Isozyme-selective metabolism of ethyl carbamate by cytochrome P450 (CYP2E1) and carboxylesterase (hydrolase A) enzymes in murine liver microsomes

Drug Metabolism and Disposition

Volumn 26, Issue 1, 1998, Pages 60-65

  Lee, Raymond P ^b   Parkinson, Andrew ^b   Forkert, Poh Gek ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; DIMETHYLNITROSAMINE; DIMETHYLNITROSAMINE DEMETHYLASE; URETHAN;

ANIMAL TISSUE; ARTICLE; DEMETHYLATION; DRUG HYDROLYSIS; DRUG PROTEIN BINDING; ENZYME ACTIVITY; ENZYME SPECIFICITY; LIVER MICROSOME METABOLISM; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; CARBON RADIOISOTOPES; CARBOXYLESTERASE; CARBOXYLIC ESTER HYDROLASES; CARCINOGENS; CATALYSIS; CHOLINESTERASE INHIBITORS; CYTOCHROME P-450 CYP2E1; ENZYME INHIBITORS; FEMALE; IMMUNOBLOTTING; MICE; MICE, INBRED STRAINS; MICROSOMES, LIVER; PARAOXON; PHENYLMETHYLSULFONYL FLUORIDE; PROTEIN BINDING; PROTEINS; URETHANE;

EID: 0031916675     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Carlson GP (1994) The effect of inducers and inhibitors of urethane metabolism on its in vitro and in vivo metabolism in rats. Cancer Lett 87:145-150.
2. Dahl GA, Miller JA and Miller EC (1978) Vinyl carbamate as a promutagen and a more carcinogenic analog of ethyl carbamate. Cancer Res 38:3793-3804.
3. Forkert PG (1995) CYP2E1 is preferentially expressed in Clara cells of murine lung: localization by in situ hybridization and immunohistochemical methods. Am J Respir Cell Mol Biol 12:589-596.
4. Forkert PG, Dowsley TF, Lee RP, Hong J-Y and Ulreich JB (1996) Differential formation of 1,1-dichloroethylene-metabolites in the lungs of adult and weanling male and female mice: correlation with severities of bronchiolar cytotoxicity. J Pharmacol Exp Ther 279:1484-1490.
5. Forkert PG, Redza ZM, Mangos S, Park SS and Tam SP (1994) Induction and regulation of CYP2E1 in murine liver after acute and chronic acetone administration. Drug Metab Dispos 22:248-253.
6. Forkert PG, Stringer V and Troughton KM (1986) Pulmonary toxicity of 1,1-dichloroethylene: correlation of early changes with covalent binding. Can J Physiol Pharmacol 64:112-121.
7. 6-ethenoadenosine. Chem Res Toxicol 4:413-421.
8. Guengerich FP, Kim DH and Iwasaki M (1991) Role of human cytochrome P-450 IIE1 in the oxidation of many low molecular weight cancer suspects. Chem Res Toxicol 4:168-179.
9. Hong J-Y, Pan J, Ning SM and Yang CS (1989) Molecular basis for the sex-related difference in renal N-nitrosodimethylamine demethylase in C3H/HeJ mice. Cancer Res 49:2973-2979.
10. Johansson I, Ekström G, Scholte B, Puzycki D, Jörnvall H and Ingelman-Sundberg M (1988) Ethanol-, fasting-, and acetone-inducible cytochromes P-450 in rat liver: regulation and characteristics of enzymes belonging to the IIB and IIE gene subfamilies. Biochemistry 27:1925-1934.
11. Kaye AM (1960) A study of the relationship between the rate of ethyl carbamate (urethan) catabolism and urethan carcinogenesis. Cancer Res 20:237-241.
12. Ko IY, Park SS, Song BJ, Patten C, Tan YM, Hah YC, Yang CS and Gelboin HV (1987) Monoclonal antibodies to ethanol-induced rat liver cytochrome P-450 that metabolizes aniline and nitrosamines. Cancer Res 47:3101-3109.
13. Kurata N, Hurst HE, Benz FW, Kemper RA and Waddell WJ (1991a) Studies on inhibition and induction of metabolism of ethyl carbamate by acetone and related compounds: evidence for metabolism by cytochromes P-450. Drug Metab Dispos 19:388-393.
14. Kurata N, Hurst HE, Kemper RA and Waddell WJ (1991b) Studies on induction of metabolism of ethyl carbamate in mice by ethanol. Drug Metab Dispos 19:239-240.
15. Lee RP and Forkert PG (1994) In vitro biotransformation of 1,1-dichloroethylene by hepatic cytochrome P450 2E1 in mice. J Pharmacol Exp Ther 270:371-376.
16. 6-Ethenoadenosine formation, mutagenicity and murine tumor induction as indicators of the generation of an electrophilic epoxide metabolite of the closely related carcinogens ethyl carbamate (urethane) and vinyl carbamate. Carcinogenesis (Lond) 11:463-473.
17. Lowry OH, Rosebrough NJ, Farr AL and Randall RJ (1951) Protein measurement with the Folin phenol reagent. J Biol Chem 193:265-275 (1951).
18. McCracken NW, Blain PG and Williams FM (1993) Nature and role of xenobiotic metabolizing esterases in rat liver, lung, skin and blood. Biochem Pharmacol 45:31-36.
19. Miller JA and Miller EC (1983) The metabolic activation and nucleic acid adducts of naturally occurring carcinogens: recent results with ethyl carbamate and the spice flavors safrole and estragole. Br J Cancer 48:1-15.
20. Mirvish SS (1968) The carcinogenic action and metabolism of urethan and N-hydroxyurethan. Adv Cancer Res 21:1-42.
21. Mirvish SS and Kaye AM (1964) The catabolism of urethane by mouse-liver homogenates. Biochem Biophys Acta 82:397-402.
22. Morgan EW, Yan B, Greenway D and Parkinson A (1994a) Regulation of two rat liver microsomal carboxylesterase isozymes: species differences, tissue distribution, and the effects of age, sex, and xenobiotic treatment of rats. Arch Biochem Biophys 315:513-526.
23. Morgan EW, Yan B, Greenway D, Peterson DR and Parkinson A (1994b) Purification and characterization of two rat liver microsomal carboxylesterases (hydrolase A and B). Arch Biochem Biophys 315:495-512.
24. Neal RA (1967) Studies on the metabolism of diethyl 4-nitrophenyl phosphothionate (parathion) in vitro. Biochem J 103:183-191.
25. Nettleship A, Henshaw PS and Meyer HL (1943) Induction of pulmonary tumors in mice with ethyl carbamate (urethane). J Natl Cancer Inst 4:309-319.
26. Nomier AA, Ioannou YM, Sanders JM and Matthews HB (1989) Comparative metabolism and disposition of ethyl carbamate (urethane) in male Fischer 344 rats and male B6C3F1 mice. Toxicol Appl Pharmacol 97:203-215.
27. Page DA and Carlson GP (1994) The effect of pyridine on the in vitro and in vivo metabolism of ethyl carbamate (urethane) by rat and mouse. Carcinogenesis (Lond) 15:2177-2181.
28. Park SS, Ko IY, Patten C, Yang CS and Gelboin HV (1986) Monoclonal antibodies to ethanol-induced cytochrome P450 that inhibit aniline and nitrosoamine metabolism. Biochem Pharmacol 35:2855-2858.
29. 14C]ethyl carbamate (urethan). Carcinogenesis (Lond) 3:539-546.
30. 3H sodium borohydride, in The Role of Cyclic Nucleic Acid Adducts in Carcinogenesis and Mutagenesis (Singer B and Bartsch H eds) IARC Scientific Publication 70, pp 109-125, International Agency for Research on Cancer, Lyon, France.
31. Skipper HE, Bennett LL Jr, Bryan CE, White L Jr, Newton MA and Simpson L (1951) Carbamates in the chemotherapy of leukemia: over-all tracer studies on carbonyl-labeled urethan, methylene-labeled urethan and methylene-labeled ethyl alcohol. Cancer Res 11:46-51.
32. Smith-Gill SJ, Wilson AC, Potter M, Prager EM, Feldmann RJ and Mainhart CR (1982) Mapping the antigenic epitope for a monoclonal antibody against lysozyme. J Immunol 128:314-322.
33. Tannenbaum A and Silverstone H (1958) Urethan (ethyl carbamate) as a multipotential carcinogen. Cancer Res 18:1225-1231.
34. Yamamoto T, Pierce WM, Hurst HE, Chen D and Waddell WJ (1990) Ethyl carbamate metabolism: in vivo inhibitors and in vitro enzymatic systems. Drug Metab Dispos 18:276-280.