α,β-Unsaturated aldehydes adducts to actin and albumin as potential biomarkers of carbonylation damage

REFERENCES

• Aldini G, Dalle-Donne I, Maffei Facino R, Milzani A, Carini M. Intervention strategies to inhibit protein carbonylation by lipoxidation-derived reactive carbonyls. Med Res Rev 2006 Oct 16; [Epub ahead of print] PMID: 17044003.
   Google Scholar
• Lovell MA, Xie C, Markesbery WR. Acrolein is increased in Alzheimer's disease brain and is toxic to primary hippocampal cultures. Neurobiol Aging 2001; 22: 187–194.
   PubMed Web of Science ®Google Scholar
• Rahman I, van Schadewijk AA, Crowther AJ et al. 4-Hydroxy-2-nonenal, a specific lipid peroxidation product, is elevated in lungs of patients with chronic obstructive pulmonary disease. Am J Respir Grit Care Med 2002; 166: 490–495.
   PubMed Web of Science ®Google Scholar
• Barreiro E, de la Puente B, Minguella J et al. Oxidative stress and respiratory muscle dysfunction in severe chronic obstructive pulmonary disease. Am J Respir Grit Care Med 2005; 171: 1116–1124.
   PubMed Web of Science ®Google Scholar
• Shao, B, Fu X, McDonald TO et al. Acrolein impairs ATP binding cassette transporter Al-dependent cholesterol export from cells through site-specific modification of apolipoprotein A-I. J Biol Chem 2005; 280: 36386–36396.
   PubMed Web of Science ®Google Scholar
• Williams TI, Lynn BC, Markesbery WR, Lovell MA. Increased levels of 4-hydroxynonenal and acrolein, neurotoxic markers of lipid peroxidation, in the brain in mild cognitive impairment and early Alzheimer's disease. Neurobiol Aging 2006; 27: 1094–1099.
   PubMed Web of Science ®Google Scholar
• Dalle-Donne I, Rossi R, Colombo R, Giustarini D, Milzani, A. Biomarkers of oxidative damage in human disease. Clin Chem 2006; 52: 601–623.
   PubMed Web of Science ®Google Scholar
• Butterfield DA, Reed T, Perluigi M et al. Elevated protein-bound levels of the lipid peroxidation product, 4-hydroxy-2-nonenal, in brain from persons with mild cognitive impairment. Neurosci Lett 2006; 397: 170–173.
   PubMed Web of Science ®Google Scholar
• Odetti P, Traverso N, Monacelli F et al. Vitamin E-coated filter decreases levels of free 4-hydroxy1-2-nonenal during haemodialysis sessions. Free Radic Res 2006; 40: 207–212.
   PubMed Web of Science ®Google Scholar
• Siems WG, Brenke R, Beier A, Grune T. Oxidative stress in chronic lymphoedema. Q J Med 2002; 95: 803–809.
   Google Scholar
• Sakata K, Kashiwagi K, Sharmin S et al. Increase in putrescine, amine oxidase, and acrolein in plasma of renal failure patients. Biochem Biophys Res Commun 2003; 305: 143–149.
   PubMed Web of Science ®Google Scholar
• Satoh, K, Yamada S, Koike Y et al. A 1-hour enzyme-linked immunosorbent assay for quantitation of acrolein- and hydroxynonenal-modified proteins by epitope-bound casein matrix method. Anal Biochem 1999; 270: 323–328.
   PubMed Web of Science ®Google Scholar
• Carini M, Aldini G, Maffei Facino R. Sequestering agents of intermediate reactive aldehydes as inhibitors of advanced lipoxidation end-products (ALEs). In: Dalle-Donne I, Scaloni A, Butterfield DA. (eds) Redox Proteomics: From Protein Modifications to Cellular Dysfunction and Disease. New York: John Wiley, 2006; 877–929.
   Google Scholar
• Volkel W, Alvarez-Sanchez R, Weick I, Mally A, Dekant W, Pahler A. Glutathione conjugates of 4-hydroxy-2(E)-nonenal as biomarkers of hepatic oxidative stress-induced lipid peroxidation in rats. Free Radic Biol Med. 2005; 38: 1526–1536.
   PubMed Web of Science ®Google Scholar
• Orioli M, Aldini G, Beretta G, Facino RM, Carini M. LC-ESI-MS/MS determination of 4-hydroxy-trans-2-nonenal Michael adducts with cysteine and histidine-containing peptides as early markers of oxidative stress in excitable tissues. J Chromatogr B Anal Technol Biomed Life Sci 2005; 827: 109–118.
   PubMed Web of Science ®Google Scholar
• Esterbauer H, Cheeseman KH. Determination of aldehydic lipid peroxidation products: malonaldehyde and 4-hydroxynonenal. Methods Enzymol 1990; 186: 407–421.
   PubMed Web of Science ®Google Scholar
• Strohmaier H, Hinghofer-Szalkay H, Schaur RJ. Detection of 4-hydroxynonenal (HNE) as a physiological component in human plasma. J Lipid Medial Cell Signal 1995; 11: 51–61.
   PubMedGoogle Scholar
• Spies-Martin D, Sommerburg O, Langhans CD, Leichsenring M. Measurement of 4-hydroxynonenal in small volume blood plasma samples: modification of a gas chromatographic-mass spectrometric method for clinical settings. J Chromatogr B Anal Technol Biomed Life Sci 2002; 774: 231–239.
   PubMed Web of Science ®Google Scholar
• 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. Biochem Biophys Res Commun 1995; 212: 1068–1073.
   PubMed Web of Science ®Google Scholar
• Shibamoto T. Analytical methods for trace levels of reactive carbonyl compounds formed in lipid peroxidation systems. J Pharm Biomed Anal 2006; 41: 12–25.
   PubMed Web of Science ®Google Scholar
• Salomon RG, Kaur K, Podrez E, Hoff HF, Krushinsky AV, Sayre LM. FINE-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 2000; 13: 557–564.
   PubMed Web of Science ®Google Scholar
• Siems WG, Grune T. Intracellular metabolism of 4-hydroxynonenal. Mol Aspects Med 2003; 24: 167–175.
   PubMedGoogle Scholar
• Chevion M, Berenshtein E, Stadtman ER. Human studies related to protein oxidation: protein carbonyl content as a marker of damage. Free Radic Res 2000; 33 ( Suppl): S99-S108.
   Google Scholar
• Himmelfarb J, McMonagle E, Freedman S et al. The PICARD Group. Oxidative stress is increased in critically ill patients with acute renal failure. J Am Soc Nephrol 2004; 15: 2449–2456.
   PubMed Web of Science ®Google Scholar
• Pupim LB, Himmelfarb J, McMonagle E, Shyr Y, Ikizler TA. Influence of initiation of maintenance hemodialysis on biomarkers of inflammation and oxidative stress. Kidney Int 2004; 65: 2371–2379.
   PubMed Web of Science ®Google Scholar
• Oh-Ishi M, Ueno T, Maeda T. Proteomic method detects oxidatively induced protein carbonyls in muscles of a diabetes model Otsuka Long-Evans Tokushima Fatty (OLETF) rat. Free Radic Biol Med 2003; 34: 11–22.
   PubMed Web of Science ®Google Scholar
• Aksenov MY, Aksenova MV, Butterfield DA, Geddes JW, Markesbery WR. Protein oxidation in the brain in Alzheimer's disease. Neuroscience 2001; 103: 373–383.
   PubMed Web of Science ®Google Scholar
• Barreiro E, Gea J, Di Falco M, Kriazhev L, James S, Hussain SN. Protein carbonyl formation in the diaphragm. Am J Respir Cell Mol Biol 2005; 32: 9–17.
   PubMed Web of Science ®Google Scholar
• Powell SR, Gurzenda EM, Wahezi SE. Actin is oxidized during myocardial ischemia. Free Radic Biol Med 2001; 30: 1171–1176.
   PubMed Web of Science ®Google Scholar
• Mera K, Anraku M, Kitamura K et al. Oxidation and carboxy methyl lysine-modification of albumin: possible involvement in the progression of oxidative stress in hemodialysis patients. Hypert ens Res 2005; 28: 973–980.
   PubMed Web of Science ®Google Scholar
• Toyokuni S, Yamada S, Kashima M et al. Serum 4-hydroxy-2-nonenal-modified albumin is elevated in patients with type 2 diabetes mellitus. Antioxid Redox Signal 2000; 2: 681–685.
   PubMed Web of Science ®Google Scholar
• Aldini G, Dalle-Donne I, Vistoli G, Maffei Facino R, Carini M. Covalent modification of actin by 4-hydroxy-trans-2-nonenal (HNE): LC-ESI-MS/MS evidence for Cys374 Michael adduction. J Mass Spectrom 2005; 40: 946–954.
   PubMed Web of Science ®Google Scholar
• Aldini G, Gamberoni L, Orioli M et al. Mass spectrometric characterization of covalent modification of human serum albumin by 4-hydroxy-trans-2-nonenal. J Mass Spectrom 2006; 41: 1149–1161.
   PubMed Web of Science ®Google Scholar
• Szapacs ME, Riggins JN, Zimmerman LJ, Liebler DC. Covalent adduction of human serum albumin by 4-hydroxy-2-nonenal: kinetic analysis of competing alkylation reactions. Biochemistry 2006; 45: 10521–10528.
   PubMed Web of Science ®Google Scholar
• Diaz N, Suarez D, Sordo TL, Merz KM Jr. Molecular dynamics study of the IIA binding site in human serum albumin: influence of the protonation state of Lys195 and Lys199. J Med Chem 2001; 44: 250–260.
   PubMed Web of Science ®Google Scholar
• Fenaille F, Tabet JC, Guy PA. Immunoaffinity purification and characterization of 4-Hydroxy-2-nonenal- and malondialdehyde-modified peptides by electrospray ionization tandem mass spectrometry. Anal Chem 2002; 74: 6298–6304.
   PubMed Web of Science ®Google Scholar
• Dalle-Donne I, Aldini G, Carini M, Colombo R, Rossi R, Milzani A. Protein carbonylation, cellular dysfunction, and disease progression. J Cell Mol Med 2006; 10: 389–406.
   PubMed Web of Science ®Google Scholar
• 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. Chem Med Chem 2006; 10: 1045–1058.
   Google Scholar
• Agarwal R Chronic kidney disease is associated with oxidative stress independent of hypertension. Clin Nephrol 2004; 61: 377–383.
   PubMed Web of Science ®Google Scholar
• Simic DV, Mimic-Oka J, Pljesa-Ercegovac M et al. Byproducts of oxidative protein damage and antioxidant enzyme activities in plasma of patients with different degrees of essential hypertension. J Hum Hypert ens 2006; 20: 149–155.
   PubMed Web of Science ®Google Scholar