The role of different cytochrome P450 isoforms in in vitro chloroform metabolism

Journal of Biochemical Toxicology

Volumn 11, Issue 6, 1996, Pages 305-312

  Testai, Emanuela ^a   De Curtis, Valentina ^a   Gemma, Simonetta ^a   Fabrizi, Laura ^a   Gervasi, PierGiovanni ^b   Vittozzi, Luciano ^a  

^a ISTITUTO SUPERIORE DI SANITÀ   (Italy)

^b CNR   (Italy)

Author keywords

Chloroform Bioactivation; P450 Isoforms; Rat Liver Microsomes

Indexed keywords

ACETONE; BETA NAPHTHOFLAVONE; CHLOROFORM; CYP2C11 PROTEIN, RAT; CYTOCHROME P450; CYTOCHROME P450 2E1; DEXAMETHASONE; ISOENZYME; PHENOBARBITAL; PYRAZOLE; PYRAZOLE DERIVATIVE; STEROID 16ALPHA MONOOXYGENASE; STEROID MONOOXYGENASE; UNSPECIFIC MONOOXYGENASE;

ANIMAL; ARTICLE; BIOSYNTHESIS; BIOTRANSFORMATION; DRUG EFFECT; DRUG POTENTIATION; ENZYME INDUCTION; ENZYMOLOGY; LIVER MICROSOME; MALE; METABOLISM; RAT; SPRAGUE DAWLEY RAT;

ACETONE; ANIMALS; ARYL HYDROCARBON HYDROXYLASES; BETA-NAPHTHOFLAVONE; BIOTRANSFORMATION; CHLOROFORM; CYTOCHROME P-450 CYP2E1; CYTOCHROME P-450 ENZYME SYSTEM; DEXAMETHASONE; DRUG SYNERGISM; ENZYME INDUCTION; ISOENZYMES; MALE; MICROSOMES, LIVER; PHENOBARBITAL; PYRAZOLES; RATS; RATS, SPRAGUE-DAWLEY; STEROID 16-ALPHA-HYDROXYLASE; STEROID HYDROXYLASES;

EID: 0030323264     PISSN: 08872082     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-7146(1996)11:6<305::AID-JBT6>3.0.CO;2-O     Document Type: Article

References (48)

1. WHO (1994). IPCS Environmental Health Criteria 163: Chloroform, Geneva: WHO.
2. A. B. Eschenbrenner and E. Miller (1945). Induction of hepatomas in mice by repeated oral administration of chloroform, with observations on sex differences. J. Natl. Cancer Inst., 5, 251-255.
3. R. H. Reitz, T. R. Fox, and J. F. Quast (1982). Mechanistic considerations for carcinogenic risk estimation: Chloroform. Environ. Health Perspect., 46, 163-168.
4. R. H. Reitz, A. L. Mendrala, R. A. Corley, J. F. Quast, M. L. Gargas, M. E. Andersen, D. A. Staats, and R. B. Conolly (1990). Estimating the risk of liver cancer associated with human exposures to chloroform using physiologically based pharmacokinetic modeling. Toxicol. Appl. Pharmacol., 105, 443-459.
5. J. L. Larson, D. C. Wolf, and B. E. Butterworth (1993). Acute hepatotoxic and nephrotoxic effects of chloroform in male F-344 rats and female B6C3F1 mice. Fund. Appl. Toxicol., 20, 302-315.
6. S. L. Rosenthal (1987). A review of the mutagenicity of chloroform, Environ. Mol. Mut., 10, 211-226.
7. A. Colacci, S. Bartoli, B. Bonora, L. Guidotti, G. Lattanzi, M. Mazzullo, A. Niero, P. Perocco, P. Silingardi, and S. Grilli (1991). Chloroform bioactivation leading to nucleic acids binding. Tumori, 77, 285-290.
8. 3 bioactivation, toxicokinetics, toxicity and induced compensatory cell proliferation in B6C3F1 male mice. Toxicol. Appl. Pharmacol., 141, 394-402.
9. K. F. Ilett, W. D. Reid, I. G. Sipes, and G. Krishna (1973). Chloroform toxicity in mice: Correlation of renal and hepatic necrosis with covalent binding of metabolites to tissue macromolecules. Exp. Mol. Pathol., 19, 215-229.
10. B. R. Brown, Jr., I. G. Sipes, and A. M. Sagalyn (1974). Mechanisms of acute hepatic toxicity chloroform, halotane and gluthatione, Anesthesiology, 41, 554-561.
11. D. Mansuy, P. Beaune, T. H. Cresteil, M. Lange, and J. P. Leroux (1977). Evidence for phosgene formation during liver microsomal oxidation of chloroform. Biochem. Biophys. Res. Commun., 79, 513-517.
12. L. R. Pohl, B. Bhooshan, N. F. Whittaker, and G. Krishna (1977). Phosgene: A metabolite of chloroform. Biochem. Biophys. Res. Commun., 79, 684-691.
13. A. Tomasi, E. Albano, F. Biasi, T. F. Slater, V. Vannini, and M. U. Dianzani (1985). Activation of chloroform and related trihalomethanes to free radical intermediates in isolated hepatocites and in the rat in vivo as detected by the ESR-spin trapping technique. Chem. Biol. Interact., 55, 303-316.
14. E. Testai, S. Di Marzio, A. di Domenico, A. Piccardi, and L. Vittozzi (1995). An in vitro investigation of the reductive metabolites of chloroform. Arch. Toxicol., 70, 83-88.
15. R. V. Branchflower, R. D. Schulick, J. W. George, and L. R. Pohl (1983). Comparison of the effects of methyl-N-butyl ketone and phenobarbital on rat liver cytochromes P-450 and the metabolism of chloroform to phosgene. Toxicol. Appl. Pharmacol., 71, 414-421.
16. A. Sato, T. Nakajima, and Y. Koyama (1980). Effects of chronic ethanol consumption on hepatic metabolism of aromatic and chlorinated hydrocarbons in rats. Br. J. Ind. Med., 37, 382-386.
17. J. F. Brady D. Li, H. Ishizaki, M. Lee, S. M. Ning, F. Xiao, and C. S. Yang (1989). Induction of cytochromes P450IIE1 and P450IIB1 by secondary ketones and the role of P450IIE1 in chloroform metabolism. Toxicol. Appl. Pharmacol., 100, 342-349.
18. 3 metabolism in hepatic microsomes from Osborne-Mendel rats. Environ. Health Perspect., 102, 25-30.
19. J. G. Lavigne and C. Marchand (1974). The role of metabolism in chloroform hepatotoxicity. Toxicol. Appl. Pharmacol., 29, 312-326.
20. 2H)-chloroform. Chem. Biol. Interact., 37, 207-217.
21. V. De Curtis, S. Gemma, M. Sbraccia, E. Testai, and L. Vittozzi (1994). The contribution of electrophilic and radicalic intermediates to phospholipid adducts formed by halomethanes in vivo. J. Biochem. Toxicol., 9(6), 305-310.
22. E. Testai and L. Vittozzi (1986). Biochemical alterations elicited in rat liver microsomes by oxidation and reduction products of chloroform metabolism. Chem. Biol. Interact., 59, 157-171.
23. T. Nakajima, E. Elovaara, S. S. Park, H. V. Gelboin, and H. Vainio (1991). Immunochemical detection of cytochrome P450 isozymes induced in rat liver by n-hexane, 2-hexanone and acetonyl-acetone. Arch. Toxicol. 65, 542-547.
24. T. Nakajima, E. Elovaara, T. Okino, H. V. Gelboin, M. Klockars, V. Riihimaki, T. Aoyama, and H. Vainio (1995). Different contributions of cytochrome P450 2E1 and P450 2B1 /2 to chloroform hepatotoxicity in rat. Toxicol. Appl. Pharmacol., 133, 215-222.
25. A. B. Kobusch, G. L. Plaa, and P. Du Souich (1989). Effects of acetone and methyl n-butyl ketone on hepatic mixed-function oxidase. Biochem. Pharmacol., 38, 3461-3467.
26. 3 hepatotoxicity and lethality by various alcohols. Fund. Appl. Toxicol., 15, 429-440.
27. C. M. MacDonald, J. Dow, and M. R. Moore (1977). A possible protective role for sulfhydryl compounds in acute alcoholic liver injury. Biochem. Pharmacol., 26, 1529-1533.
28. Y. Israel, H. Kalant, H. Orrego, J. M. Khanna, L. Videla, and J. M. Phillips (1975). Experimental alcohol-induced hepatic necrosis. Suppression by propylthiouracil. Proc. Natl. Acad. Sci. U.S.A., 72, 1137-1141.
29. 3-hepatotoxicity. Biochem. Biophys. Res. Commun., 161, 615-618.
30. C. D. Klaassen and G. L. Plaa (1969). Comparison of the biochemical alterations elicited in livers from rats treated with carbon tetrachloride, chloroform, 1,1,2-trichloroethane and 1,1,1-trichloroethane. Biochem. Pharmacol., 18, 2019-2027.
31. B. R. Brown, Jr. (1972). Hepatic microsomal lipoperoxidation and inhalation anesthetics: A biochemical and morphologic study in the rat. Anesthesiology, 36, 458-465.
32. Y. Masuda, I. Yano, and T. Murano (1980). Comparative studies on the hepatotoxic actions of chloroform and related halogenomethanes in normal and phenobarbital-pretreated animals. J. Pharm. Dyn., 3, 53-64.
33. 3 metabolites to microsomal phospholipids. Chem. Biol. Interact., 85, 229-242.
34. V. I. Oyama and H. Eagle (1956). Measurement of cell growth in tissue culture with a phenol reagent (Folin-Ciocalteus). Proc. Soc. Exp. Biol. Med., 91, 305-307.
35. T. Omura and R. Sato (1964). The carbon monoxide binding pigment of liver microsomes. J. Biol. Chem., 239, 2370-2378.
36. M. D. Burke and R. T. Mayer (1974). Ethoxyresorufin: Direct fluorimetric assay of a microsomal O-dealkylation which is preferentially inducible by 3-methylcolanthrene. Drug Metab. Dispos., 2, 583-588.
37. I. Y. Ko, S. S. Park, B. J. Song, C. Patten, Y. Tan, C. S. Yang, and H. V. Gelboin (1987). Monoclonal antibodies to ethanol-induced rat liver cytochrome P450 that metabolizes aniline and nitrosamines. Cancer Res., 47, 3101-3106.
38. M. W. Anders and G. J. Mannering (1966). Inhibition of drug metabolism. Mol. Pharmacol., 2, 319-323.
39. U.K. Laemmli (1970). Cleavage of structural proteins during the assembly of the head of the bacteriophage T4. Nature, 227, 680-683.
40. H. Towbin, P. Stachelin, and J. Gordom (1979). Electrophoretic transfer of proteins from polyacrylamide gels to nitrocellulose sheets: Procedure and some applications. Proc. Natl. Acad. Sci. U.S.A., 76, 4350-4354.
41. E. Testai, S. Di Marzio, and L. Vittozzi (1990). Multiple activation of chloroform in hepatic microsomes from un-induced B6C3F1 mice. Toxicol. Appl. Pharmacol., 104, 496-503.
42. S. Gemma, P. Ade, M. Sbraccia, E. Testai, and L. Vittozzi (1996). In vitro quantitative determination of phospholipid adducts of chloroform intermediates in hepatic and renal microsomes from different rodent strains. Environ. Toxicol. Pharmacol., 2, 233-242.
43. E. L. Docks and G. Krishna (1976). The role of gluthatione in chloroform-induced hepatotoxicity. Exp. Mol. Pathol., 24, 13-22.
44. J. H. Smith, K. Maita, S. D. Sleight, and J. B. Hook (1983). Mechanism of chloroform nephrotoxicity: I. Time course of chloroform toxicity in male and female mice. Toxicol. Appl. Pharmacol., 70, 467-479.
45. W. R. Hewitt, H. Miyajima, M. G. Cote, and G. L. Plaa (1980). Acute alteration of chloroform-induced hepato-and nephrotoxicity by N-hexane, methil-N-butyl ketone, and 2,5-hexanedione. Toxicol. Appl. Pharmacol., 53, 230-248.
46. E. M. Brown and W. R. Hewitt (1984). Dose-response relationships in ketone-induced potentiation of chloroform hepato- and nephrotoxicity. Toxicol. Appl. Pharmacol., 76, 437-453.
47. W. R. Hewitt, E. M. Brown, and G. L. Plaa (1983). Relationship between the carbon skeleton length of ketonic solvents and potentiation of chloroform-induced hepatotoxicity in rats. Toxicol. Lett., 16, 297-304.
48. I. Chu, D. C. Villeneuve, V. E. Secours, and G. C. Becking (1982). Toxicity of trihalomethanes: I. The acute and subacute toxicity of chloroform, bromochloromethane, chlorodibromomethane and bromoform in rats. J. Environ. Sci. Health, B17, 205-224.