Cob(I)alamin for trapping butadiene epoxides in metabolism with rat S9 and for determining associated kinetic parameters

Chemical Research in Toxicology

Volumn 22, Issue 9, 2009, Pages 1509-1516

  Motwani, Hitesh V ^a,b   Fred, Charlotta ^a,c   Haglund, Johanna ^a,c   Golding, Bernard T ^b   Törnqvist, Margareta ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b NEWCASTLE UNIVERSITY   (United Kingdom)

^c ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 EPOXY 3 BUTENE; 1,2 EPOXY 3,4 BUTANEDIOL; BUTADIENE DIEPOXIDE; BUTANEDIOL; CYANOCOBALAMIN; CYTOCHROME P450; EPOXIDE; EPOXIDE HYDROLASE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; HYDROLYSIS; KINETICS; LIQUID CHROMATOGRAPHY; NONHUMAN; OXIDATION; QUANTITATIVE ANALYSIS; RAT; SYNTHESIS;

RATTUS;

EID: 70349307489     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx900088w     Document Type: Article

References (41)

1. 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.
2. 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. (Pubitemid 20162599)
3. Stump, F. D., and Dropkin, D. L. (1985) Gas chromatographic method for quantitative determination of C2 to C13 hydrocarbons in roadway vehicle emissions. Anal. Chem. 57, 2629-2634.
4. Gustafson, P., Barregård, L., Strandberg, B., and Sällsten, G. (2007) The impact of domestic wood burning on personal, indoor and outdoor levels of 1,3-butadiene, benzene, formaldehyde and acetaldehyde. J. Environ. Monit. 9, 23-32. (Pubitemid 46084824)
5. Santos-Burgoa, C., Matanoski, G. M., Zeger, S., and Schwartz, L. (1992) Lymphohematopoietic cancer in styrene-butadiene polymerization workers. Am. J. Epidemiol. 136, 843-854.
6. Sielken, R. L., Jr., Valdez-Flores, C., Gargas, M. L., Kirman, C. R., Teta, M. J., and Delzell, E. (2007) Cancer risk assessment for 1,3- butadiene: Dose-response modeling from an epidemiological perspective. Chem.-Biol. Interact. 166, 140-149. (Pubitemid 46413215)
7. International Agency for Research on Cancer (IARC). (2008) 1,3- Butadiene. IARC Monographs Evaluation of Carcinogenic Risks to Humans, Vol.97.
8. Huff, J. E., Melnick, R. L., Solleveld, H. A., Haseman, J. K., Powers, M., and Miller, R. A. (1985) Multiple organ carcinogenicity of 1,3- butadiene in B6C3F1 mice after 60 weeks of inhalation exposure. Science 227, 548-549.
9. Owen, P. E., and Glaister, J. R. (1990) Inhalation toxicity and carcinogenicity of 1,3-butadiene in Sprague-Dawley rats. Environ. Health Perspect. 86, 19-25. (Pubitemid 20298810)
10. Sharer, J. E., Duescher, R. J., and Elfarra, A. A. (1992) Species and tissue differences in the microsomal oxidation of 1,3-butadiene and the glutathione conjugation of butadiene monoxide in mice and rats. Possible role in 1,3-butadiene-induced toxicity. Drug Metab. Dispos. 20, 658-664.
11. Csanady, G. A., Guengerich, F. P., and Bond, J. A. (1992) Comparison of the biotransformation of 1,3-butadiene and its metabolite, butadiene monoepoxide, by hepatic and pulmonary tissues from humans, rats and mice. Carcinogenesis 13, 1143-1153.
12. 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. (Pubitemid 24124417)
13. Duescher, R. J., and Elfarra, A. A. (1994) Human liver microsomes are efficient catalysts of 1,3-butadiene oxidation: evidence for major roles by cytochromes P450 2A6 and 2E1. Arch. Biochem. Biophys. 311, 342-349.
14. Seaton, M. J., Follansbee, M. H., and Bond, J. A. (1995) Oxidation of 1,2-epoxy-3-butene to 1,2:3,4-diepoxybutane by cDNA-expressed human cytochromes P450 2E1 and 3A4 and human, mouse and rat liver microsomes. Carcinogenesis 16, 2287-2293.
15. Kemper, R. A., Elfarra, A. A., and Myers, S. R. (1998) Metabolism of 3-butene-1,2-diol in B6C3F1 mice, evidence for involvement of alcohol dehydrogenase and cytochrome P450. Drug Metab. Dispos. 26, 914-920.
16. Boogaard, P. J., Sumner, S. C., and Bond, J. A. (1996) Glutathione conjugation of 1,2:3,4-diepoxybutane in human liver and rat and mouse liver and lung in vitro. Toxicol. Appl. Pharmacol. 136, 307-316. (Pubitemid 26070895)
17. Sharer, J. E., Duescher, R. J., and Elfarra, A. A. (1991) Formation, stability, and rearrangements of the glutathione conjugates of butadiene monoxide: Evidence for the formation of stable sulfurane intermediates. Chem. Res. Toxicol. 4, 430-436.
18. Sharer, J. E., and Elfarra, A. A. (1992) S-(2-Hydroxy-3-buten-1- yl)glutathione and S-(1-hydroxy-3-buten-2-yl)glutathione are in vivo metabolites of butadiene monoxide: Detection and quantitation in bile. Chem. Res. Toxicol. 5, 787-790.
19. Kemper, R. A., Krause, R. J., and Elfarra, A. A. (2001) Metabolism of butadiene monoxide by freshly isolated hepatocytes from mice and rats: Different partitioning between oxidative, hydrolytic, and conjugation pathways. Drug Metab. Dispos. 29 (6), 830-836.
20. Krause, R. J., Sharer, J. E., and Elfarra, A. A. (1997) Epoxide hydrolase-dependent metabolism of butadiene monoxide to 3-butene- 1,2-diol in mouse, rat, and human liver. Drug Metab. Dispos. 25, 1013-1015.
21. U.S. Environmental Protection Agency (US EPA) National Center for Environmental Assessment Office of Research and Development. (2002) Health assessment of 1,3-butadiene. Washington, DC.
22. Boogaard, P. J., and Bond, J. A. (1996) The role of hydrolysis in the detoxification of 1,2:3,4-diepoxybutane by human, rat, and mouse liver and lung in vitro. Toxicol. Appl. Pharmacol. 141, 617-627. (Pubitemid 27046388)
23. 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.
24. Cheng, X., and Ruth, J. A. (1993) A simplified methodology for quantitation of butadiene metabolites. Application to the study of 1,3- butadiene metabolism by rat liver microsomes. Drug Metab. Dispos. 21, 121-124. (Pubitemid 23052231)
25. Munter, T., Cottrell, L., Golding, B. T., and Watson, W. P. (2003) Detoxication pathways involving glutathione and epoxide hydrolase in the in vitro metabolism of chloroprene. Chem. Res. Toxicol. 16, 1287-1297. (Pubitemid 37315218)
26. Preussmann, R., Schneider, H., and Epple, F. (1969) Identification of alkylating agents. II. Identification of different classes of alkylating agents by a modification of the color reaction with 4-(4-nitrobenzyl)- pyridine (NBP). Arzneimittelforschung 19, 1059-1073.
27. Preussmann, R., Arjungi, K. N., and Ebers, G. (1976) Letter: In vitro detection of nitrosamines and other indirect alkylating agents by reaction with 3,4-dichlorothiophenol in the presence of rat liver microsomes. Cancer Res. 36, 2459-2462.
28. Haglund, J., Rafiq, A., Ehrenberg, L., Golding, B. T., and Törnqvist, M. (2000) Transalkylation of phosphotriesters using cob(I)alamin: Toward specific determination of DNA-phosphate adducts. Chem. Res. Toxicol. 13, 253-256. (Pubitemid 30241651)
29. Haglund, J., Magnusson, A.-L., Ehrenberg, L., and Törnqvist, M. (2003) Introduction of Cob(I)alamin as an analytical tool: Application to reaction-kinetic studies of oxiranes. Toxicol. Environ. Chem. 85 (4-6), 81-94. (Pubitemid 38448920)
30. Fred, C., Haglund, J., Alsberg, T., Rydberg, P., Minten, J., and Törnqvist, M. (2004) Characterization of alkyl-cobalamins formed on trapping of epoxide metabolites of 1,3-butadiene. J. Sep. Sci. 27, 607-612. (Pubitemid 38735651)
31. Haglund, J., Silvari, V., Esmans, E., and Törnqvist, M. (2006) Cobalamin as an analytical tool for analysis of oxirane metabolites of 1,3-butadiene: development and validation of the method. J. Chromatogr. A 1119, 246-250. (Pubitemid 43831885)
32. Golding, B. T., Slaich, P. K., Kennedy, G., Bleasdale, C., and Watson, W. P. (1996) Mechanisms of formation of adducts from reactions of glycidaldehyde with 2′-deoxyguanosine and/or guanosine. Chem. Res. Toxicol. 9, 147-157. (Pubitemid 26041282)
33. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Randall, R. J. (1951) Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275.
34. Schrauzer, G. N., and Deutsch, E. (1969) Reactions of cobalt(I) supernucleophiles. The alkylation of vitamin B12s cobaloximes(I), and related compounds. J. Am. Chem. Soc. 91, 3341-3350.
35. 12) using reversed phase high performance liquid chromatography with electrospray tandem mass spectrometry and ultraviolet diode array detection. Rapid Commun. Mass Spectrom. 15, 2438-2445.
36. Dixon, R. M., Golding, B. T., Howarth, O. W., and Murphy, J. L. (1983) Synthesis and characterization by proton NMR spectroscopy of diastereoisomeric hydroxy- and dihydroxyalkylcobalamins. J. Chem. Soc., Chem. Commun. 243-245.
37. Ross, M. A., Pohl, T. M., Piazza, K., Thomas, M., Fox, B., and Whalen, D. L. (1982) Vinyl epoxides hydrolysis reactions. J. Am. Chem. Soc. 104, 1658-1665.
38. Ross, W. C. J. (1950) The reactions of certain epoxides in aqueous solutions. J. Chem. Soc. 2257-2272.
39. Fred, C., Törnqvist, M., and Granath, F. (2008) Evaluation of cancer tests of 1,3-butadiene using internal dose, genotoxic potency, and a multiplicative risk model. Cancer Res. 68, 8014-8021.
40. Kemper, R. A., and Elfarra, A. A. (1996) Oxidation of 3-butene-1,2- diol by alcohol dehydrogenase. Chem. Res. Toxicol. 9, 1127-1134. (Pubitemid 26347965)
41. Boysen, G., Georgieva, N. I., Upton, P. B., Jayaraj, K., Li, Y., Walker, V. E., and Swenberg, J. A. (2005) Analysis of diepoxide-specific cyclic N-terminal globin adducts in mice and rats after inhalation to 1,3- butadiene. Cancer Res. 64, 8517-8520. (Pubitemid 39552062)