Biotransformation of 12C- and 2-13C-labeled methyl tert-butyl ether, ethyl tert-butyl ether, and tert-butyl alcohol in rats: Identification of metabolites in urine by 13C nuclear magnetic resonance and gas chromatography/mass spectrometry

Chemical Research in Toxicology

Volumn 11, Issue 6, 1998, Pages 651-658

  Bernauer, Ulrike ^a   Amberg, Alexander ^a   Scheutzow, Dieter ^a   Dekant, Wolfgang ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

TERT BUTYL ALCOHOL; TERT BUTYL ETHYL ETHER; TERT BUTYL METHYL ETHER; UNCLASSIFIED DRUG; CARBON; ETHER DERIVATIVE; ETHYL TERT BUTYL ETHER; ETHYL TERT-BUTYL ETHER; METHYL TERT-BUTYL ETHER;

ACUTE TOXICITY; ALCOHOL METABOLISM; ALCOHOL OXIDATION; ANALYTIC METHOD; ANIMAL EXPERIMENT; ARTICLE; BIOTRANSFORMATION; CHEMICAL CARCINOGENESIS; DRUG URINE LEVEL; FEMALE; MALE; MOUSE; NONHUMAN; ANIMAL; FISCHER 344 RAT; HUMAN; MASS FRAGMENTOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT;

ANIMALS; BIOTRANSFORMATION; CARBON ISOTOPES; ETHYL ETHERS; FEMALE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; METHYL ETHERS; RATS; RATS, INBRED F344; TERT-BUTYL ALCOHOL;

EID: 0031596435     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970215v     Document Type: Article

References (33)

1. Costantini, M. G. (1993) Health effects of oxygenated fuels. Environ. Health Perspect. 6, 151-160.
2. White, R. D., Daughtrey, W. C., and Wells, M. S. (1995) Health effects of inhaled tertiary amyl methyl ether and ethyl tertiary butyl ether. Toxicol. Lett. 82/83, 719-724.
3. Burleigh-Flayer, H. D., Chun, J. S., and Kintigh, W. J. (1992) Methyl tertiary butyl ether: vapor inhalation oncogenicity study in CD-1 mice. BRRC Project Number 91N0013A, Bushy Bun Research Center, Export, PA.
4. 2U-globulin nephropathy and associated cell proliferation in male Fischer 344 rats dosed with tert-butyl alcohol. Environ. Health Perspect. 101, 281-286.
5. Borghoff, S. J., Prescott-Mathews, J. S., and Poet, T. S. (1996) The mechanism of male rat kidney tumors induced by methyl tertbutyl ether and its relevance in assessing human risk. CIIT Activities 16, 1-8.
6. Scientific Advisory Board on Toxic Air Pollutants. (1995) Summary of the carcinogenicity assessment of MTBE. Environ. Health Perspect. 103, 420-422.
7. 2u-globulin nephropathy. Toxicol. Appl. Pharmacol. 97, 35-46.
8. Belpoggi, F., Soffritti, M., and Maltoni, C. (1995) Methyl-tertiary-butyl ether (MTBE) - a gasoline additive - causes testicular and lymphohaernatopoietic cancers in rats. Toxicol. Ind. Health 11, 119-149.
9. Duffy, J. S., Del Pup, J. A., and Kneiss, J. J. (1992) Toxicological evaluation of methyl tertiary butyl ether (MTBE): testing performed under TSCA consent agreement. J. Soil Contain. 1, 29-37.
10. Johanson, G., Nihlén, A., and Löf, A. (1995) Disposition and acute effects of inhaled MTBE and ETBE in male volunteers. The International Toxicologist, International Congress of Toxicology-VII, Seattle, WA, July 2-6, 68-W-62.
11. Johanson, G., Nihlén, A., and Löf, A. (1995) Toxicokinetics and acute effects of MTBE and ETBE in male volunteers. Toxicol. Lett. 83, 713-718.
12. Gordian, M. E., Huelsman, M. D., Brecht, M. L., and Fisher, D. G. (1995) Health effects of methyl tertiary butyl ether (MTBE) in gasoline in Alaska. Alaska Med. 37, 101-103.
13. Loizou, G. D., Urban, G., Dekant, W., and Anders, M. W. (1994) Gas-uptake pharmacokinetics of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123). Drug Metab. Dispos. 22, 511-517.
14. Henderson, R. F., Sabourin, P. J., Bechtold, W. E., Steinberg, B., and Chang, I. Y. (1993) Disposition of inhaled isobutene in F344/N rats. Toxicol. Appl. Pharmacol. 123, 50-61.
15. Kropf, H. (1975) Herstellung von Alkoholen durch Aufbaureaktionen. In Houben-Weyl. Handbuch der organischen Chemie, pp 1021-1022.
16. Hünig, S., Märkl, G., and Sauer, J. (1979) Integriertes organisches Praktikum, Verlag Chemie, Weinheim.
17. Meerwein, H. (1975) Äther. In Houben-Weyl. Handbuch der organischen Chemie, p 14.
18. 13C NMR spectra of urines and biochemical and histopathological examinations. J. Appl. Toxicol. 7, 23-34.
19. Nicholson, J. K., and Wilson, I. D. (1987) High-resolution nuclear magnetic resonance spectroscopy of biological samples as an aid to drug development. Prog. Drug Res. 31, 427-479.
20. Miller, M. J., Ferdinandi, E. S., Klan, M., Andrews, L. S., Douglas, J. F., and Kneiss, J. J. (1997) Pharmacokinetics and disposition of methyl-tert-butyl ether in Fischer 344 rats. J. Appl. Toxicol, 17, S3-S12.
21. HEI. (1996) The potential health effects of oxygenates added to gasoline. Health Effects Institute, Cambridge, MA.
22. Brady, J. F., Xiao, F., Ning, S. M., and Yang, C. S. (1990) Metabolism of methyl tertiary-butyl ether by rat hepatic microsomes. Arch. Toxicol. 64, 157-160.
23. Hong, J.-Y., Yang, C. S., Lee, M., Wang, Y.-Y., Huang, W.-Q., Tan, Y., Patten, C. J., and Bondoc, F. Y. (1997) Role of cytochromea P450 in the metabolism of methyl tert-butyl ether in human livers. Arch. Toxicol. 71, 266-269.
24. Brady, J. F., Lee, M. J., Li, M., Ishizaki, H., and Yang, C. S. (1988) Diethyl ether as substrate for acetone/ethanol-inducible cytochrome P-450 and as an inducer for cytochrome(s) P-450. Mol. Pharmacol. 33, 148-154.
25. Krämer, A., Staudinger, H., and Ullrich, V. (1974) Effect of n-hexane inhalation on the monooxygenase system in mice liver microsomes. Chem.-Biol. Interact. 8, 11-18.
26. Kamil, I. A., Smith, J. N., and Williams, R. T. (1953) The metabolism of aliphatic alcohols. The glucuronic acid conjugation of acyclic aliphatic alcohols. Biochem. J. 53, 129-136.
27. Falany, C. N., and Wilborn, T. W. (1994) Biochemistry of cytosolic sulfotransferases involved in bioactivation. In Conjugation-dependent carcinogenicity and toxicity of foreign compounds (Anders, M. W., and Dekant, W., Eds.) pp 330-329, Academic Press, San Diego.
28. Cederbaum, A. I., and Cohen, G. (1980) Oxidative demethylation of tert-butyl alcohol by rat liver microsomes. Biochem. Biophys. Res. Commun. 97, 730-736.
29. Cederbaum, A. I., Qureshi, A., and Cohen, G. (1983) Production of formaldehyde and acetone by hydroxyl-radical generating systems during the metabolism of tertiary butyl alcohol. Biochem. Pharmacol. 32, 3517-3524.
30. Poet, T. S., Valentine, J. L., and Borghoff, S. J. (1997) Pharmacokinetics of tertiary butyl alcohol in male and female Fischer 344 rats. Toxicol. Lett. 92, 179-186.
31. Lindamood, C. D., Farnell, D. R., Giles, H. D., Prejean, J. D., Collins, J. J., Takahashi, K., and Maronpot, R. R. (1992) Subchronic toxicity studies of tert-butyl alcohol in rats and mice. Fundam. Appl. Toxicol. 19, 91-100.
32. 2u-globulin nephropathy and enhanced renal cell proliferation in male Fischer-344 rats. Toxicol. Appl. Pharmacol. 143, 301-314.
33. Poet, T. S., and Borghoff, S. J. (1997) In vitro uptake of methyl tert-butyl ether in male rat kidney: use of a two-compartment model to describe protein interactions. Toxicol. Appl. Pharmacol. 145, 340-348.