Adductomics: Characterizing exposures to reactive electrophiles

Toxicology Letters

Volumn 213, Issue 1, 2012, Pages 83-90

  Rappaport, Stephen M ^a   Li, He ^a   Grigoryan, Hasmik ^a   Funk, William E ^b   Williams, Evan R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NORTHWESTERN UNIVERSITY   (United States)

Author keywords

Adductome; Cys34; Exposome; HSA; Reactive electrophiles; Selected reaction monitoring

Indexed keywords

1,4 BENZOQUINONE; BENZENE; CYSTEINE; DICLOFENAC; ELECTROPHILE; GLUTATHIONE; HEMOGLOBIN; HORMONE; HUMAN SERUM ALBUMIN; METAL; ORGANIC COMPOUND; PARACETAMOL; REACTIVE ELECTROPHILE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG; XENOBIOTIC AGENT;

ARTICLE; BIOLOGICAL MONITORING; BLOOD; CANCER RISK; CARDIOVASCULAR DISEASE; CHINESE; DIETARY INTAKE; DNA ADDUCT; DRUG USE; ENVIRONMENTAL EXPOSURE; GENETIC ASSOCIATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; INDUSTRIAL WORKER; LIPID PEROXIDATION; MAJOR CLINICAL STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

DNA ADDUCTS; ENVIRONMENTAL EXPOSURE; ENVIRONMENTAL MONITORING; HUMANS; NOXAE; PROTEINS; SULFHYDRYL COMPOUNDS; TOXICOLOGY; XENOBIOTICS;

EID: 84864300656     PISSN: 03784274     EISSN: 18793169     Source Type: Journal    
DOI: 10.1016/j.toxlet.2011.04.002     Document Type: Article

References (56)

1. 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. J. Mass Spectrom. 2006, 41:1149-1161.
2. Aldini G., Vistoli G., Regazzoni L., Gamberoni L., Facino R.M., 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, 21:824-835.
3. Ames B.N. Dietary carcinogens and anticarcinogens, oxygen radicals and degenerative diseases. Science 1983, 221:1256-1264.
4. Armstrong B., Doll R. Environmental factors and cancer incidence and mortality in different countries, with special reference to dietary practices. Int. J. Cancer 1975, 15:617-631.
5. Beck J.L., Ambahera S., Yong S.R., Sheil M.M., de Jersey J., Ralph S.F. Direct observation of covalent adducts with Cys34 of human serum albumin using mass spectrometry. Anal. Biochem. 2004, 325:326-336.
6. Blair I.A. Endogenous glutathione adducts. Curr. Drug Metab. 2006, 7:853-872.
7. Blair I.A. Analysis of endogenous glutathione-adducts and their metabolites. Biomed. Chromatogr. 2010, 24:29-38.
8. Brodie B.B., Reid W.D., Cho A.K., Sipes G., Krishna G., Gillette J.R. Possible mechanism of liver necrosis caused by aromatic organic compounds. Proc. Natl. Acad. Sci. U. S. A. 1971, 68:160-164.
9. Carballal S., Alvarez B., Turell L., Botti H., Freeman B.A., Radi R. Sulfenic acid in human serum albumin. Amino Acids 2007, 32:543-551.
10. Carballal S., Radi R., Kirk M.C., Barnes S., Freeman B.A., Alvarez B. Sulfenic acid formation in human serum albumin by hydrogen peroxide and peroxynitrite. Biochemistry 2003, 42:9906-9914.
11. CDC Fourth National Report on Human Exposure to Environmental Chemicals. National Center for Environmental Health 2009, Centers for Disease Control and Prevention, Atlanta, GA.
12. Christodoulou J., Sadler P.J., Tucker A. 1H NMR of albumin in human blood plasma: drug binding and redox reactions at Cys34. FEBS Lett. 1995, 376:1-5.
13. Dalle-Donne I., Rossi R., Colombo R., Giustarini D., Milzani A. Biomarkers of oxidative damage in human disease. Clin. Chem. 2006, 52:601-623.
14. Furne J.K., Springfield J.R., Ho S.B., Levitt M.D. Simplification of the end-alveolar carbon monoxide technique to assess erythrocyte survival. J Lab Clin Med 2003, 142:52-57.
15. Funk W.E., Li H., Iavarone A.T., Williams E.R., Riby J., Rappaport S.M. Enrichment of cysteinyl adducts of human serum albumin. Anal. Biochem. 2010, 400:61-68.
16. Granath F., Ehrenberg L., Tornqvist M. Degree of alkylation of macromolecules in vivo from variable exposure. Mutat. Res. 1992, 284:297-306.
17. He X.M., Carter D.C. Atomic structure and chemistry of human serum albumin. Nature 1992, 358:209-215.
18. Hecht S.S. Tobacco carcinogens, their biomarkers and tobacco-induced cancer. Nat. Rev. Cancer 2003, 3:733-744.
19. Kanaly R.A., Hanaoka T., Sugimura H., Toda H., Matsui S., Matsuda T. Development of the adductome approach to detect DNA damage in humans. Antioxid. Redox Signal. 2006, 8:993-1001.
20. Kanaly R.A., Matsui S., Hanaoka T., Matsuda T. Application of the adductome approach to assess intertissue DNA damage variations in human lung and esophagus. Mutat. Res. 2007, 625:83-93.
21. Kato H., Tillotson J., Nichaman M.Z., Rhoads G.G., Hamilton H.B. Epidemiologic studies of coronary heart disease and stroke in Japanese men living in Japan, Hawaii and California. Am. J. Epidemiol. 1973, 97:372-385.
22. Li H., Grigoryan H., Funk W.E., Lu S.S., Rose S., Williams E.R., Rappaport S.M. Profiling Cys34 adducts of human serum albumin by fixed-step selected reaction monitoring. Mol Cell Proteomics 2011, 10(3):1-14. M110.004606.
23. Lichtenstein P., Holm N.V., Verkasalo P.K., Iliadou A., Kaprio J., Koskenvuo M., Pukkala E., Skytthe A., Hemminki K. Environmental and heritable factors in the causation of cancer--analyses of cohorts of twins from Sweden, Denmark, and Finland. N. Engl. J. Med. 2000, 343:78-85.
24. Liebler D.C. Protein damage by reactive electrophiles: targets and consequences. Chem. Res. Toxicol. 2008, 21:117-128.
25. Lin Y.S., Vermeulen R., Tsai C.H., Waidyanatha S., Lan Q., Rothman N., Smith M.T., Zhang L., Shen M., Li G., Yin S., Kim S., Rappaport S.M. Albumin adducts of electrophilic benzene metabolites in benzene-exposed and control workers. Environ. Health Perspect. 2007, 115:28-34.
26. Lindstrom A.B., Yeowell-O'Connell K., Waidyanatha S., McDonald T.A., Golding B.T., Rappaport S.M. Formation of hemoglobin and albumin adducts of benzene oxide in mouse, rat, and human blood. Chem. Res. Toxicol. 1998, 11:302-310.
27. Manolio T.A., Collins F.S., Cox N.J., Goldstein D.B., Hindorff L.A., Hunter D.J., McCarthy M.I., Ramos E.M., Cardon L.R., Chakravarti A., Cho J.H., Guttmacher A.E., Kong A., Kruglyak L., Mardis E., Rotimi C.N., Slatkin M., Valle D., Whittemore A.S., Boehnke M., Clark A.G., Eichler E.E., Gibson G., Haines J.L., Mackay T.F., McCarroll S.A., Visscher P.M. Finding the missing heritability of complex diseases. Nature 2009, 461:747-753.
28. Merrick B.A. The plasma proteome, adductome and idiosyncratic toxicity in toxicoproteomics research. Brief. Funct. Genomic Proteomic 2008, 7:35-49.
29. Miller E.C., Miller J.A. Mechanisms of chemical carcinogenesis: nature of proximate carcinogens and interactions with macromolecules. Pharmacol. Rev. 1966, 18:805-838.
30. Ollier W., Sprosen T., Peakman T. UK Biobank: from concept to reality. Pharmacogenomics 2005, 6:639-646.
31. Olsen J.V., Blagoev B., Gnad F., Macek B., Kumar C., Mortensen P., Mann M. Global, in vivo, and site-specific phosphorylation dynamics in signaling networks. Cell 2006, 127:635-648.
32. Ong S.E., Mittler G., Mann M. Identifying and quantifying in vivo methylation sites by heavy methyl SILAC. Nat. Methods 2004, 1:119-126.
33. Patel C.J., Bhattacharya J., Butte A.J. An Environment-Wide Association study (EWAS) on type 2 diabetes mellitus. PLoS One 2010, 5:e10746.
34. Peto J. Cancer epidemiology in the last century and the next decade. Nature 2001, 411:390-395.
35. Rappaport S.M. Implications of the exposome for exposure science. J. Expo. Sci. Environ. Epidemiol. 2011, 21:5-9.
36. Rappaport S.M., Kim S., Lan Q., Li G., Vermeulen R., Waidyanatha S., Zhang L., Yin S., Smith M.T., Rothman N. Human benzene metabolism following occupational and environmental exposures. Chem. Biol. Interact. 2010, 184:189-195.
37. Rappaport S.M., Smith M.T. Environment and disease risks. Science 2010, 330:460-461.
38. Rappaport S.M., Waidyanatha S., Qu Q., Shore R., Jin X., Cohen B., Chen L.C., Melikian A.A., Li G., Yin S., Yan H., Xu B., Mu R., Li Y., Zhang X., Li K. Albumin adducts of benzene oxide and 1,4-benzoquinone as measures of human benzene metabolism. Cancer Res. 2002, 62:1330-1337.
39. Rodgers A., Ezzati M., Vander Hoorn S., Lopez A.D., Lin R.B., Murray C.J. Distribution of major health risks: findings from the global burden of disease study. PLoS Med. 2004, 1:e27.
40. Rubino F.M., Pitton M., Di Fabio D., Colombi A. Toward an " omic" physiopathology of reactive chemicals: thirty years of mass spectrometric study of the protein adducts with endogenous and xenobiotic compounds. Mass Spectrom. Rev. 2009, 28:725-784.
41. Saracci R., Vineis P. Disease proportions attributable to environment. Environ. Health 2007, 6:38.
42. Scholz K., Dekant W., Volkel W., Pahler A. Rapid detection and identification of N-acetyl-l-cysteine thioethers using constant neutral loss and theoretical multiple reaction monitoring combined with enhanced product-ion scans on a linear ion trap mass spectrometer. J. Am. Soc. Mass Spectrom. 2005, 16:1976-1984.
43. Sengupta S., Chen H., Togawa T., DiBello P.M., Majors A.K., Budy B., Ketterer M.E., Jacobsen D.W. Albumin thiolate anion is an intermediate in the formation of albumin-S-S-homocysteine. J. Biol. Chem. 2001, 276:30111-30117.
44. Smith C.J., Perfetti T.A., Garg R., Hansch C. IARC carcinogens reported in cigarette mainstream smoke and their calculated log P values. Food Chem. Toxicol. 2003, 41:807-817.
45. Smith M.T., Rappaport S.M. Building exposure biology centers to put the E into " G×E" interaction studies. Environ. Health Perspect. 2009, 117:A334-A335.
46. Stewart A.J., Blindauer C.A., Berezenko S., Sleep D., Tooth D., Sadler P.J. Role of Tyr84 in controlling the reactivity of Cys34 of human albumin. FASEB J. 2005, 272:353-362.
47. Tornqvist M., Fred C., Haglund J., Helleberg H., Paulsson B., Rydberg P. Protein adducts: quantitative and qualitative aspects of their formation, analysis and applications. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 2002, 778:279-308.
48. Troester M.A., Lindstrom A.B., Waidyanatha S., Kupper L.L., Rappaport S.M. Stability of hemoglobin and albumin adducts of naphthalene oxide, 1,2- naphthoquinone, and 1,4-naphthoquinone. Toxicol. Sci. 2002, 68:314-321.
49. Turell L., Botti H., Carballal S., Ferrer-Sueta G., Souza J.M., Duran R., Freeman B.A., Radi R., Alvarez B. Reactivity of sulfenic acid in human serum albumin. Biochemistry 2008, 47:358-367.
50. Wagner S., Scholz K., Donegan M., Burton L., Wingate J., Volkel W. Metabonomics and biomarker discovery: LC-MS metabolic profiling and constant neutral loss scanning combined with multivariate data analysis for mercapturic acid analysis. Anal. Chem. 2006, 78:1296-1305.
51. Wagner S., Scholz K., Sieber M., Kellert M., Voelkel W. Tools in metabonomics: an integrated validation approach for LC-MS metabolic profiling of mercapturic acids in human urine. Anal. Chem. 2007, 79:2918-2926.
52. Wild C.P. Complementing the genome with an " exposome" : the outstanding challenge of environmental exposure measurement in molecular epidemiology. Cancer Epidemiol. Biomarkers Prev. 2005, 14:1847-1850.
53. Willett W.C. Balancing life-style and genomics research for disease prevention. Science 2002, 296:695-698.
54. Yeowell-O'Connell K., Rothman N., Smith M.T., Hayes R.B., Li G., Waidyanatha S., Dosemeci M., Zhang L., Yin S., Titenko-Holland N., Rappaport S.M. Hemoglobin and albumin adducts of benzene oxide among workers exposed to high levels of benzene. Carcinogenesis 1998, 19:1565-1571.
55. Zhan X., Desiderio D.M. Nitroproteins from a human pituitary adenoma tissue discovered with a nitrotyrosine affinity column and tandem mass spectrometry. Anal. Biochem. 2006, 354:279-289.
56. Zhang J., Sprung R., Pei J., Tan X., Kim S., Zhu H., Liu C.F., Grishin N.V., Zhao Y. Lysine acetylation is a highly abundant and evolutionarily conserved modification in Escherichia coli. Mol. Cell. Proteomics 2009, 8:215-225.