1480
G. Aldini et al.
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. Plasmaproteinhomocysteinylationinuremia. Clinical
Chemistry and Laboratory Medicine 2007; 45: 1678.
presented here seems to offer the potential for reaching these
goals, and will be further implemented by quantitative anal-
ysis in MRM mode, using isotopically labeled derivatives of
the carbonylated tag peptides.
Thus the combined LC-MS/MS approaches (in both pre-
cursor ion and MRM mode) could well be successful in
oxidative stress-related research, where detailed character-
ization and quantitation of covalently modified proteins is
particularly important.
Supplementary material
Supplementary electronic material for this paper is available
com/jpages/1076-5174/suppmat/.
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.
Acknowledgements
This study was partially supported by FIRST (University of Milan).
J.D.Baggott kindly edited the manuscript.
REFERENCES
19. Papac DI, Shahrokh Z. Mass spectrometry innovation in drug
discovery and development. Pharmaceutical Research 2001; 18:
131.
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.
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 chro-
matography/atmospheric pressure ionization-mass spectrome-
try in drug metabolism studies. 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
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 admin-
istration 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.
Copyright 2008 John Wiley & Sons, Ltd.
J. Mass Spectrom. 2008; 43: 1470–1481
DOI: 10.1002/jms