Capillary HPLC-accurate mass MS/MS quantitation of N7-(2,3,4-trihydroxybut- 1-yl)-guanine adducts of 1,3-butadiene in human leukocyte DNA

Chemical Research in Toxicology

Volumn 26, Issue 10, 2013, Pages 1486-1497

  Sangaraju, Dewakar ^a   Villalta, Peter ^a   Goggin, Melissa ^a   Agunsoye, Maria O ^a   Campbell, Colin ^a   Tretyakova, Natalia ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; 1,3 BUTADIENE; 3,4 EPOXY 1,2 DIOL; BIOLOGICAL MARKER; BUTADIENE DIEPOXIDE; EPOXIDE; GUANINE DERIVATIVE; N7 (2,3,4 TRIHYDROXYBUT 1 YL)GUANINE; NUCLEIC ACID BASE; UNCLASSIFIED DRUG;

ACCURACY; ADULT; ANALYTIC METHOD; ARTICLE; CELL LEVEL; CLINICAL ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DNA ADDUCT; DNA ALKYLATION; ELECTROSPRAY MASS SPECTROMETRY; ENVIRONMENTAL EXPOSURE; FEMALE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROLYSIS; ISOTOPE DILUTION ASSAY; LEUKOCYTE; MALE; MASS SPECTROMETER; OCCUPATIONAL EXPOSURE; QUANTITATIVE ASSAY; REPRODUCIBILITY; SENSITIVITY AND SPECIFICITY; SMOKING; SMOKING CESSATION; SOLID PHASE EXTRACTION; ULTRAFILTRATION; VALIDITY;

ADULT; BIOLOGICAL MARKERS; BUTADIENES; CELL LINE, TUMOR; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; DNA ADDUCTS; FEMALE; GUANINE; HUMANS; LEUKOCYTES; MALE; MIDDLE AGED; SMOKING; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; YOUNG ADULT;

EID: 84886674849     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx400213m     Document Type: Article

References (56)

1. Owen, P. E., Glaister, J. R., Gaunt, I. F., and Pullinger, D. H. (1987) Inhalation toxicity studies with 1,3-butadiene. 3. Two year toxicity/ carcinogenicity study in rats Am. Ind. Hyg. Assoc. J. 48, 407-413
2. Melnick, R. L., Huff, J., Chou, B. J., and Miller, R. A. (1990) Carcinogenicity of 1,3-butadiene in C57BL/6 x C3H F1 mice at low exposure concentrations Cancer Res. 50, 6592-6599
3. Himmelstein, M. W., Acquavella, J. F., Recio, L., Medinsky, M. A., and Bond, J. A. (1997) Toxicology and epidemiology of 1,3-butadiene Crit. Rev. Toxicol. 27, 1-108
4. Cheng, H., Sathiakumar, N., Graff, J., Matthews, R., and Delzell, E. (2007) 1,3-Butadiene and leukemia among synthetic rubber industry workers: exposure-response relationships Chem. Biol. Interact. 166, 15-24
5. Delzell, E., Sathiakumar, N., Hovinga, M., Macaluso, M., Julian, J., Larson, R., Cole, P., and Muir, D. C. (1996) A follow-up study of synthetic rubber workers Toxicology 113, 182-189
6. Sathiakumar, N., Graff, J., Macaluso, M., Maldonado, G., Matthews, R., and Delzell, E. (2005) An updated study of mortality among North American synthetic rubber industry workers Occup. Environ. Med. 62, 822-829
7. Fajen, J. M., Roberts, D. R., Ungers, L. J., and Krishnan, E. R. (1990) Occupational exposure of workers to 1,3-butadiene Environ. Health Perspect. 86, 11-18
8. Hecht, S. S. (1999) Tobacco smoke carcinogens and lung cancer J. Natl. Cancer Inst. 91, 1194-1210
9. Grant, R. L., Leopold, V., McCant, D., and Honeycutt, M. (2007) Spatial and temporal trend evaluation of ambient concentrations of 1,3-butadiene and chloroprene in Texas Chem. Biol. Interact. 166, 44-51
10. Pelz, N., Dempster, N. M., and Shore, P. R. (1990) Analysis of low molecular weight hydrocarbons including 1,3-butadiene in engine exhaust gases using an aluminum oxide porous-layer open-tubular fused-silica column J. Chromatogr. Sci. 28, 230-235
11. U.S. Department of Health and Human Services. Public HealthStatement for 1,3-Butadiene, (2013. Agency for Toxic Substances and Disease Registry. http://www.atsdr.cdc.gov/PHS/PHS.asp?id=457&tid=81 (accessed July 26, 2013).
12. Kirman, C. R., Albertini, R. A., and Gargas, M. L. (2010) 1,3-Butadiene: III. Assessing carcinogenic modes of action Crit. Rev. Toxicol. 40 (Suppl 1) 74-92
13. Cochrane, J. E. and Skopek, T. R. (1994) Mutagenicity of butadiene and its epoxide metabolites: I. Mutagenic potential of 1,2-epoxybutene, 1,2,3,4-diepoxybutane and 3,4-epoxy-1,2-butanediol in cultured human lymphoblasts Carcinogenesis 15, 713-717
14. Koc, H., Tretyakova, N. Y., Walker, V. E., Henderson, R. F., and Swenberg, J. A. (1999) Molecular dosimetry of N-7 guanine adduct formation in mice and rats exposed to 1,3-butadiene Chem. Res. Toxicol. 12, 566-574
15. Koivisto, P., Kilpelainen, I., Rasanen, I., Adler, I. D., Pacchierotti, F., and Peltonen, K. (1999) Butadiene diolepoxide- and diepoxybutane-derived DNA adducts at N7-guanine: a high occurrence of diolepoxide-derived adducts in mouse lung after 1,3-butadiene exposure Carcinogenesis 20, 1253-1259
16. Perez, H. L., Lahdetie, J., Landin, H., Kilpelainen, I., Koivisto, P., Peltonen, K., and Osterman-Golkar, S. (1997) Haemoglobin adducts of epoxybutanediol from exposure to 1,3-butadiene or butadiene epoxides Chem. Biol. Interact. 105, 181-198
17. Swenberg, J. A., Christova-Gueorguieva, N. I., Upton, P. B., Ranasinghe, A., Scheller, N., Wu, K. Y., Yen, T. Y., and Hayes, R. (2000) 1,3-butadiene: cancer, mutations, and adducts. Part V: Hemoglobin adducts as biomarkers of 1,3-butadiene exposure and metabolism Res. Rep.-Health Eff. Inst. 191-210
18. Krause, R. J. and Elfarra, A. A. (1997) Oxidation of butadiene monoxide to meso- and (±)-diepoxybutane by cDNA-expressed human cytochrome P450s and by mouse, rat, and human liver microsomes: evidence for preferential hydration of meso-diepoxybutane in rat and human liver microsomes Arch. Biochem. Biophys. 337, 176-184
19. Oe, T., Kambouris, S. J., Walker, V. E., Meng, Q., Recio, L., Wherli, S., Chaudhary, A. K., and Blair, I. A. (1999) Persistence of N7-(2,3,4- trihydroxybutyl)guanine adducts in the livers of mice and rats exposed to 1,3-butadiene Chem. Res. Toxicol. 12, 247-257
20. Park, S., Anderson, C., Loeber, R., Seetharaman, M., Jones, R., and Tretyakova, N. (2005) Interstrand and intrastrand DNA-DNA cross-linking by 1,2,3,4-diepoxybutane: role of stereochemistry J. Am. Chem. Soc. 127, 14355-14365
21. +-MS/MS methods for quantitative analysis of exocyclic dA adducts in the DNA of laboratory animals exposed to 1,3-butadiene Chem. Res. Toxicol. 23, 808-812
22. Goggin, M., Anderson, C., Park, S., Swenberg, J., Walker, V., and Tretyakova, N. (2008) Quantitative high-performance liquid chromatography- electrospray ionization-tandem mass spectrometry analysis of the adenine-guanine cross-links of 1,2,3,4-diepoxybutane in tissues of butadiene-exposed B6C3F1 mice Chem. Res. Toxicol. 21, 1163-1170
23. Park, S. and Tretyakova, N. (2004) Structural characterization of the major DNA-DNA cross-link of 1,2,3,4-diepoxybutane Chem. Res. Toxicol. 17, 129-136
24. Seneviratne, U., Antsypovich, S., Goggin, M., Dorr, D. Q., Guza, R., Moser, A., Thompson, C., York, D. M., and Tretyakova, N. (2010) Exocyclic deoxyadenosine adducts of 1,2,3,4-diepoxybutane: synthesis, structural elucidation, and mechanistic studies Chem. Res. Toxicol. 23, 118-133
25. Tretyakova, N. Y., Chiang, S. Y., Walker, V. E., and Swenberg, J. A. (1998) Quantitative analysis of 1,3-butadiene-induced DNA adducts in vivo and in vitro using liquid chromatography electrospray ionization tandem mass spectrometry J. Mass Spectrom 33, 363-376
26. Goggin, M., Sangaraju, D., Walker, V. E., Wickliffe, J., Swenberg, J. A., and Tretyakova, N. (2011) Persistence and repair of bifunctional DNA adducts in tissues of laboratory animals exposed to 1,3-butadiene by inhalation Chem. Res. Toxicol. 24, 809-817
27. Blair, I. A., Oe, T., Kambouris, S., and Chaudhary, A. K. (2000) 1,3-butadiene: cancer, mutations, and adducts. Part IV: Molecular dosimetry of 1,3-butadiene Res. Rep.-Health Eff. Inst. 151-190
28. Gates, K. S., Nooner, T., and Dutta, S. (2004) Biologically relevant chemical reactions of N7-alkylguanine residues in DNA Chem. Res. Toxicol. 17, 839-856
29. Albertini, R. J., Sram, R. J., Vacek, P. M., Lynch, J., Wright, M., Nicklas, J. A., Boogaard, P. J., Henderson, R. F., Swenberg, J. A., Tates, A. D., and Ward, J. B., Jr. (2001) Biomarkers for assessing occupational exposures to 1,3-butadiene Chem. Biol. Interact. 135-136, 429-453
30. Boysen, G., Georgieva, N. I., Bordeerat, N. K., Sram, R. J., Vacek, P., Albertini, R. J., and Swenberg, J. A. (2012) Formation of 1,2:3,4-diepoxybutane- specific hemoglobin adducts in 1,3-butadiene exposed workers Toxicol. Sci. 125, 30-40
31. Balbo, S., Villalta, P. W., and Hecht, S. S. (2011) Quantitation of 7-ethylguanine in leukocyte DNA from smokers and nonsmokers by liquid chromatography-nanoelectrospray-high resolution tandem mass spectrometry Chem. Res. Toxicol. 24, 1729-1734
32. Michaelson-Richie, E. D., Ming, X., Codreanu, S. G., Loeber, R. L., Liebler, D. C., Campbell, C., and Tretyakova, N. Y. (2011) Mechlorethamine- induced DNA - protein cross-linking in human fibrosarcoma (HT1080) cells J. Proteome Res. 10, 2785-2796
33. Hecht, S. S. (2003) Tobacco carcinogens, their biomarkers and tobacco-induced cancer Nat. Rev. Cancer 3, 733-744
34. +-MS/MS analysis of N7-guanine-N7-guanine DNA cross-links in tissues of mice exposed to 1,3-butadiene Chem. Res. Toxicol. 20, 839-847
35. Brunnemann, K. D., Kagan, M. R., Cox, J. E., and Hoffmann, D. (1990) Analysis of 1,3-butadiene and other selected gas-phase components in cigarette mainstream and sidestream smoke by gas chromatography-mass selective detection Carcinogenesis 11, 1863-1868
36. Swenberg, J. A., Bordeerat, N. K., Boysen, G., Carro, S., Georgieva, N. I., Nakamura, J., Troutman, J. M., Upton, P. B., Albertini, R. J., Vacek, P. M., Walker, V. E., Sram, R. J., Goggin, M., and Tretyakova, N. (2011) 1,3-Butadiene: Biomarkers and application to risk assessment Chem. Biol. Interact. 192, 150-154
37. Tretyakova, N. Y., Michaelson-Richie, E. D., Gherezghiher, T. B., Kurtz, J., Ming, X., Wickramaratne, S., Campion, M., Kanugula, S., Pegg, A. E., and Campbell, C. (2013) DNA-reactive protein monoepoxides induce cell death and mutagenesis in mammalian cells Biochemistry 52, 3171-3181
38. Gherezghiher, T. B., Ming, X., Villalta, P. W., Campbell, C., and Tretyakova, N. Y. (2013) 1,2,3,4-Diepoxybutane-induced DNA-protein cross-linking in human fibrosarcoma (HT1080) cells J. Proteome Res. 12, 2151-2164
39. 6-gamma- HMHP-dA) adducts by human and archebacterial DNA polymerases J. Biol. Chem. 287, 38800-38811
40. Rodriguez, D. A., Kowalczyk, A., Ward, J. B., Jr., Harris, C. M., Harris, T. M., and Lloyd, R. S. (2001) Point mutations induced by 1,2-epoxy-3-butene N1 deoxyinosine adducts Environ. Mol. Mutagen. 38, 292-296
41. Carmical, J. R., Kowalczyk, A., Zou, Y., Van Houten, B., Nechev, L. V., Harris, C. M., Harris, T. M., and Lloyd, R. S. (2000) Butadiene-induced intrastrand DNA cross-links: a possible role in deletion mutagenesis J. Biol. Chem. 275, 19482-19489
42. Boysen, G., Pachkowski, B. F., Nakamura, J., and Swenberg, J. A. (2009) The formation and biological significance of N7-guanine adducts Mutat. Res. 678, 76-94
43. Cote, I. L. and Bayard, S. P. (1990) Cancer risk assessment of 1,3-butadiene Environ. Health Perspect. 86, 149-153
44. Neligan, R. E. (1962) Hydrocarbons in the Los Angeles atmosphere. A comparison between the hydrocarbons in automobile exhaust and those found in the Los Angeles atmosphere Arch. Environ. Health 5, 581-591
45. United States Department of Labor. Safety and Health Topics,1,3- Butadiene, 2013. Occupational Safety & Health Administration. https://www.osha.gov/SLTC/butadiene/index.html#standards (accessed July 26, 2013).
46. van Sittert, N. J., Megens, H. J., Watson, W. P., and Boogaard, P. J. (2000) Biomarkers of exposure to 1,3-butadiene as a basis for cancer risk assessment Toxicol. Sci. 56, 189-202
47. Fustinoni, S., Soleo, L., Warholm, M., Begemann, P., Rannug, A., Neumann, H. G., Swenberg, J. A., Vimercati, L., and Colombi, A. (2002) Influence of metabolic genotypes on biomarkers of exposure to 1,3-butadiene in humans Cancer Epidemiol., Biomarkers Prev. 11, 1082-1090
48. Vacek, P. M., Albertini, R. J., Sram, R. J., Upton, P., and Swenberg, J. A. (2010) Hemoglobin adducts in 1,3-butadiene exposed Czech workers: female-male comparisons Chem. Biol. Interact. 188, 668-676
49. De Bont, R. and van Larebeke, N. (2004) Endogenous DNA damage in humans: a review of quantitative data Mutagenesis 19, 169-185
50. Chen, H. J., Lin, G. J., and Lin, W. P. (2010) Simultaneous quantification of three lipid peroxidation-derived etheno adducts in human DNA by stable isotope dilution nanoflow liquid chromatography nanospray ionization tandem mass spectrometry Anal. Chem. 82, 4486-4493
51. Chen, H. J. and Lin, W. P. (2011) Quantitative analysis of multiple exocyclic DNA adducts in human salivary DNA by stable isotope dilution nanoflow liquid chromatography nanospray ionization tandem mass spectrometry Anal. Chem. 83, 8543-8551
52. 2-propanodeoxyguanosine adducts in human leukocyte DNA from smokers and nonsmokers Chem. Res. Toxicol. 24, 119-124
53. Matsuda, T., Tao, H., Goto, M., Yamada, H., Suzuki, M., Wu, Y., Xiao, N., He, Q., Guo, W., Cai, Z., Kurabe, N., Ishino, K., Matsushima, Y., Shinmura, K., Konno, H., Maekawa, M., Wang, Y., and Sugimura, H. (2013) Lipid peroxidation-induced DNA adducts in human gastric mucosa Carcinogenesis 34, 121-127
54. Nair, J., Carmichael, P. L., Fernando, R. C., Phillips, D. H., Strain, A. J., and Bartsch, H. (1998) Lipid peroxidation-induced etheno-DNA adducts in the liver of patients with the genetic metal storage disorders Wilson's disease and primary hemochromatosis Cancer Epidemiol. Biomarkers Prev. 7, 435-440
55. Bartsch, H. (1996) DNA adducts in human carcinogenesis: etiological relevance and structure-activity relationship Mutat. Res. 340, 67-79
56. Zhao, C., Vodicka, P., Sram1, R. J., and Hemminki, K. (2000) Human DNA adducts of 1,3-butadiene, an important environmental carcinogen Carcinogenesis 21, 107-111