MS analysis; Oxidative stress; Precursor ion scan; Reactive carbonyl species

Indexed keywords

ALDEHYDES; AMINES; BODY FLUIDS; CARBONYLATION; CHROMATOGRAPHIC ANALYSIS; DERIVATIVES; ELECTROSPRAY IONIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IONIZATION OF LIQUIDS; IONS; IRON COMPOUNDS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; ORGANIC COMPOUNDS; PLASMAS; PROTEINS; SCANNING;

CYS34; HUMAN SERUM ALBUMIN; LC-ESI-MS/MS ANALYSIS; PRECURSOR-ION SCAN; REACTIVE CARBONYL SPECIES;

ION CHROMATOGRAPHY;

2,2' AZOBIS(2 AMIDINOPROPANE); 4 HYDROXYNONENAL; ACROLEIN; ALDEHYDE DERIVATIVE; CYSTEINE; CYSTEINE 34; HUMAN SERUM ALBUMIN; HYDROGEN PEROXIDE; IRON; KETONE DERIVATIVE; LOW DENSITY LIPOPROTEIN; PEPTIDE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CARBONYLATION; CHEMICAL MODIFICATION; CONTROLLED STUDY; COVALENT BOND; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; LIQUID CHROMATOGRAPHY; OXIDATIVE STRESS; PRIORITY JOURNAL; TANDEM MASS SPECTROMETRY;

ADULT; BLOOD CHEMICAL ANALYSIS; BLOOD VESSELS; CYSTEINE; FEMALE; HUMANS; MALE; OXIDATIVE STRESS; REACTIVE OXYGEN SPECIES; SERUM ALBUMIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 55249111076     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1419     Document Type: Article

References (34)

1. Poli G, Schaur RJ. 4-Hydroxynonenal in the pathomechanisms of oxidative stress. IUBMB Life 2000; 50: 315.
2. Leonarduzzi G, Chiarpotto E, Biasi F, Poli G. 4-Hydroxynonenal and cholesterol oxidation products in atherosclerosis. Molecular Nutrition and Food Research 2005; 49: 1044.
3. Uchida K. 4-Hydroxy-2-nonenal: a product and mediator of oxidative stress. Progress in Lipid Research 2003; 42: 318.
4. Aldini G, Dalle-Donne I, Facino RM, Milzani A, Carini M. Intervention strategies to inhibit protein carbonylation by lipoxidation-derived reactive carbonyls. Medicinal Research Reviews 2007; 27: 817.
5. Dalle-Donne I, Aldini G, Carini M, Colombo R, Rossi R, Milzani A. Protein carbonylation, cellular dysfunction, and disease progression. Journal of Cellular and Molecular Medicine 2006; 10: 389.
6. Shibamoto T. Analytical methods for trace levels of reactive carbonyl compounds formed in lipid peroxidation systems. Journal of Pharmaceutical and Biomedical Analysis 2006; 41: 12.
7. Zarkovic N. 4-hydroxynonenal as a bioactive marker of pathophysiological processes. Molecular Aspects of Medicine 2003; 24: 281.
8. Mera K, Anraku M, Kitamura K, Nakajou K, Maruyama T, Otagiri M. The structure and function of oxidized albumin in hemodialysis patients: its role in elevated oxidative stress via neutrophil burst. Biochemical and Biophysical Research Communications 2005; 334: 1322.
9. Anraku M, Kitamura K, Shinohara A, Adachi M, Suenga A, Maruyama T, Miyanaka K, Miyoshi T, Shiraishi N, Nonoguchi H, Otagiri M, Tomita K. Intravenous iron administration induces oxidation of serum albumin in hemodialysis patients. Kidney International 2004; 66: 841.
10. Dalle-Donne I, Giustarini D, Colombo R, Rossi R, Milzani A. Protein carbonylation in human diseases. Trends in Molecular Medicine 2003; 9: 169.
11. Aldini G, Vistoli G, Regazzoni L, Gamberoni L, Facino RM, Yamaguchi S, Uchida K, Carini M. Albumin is the main nucleophilic target of human plasma: a protective role against pro-atherogenic electrophilic reactive carbonyl species? Chem Res Toxicol. 2008; 21: 824 .
12. Aldini G, Gamberoni L, Orioli M, Beretta G, Regazzoni L, Maffei Facino R, Carini M. Mass spectrometric characterization of covalent modification of human serum albumin by 4-hydroxy-trans-2-nonenal. Journal of Mass Spectrometry 2006; 41: 1149.
13. Aldini G, Orioli M, Carini M. Alpha, beta-unsaturated aldehydes adducts to actin and albumin as potential biomarkers of carbonylation damage. Redox Report 2007; 12: 20.
14. Tallman KA, Kim HY, Ji JX, Szapacs ME, Yin H, McIntosh TJ, Liebler DC, Porter NA. Phospholipid-protein adducts of lipid peroxidation: synthesis and study of new biotinylated phosphatidylcholines. Chemical Research in Toxicology 2007; 20: 227.
15. Bar-Or D, Heyborne KD, Bar-Or R, Rael LT, Winkler JV, Navot D. Cysteinylation of maternal plasma albumin and its association with intrauterine growth restriction. Prenatal Diagnosis 2005; 25: 245.
16. Perna AF, Acanfora F, Luciano MG, Pulzella P, Capasso R, Satta E, Cinzia L, Pollastro RM, Iannelli S, Ingrosso D, De Santo NG. Plasmaprotein homocysteinylation in uremia. Clinical Chemistry and Laboratory Medicine 2007; 45: 1678.
17. Musante L, Bruschi M, Candiano G, Petretto A, Dimasi N, Del Boccio P, Urbani A, Rialdi G, Ghiggeri GM. Characterization of oxidation end product of plasma albumin 'in vivo'. Biochemical and Biophysical Research Communications 2006; 349: 668.
18. Musante L, Candiano G, Petretto A, Bruschi M, Dimasi N, Caridi G, Pavone B, Del Boccio P, Galliano M, Urbani A, Scolari F, Vincenti F, Ghiggeri GM. Active focal segmental glomerulosclerosis is associated with massive oxidation of plasma albumin. Journal of the American Society of Nephrology 2007; 18: 799.
19. Papac DI, Shahrokh Z. Mass spectrometry innovation in drug discovery and development. Pharmaceutical Research 2001; 18: 131.
20. Zhang JY, Wang Y, Dudkowski C, Yang D, Chang M, Yuan J, Paulson SK, Breau AP. Characterization of metabolites of celecoxib in rabbits by liquid chromatography/tandem mass spectrometry. Journal of Mass Spectrometry 2000; 35: 1259.
21. Kostiainen R, Kotiaho T, Kuuranne T, Auriola S. Liquid chromatography/atmospheric pressure ionization-mass spectrometry indrugmetabolismstudies. Journal of Mass Spectrometry 2003; 384: 357.
22. Liu DQ, Hop CE. Strategies for characterization of drug metabolites using liquid chromatography-tandem mass spectrometry in conjunction with chemical derivatization and on-line H/D exchange approaches. Journal of Pharmaceutical and Biomedical Analysis 2005; 37: 1.
23. Orioli M, Aldini G, Benfatto MC, Facino RM, Carini M. HNE Michael adducts to histidine and histidine-containing peptides as biomarkers of lipid-derived carbonyl stress in urines: LC-MS/MS profiling in Zucker obese rats. Analytical Chemistry 2007; 79: 9174.
24. Young CL, Woolfitt AR, McWilliams LG, Moura H, Boyer AE, Barr JR. Survey of albumin purification methods for the analysis of albumin-organic toxicant adducts by liquid chromatography-electrospray ionization-tandem mass spectrometry. Proteomics 2005; 5: 4973.
25. Havel RJ, Eder HA, Bragdon JH. The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum. Journal of Clinical Investigation 1955; 34: 1345.
26. Vieira O, Escargueil-Blanc I, Jurgens G, Borner C, Almeida L, Salvayre R, Negre-Salvayre A. Oxidized LDLs alter the activity of the ubiquitin-proteasome pathway: potential role in oxidized LDL-induced apoptosis. FASEB Journal 2000; 14: 532.
27. Vieira O, Escargueil-Blanc I, Meilhac O, Basile JP, Laranjinha J, Almeida L, Salvayre R, Negre-Salvayre A. Effect of dietary phenolic compounds on apoptosis of human cultured endothelial cells induced by oxidized LDL. British Journal of Pharmacology 1998; 123: 565.
28. Atkin MA, Gasper A, Ullegaddi R, Powers HJ. Oxidative susceptibility of unfractionated serum or plasma: response to antioxidants in vitro and to antioxidant supplementation. Clinical Chemistry 2005; 51: 2138.
29. Agil A, Fuller CJ, Jialal I. Susceptibility of plasma to ferrous iron/hydrogen peroxide-mediated oxidation: demonstration of a possible Fenton reaction. Clinical Chemistry 1995; 41: 220.
30. Uchida K, Osawa T, Hiai H, Toyokuni S. 4-Hydroxy-2-nonenal-trapping ELISA: direct evidence for the release of a cytotoxic aldehyde from oxidized low density lipoproteins. Biochemical and Biophysical Research Communications 1995; 212: 1068.
31. Uchida K, Kanematsu M, Morimitsu Y, Osawa T, Noguchi N, Niki E. Acrolein is a product of lipid peroxidation reaction. Formation of free acrolein and its conjugate with lysine residues in oxidized low density lipoproteins. Journal of Biological Chemistry 1998; 273: 16058.
32. Jacob C, Holme AL, Fry FH. The sulfinic acid switch in proteins. Organic and Biomolecular Chemistry 2004; 14: 19532.
33. Carballal S, Alvarez B, Turell L, Botti H, Freeman BA, Radi R. Sulfenic acid in human serum albumin. Amino Acids 2007; 32: 543.
34. Aldini G, Dalle-Donne I, Colombo R, Maffei Facino R, Milzani A, Carini M. Lipoxidation-derived reactive carbonyl species as potential drug targets in preventing protein carbonylation and related cellular dysfunction. ChemMedChem 2006; 10: 1045.