Analysis of Nε-Ethyllysine in Human Plasma Proteins by Gas Chromatography-Negative Ion Chemical Ionization/Mass Spectrometry as a Biomarker for Exposure to Acetaldehyde and Alcohol

Alcoholism: Clinical and Experimental Research

Volumn 36, Issue 6, 2012, Pages 1013-1020

  Mabuchi, Ryota ^a   Kurita, Aya ^a   Miyoshi, Noriyuki ^a   Yokoyama, Akira ^a,b   Furuta, Takumi ^a   Goda, Toshinao ^a   Suwa, Yoshihide ^c   Kan, Toshiyuki ^a   Amagai, Takashi ^a   Ohshima, Hiroshi ^a  

^a UNIVERSITY OF SHIZUOKA   (Japan)

^b KURIHAMA NATIONAL HOSPITAL   (Japan)

^c SUNTORY LTD   (Japan)

Author keywords

Acetaldehyde; Alcohol; GC NCI MS; Pentafluorobenzyl Derivatives

Indexed keywords

ACETALDEHYDE; ALCOHOL; AMINO ACID; BIOLOGICAL MARKER; BROMINE DERIVATIVE; LYSINE; N EPSILON ETHYLLYSINE; PENTAFLUOROBENZYL BROMIDE; PLASMA PROTEIN; PRONASE; PRONASE E; STABLE ISOTOPE; UNCLASSIFIED DRUG;

ARTICLE; CLINICAL ARTICLE; CONTROLLED STUDY; DERIVATIZATION; GAS CHROMATOGRAPHY NEGATIVE ION CHEMICAL IONIZATION MASS SPECTROMETRY; HUMAN; ISOTOPE LABELING; MASS FRAGMENTOGRAPHY; PRIORITY JOURNAL; PROTEIN HYDROLYSIS; PROTEIN PURIFICATION; QUANTITATIVE ANALYSIS; SENSITIVITY AND SPECIFICITY;

EID: 84861745062     PISSN: 01456008     EISSN: 15300277     Source Type: Journal    
DOI: 10.1111/j.1530-0277.2011.01705.x     Document Type: Article

References (38)

1. Albano E (2006) Alcohol, oxidative stress and free radical damage. Proc Nutr Soc 65:278-290.
2. Baan R, Straif K, Grosse Y, Secretan B, El Ghissassi F, Bouvard V, Altieri A, Cogliano V; WHO International Agency for Research on Cancer Monograph Working Group (2007) Carcinogenicity of alcoholic beverages. Lancet Oncol 8:292-293.
3. Behrens UJ, Hoerner M, Lasker JM, Lieber CS (1988) Formation of acetaldehyde adducts with ethanol-inducible P450IIE1 in vivo. Biochem Biophys Res Commun 154:584-590.
4. Bootorabi F, Jänis J, Valjakka J, Isoniemi S, Vainiotalo P, Vullo D, Supuran CT, Waheed A, Sly WS, Niemelä O, Parkkila S (2008) Modification of carbonic anhydrase II with acetaldehyde, the first metabolite of ethanol, leads to decreased enzyme activity. BMC Biochem 9:32.
5. Braun KP, Pavlovich JG, Jones DR, Peterson CM (1997) Stable acetaldehyde adducts: structural characterization of acetaldehyde adducts of human hemoglobin N-terminal beta-globin chain peptides. Alcohol Clin Exp Res 21:40-43.
6. Donohue TM Jr, Tuma DJ, Sorrell MF (1983) Acetaldehyde adducts with proteins: binding of [14C]acetaldehyde to serum albumin. Arch Biochem Biophys 220:239-246.
7. Druesne-Pecollo N, Tehard B, Mallet Y, Gerber M, Norat T, Hercberg S, Latino-Martel P (2009) Alcohol and genetic polymorphisms: effect on risk of alcohol-related cancer. Lancet Oncol 10:173-180.
8. Gaines KC, Salhany JM, Tuma DJ, Sorrell MF (1977) Reaction of acetaldehyde with human erythrocyte membrane proteins. FEBS Lett 75:115-119.
9. Harada S, Zhang S (1993) New strategy for detection of ALDH2 mutant. Alcohol Alcohol 28(SUPPL):11-13.
10. Hazen SL, Hsu FF, d'Avignon A, Heinecke JW (1998) Human neutrophils employ myeloperoxidase to convert alpha-amino acids to a battery of reactive aldehydes: a pathway for aldehyde generation at sites of inflammation. Biochemistry 37:6864-6873.
11. IARC Working Group on the Evaluation of Carcinogenic Risks to Humans (1999) Re-evaluation of some organic chemicals, hydrazine and hydrogen peroxide. IARC Monogr Eval Carcinog Risks Hum 71:319-335.
12. IARC Working Group on the Evaluation of Carcinogenic Risks to Humans(2010) Alcohol consumption and ethyl carbamate. IARC Monogr Eval Carcinog Risks Hum 96:1278-1279.
13. Jukkola A, Niemelä O (1989) Covalent binding of acetaldehyde to type III collagen. Biochem Biophys Res Commun 159:163-169.
14. Lin RC, Shahidi S, Lumeng L (1993) Production of antibodies that recognize the heterogeneity of immunoreactive sites in human hemoglobin chemically modified by acetaldehyde. Alcohol Clin Exp Res 17:882-886.
15. Mawhinney TP, Robinett RS, Atalay A, Madson MA (1986) Analysis of amino acids as their tert.-butyldimethylsilyl derivatives by gas-liquid chromatography and mass spectrometry. J Chromatogr 358:231-242.
16. Moncada C, Israel Y (1999) Generation of acetate and production of ethyl-lysine in the reaction of acetaldehyde plus serum albumin. Alcohol 17:87-91.
17. Niemelä O, Israel Y, Mizoi Y, Fukunaga T, Eriksson CJ (1990) Hemoglobin-acetaldehyde adducts in human volunteers following acute ethanol ingestion. Alcohol Clin Exp Res 14:838-841.
18. Niemelä O, Parkkila S (2004) Alcoholic macrocytosis-is there a role for acetaldehyde and adducts? Addict Biol 9:3-10.
19. Oneta CM, Lieber CS, Li J, Rüttimann S, Schmid B, Lattmann J, Rosman AS, Seitz HK (2002) Dynamics of cytochrome P4502E1 activity in man: induction by ethanol and disappearance during withdrawal phase. J Hepatol 36:47-52.
20. Peterson CM, Nguyen LB (1985) Clinical implications of acetaldehyde adducts with hemoglobin. Prog Clin Biol Res 183:19-30.
21. San George RC, Hoberman HD (1986) Reaction of acetaldehyde with hemoglobin. J Biol Chem 261:6811-6821.
22. Savolainen MJ, Baraona E, Lieber CS (1987) Acetaldehyde binding increases the catabolism of rat serum low-density lipoproteins. Life Sci 40:841-846.
23. Secretan B, Straif K, Baan R, Grosse Y, El Ghissassi F, Bouvard V, Benbrahim-Tallaa L, Guha N, Freeman C, Galichet L, Cogliano V; WHO International Agency for Research on Cancer Monograph Working Group (2009) A review of human carcinogens-Part E: tobacco, areca nut, alcohol, coal smoke, and salted fish. Lancet Oncol 10:1033-1034.
24. Seitz HK, Stickel F (2007) Molecular mechanisms of alcohol-mediated carcinogenesis. Nat Rev Cancer 7:599-612.
25. Stevens VJ, Fantl WJ, Newman CB, Sims RV, Cerami A, Peterson CM (1981) Acetaldehyde adducts with hemoglobin. J Clin Invest 67:361-369.
26. Thiele GM, Tuma DJ, Miller JA, Wegter KM, McDonald TL, Klassen LW (1998) Monoclonal and polyclonal antibodies recognizing acetaldehyde-protein adducts. Biochem Pharmacol 56:1515-1523.
27. Thiele GM, Wegter KM, Sorrell MF, Tuma DJ, McDonald TL, Klassen LW (1994) Specificity of N-ethyl lysine of a monoclonal antibody to acetaldehyde-modified proteins prepared under reducing conditions. Biochem Pharmacol 48:183-189.
28. Toennes SW, Wagner MG, Kauert GF (2010) Application of LC-TOF MS to analysis of hemoglobin acetaldehyde adducts in alcohol detoxification patients. Anal Bioanal Chem 398:769-777.
29. Tuma DJ, Donohue TM Jr, Medina VA, Sorrell MF (1984) Enhancement of acetaldehyde-protein adduct formation by L-ascorbate. Arch Biochem Biophys 234:377-381.
30. Tuma DJ, Hoffman T, Sorrell MF (1991) The chemistry of acetaldehyde-protein adducts. Alcohol Alcohol SUPPL 1:271-276.
31. Tuma DJ, Jennett RB, Sorrell MF (1987a) The interaction of acetaldehyde with tubulin. Ann N Y Acad Sci 492:277-286.
32. Tuma DJ, Newman MR, Donohue TM Jr, Sorrell MF (1987b) Covalent binding of acetaldehyde to proteins: participation of lysine residues. Alcohol Clin Exp Res 11:579-584.
33. 2-ethyldeoxyguanosine. Chem Res Toxicol 19:319-324.
34. Warnakulasuriya S, Parkkila S, Nagao T, Preedy VR, Pasanen M, Koivisto H, Niemelä O (2008) Demonstration of ethanol-induced protein adducts in oral leukoplakia (precancer) and cancer. J Oral Pathol Med 37:157-165.
35. Wickramasinghe SN, Gardner B, Barden G (1986) Cytotoxic protein molecules generated as a consequence of ethanol metabolism in vitro and in vivo. Lancet 2:823-826.
36. Xu Y, Carr LG, Bosron WF, Li TK (1988) Genotyping of human alcohol dehydrogenases at the ADH2 and ADH3 loci following DNA sequence amplification. Genomics 2:209-214.
37. Yokoyama A, Omori T (2005) Genetic polymorphisms of alcohol and aldehyde dehydrogenases and risk for esophageal and head and neck cancers. Alcohol 35:175-185.
38. Zhu Y, Fillenwarth MJ, Crabb D, Lumeng L, Lin RC (1996) Identification of the 37-kd rat liver protein that forms an acetaldehyde adduct in vivo as delta 4-3-ketosteroid 5 beta-reductase. Hepatology 23:115-122.