Water-soluble α,β-unsaturated aldehydes of cigarette smoke induce carbonylation of human serum albumin

Antioxidants and Redox Signaling

Volumn 12, Issue 3, 2010, Pages 349-364

  Colombo, Graziano ^a   Aldini, Giancarlo ^a   Orioli, Marica ^a   Giustarini, Daniela ^b   Gornati, Rosalba ^c   Rossi, Ranieri ^b   Colombo, Roberto ^a   Carini, Marina ^a   Milzani, Aldo ^a   Dalle Donne, Isabella ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

^c UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DINITROPHENYLHYDRAZINE; ACROLEIN; ALDEHYDE; ALPHA BETA UNSATURATED ALDEHYDE; ANTIOXIDANT; CARBONYL DERIVATIVE; CIGARETTE SMOKE; CROTONALDEHYDE; FLUORESCENT DYE; HUMAN SERUM ALBUMIN; HYDRALAZINE; PLASMA PROTEIN; PYRIDOXAMINE; SCHIFF BASE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CAPILLARY CHROMATOGRAPHY; CARDIOVASCULAR DISEASE; CIGARETTE SMOKING; CONCENTRATION (PARAMETERS); DERIVATIZATION; FLUORESCENCE ANALYSIS; HUMAN; IMMUNOHISTOCHEMISTRY; LUNG LAVAGE; NANOANALYSIS; PRIORITY JOURNAL; PROTEIN CARBONYLATION; SPECTROPHOTOMETRY; TANDEM MASS SPECTROMETRY;

ACROLEIN; ALDEHYDES; ARGININE; BLOTTING, WESTERN; CHROMATOGRAPHY, LIQUID; ELECTROPHORESIS, POLYACRYLAMIDE GEL; HUMANS; LYSINE; PROTEIN CARBONYLATION; SERUM ALBUMIN; SMOKE; TANDEM MASS SPECTROMETRY; TOBACCO;

EID: 75149171356     PISSN: 15230864     EISSN: None     Source Type: Journal    
DOI: 10.1089/ars.2009.2806     Document Type: Article

References (53)

1. Aldini G, Dalle-Donne I, Facino RM, Milzani A, and Carini M. Intervention strategies to inhibit protein carbonylation by lipoxidation-derived reactive carbonyls. Med Res Rev 27: 817-868, 2007.
2. Aldini G, Dalle-Donne I, Vistoli G, Maffei Facino R, and 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 40: 946-954, 2005.
3. Aldini G, Gamberoni L, Orioli M, Beretta G, Regazzoni L, Maffei Facino R, and Carini M. Mass spectrometric characterization of covalent modification of human serum albumin by 4-hydroxy-trans-2-nonenal. J Mass Spectrom 41: 1149-1161, 2006.
4. Aldini G, Vistoli G, Regazzoni L, Gamberoni L, Facino RM, Yamaguchi S, Uchida K, and Carini M. 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, 2008.
5. Andreoli R, Manini P, Corradi M, Mutti A, and Niessen WM. Determination of patterns of biologically relevant aldehydes in exhaled breath condensate of healthy subjects by liquid chromatography=atmospheric chemical ionization tandem mass spectrometry. Rapid Commun Mass Spectrom 17: 637-645, 2003.
6. Annovazzi L, Cattaneo V, Viglio S, Perani E, Zanone C, Rota C, Pecora F, Cetta G, Silvestri M, and Iadarola P. High-performance liquid chromatography and capillary electro-phoresis: methodological challenges for the determination of biologically relevant low-aliphatic aldehydes in human saliva. Electrophoresis 25: 1255-1263, 2004.
7. Anraku M, Kitamura K, Shinohara A, Adachi M, Suenga A, Maruyama T, Miyanaka K, Miyoshi T, Shiraishi N, Non-oguchi H, Otagiri M, and Tomita K. Intravenous iron administration induces oxidation of serum albumin in hemodialysis patients. Kidney Int 66: 841-848, 2004. Erratum in: Kidney Int 66: 1304, 2004.
8. Anraku M, Yamasaki K, Maruyama T, Kragh-Hansen U, and Otagiri M. Effect of oxidative stress on the structure and function of human serum albumin. Pharm Res 18: 632-639, 2001. (Pubitemid 32595791)
9. Bartecchi CE, Mackenzie TD, and Schier RW. The human costs of tobacco use. N Engl J Med 330: 907-912, 1994.
10. Bourdon E and Blache D. The importance of proteins in defense against oxidation. Antioxid Redox Signal 3: 293-311, 2001.
11. Burcham PC and Pyke SM. Hydralazine inhibits rapid acrolein-induced protein oligomerization: role of aldehyde scavenging and adduct trapping in cross-link blocking and cytoprotection. Mol Pharmacol 69: 1056-1065, 2006.
12. Carballal S, Radi R, Kirk MC, Barnes S, Freeman BA, and Alvarez B. Sulfenic acid formation in human serum albumin by hydrogen peroxide and peroxynitrite. Biochemistry 42: 9906-9914, 2003.
13. Carmella SG, Chen M, Zhang Y, Zhang S, Hatsukami DK, and Hecht SS. Quantitation of acrolein-derived (3-hydro-xypropyl)mercapturic acid in human urine by liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry: effects of cigarette smoking. Chem Res Toxicol 20: 986-990, 2007.
14. Clunes LA, Bridges A, Alexis N, and Tarran R. In vivo versus in vitro airway surface liquid nicotine levels following cigarette smoke exposure. J Anal Toxicol 32: 201-207, 2008.
15. Conklin DJ, Haberzettl P, Prough RA, and Bhatnagar A. Glutathione S-transferase P protects against endothelial dysfunction induced by exposure to tobacco smoke. Am J Physiol Heart Circ Physiol 2009, doi:10.1152=ajpheart.00867. 2008.
16. Csiszar A, Labinskyy N, Podlutsky A, Kaminski PM, Wolin MS, Zhang C, Mukhopadhyay P, Pacher P, Hu F, de Cabo R, Ballabh P, and Ungvari Z. Vasoprotective effects of resver-atrol and SIRT1: attenuation of cigarette smoke-induced oxidative stress and proinflammatory phenotypic alterations. Am J Physiol Heart Circ Physiol 294: H2721-H2735, 2008.
17. Dalle-Donne I, Aldini G, Carini M, Colombo R, Rossi R, and Milzani A. Protein carbonylation, cellular dysfunction, and disease progression. J Cell Mol Med 10: 389-406, 2006.
18. Dalle-Donne I, Carini M, Vistoli G, Gamberoni L, Giustarini D, Colombo R, Maffei Facino R, Rossi R, Milzani A, and Aldini G. Actin Cys374 as a nucleophilic target of alpha, beta-unsaturated aldehydes. Free Radic Biol Med 42: 583-598, 2007.
19. Dalle-Donne I, Rossi R, Gagliano N, Milzani A, Di Simplicio P, and Colombo R. Actin carbonylation: from simple marker of protein oxidation to relevant sign of severe functional impairment. Free Radic Biol Med 31: 1075-1083, 2001.
20. Dalle-Donne I, Rossi R, Giustarini D, Milzani A, and Colombo R. Protein carbonyl groups as biomarkers of oxidative stress. Clin Chim Acta 329: 23-38, 2003.
21. Eckenhoff RG, Petersen CE, Ha CE, and Bhagavan NV. Inhaled anesthetic binding sites in human serum albumin. J Biol Chem 275: 30439-30444, 2000.
22. Esterbauer H, Schaur RJ, and Zollner H. Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde, and related aldehydes. Free Radic Biol Med 11: 81-128, 1991.
23. Faure P, Troncy L, Lecomte M, Wiernsperger N, Lagarde M, Ruggiero D, and Halimi S. Albumin antioxidant capacity is modified by methylglyoxal. Diabetes Metab 31: 169-177, 2005.
24. Galvani S, Coatrieux C, Elbaz M, Grazide MH, Thiers JC, Parini A, Uchida K, Kamar N, Rostaing L, Baltas M, Salvayre R, and Nègre-Salvayre A. Carbonyl scavenger and anti-atherogenic effects of hydrazine derivatives. Free Radic Biol Med 45: 1457-1467, 2008.
25. Guex N and Peitsch MC. SWISS-MODEL and the Swiss-Pdbviewer: an environment for comparative protein modeling. Electrophoresis 18: 2714-2723, 1997.
26. Han P, Zhou X, Huang B, Zhang X, and Chen C. On-gel fluorescent visualization and the site identification of S-nitrosylated proteins. Anal Biochem 377: 150-155, 2008.
27. Himmelfarb J and McMonagle E. Albumin is the major plasma protein target of oxidant stress in uremia. Kidney Int 60: 358-363, 2001.
28. Hoffmann D, Hoffmann I, and El-Bayoumy K. The less harmful cigarette: a controversial issue: a tribute to Ernst L. Wynder. Chem Res Toxicol 14: 767-790, 2001.
29. Ishii T, Matsuse T, Igarashi H, Masuda M, Teramoto S, and Ouchi Y. Tobacco smoke reduces viability in human lung fibroblasts: protective effect of glutathione S-transferase P1. Am J Physiol Lung Cell Mol Physiol 280: L1189-L1195, 2001.
30. Kawakami A, Kubota K, Yamada N, Tagami U, Takehana K, Sonaka I, Suzuki E, and Hirayama K. Identification and characterization of oxidized human serum albumin: a slight structural change impairs its ligand-binding and antioxidant functions. FEBS J 273: 3346-3357, 2006.
31. Levine RL, Wehr N, Williams JA, Stadtman ER, and Shacter E. Determination of carbonyl groups in oxidized proteins. Methods Mol Biol 99: 15-24, 2000.
32. Levine RL, Williams JA, Stadtman ER, and Shacter E. Car-bonyl assays for determination of oxidatively modified proteins. Methods Enzymol 233: 346-357, 1994.
33. Lu X, Cai J, Kong H, Wu M, Hua R, Zhao M, Liu J, and Xu G. Analysis of cigarette smoke condensates by comprehensive two-dimensional gas chromatography=time-of-flight mass spectrometry I acidic fraction. Anal Chem 75: 4441-4451, 2003.
34. Marangon K, Devaraj S, and Jialal I. Measurement of protein carbonyls in plasma of smokers and in oxidized LDL by an ELISA. Clin Chem 45: 577-578, 1999.
35. Mera K, Anraku M, Kitamura K, Nakajou K, Maruyama T, Tomita K, and Otagiri M. Oxidation and carboxy methyl lysine-modification of albumin: possible involvement in the progression of oxidative stress in hemodialysis patients. Hypertens Res 28: 973-980, 2005.
36. Nagai K, Betsuyaku T, Kondo T, Nasuhara Y, and Nishimura M. Long term smoking with age builds up excessive oxidative stress in bronchoalveolar lavage fluid. Thorax 61: 496-502, 2006.
37. Nagai K, Betsuyaku T, Konno S, Ito Y, Nasuhara Y, Hizawa N, Kondo T, and Nishimura M. Diversity of protein car-bonylation in allergic airway inflammation. Free Radic Res 42: 921-929, 2008.
38. Oettl K and Stauber RE. Physiological and pathological changes in the redox state of human serum albumin critically influence its binding properties. Br J Pharmacol 151: 580-590, 2007.
39. Oettl K, Stadlbauer V, Petter F, Greilberger J, Putz-Bankuti C, Hallström S, Lackner C, and Stauber RE. Oxidative damage of albumin in advanced liver disease. Biochim Biophys Acta 1782: 469-473, 2008.
40. Olsen JV, de Godoy LM, Li G, Macek B, Mortensen P, Pesch R, Makarov A, Lange O, Horning S, and Mann M. Parts per million mass accuracy on an Orbitrap mass spectrometer via lock mass injection into a C-trap. Mol Cell Proteomics 4: 2010-2021, 2005.
41. O'Neill CA, Halliwell B, van der Vliet A, Davis PA, Packer L, Tritschler H, Strohman WJ, Rieland T, Cross CE, and Reznick AZ. Aldehyde-induced protein modifications in human plasma: protection by glutathione and dihydrolipoic acid. J Lab Clin Med 124: 359-370, 1994.
42. Onorato JM, Jenkins AJ, Thorpe SR, and Baynes JW. Pyr-idoxamine, an inhibitor of advanced glycation reactions, also inhibits advanced lipoxidation reactions: mechanism of action of pyridoxamine. J Biol Chem 275: 21177-21184, 2000.
43. Panda K, Chattopadhyay R, Ghosh MK, Chattopadhyay DJ, and Chatterjee IB. Vitamin C prevents cigarette smoke induced oxidative damage of proteins and increased prote-olysis Free Radic Biol Med 27: 1064-1079, 1999.
44. Peters T Jr. The albumin molecule: structure and chemical properties. In: All about Albumin: Biochemistry, Genetics, and Medical Applications, edited by Peters T Jr. San Diego, CA: Academic Press, 1996, pp. 9-75.
45. Pignatelli B, Li CQ, Boffetta P, Chen Q, Ahrens W, Nyberg F, Mukeria A, Bruske-Hohlfeld I, Fortes C, Constantinescu V, Ischiropoulos H, and Ohshima H. Nitrated and oxidized plasma proteins in smokers and lung cancer patients. Cancer Res 61: 778-784, 2001.
46. Pryor WA and Stone K. Oxidants in cigarette smoke: radicals, hydrogen peroxides, peroxynitrate and peroxynitrite. Ann N Y Acad Sci 686: 12-28, 1993.
47. Reznick AZ, Cross CE, Hu ML, Suzuki YJ, Khwaja S, Safadi A, Motchnik PA, Packer L, and Halliwell B. Modification of plasma proteins by cigarette smoke as measured by protein carbonyl formation. Biochem J 286: 607-611, 1992.
48. Rossi R, Giustarini D, Milzani A, and Dalle-Donne I. Cy-steinylation and homocysteinylation of plasma protein thiols during ageing of healthy human beings. J Cell Mol Med 2008, doi:10.1111=j.1582-4934.2008.00417.x.
49. Schmitt A, Schmitt J, Münch G, and Gasic-Milencovic J. Characterization of advanced glycation end products for biochemical studies: side chain modifications and fluorescence characteristics. Anal Biochem 338: 201-215, 2005. (Pubitemid 40312584)
50. Suzuki M, Betsuyaku T, Ito Y, Nagai K, Nasuhara Y, Kaga K, Kondo S, and Nishimura M. Down-regulated NF-E2-related factor 2 in pulmonary macrophages of aged smokers and patients with chronic obstructive pulmonary disease. Am J Respir Cell Mol Biol 39: 673-682, 2008.
51. Turell L, Botti H, Carballal S, Ferrer-Sueta G, Souza JM, Durán R, Freeman BA, Radi R, and Alvarez B. Reactivity of sulfenic acid in human serum albumin. Biochemistry 47: 358-367, 2008.
52. Turell L, Botti H, Carballal S, Radi R, and Alvarez B. Sul-fenic acid: a key intermediate in albumin thiol oxidation. J Chromatogr B Analyt Technol Biomed Life Sci 877: 3384-3392, 2008.
53. Weiner D, Levy Y, Khankin EV, and Reznick AZ. Inhibition of salivary amylase activity by cigarette smoke aldehydes. J Physiol Pharmacol 59: 727-737, 2008.