Identification of benzene oxide as a product of benzene metabolism by mouse, rat, and human liver microsomes

Carcinogenesis

Volumn 18, Issue 9, 1997, Pages 1695-1700

  Lovern, Mark R ^a,b   Turner, Max J ^b   Meyer, Mark ^c   Kedderis, Gregory L ^b   Bechtold, William E ^c   Schlosser, Paul M ^b  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

^b CIIT CENTERS FOR HEALTH RESEARCH   (United States)

^c LOVELACE RESPIRATORY RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; BENZENE DERIVATIVE; CARBON 14; DICHLOROMETHANE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SODIUM DIHYDROGEN PHOSPHATE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; LIVER MICROSOME METABOLISM; MALE; MASS SPECTROMETRY; METABOLISM; MOUSE; NONHUMAN; OXIDATION; PRIORITY JOURNAL; RADIOASSAY; RAT;

ANIMALS; BENZENE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYCLOHEXANES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; MALE; MICE; MICROSOMES, LIVER; RATS; RATS, INBRED F344; SPECIES SPECIFICITY;

EID: 0031408978     PISSN: 01433334     EISSN: None     Source Type: Journal    
DOI: 10.1093/carcin/18.9.1695     Document Type: Article

References (34)

1. Ayres, P.H. and Taylor, W.D. (1989) Solvents. In Hayes, A.H. (ed.) Principles and Methods of Toxicology. 2nd Edn. Raven Press Ltd, New York, pp. 111-135.
2. Wallace, L. (1990) Major sources of exposure to benzene and other volatile organic chemicals. Risk Anal., 10, 59-64.
3. Infante, P.E., Rinsky, R.A., Wagoner, J.K. and Young, R.J. (1977) Leukemia in benzene workers. Lancet, 2, 76-78.
4. Runion, H.E. and Scott, L.M. (1985) Benzene exposure in the United States 1978-1983: an overview. Am. J. Ind. Med., 7, 385-393.
5. Travis, L.B., Li, C.Y., Zhang, Z.N., Li, D.G., Yin, S.N., Chow, W.H., Li, G.L. Dosemeci, M., Blot, W., Fraumeni, J.F., Jr., Hayes, R.B. and Linet, M.S. (1994) Hematopoetic malignancies and related disorders among benzene-exposed workers in China. Leuk. Lymphoma., 14, 91-102.
6. Xia, Z.L., Jin, X.P., Lu, P.L., Gu, X.Q., LaPorte, R.E. and Tajima, N. (1995) Ascertainment corrected prevalence rate (ACPR) of leukopenia in workers exposed to benzene in small-scale industries calculated with capture-recapture methods. Biomed. Environ. Sci., 8, 30-34.
7. MacEachern, L., Snyder, R. and Laskin, D.L. (1992) Alterations in the morphology and functional activity of bone marrow phagocytes following benzene treatment of mice. Toxicol. Appl. Pharmacol., 117, 147-154.
8. Snyder, C.A., Goldstein, B.D., Sellakumar, A., Wolman, S.R., Bromberg, I. and Laskin, S. (1978) Hematotoxicity of inhaled benzene to Sprague-Dawley rats and AKR mice at 300 ppm. J. Toxicol. Environ. Health, 4, 605-619.
9. Sammett, D., Lee, E.W., Kocsis, J.J. and Snyder, R. (1979) Partial hepatectomy reduces both metabolism and toxicity of benzene. J. Toxicol. Environ. Health 5, 785-792.
10. Rothman, N., Smith, M.T., Yin, S.N., Haas, R., Campleman, S., Hoener, B.A., Bechtold, W., Zhang, L.P. and the NCI-CAPM Collaborative Study. (1995) Biomarker study of workers exposed to benzene. Proceedings, Benzene '95 Conference, June 17-10, Environmental and Occupational Health Sciences Institute, Piscataway, NJ.
11. 14C]benzene. Biochem. J., 54, 231-238.
12. Porteous, J.W. and Williams, R.T. (1949) Studies in detoxication. 19. The metabolism of benzene. Biochem. J., 44, 46-61.
13. Jerina, D., Daly, J., Witkop, B., Zaltzman-Nirenberg, P. and Udenfriend, S. (1968) Role of the arene oxide-oxepin system in the metabolism of aromatic substances. I. In-vitro conversion of benzene oxide to a premercapturic acid and dihydrodiol. Arch. Biochem. Biophys., 128, 176-193.
14. Lindstrom, A.B., Yeowell-O'Connell, K., Waidyanatha, S., Golding, B.T., Tomero-Velez, R. and Rappaport, S.M. (1997) Measurement of benzene oxide in the blood of rats following admistration of benzene. Carcinogenesis (in press).
15. Davies, S.G. and Whitham, G.H. (1977) Benzene oxide-oxepin. Oxidation to muconaldehyde. J. Chem. Soc., Perkin Trans., 11, 1346-1347.
16. Seaton, M.J., Schlosser, P.M., Bond, J.A. and Medinsky, M.A. (1994) Benzene metabolism by human liver microsomes in relation to cytochrome P450 E1 activity. Carcinogenesis, 15, 1799-1906.
17. 3H] labeled benzene oxide. J. Labeled Compounds Radiopharm., 13, 471-479.
18. van Tramelen, E.E. (1955) The reaction of cyclohexadiene-1,4 with electrophilic reagents. J. Am. Chem. Soc., 77, 1704-1706.
19. Gillard, J.R., Newlands, M.J., Bridson, J.N. and Burnell, D.J. (1991) π-Facial stereoselectivity in the Diers-Alder reactions of benzene oxides. Can. J. Chem., 69, 1337-1343.
20. Vogel, E. and Gunther, H. (1967) Benzene oxide-oxepin valence tautomerism. Angew. Chem., 6, 385-476.
21. Dahl, A.R., Benson, J.M., Hanson, R.L. and Rothenberg, S.J. (1984) The fractionation of environmental samples according to volatility by vacuum line-cryogenic distillation. Am. Ind. Hyg. Assoc. J., 45, 193-198.
22. Csanády, 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.
23. Kedderis, G.L., Batra, R. and Koop, D.R. (1993) Epoxidation of acrylonitrile by rat and human cytochromes P450. Chem. Res. Toxicol., 6, 866-871.
24. Lowry, O.H., Rosenbrough, N.F., Farr, A.L. and Randall, R.J. (1951) Protein measurements with the Folin phenol reagent. J. Biol. Chem., 193, 265-275.
25. Schlosser, P.M., Bond, J.A. and Medinsky, M.A. (1993) Benzene and phenol metabolism by mouse and rat liver. Carcinogenesis, 14, 2477-2486.
26. Bechtold, W.E., Sabourin, P.J. and Henderson, R.F. (1988) A reverse isotope dilution method for determining benzene and metabolites in tissues. J. Anal. Toxicol., 12, 176-179.
27. Kasparek, G.J. and Bruice, T.C. (1972) The mechanism of the aromatization of arene oxides. J. Am. Chem. Soc., 94, 198-202.
28. Arms, A.D. and Travis, C.C. (1988) Reference Physiological Parameters in Pharmacokinetic Modeling. U.S.E.P.A. 600/6-88/004, Final Report, NTIS, PB88-196019.
29. Guy, R.L., Hu, P., Witz, G., Goldstein, B.D. and Snyder, R. (1991) Depression of iron uptake into erythrocytes in mice by treatment with the combined benzene metabolites p-benzoquinone, muconaldehyde and hydroquinone. J. Appl. Toxicol., 11, 443-446.
30. Snyder, R., Dimitriadis, E., Guy, R., Hu, P., Cooper, K., Bauer, H., Witz, G. and Goldstein, B. D. (1989) Studies on the mechanism of benzene toxicity. Environ. Health Perspect., 82, 31-35.
31. Barale, R., Marrazzini, A., Betti, C., Vangelisti, V., Loprieno, N. and Barrai, I. (1990) Genotoxicity of two metabolites of benzene: phenol and hydroquinone show strong synergistic effects in vivo. Mutat. Res., 244, 15-20.
32. Eastmond, D.A., Smith, M.T. and Irons, R.D. (1987) An interaction of benzene metabolites reproduces the myelotoxicity observed with benzene. Toxicol. Appl. Pharmacol., 91, 85-95.
33. Ehrenberg, L. and Hussain, S. (1981) Genetic toxicity of some important epoxides. Mutat. Res., 86, 1-113.
34. 6]benzene. Cancer Res. 54, 4907-4914.