Evaluation of three simple direct or indirect carbonyl detection methods for characterization of oxidative modifications of proteins

References

• Alderton AL, Faustman C, Liebler DC, Hill DW. 2003. Induction of redox instability of bovine myoglobin by adduction with 4-hydroxy-2-nonenal. Biochemistry 42:4398–4405.
   PubMed Web of Science ®Google Scholar
• Aldini G, Dalle-Donne I, Colombo R, Maffei Facino R, Milzani A, Carini M. 2006. Lipoxidation-derived reactive carbonyl species as potential drug targets in preventing protein carbonylation and related cellular dysfunction. ChemMedChem 1:1045–1058.
   PubMed Web of Science ®Google Scholar
• Aldini G, Dalle-Donne I, Facino RM, Milzani A, Carini M. 2007. Intervention strategies to inhibit protein carbonylation by lipoxidation-derived reactive carbonyls. Med Res Rev 27:817–868.
   PubMed Web of Science ®Google Scholar
• Argüelles S, Machado A, Ayala A. 2006. “In vitro” effect of lipid peroxidation metabolites on elongation factor-2. Biochim Biophys Acta 1760:445–452.
   PubMedGoogle Scholar
• Borovic S, Rabuzin F, Waeg G, Zarkovic N. 2006. Enzyme-linked immunosorbent assay for 4-hydroxynonenal-histidine conjugates. Free Radic Res 40:809–820.
   PubMed Web of Science ®Google Scholar
• Bruenner BA, Jones AD, German JB. 1995. Direct characterization of protein adducts of the lipid peroxidation product 4-hydroxy-2-nonenal using electrospray mass spectrometry. Chem Res Toxicol 8:552–559.
   PubMed Web of Science ®Google Scholar
• Butterfield DA, Galvan V, Lange MB, Tang H, Sowell RA, Spilman P, Fombonne J, Gorostiza O, Zhang J, Sultana R, Bredesen DE. 2010. In vivo oxidative stress in brain of Alzheimer disease transgenic mice: Requirement for methionine 35 in amyloid beta-peptide of APP. Free Radic Biol Med 48:136–144.
   PubMed Web of Science ®Google Scholar
• Codreanu SG, Zhang B, Sobecki SM, Billheimer DD, Liebler DC. 2009. Global analysis of protein damage by the lipid electrophile 4-hydroxy-2-nonenal. Mol Cell Proteomics 8:670–680.
   PubMed Web of Science ®Google Scholar
• Dalle-Donne I, Aldini G, Carini M, Colombo R, Rossi R, Milzani A. 2006a. Protein carbonylation, cellular dysfunction, and disease progression. J Cell Mol Med 10:389–406.
   PubMed Web of Science ®Google Scholar
• Dalle-Donne I, Giustarini D, Colombo R, Rossi R, Milzani A. 2003. Protein carbonylation in human diseases. Trends Mol Med 9:169–176.
   PubMed Web of Science ®Google Scholar
• Dalle-Donne I, Rossi R, Colombo R, Giustarini D, Milzani A. 2006b. Biomarkers of oxidative damage in human disease. Clin Chem 52:601–623.
   PubMed Web of Science ®Google Scholar
• Doorn JA, Petersen DR. 2003. Covalent adduction of nucleophilic amino acids by 4-hydroxynonenal and 4-oxononenal. Chem Biol Interact 143–144:93–100.
   PubMed Web of Science ®Google Scholar
• Doorn JA, Petersen DR. 2002. Covalent modification of amino acid nucleophiles by the lipid peroxidation products 4-hydroxy-2-nonenal and 4-oxo-2-nonenal. Chem Res Toxicol 15:1445–1450.
   PubMed Web of Science ®Google Scholar
• Esterbauer H, Schaur RJ, Zollner H. 1991. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde and related aldehydes. Free Radic Biol Med 11:81–128.
   PubMed Web of Science ®Google Scholar
• Grimsrud PA, Xie H, Griffin TJ, Bernlohr DA. 2008. Oxidative stress and covalent modification of protein with bioactive aldehydes. J Biol Chem 283:21837–21841.
   PubMed Web of Science ®Google Scholar
• Jouanin I, Sreevani V, Rathahao E, Gueraud F, Paris A. 2008. Synthesis of the lipid peroxidation product 4-hydroxy-2(E)-nonenal with C-13 stable isotope incorporation. J Label Compds Radiopharm 51:87–92.
   Web of Science ®Google Scholar
• Kohen R, Nyska A. 2002. Oxidation of biological systems: oxidative stress phenomena, antioxidants, redox reactions, and methods for their quantification. Toxicol Pathol 30:620–650.
   PubMed Web of Science ®Google Scholar
• Lesgards JF, Frayne IR, Comte B, Busseuil D, Rhéaume E, Tardif JC, Rosiers CD. 2009. Differential distribution of 4-hydroxynonenal adducts to sulfur and nitrogen residues in blood proteins as revealed using Raney nickel and gas chromatography-mass spectrometry. Free Radic Biol Med 47:1375–1385.
   PubMedGoogle Scholar
• Loguercio C, Federico A. 2003. Oxidative stress in viral and alcoholic hepatitis. Free Radic Biol Med 34:1–10.
   PubMed Web of Science ®Google Scholar
• Levine RL, Garland D, Oliver CN, Amici A, Climent I, Lenz AG, Ahn BW, Shaltiel S, Stadtman ER. 1990. Determination of carbonyl content in oxidatively modified proteins. Meth Enzymol 186:464–478.
   PubMed Web of Science ®Google Scholar
• Levine RL, Williams JA, Stadtman ER, Shacter E. 1994. Carbonyl assays for determination of oxidatively modified proteins. Meth Enzymol 233:346–357.
   PubMed Web of Science ®Google Scholar
• LoPachin RM, Gavin T, Petersen DR, Barber DS. 2009. Molecular mechanisms of 4-hydroxy-2-nonenal and acrolein toxicity: nucleophilic targets and adduct formation. Chem Res Toxicol 22:1499–1508.
   PubMed Web of Science ®Google Scholar
• Nadkarni DV, Sayre LM. 1995. Structural definition of early lysine and histidine adduction chemistry of 4-hydroxynonenal. Chem Res Toxicol 8:284–291.
   PubMed Web of Science ®Google Scholar
• Negre-Salvayre A, Auge N, Ayala V, Basaga H, Boada J, Brenke R, Chapple S, Cohen G, Feher J, Grune T, Lengyel G, Mann GE, Pamplona R, Poli G, Portero-Otin M, Riahi Y, Salvayre R, Sasson S, Serrano J, Shamni O, Siems W, Siow RC, Wiswedel I, Zarkovic K, Zarkovic N. 2010. Pathological aspects of lipid peroxidation. Free Radic Res 44:1125–1171.
   PubMed Web of Science ®Google Scholar
• Negre-Salvayre A, Coatrieux C, Ingueneau C, Salvayre R. 2008. Advanced lipid peroxidation end products in oxidative damage to proteins. Potential role in diseases and therapeutic prospects for the inhibitors. Br J Pharmacol 153:6–20.
   PubMed Web of Science ®Google Scholar
• Nyström T. 2005. Role of oxidative carbonylation in protein quality control and senescence. EMBO J 24:1311–1317.
   PubMed Web of Science ®Google Scholar
• Petersen DR, Doorn JA. 2004. Reactions of 4-hydroxynonenal with proteins and cellular targets. Free Radic Biol Med 37:937–945.
   PubMed Web of Science ®Google Scholar
• Poli G, Biasi F, Leonarduzzi G. 2008. 4-Hydroxynonenal-protein adducts: A reliable biomarker of lipid oxidation in liver diseases. Mol Aspects Med 29:67–71.
   PubMed Web of Science ®Google Scholar
• Reed T, Perluigi M, Sultana R, Pierce WM, Klein JB, Turner DM, Coccia R, Markesbery WR, Butterfield DA. 2008. Redox proteomic identification of 4-hydroxy-2-nonenal-modified brain proteins in amnestic mild cognitive impairment: insight into the role of lipid peroxidation in the progression and pathogenesis of Alzheimer’s disease. Neurobiol Dis 30:107–120.
   PubMed Web of Science ®Google Scholar
• Requena JR, Levine RL, Stadtman ER. 2003. Recent advances in the analysis of oxidized proteins. Amino Acids 25:221–226.
   PubMed Web of Science ®Google Scholar
• Roe MR, Xie H, Bandhakavi S, Griffin TJ. 2007. Proteomic mapping of 4-hydroxynonenal protein modification sites by solid-phase hydrazide chemistry and mass spectrometry. Anal Chem 79:3747–3756.
   PubMed Web of Science ®Google Scholar
• Roede JR, Carbone DL, Doorn JA, Kirichenko OV, Reigan P, Petersen DR. 2008. In vitro and in silico characterization of peroxiredoxin 6 modified by 4-hydroxynonenal and 4-oxononenal. Chem Res Toxicol 21:2289–2299.
   PubMed Web of Science ®Google Scholar
• Salto R, Girón MD, del Mar Sola M, Vargas AM. 1999. Evolution of pyruvate carboxylase and other biotin containing enzymes in developing rat liver and kidney. Mol Cell Biochem 200:111–117.
   PubMedGoogle Scholar
• Sayre LM, Lin D, Yuan Q, Zhu X, Tang X. 2006. Protein adducts generated from products of lipid oxidation: focus on HNE and one. Drug Metab Rev 38:651–675.
   PubMed Web of Science ®Google Scholar
• Schaffner W, Weissmann C. 1973. A rapid, sensitive, and specific method for the determination of protein in dilute solution. Anal Biochem 56:502–514.
   PubMed Web of Science ®Google Scholar
• Spickett CM, Wiswedel I, Siems W, Zarkovic K, Zarkovic N. 2010. Advances in methods for the determination of biologically relevant lipid peroxidation products. Free Radic Res 44:1172–1202.
   PubMed Web of Science ®Google Scholar
• Stadtman ER, Berlett BS. 1997. Reactive oxygen-mediated protein oxidation in aging and disease. Chem Res Toxicol 10:485–494.
   PubMed Web of Science ®Google Scholar
• Vaishnav RA, Getchell ML, Poon HF, Barnett KR, Hunter SA, Pierce WM, Klein JB, Butterfield DA, Getchell TV. 2007. Oxidative stress in the aging murine olfactory bulb: redox proteomics and cellular localization. J Neurosci Res 85:373–385.
   PubMedGoogle Scholar
• Valko M, Leibfritz D, Moncol J, Cronin MT, Mazur M, Telser J. 2007. Free radicals and antioxidants in normal physiological functions and human disease. Int J Biochem Cell Biol 39:44–84.
   PubMed Web of Science ®Google Scholar
• Véronneau M, Comte B, Des Rosiers C. 2002. Quantitative gas chromatographic-mass spectrometric assay of 4-hydroxynonenal bound to thiol proteins in ischemic/reperfused rat hearts. Free Radic Biol Med 33:1380–1388.
   PubMedGoogle Scholar
• Vila A, Tallman KA, Jacobs AT, Liebler DC, Porter NA, Marnett LJ. 2008. Identification of protein targets of 4-hydroxynonenal using click chemistry for ex vivo biotinylation of azido and alkynyl derivatives. Chem Res Toxicol 21:432–444.
   PubMed Web of Science ®Google Scholar
• Waeg G, Dimsity G, Esterbauer H. 1996. Monoclonal antibodies for detection of 4-hydroxynonenal modified proteins. Free Radic Res 25:149–159.
   PubMed Web of Science ®Google Scholar
• Waris G, Ahsan H. 2006. Reactive oxygen species: role in the development of cancer and various chronic conditions. J Carcinog 5:14.
   PubMedGoogle Scholar
• Zarkovic N, Cipak Gasparovic A, Cindric M, Waeg G, Borovic Sunjic S, Mrakovcic L, Jaganjac M, Kolenc D, Andrisic L, Gveric Ahmetasevic S, Katusic A, Cherkas A, Juric Sekhar G, Wildburger R, Zarkovic K. (2009) 4-Hydroxynonenal-protein adducts as biomarkers of oxidative stress, lipid peroxidation and oxidative homeostasis. In: Free Radicals, Health and Lifestyle. Caporossi FPD, Sabatini S, (eds.). Bologna, Italy: Medimond Srl. pp 37–45.
   Google Scholar