Effects of phenethyl isothiocyanate on acetaminophen metabolism and hepatotoxicity in mice

Toxicology and Applied Pharmacology

Volumn 144, Issue 2, 1997, Pages 306-314

  Li, Yan ^a,b   Wang, Er Jia ^a   Chen, Laishun ^a   Stein, Adam P ^a   Reuhl, Kenneth R ^a   Yang, Chung S ^a  

^a RUTGERS UNIVERSITY   (United States)

^b INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE AMINOTRANSFERASE; GLUTATHIONE; LACTATE DEHYDROGENASE; PARACETAMOL; PHENETHYL ISOTHIOCYANATE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; DRUG METABOLISM; HISTOPATHOLOGY; INTRAGASTRIC DRUG ADMINISTRATION; LIVER TOXICITY; MALE; MORTALITY; MOUSE; NONHUMAN;

EID: 0031172563     PISSN: 0041008X     EISSN: None     Source Type: Journal    
DOI: 10.1006/taap.1997.8134     Document Type: Article

References (51)

1. Beyeler, S., Testa, B., and Perrissoud, D. (1988). Flavonoids as inhibitors of rat liver monooxygenase activities. Biochem. Pharmacol 37, 1971-1979.
2. Burk, R. F., Hill, K. E., Hunt, R. W., and Martin, A. E. (1990). Isoniazid potentiation of acetaminophen hepatotoxicity in the rat and 4-methylpyrazole inhibition of it. Res. Commun. Chem. Pathol. Pharmacol. 69, 115-118.
3. Chung, F-L., Juchatz, A., Vitarius, J., and Hecht, S. S. (1984). Effects of dietary compounds on α-hydroxylation of N-nitrosopyrrolidine and N′-nitrosonornicotine in rat target tissues. Cancer Res. 44, 2924-2928.
4. Chung, F-L., Morse, M. A., and Eklind, K. I. (1992). New potential chemopreventive agents for lung carcinogenesis of tobacco-specific nitrosamine. Cancer Res. 52, 2719s-2722s.
5. Corcoran, G. B., Mitchell, J. R., Vaishnav, Y. N., and Horning E. C. (1980). Evidence that acetaminophen and N-hydroxyacetaminophen from a common arylating intermediate, N-acetyl-p-benzoquinone imine. Mol. Pharmacol. 18, 536-542.
6. Corcoran, G. B., Todd, E. L., Racz, W. J., Hughes, H., Smith, C. V., and Mitchell, J. R. (1984). Effects of N-acetylcysteine on the disposition and metabolism of acetaminophen in mice. J. Pharmacol. Exp. Ther. 232, 857-863.
7. Dahlin, D. C., Miwa, G. T., Lu, A. Y. H., and Nelson, S. D. (1984). N-Acetyl-p-benzoquinone imine: A cytochrome P-450-mediated oxidation product of acetaminophen. Proc. Natl. Acad. Sci. USA 81, 1327-1331.
8. Davies, M., Simmons, C. J., Harrison, N. G., and Williams, R. (1976). Paracetamol overdose in man: Relationship between pattern of urinary metabolites and severity of liver damage. Q. J. Med. 45, (178), 181-191.
9. Davies, M. H., and Schnell, R. C. (1991). Oltipraz-induced amelioration of acetaminophen hepatotoxicity in hamsters. II. Competitive shunt in metabolism via glucuronidation. Toxicol. Appl. Pharmacol. 109, 29-40.
10. Gregus, Z., Madhu, C., and Klaassen, C. D. (1988). Species variation in toxication and detoxication of acetaminophen in vivo: A comparative study of biliary and urinary excretion of acetaminophen metabolites. J. Pharmacol. Exp. Ther. 244, 91-98.
11. Guo, Z., Smith, T. J., Wang, E., Sadrieh, N., Ma, Q., Thomas P. E., and Yang, C. S. (1992). Effects of phenethyl isothiocyanate, a carcinogenesis inhibitor, on xenobiotic-metabolizing enzymes and nitrosamine metabolism in rats. Carcinogenesis 13, 2205-2210.
12. Guo, Z., Smith, T. J., Wang, E., Eklind, K. I., Chung, F-L., and Yang, C. S. (1993). Structure-activity relationships of arylalkyl isothiocyanates for the inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone metabolism and modulation of xenobiotic-metabolizing enzymes in rats and mice. Carcinogenesis 14, 1167-1173.
13. Harvison, P. J., Guengerich, F. P., Rashed, M. S., and Nelson, S. D. (1988). Cytochrome P450 isozyme selectivity in the oxidation of acetaminophen. Chem. Res. Toxicol. 1, 47-52.
14. Hinson, J. A., Nelson, S. D., and Mitchell, J. R. (1977). Studies on the microsomal formation of arylating metabolites of acetaminophen and phenacetin. Mol. Pharmacol. 13, 625-633.
15. Hjelle, J. J., and Klaassen, C. D. (1984). Glucuronidation and biliary excretion of acetaminophen in rats. J. Pharmacol. Exp. Ther. 228, 407-413.
16. Hu, J. J., Lee, M. J., Vapiwala, M., Reuhl, K., Thomas, P. E., and Yang, C. S. (1993). Sex-related differences in mouse renal metabolism and toxicity of acetaminophen. Toxicol. Appl. Pharmacol. 122, 16-29.
17. Ishizaki, H., Brady, J. F., Ning, S. M., and Yang, C. S. (1990). Effect of phenethyl isothiocyanate on microsomal N-nitrosodimethylamine metabolism and other monooxygenase activities. Xenobiotica 20, 255-264.
18. Jackson, J. E. (1982). Cimetidine protects against acetaminophen toxicity. Life Sci. 31, 31-35.
19. Jollow, D. J., Mitchell, J. R., Potter, W. Z., Davis, D. C., Gillette, J. R., and Brodie, B. B. (1973). Acetaminophen-induced hepatic necrosis II. Role of covalent binding in vivo. J. Pharmacol. Exp. Ther. 187, 195-202.
20. Jollow, D. J., Thorgeirsson, S. S., Potter, W. Z., Hashimoto, M., and Mitchell, J. R. (1974). Acetaminophen-induced hepatic necrosis. Pharmacology 12, 251-271.
21. Kadri, A. Z., Fisher, R., and Winterton, M. C. (1988). Cimetidine and paracetamol hepatotoxicity. Hum. Toxicol. 7, 205.
22. Lesser, P. B., Vietti, M. M., and Clark, W. D. (1986) Lethal enhancement of therapeutic doses of acetaminophen by alcohol. Dig. Dis. Sci. 31, 103-105.
23. Lin, M. C., Wang, E-J., Patten, C., Lee, M-J., Xiao, F., Reuhl, K. R., and Yang, C. S. (1996). Protective effect of diallyl sulfone against acetaminophen-induced hepatotoxicity in mice. J. Biochem. Toxicol. 11, 11-19.
24. Madhu, C., and Klaassen, C. D. (1991). Protective effect of pregnenolone-16α-carbonitrile on acetaminophen-induced hepatotoxicity in hamster. Toxicol. Appl. Pharmacol. 109, 305-313.
25. Madhu, C., Maziasz, T., and Klaassen, C. D. (1992). Effect of pregnenolone-16α-carbonitrile and dexamethasone on acetaminophen-induced hepatotoxicity in mice. Toxicol. Appl. Pharmacol. 115, 191-198.
26. Michael, C. S., and Frederick, W. O. (1983). Acetaminophen and its toxicity. J. Appl. Toxicol. 3, 96-111.
27. Mitchell, J. R., Jollow, D. J., Potter, W. Z., Gillette, J. R., and Brodie, B. B. (1973). Acetaminophen-induced hepatic necrosis. IV. Protective role of glutathione. J. Pharmacol. Exp. Ther. 187, 211-217.
28. Morgan, E. T., Koop, D. R., and Coon, M. J. (1983). Comparison of six rabbit liver cytochrome P450 isozymes in formation of a reactive metabolite of acetaminophen. Biochem. Biophys. Res. Commun. 112, 8-13.
29. Morse, M. A., Wang, C-X., Stoner, G. D., Mandal, S., Conran, P. B., Amin, S. G., Hecht, S. S., and Chung, F-L. (1989a). Inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA adduct formation and tumorigenicity in the lung of F344 rats by dietary phenethyl isothiocyanate. Cancer. Res. 49, 549-553.
30. 6-methylguanine formation, and metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in A/J mouse lung. Cancer Res. 49, 2894-2897.
31. Morse, M. A., Eklind, K. I., Amin, S. G., Hecht, S. S., and Chung, F-L. (1989c). Effects of alkyl chain length on the inhibition of NNK-induced lung neoplasia in A/J mice by arylalkyl isothiocyanates. Carcinogenesis 10, 1757-1759.
32. Morse, M. A., Reinhardt, J. C., Amin, S. G., Hecht, S. S., Stoner, G. D., and Chung, F-L. (1990). Effect of dietary aromatic isothiocyanates fed subsequent to the administration of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone on lung tumorigenicity in mice. Cancer Lett. 49, 225-230.
33. Nolan, C. M., Sandblom, R. E., Thummel, K. E., Slattery, J. T., and Nelson, S. D. (1994). Hepatotoxicity associated with acetaminophen usage in patients receiving multiple drug therapy for tuberculosis. Chest 105, 408-411.
34. Patten, C. J., Thomas, P. E., Guy, R. L., Lee, M. L., Gonzalez, F. J., Guengerich, F. P., and Yang, C. S. (1993). Cytochrome P450 enzymes involved in acetaminophen activation by rat and human liver microsomes and their kinetics. Chem. Res. Toxicol. 6, 511-518.
35. Patten, C. J., Ishizaki, H., Aoyama, T., Lee, M., Ning, S. M., Huang, W., Gonzalez, F. J., and Yang, C. S. (1992). Catalytic properties of the human cytochrome P450 2E1 produced by cDNA expression in mammalian cells. Arch. Biochem. Biophys. 299, 163-171.
36. Pessayre, D., Dolder, A., Artigou, J. Y., Wandscheer, J. C., Descatoire, V., Degott, C., and Benhamou, J. P. (1979). Effects of fasting on metabolite-mediated hepatotoxicity in the rat. Gastroenterology 77, 264-271.
37. Peterson, F. J., Holloway, D. E., Erickson, R. R., Duquette, P. H., McClain, C. L., and Holtzman, J. L. (1980). Ethanol induction of acetaminophen toxicity and metabolism. Life Sci. 27, 1705-1711.
38. Raucy, J. L., Lasker, J. M., Lieber, C. S., and Black, M. (1989). Acetaminophen activation by human liver cytochromes P450 IIE1 and P450 1A2. Arch. Biochem. Biophys. 271, 270-283.
39. Reiners, J. J., Cantu, A. R., Pavone, A., Smith, S. C., Gardner, C. R., and Laskin, D. J. (1990). Fluorescence assay for per-cell estimation of cytochrome P-450-dependent monooxygenase activities in keratinocyte suspensions and culture. Anal. Biochem. 188, 317-324.
40. Robert, D. W., Bucci, T. J., Benson, R. W., Warbritton, A. R., McRae, T. A., Pumford, N. R., and Hinson, J. A. (1991). Immunohistochemical localization and quantification of the 3-(cysteine-S-yl)-acetaminophen protein adduct in acetaminophen hepatotoxicity. Am. J. Pathol. 138, 359-371.
41. Rundgren, M., Porubek, D. J., Harvison, P. J., Cotgreave, I. A., Moldeus, P., and Nelson, S. D. (1988). Comparative cytotoxic effect of N-acetyl-p-benzoquinone imine and two dimethylated analogues. Mol. Pharmacol. 34, 566-572.
42. Sato, C., Matsuda, Y., and Lieber, C. S. (1981). Increased hepatotoxicity of acetaminophen after chronic ethanol consumption in the rat. Gastroenterology 80, 140-148.
43. Smith, T. J., Guo, Z. Y, Thomas, P. E., Chung, F-L., Morse, M. A., Eikind, K. I., and Yang, C. S. (1990). Metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in mouse lung microsomes and its inhibition by isothiocyanates. Cancer Res. 50, 6817-6822.
44. Smith, T. J., Guo, Z. Y., Li, Q., Ning, M., Thomas, P. E., and Yang, C. S. (1993). Mechanisms of inhibition of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone bioactivation in mouse by dietary phenethyl isothiocyanate. Cancer Res. 53, 3276-3282.
45. Sones, K., Heaney, R. K., and Fenwick, G. R. (1984). An estimate of the mean daily intake of glucosinolates from cruciferous vegetables in the UK. J. Sci. Food Agric. 35, 715-720.
46. Stoner, G. D., Morrissey, D. T., Heur, Y. H., Daniel, E. M., Galati, A. J., and Wagner, S. A. (1991). Inhibitory effects of phenethyl isothiocyanate on N-nitrosobenzylmethylamine carcinogenesis in the rat esophagus. Cancer Res. 51, 2063-2068.
47. Thomas, P. E., Reik, L. M., Ryan, D. E., and Levin, W. (1983). Induction of two immunochemically related rat liver cytochrome P-450 isozymes, cytochromes P450c and P-450d, by structurally diverse xenobiotics. J. Biol. Chem. 258, 4590-4598.
48. Thummel, K. E., Lee, C. A., Kunze, K. L., Nelson, S. D., and Slattery, J. T. (1993). Oxidation of acetaminophen to N-acetyl-p-aminobenzoquinone imine by human CYP 3A4. Biochem. Pharmacol. 45, 1563-1569.
49. Wang, E-J., Li, Y., Lin, M., Chen, L., Stein, A. P., Reuhl, K. R., and Yang, C. S. (1996). Protective effects of garlic and related organosulfur compounds on acetaminophen-induced hepatotoxicity in mice. Toxicol. Appl. Pharmacol. 136, 146-154.
50. Wattenberg, L. W. (1992). Inhibition of carcinogenesis by minor dietary constituents. Cancer Res. 52, 2085s-2091s.
51. Yang, C. S., Patten, C. J., Ishizaki, H., and Yoo, J-S. H. (1991). Induction, purification, and characterization of cytochrome P450IIE1. Methods Enzymol. 206, 595-603.