Analysis of diepoxide-specific cyclic N-terminal globin adducts in mice and rats after inhalation exposure to 1,3-butadiene

Cancer Research

Volumn 64, Issue 23, 2004, Pages 8517-8520

  Boysen, Gunnar ^a   Georgieva, Nadia I ^a   Upton, Patricia B ^a   Jayaraj, Karupiah ^a   Li, Yutai ^a   Walker, Vernon E ^b   Swenberg, James A ^a,c  

^a University of North Carolina at Chapel Hill   (United States)

^b LOVELACE RESPIRATORY RESEARCH INSTITUTE   (United States)

^c IL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIHYDROXYBUTYLVALINE; 1,3 BUTADIENE; 1,3 BUTANEDIENE; 2 HYDROXY 3 BUTENYLVALINE; 3 BUTENE 1,2 DIOL; 3,4 EPOXY 1,2 BUTANEDIOL; BUTADIENE DIEPOXIDE; CARCINOGEN; EPOXIDE; GLOBIN; INDUSTRIAL CHEMICAL; N,N (2,3 DIHYDROXY 1,4 BUTADIYL)VALINE; RUBBER; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CANCER SUSCEPTIBILITY; CONTROLLED STUDY; DNA ADDUCT; EPOXIDATION; FEMALE; GAS CHROMATOGRAPHY; HYDROLYSIS; IMMUNOAFFINITY CHROMATOGRAPHY; INHALATION; LEUKEMIA; METABOLISM; MOUSE; NONHUMAN; OCCUPATIONAL EXPOSURE; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; RAT; SPECIES DIFFERENCE; TANDEM MASS SPECTROMETRY;

AMINO ACID SEQUENCE; ANIMALS; BUTADIENES; CARCINOGENS; CHROMATOGRAPHY, LIQUID; EPOXY COMPOUNDS; FEMALE; GLOBINS; HUMANS; INHALATION EXPOSURE; MASS SPECTROMETRY; MICE; PYRROLIDINES; RABBITS; RATS; RATS, INBRED F344; VALINE;

EID: 9244249860     PISSN: 00085472     EISSN: None     Source Type: Journal    
DOI: 10.1158/0008-5472.CAN-04-3184     Document Type: Article

References (21)

1. Himmelstein MW, Acquavella JF, Recio L, Medinsky MA, Bond JA. Toxicology and epidemiology of 1,3-butadiene. Crit Rev Toxicol 1997;27:1-108.
2. Rydberg P, Magnusson AL, Zorcec V, Granath F, Törnqvist M. Adducts to N-terminal valines in hemoglobin from butadiene metabolites. Chem Biol Interact 1996;101:193-205.
3. Basile A, Ferranti P, Pocsfalvi G, et al. A novel approach for identification and measurement of hemoglobin adducts with 1,2,3,4-diepoxybutane by liquid chromatography/electrospray ionisation mass spectrometry and matrix-assisted laser desorption/ionisation tandem mass spectrometry. Rapid Commun Mass Spectrom 2001;15:527-40.
4. Miraglia N, Basile A, Fieri M, et al. Ion trap mass spectrometry in the structural analysis of haemoglobin peptides modified by epichlorohydrin and diepoxybutane. Rapid Commun Mass Spectrom 2002;16:840-7.
5. Kautiainen A, Fred C, Rydberg P, Törnqvist M. A liquid chromatography tandem mass spectrometric method for in vivo dose monitoring of diepoxybutane, a metabolite of butadiene. Rapid Commun Mass Spectrom 2000;14:1848-53.
6. Fred C, Kautiainen A, Athanassiadis I, Törnqvist M. Hemoglobin adduct levels in rat and mouse treated with 1,2:3,4-diepoxybutane. Chem Res Toxicol 2004;17:785-94.
7. Swenberg JA, Koc H, Upton PB, et al. Using DNA and hemoglobin adducts to improve the risk assessment of butadiene. Chem Biol Interact 2001;135-136:387-403.
8. Jayaraj K, Georgieva NI, Gold A, et al. Synthesis and characterization of peptides containing a cyclic Va1 adduct of diepoxybutane, a possible biomarker of human exposure to butadiene. Chem Res Toxicol 2003;16:637-43.
9. Ham AJL, Ranasinghe A, Morinello EJ, et al. Immunoaffinity/gas chromatography/ high-resolution mass spectrometry method for the detection of N-2,3-ethenoguanine. Chem Res Toxicol 1999;12:1240-6.
10. Meng Q, Henderson RF, Long L, et al. Mutagenicity at the Hprt locus in T cells of female mice following inhalation exposures to low levels of 1,3-butadiene. Chem Biol Interact 2001;135-136:343-61.
11. Bevan C, Stadler JC, Elliott GS, et al. Subchronic toxicity of 4-vinylcyclohexene in rats and mice by inhalation exposure. Fund Appl Toxicol 1996;32:1-10.
12. Mowrer J, Törnqvist M, Jensen S, Ehrenberg L. Modified Edman degradation applied to hemoglobin for monitoring occupational exposure to alkylaling-agents. Tox Env Chem 1986;1:215-31.
13. Swenberg JA, Christova-Gueorguieva NI, Upton PB, et al. 1,3-Butadiene: cancer, mutations, and adducts. Part V. Hemoglobin adducts as biomarkers of butadiene exposure and metabolism. Health Effects Institute Report 92. Cambridge, MA: HEI; 2000. p. 191-209.
14. Albertini R, Clewell H, Himmelstein MW, et al. The use of non-tumor data in cancer risk assessment: reflections on butadiene, vinyl chloride, and benzene. Regul Toxicol Pharmacol 2003;37:105-32.
15. Perez HL, Lahdetie J, Landin H, et al. Haemoglobin adducts of epoxybutanediol from exposure to 1,3-butadiene or butadiene epoxides. Chem Biol Interact 1997;105:181-98.
16. Koc H, Tretyakova NY, Walker VE, Henderson RF, Swenberg JA. Molecular dosimetry of N-7 guanine adduct formation in mice and rats exposed to 1,3-butadiene. Chem Res Toxicol 1999;12:566-74.
17. Koivisto P, Kilpelainen I, Rasanen I, Adler ID, Pacchierotti F, Peltonen K. 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 (Lond) 1999;20:1253-9.
18. Krause RJ, Kemper RA, Elfarra AA. Hydroxymethylvinyl ketone: a reactive Michael acceptor formed by the oxidation of 3-butene-1,2-diol by cDNA-expressed human cytochrome P450s and mouse, rat, and human liver microsomes. Chem Res Toxicol 2001;14:1590-5.
19. 2-propanodeoxyguanosine adducts of the 1,3-butadiene metabolite, hydroxymethylvinyl ketone. Chem Res Toxicol 2003;16:1448-54.
20. Johanson G, Filser JG. PBPK model for butadiene metabolism to epoxides: quantitative species differences in metabolism. Toxicology 1996;113:40-7.
21. Henderson RF, Thornton-Manning JR, Bechtold WE, Dahl AR. Metabolism of 1,3-butadiene: species differences. Toxicology 1996;113:17-22.