The use of human in vitro metabolic parameters to explore the risk assessment of hazardous compounds: The case of ethylene dibromide

Toxicology and Applied Pharmacology

Volumn 143, Issue 1, 1997, Pages 56-69

  Ploemen, Jan Peter H T M ^a,f   Wormhoudt, Lars W ^b   Haenen, Guido R M M ^a   Oudshoorn, Martin J ^a   Commandeur, Jan N M ^b   Vermeulen, Nico P E ^b   De Waziers, Isabelle ^c   Beaune, Philippe H ^c   Watabe, Tadashi ^d   Van Bladeren, Peter J ^a,e  

^a TNO   (Netherlands)

^b VU UNIVERSITY AMSTERDAM   (Netherlands)

^c UNIVERSITÉ PARIS DESCARTES   (France)

^d TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^e WAGENINGEN UNIVERSITY   (Netherlands)

^f NV ORGANON   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DIBROMOETHANE; CYTOCHROME P450; GLUTATHIONE TRANSFERASE; ISOENZYME;

ARTICLE; CARCINOGENICITY; CONJUGATION; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME KINETICS; HUMAN; HUMAN TISSUE; IN VITRO STUDY; LIVER METABOLISM; METABOLIC PARAMETERS; METABOLISM; PREDICTION; RISK ASSESSMENT; TECHNIQUE;

EID: 0031106259     PISSN: 0041008X     EISSN: None     Source Type: Journal    
DOI: 10.1006/taap.1996.8004     Document Type: Article

References (66)

1. Andersen, M. E., Clewell III, H. J., Gargas, M. L., Smith, F. A., and Reitz, R. H. (1987). Physiologically based pharmacokinetics and risk assessment process for methylene chloride. Toxicol. Appl. Pharmacol. 87, 185-205.
2. Andersen, M. E., Clewell III, H. J., and Frederick, C. B. (1995). Applying simulation modeling to problems in toxicology and risk assessment - A short perspective. Toxicol. Appl. Pharmacol. 133, 181-187.
3. Arfellini, G., Bartoli, S., Colacci, A., Mazzullo, M., Galli, M. C., Prodi, G., and Grilli, S. (1984). In vivo and in vitro binding of 1,2-dibromoethane and 1,2-dichloroethane to macromolecules in rat and mouse organs. J. Cancer Res. Clin. Oncol. 108, 204-213.
4. Armstrong, R. N. (1991). Glutathione S-transferases: Reaction mechanism, structure, and function. Chem. Res. Toxicol. 4, 131-140.
5. Bäärnhielm, C., Dahlbäck, H., and Skanberg, I. (1986). In vivo pharmacokinetics of felodipine predicted from in vitro studies in rat, dog and man. Acta Pharmacol. Toxicol. 59, 113-122.
6. Berthou, F., Ratanasavanh, D., Riche, C., Picart, D., Voirin, T., and Guilouzo, A. (1989). Comparison of caffeine metabolism by slices, microsomes, and hepatocyte cultures from adult human liver. Xenobiotica 19, 401-410.
7. Bogaards, J. J. P., van Ommen, B., and van Bladeren, P. J. (1989). An improved method for the separation and quantification of glutathione S-transferase subunits in rat tissue using high-performance liquid chromatography. J. Chromatogr. 474, 435-440.
8. Brockmöller, J., Kerb, R., Drakoulis, N., Staffeldt, B., and Roots, I. (1994). Glutathione S-transferase M1 and its Variant A and B as host factors of bladder cancer susceptibility: A case control study. Cancer Res. 54, 4103-4111.
9. Clewell III, H. J. (1995). The application of physiologically based pharmacokinetic modeling in human health risk assessment of hazardous substances. Toxicol. Lett. 79, 207-217.
10. Edwards, K., Jackson, H., and Jones, A. R. (1970). A chemical interpretation through metabolic studies of the antifertility effects of ethylene dimethanesulphonate and ethylene dibromide. Biochem. Pharmacol. 19, 1783-1789.
11. Fiserova-Bergerova, V. (1995). Extrapolation of physiological parameters for physiologically based simulation models. Toxicol. Lett. 79, 77-86.
12. Fisher, J. W., Whittaker, T. A., Taylor, D. H., Clewell III, H. J., and Andersen, M. E. (1989). Physiologically based pharmacokinetic modeling of the pregnant rat: A multiroute exposure model for trichloroethylene and its metabolite, trichloroacetic acid. Toxicol. Appl. Pharmacol. 99, 395-414.
13. Fryer, A. A., Zhao, L., Alldersea, J., Pearson, W. R., and Strange, R. C. (1993). Use of site-directed mutagenesis of allele-specific PCR primers to identify the GSTM1 A, GSTM1 B, GSTM1 A,B and GSTM1 null polymorphisms at the glutathione S-transferase, GSTM1 locus. Biochem. J. 295, 313-315.
14. Gargas, M. L., Burgess, R. J., Voisard, D. E., Cason, G. H., and Andersen, M. E. (1989). Partition coefficients of low-molecular-weight volatile chemicals in various liquids and tissues. Toxicol. Appl. Pharmacol. 98, 87-99.
15. Guengerich, F. P., Kim, D.-H., 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.
16. Guengerich, F. P., and Turvy, C. G. (1991). Comparison of levels of several human microsomal cytochrome P-450 enzymes and epoxide hydrolase in normal and disease states using immunochemical analysis of surgical liver samples. J. Pharmacol. Exp. Ther. 256, 1189-1195.
17. Guengerich, F. P. (1994). Catalytic selectivity of human cytochrome P450 enzymes: Relevance to drug metabolism and toxicity. Toxicol. Lett. 70, 133-138.
18. Ha, H. R., Chen, J., Freiburghaus, A. U., and Follath, F. (1995). Metabolism of theophylline by cDNA-expressed human cytochromes P-450. Br. J. Clin. Pharm. 39, 321-326.
19. Habig, W. H., Pabst, M. J., and Jakoby, W. B. (1974). Glutathione S-transferases. The first step in mercapturic acid formation. J. Biol. Chem. 249, 7130-7139.
20. Hallier, E., Langhof, T., Dannappel, D., Leutbecher, M., Schröder, K., Goergens, H. W., Müller, A., and Bolt, H. M. (1993). Polymorphism of glutathione conjugation of methyl bromide, ethylene oxide and dichlbromethane in human blood: Influence on the induction of sister chromatid exchanges (SCE) in lymphocytes. Arch. Toxicol. 67, 173-178.
21. Hayes, K. A., Brennan, B., Chenery, R., and Houston, B. (1995). In vivo disposition of caffeine predicted from hepatic microsomal and hepatocyte data. Drug Metab. Dispos. 23, 349-353.
22. Hiratsuka, A., Okada, T., Nishiyama, T., Fujikawa, M., Ogura, K., Okuda, H., Watabe, T., and Watabe, T. (1994). Novel theta class glutathione S-transferase Yrs-Yrs' and Yrs'-Yrs' in rat liver cytosol: Their potent activity towards 5-sulfoxymethylchrysene, a reactive metabolite of the carcinogen 5-hydroxymethylchrysene. Biochem. Biophys. Res. Commun. 202, 278-284.
23. Houston, J. B. (1994a). Relevance of in vitro kinetic parameters to in vivo metabolism of xenobiotics. Toxic. In Vitro 8, 507-512.
24. Houston, J. B. (1994b). Utility of in vitro drug metabolism data in predicting in vivo metabolic clearance. Biochem. Pharmacol. 47, 1469-1479.
25. m values for the metabolism of isofenphos by P-450 liver enzymes in animals and human. Toxicol. Appl. Pharmacol. 120, 106-113.
26. Kremers, P., Beaune, P., Cresteil, T., De Graeve, J., Columelli, S., Leroux, J.-P., and Gielen, J. E. (1981). Cytochrome P-450 monooxygenase activities in human and rat liver microsomes. Eur. J. Biochem. 118, 599-606.
27. 7-guanyl)ethyl]glutathione, the major DNA adduct formed from 1,2-dibromoethane. Biochemistry 25, 2191-2198.
28. Leung, H.-W., and Paustenbach, D. J. (1995). Physiologically based pharmacokinetic and pharmacodynamic modeling in health risk assessment and characterization of hazardous substances. Toxicol. Lett. 79, 55-65.
29. Lin, J. H. (1995). Review. Species similarities and differences in pharmacokinetics. Drug Metab. Dispos. 23, 1008-1021.
30. Lo Bello, M., Petruzzelli, R., De Stefano, E., Tenedini, C., Barra, D., and Federici, G. (1990). Identification of a highly reactive sulphydryl group in human placental glutathione transferase by a site-directed fluorescent reagent. FEBS Lett. 263, 389-391.
31. Lowry, O. H., Rosebrough, N. J., Farr, A. L., and Ransdall, R. J. (1951). Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193, 265-275.
32. Mannervik, B., and Guthenberg, C. (1981). Glutathione transferase (human placenta). Methods Enzymol. 77, 231-235.
33. Mannervik, B. (1985). The isoenzymes of glutathione transferases. Adv. Enzymol. Rel. Areas Mol. Biol. 57, 357-417.
34. Medinsky, M. A. (1995). The application of physiologically based pharmacokinetic/pharmacodynamic (PBPK/PD) modeling to understanding the mechanism of action of hazardous substances. Toxicol. Lett. 79, 185-191.
35. Meyer, M. C., and Guttman, D. E. (1968). The binding of drugs by plasma proteins. J. Pharm. Sci. 57, 895-918.
36. Meyer, D. J., Coles, B., Pemble, S. E., Kilmore, K. S., Fraser, G. M., and Ketterer, B. (1991). Theta, a new class of glutathione transferases purified from rat and human. Biochem. J. 274, 409-414.
37. Miners, J. O., Veronese, M. E., and Birkett, D. J. (1994). Chapter 31. In vitro approaches for the prediction of human drug metabolism. Annu. Rep. Med. Chem. 29, 307-316.
38. Morimoto, M., Hagbjörk, A.-L., Nanji, A. A., Ingelman-Sundberg, M., Lindros, K. O., Fu, P. C., Albano, E., and French, S. W. (1993). Role of cytochrome P4502E1 in alcohol liver disease pathogenesis. Alcohol 10, 459-465.
39. National Toxicology Program (NTP) (1985). NTP technical report on the toxicology and carcinogenesis studies of dichloromethane in F-344/N rats and B6C3F1 mice (inhalation studies). NTP-TR-306 (board draft).
40. Newton, D. J., Wang, R. W., and Lu, A. Y. H. (1995). Cytochrome P450 inhibitors. Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab. Dispos. 23, 154-158.
41. Ogura, K., Nishiyama, T., Watabe, T., and Watabe, T. (1994). Isolation and characterization of the gene encoding rat class theta glutathione S-transferase subunit Yrs. Biochem. Biophys. Res. Commun. 205, 1250-1256.
42. Olson, W. A., Habermann, R. T., Weisburger, E. K., Ward, J. M., and Weisburger, J. H. (1973). Induction of stomach cancer in rats and mice by halogenated aliphatic fumigants. J. Natl. Cancer Inst. 51, 1993-1995.
43. Ostlund Farrants, A.-K., Meyer, D. J., Coles, B., Southan, C., Aitken, A., Johnson, P. J., and Ketterer, B. (1987). The separation of glutathione transferase subunits by using reverse-phase high-pressure liquid chromatography. Biochem. J. 245, 423-428.
44. Pemble, S., Schröder, K. R., Spencer, S. R., Meyer, D. J., Hallier, E., Bolt, H. M., Ketterer, B., and Taylor, J. B. (1994). Human glutathione S-transferase theta (GSTT1): cDNA cloning and the characterization of a genetic polymorphism. Biochem. J. 300, 271-276.
45. Ploemen, J. H. T. M., Bogaards, J. J. P., Veldink, G. A., van Ommen, B., Jansen, D. H. M., and van Bladeren, P. J. (1993). Isoenzyme selective irreversible inhibition of rat and human glutathione S-transferases by ethacrynic acid and two brominated derivatives. Biochem. Pharmacol. 45, 633-639.
46. Ploemen, J. H. T. M., Wormhoudt, L. W., van Ommen, B., Commandeur, J. N. M., Vermeulen, N. P. E., and van Bladeren, P. J. (1995). Polymorphism in the glutathione conjugation activity of human erythrocytes towards ethylene dibromide and 1,2-epoxy-3-(p-nitrophenoxy)-propane. Biochim. Biophys. Acta 1243, 469-476.
47. Powers, M. B., Voelker, R. W., Page, N. P., Weisburger, E. K., and Kraybill, H. F. (1975). Carcinogenicity of ethylene dibromide (EDB) and 1,2-dibromo-3-chloropropane (DBCP) after oral administration in rats and mice. Toxicol. Appl. Pharmacol. 33, 171.
48. Prasanna, H. R., Lu, M. H., Beland, F. A., and Hart, R. W. (1989). Inhibition of aflatoxin B1 binding to hepatic DNA by dehydroepiandrosterone in vivo. Carcinogenesis 10, 2197-2200.
49. Ramsey, J. C., Park, C. N., Ott, M. G., and Gehring, P. J. (1978). Carcinogenic risk assessment: ethylene dibromide. Toxicol. Appl. Pharmacol. 47, 411-414.
50. Ramsey, J. C., and Andersen, M. E. (1984). A physiologically based description of the inhalation pharmacokinetics of styrene in rats and humans. Toxicol. Appl. Pharmacol. 73, 159-175.
51. Shimada, T., Yamazaki, H., Mimura, M., Inui, Y., and Guengerich, F. P. (1994). Interindividual variations in human liver cytochrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: studies with liver microsomes of 30 japanese and 30 caucasians. J. Pharmacol. Exp. Ther. 270, 414-423.
52. Tamai, K., Satoh, K., Tsuchida, S., Hatayama, I., Maki, T., and Sato, K. (1990). Specific inactivation of glutathione S-transferases in class pi by SH-modifiers. Biochem. Biophys. Res. Commun. 167, 331-338.
53. Thier, R., Taylor, J. B., Pemble, S. E., Humphreys, W. G., Persmark, M., Ketterer, B., and Guengerich, F. (1993). Expression of mammalian glutathione S-transferases 5-5 in Salmonella typhimurium TA1535 leads to base-pair mutations upon exposure to dihalomethanes. Proc. Natl. Acad. Sci. USA 90, 8576-8580.
54. Valles, B., Schiller, D., Coassolo, P., De Sousa, G., Wyss, R., Jaeck, D., Viger-Chougnet, A., and Rahmani, R. (1995). Metabolism of mofarotene in hepatocytes and liver microsomes from different species. Drug Metab. Dispos. 23, 1051-1057.
55. van Bladeren, P. J., Hoogeterp, J. J., Breimer, D. D., and van der Gen, A. (1981a). The influence of disulfiram and other inhibitors of oxidative metabolism on the formation of 2-hydroxyethyl-mercapturic acid from 1,2-dibromoethane by the rat. Biochem. Pharmacol. 30, 2983-2987.
56. van Bladeren, P. J., Breimer, D. D., van Huijgevoort, J. A. T. C. M., Vermeulen, N. P. E., and van der Gen, A. (1981b). The metabolic formation of N-acetyl-S-2-hydroxyethyl-L-cysteine from tetradeutero-1,2-dibromoethane. Relative importance of oxidation and glutathione conjugation in vivo. Biochem. Pharmacol. 30, 2499-2502.
57. van Bree, L., Commandeur, J. N. M., Lambertz, L., Cornelissen, M., van Roon, M., Laterveen, H., and de Vries, J. (1990). Induction of drug metabolism by dihalogenated biphenyls. J. Biochem. Toxicol. 5, 57-62.
58. van Ommen, B., Bogaards, J. J. P., Peters, W. H. M., Blaauboer, B., and van Bladeren, P. J. (1990). Quantification of human hepatic glutathione S-transferases. Biochem. J. 269, 609-613.
59. Vos, R. M. E., Snoek, M. C., van Berkel, W. J. H., Müller, F., and van Bladeren, P. J. (1988). Differential induction of rat hepatic glutathione S-transferase isoenzymes by hexachlorobenzene and benzyl isothiocyanate: comparison with induction by phenobarbital and 3-methylcholantrene. Biochem. Pharmacol. 37, 1077-1082.
60. Ward, J. M., and Habermann, R. T. (1974a). Pathology of stomach cancer in rats and mice induced with the agricultural chemicals ethylene dibromide and dibromochloropropane. Lab. Invest. 30, 392.
61. Ward, J. M., and Habermann, R. T. (1974b). Pathology of stomach cancer in rats and mice induced with the agricultural chemicals ethylene dibromide and dibromochloropropane. Bull. Soc. Pharmacol. Environ. Pathol. 2, 10-11.
62. Wilkinson, G. R. (1987). Clearance approaches in pharmacology. Pharmacol. Rev. 39, 1-47.
63. Wolf, C. R. (1990). Metabolic factors in cancer susceptibility. Cancer Surveys 9, 437-473.
64. Wong, L. C. K., Winston, J. M., Hong, C. B., and Plotnick, H. (1982). Carcinogenicity and toxicity of 1,2-dibromoethane in the rat. Toxicol. Appl. Pharmacol. 63, 155-165.
65. Wormhoudt, L. W., Ploemen, J. H. T. M., de Waziers, I., Commandeur, J. N. M., Beaune, P. H., van Bladeren, P. J., and Vermeulen, N. P. E. Inter-individual variability in the oxidation of 1,2-dibromoethane. Use of heterologously expressed human cytochrome P450 and human liver microsomes. Chem. Biol. Inter, in press.
66. Yang, R. S. H., El-Masri, H. A., Thomas, R. S., Constan, A. A., and Tessari, J. D. (1995). The application of physiologically based pharmacokinetic/ pharmacodynamic (PBPK/PD) modeling for exploring risk assessment approaches of chemical mixtures. Toxicol. Lett. 79, 193-200.