Immunochemical identification of hepatic protein adducts derived from estragole

Chemical Research in Toxicology

Volumn 11, Issue 8, 1998, Pages 863-872

  Wakazono, Hiroshi ^d   Gardner, Iain ^a   Eliasson, Erik ^e   Coughtrie, Michael W H ^b   Kenna, J Gerald ^c   Caldwell, John ^a  

^a IMPERIAL COLLEGE SCHOOL OF MEDICINE   (United Kingdom)

^b UNIVERSITY OF DUNDEE   (United Kingdom)

^c ASTRAZENECA   (United Kingdom)

^d ONO PHARMACEUTICAL CO   (Japan)

^e KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ESTRAGOLE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CONTROLLED STUDY; COVALENT BOND; DNA ADDUCT; HYDROXYLATION; IMMUNOCHEMISTRY; LIVER MICROSOME; METABOLIC ACTIVATION; NONHUMAN; PROTEIN ANALYSIS; PROTEIN BINDING; RAT; SULFATION;

ANIMALS; ANISOLES; CELL LINE; CELLS, CULTURED; CRICETINAE; FLAVORING AGENTS; IMMUNOBLOTTING; LIVER; MALE; PROTEINS; RATS; RATS, INBRED F344; SUBCELLULAR FRACTIONS;

ANIMALIA; ORYCTOLAGUS CUNICULUS; RODENTIA;

EID: 0031815205     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9702188     Document Type: Article

References (34)

1. Leung, A. Y. (1980) Encyclopaedia of Common Natural Ingredients Used in Food, Drugs and Cosmetics, John Wiley & Sons, New York.
2. Flavor and Extract Manufacturer's Association. (1978) Scientific Literature Review of Anisole and Derivatives in Flavor Usage, FEMA, Washington, DC.
3. Drinkwater, N. R., Miller, E. C., Miller, J. A., and Pilot, H. C. (1976) Hepatocarcinogenecity of estragole (1-allyl-4-methoxybenzene) and 1′- hydroxyestragole in the mouse and mutagenicity of l-acetoxyestragole in bacteria. J. Natl. Cancer Inst. 57, 1323-1331.
4. Miller, E. C., Swanson, A. B., Phillips, D. H., Fletcher, T. L., Liem, A., and Miller, J. A. (1983) Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. Cancer Res. 43, 1124-1134.
5. Phillips, D. H., Miller, J. A., Miller, E. C., and Adams, B. (1981) Structures of the DNA adducts formed in mouse liver after administration of the proximate hepatocarcinogen 1′-hydroxyestragole. Cancer Res. 41, 176-186.
6. 32P-Post-labeling analysis of DNA adducts formed in the livers of animals trreated with safrole, estragole and other naturally occurring alkenylbenzenes. I. Adult female CD-1 mice. Carcinogenesis 5, 1613-1622.
7. Chan, V. S. W., and Caldwell, J. (1992) Comparative induction of unscheduled DNA synthesis in cultured rat hepatocytes by allylbenzenes and their 1′-hydroxy metabolites. Food Chem. Toxicol. 30, 831-836.
8. Boberg, E. W., Miller, E. C., Miller, J. A., Poland, A., and Liem, A. (1983) Strong evidence from studies with brachymorphic mice and pentachlorophenol that 1′-sulfooxysafrole is the major ultimate electrophilic and carcinogenic metabolite of l′-hydroxysafrole in mouse liver. Cancer Res. 43, 5163-5173.
9. Swanson, A. B., Miller, E. C., and Miller, J. A. (1981) The sidechain epoxidation and hydroxylation of the hepatocarcinogens safrole and estragole and some related compounds by rat and mouse liver microsomes. Biochim. Biophys. Acta 673, 504-515.
10. Luo, G., and Guenthner, T. M. (1995) Metabolism of allylbenzene 2′, 3′-oxide and estragole 2′, 3′-oxide in the isolated perfused rat liver. J. Pharmacol. Exp. Ther. 272, 588-596.
11. Hinson, D. H., and Roberts, D. W. (1992) Role of covalent and noncovalent interactions in cell toxicity: effects on proteins. Annu. Rev. Pharmacol. Toxicol. 32, 471-450.
12. Bolesterli, U. A. (1993) Specific targets of covalent drug-protein interactions in hepatocytes and their toxicological significance in drug-induced liver injury. Drug Metab. Rev. 25, 395-451.
13. Gardner, I., Bergin, P., Stening, P., Kenna, J. G., and Caldwell, J. (1996) Immunodetection of covalently modified protein adducts in livers of rats treated with methyleugenol. Chem. Res. Toxicol. 9, 713-721.
14. Eliasson, E., and Kenna, J. G. (1996) Cytochrome P450 2E1 is a cell surface autoantigen in halothane hepatitis. Mol. Pharmacol. 50, 573-582.
15. Davis, M. T., and Preston, J. F. (1981) A simple modified carbodiimide method for conjugation of small-molecular-weight compounds to immunoglobulin G with minimal protein cross-linking. Anal. Biochem. 116, 402-407.
16. Moldeus, P., Hogberg, J., and Orrenius, S. (1978). Isolation and use of liver cells. Methods Enzymol. 52, 60-71.
17. Jones, A. L., Hagen, M., Coughtrie, M. W. H., Roberts, R. C., and Glatt, H. (1995) Human platelet phnolsulfotransferase; cDNA cloning, stable expression in V79 cells and identification of a novel allelic variant of the phenol-sulfating form. Biochem. Biophys. Res. Commun. 208, 855-862.
18. Fujiki, Y., Hubbard, A. L., Fowler, S., and Lazarow, P. B. (1982) Isolation of intracellular membranes by means of sodium carbonate treatment: application to endoplasmic reticulum. J. Cell Biol. 93, 97-102.
19. Nilsson, O. S., and Dallner, G. (1977) Enzyme and phospholipid asymmetry in liver microsomal membranes. J. Cell Biol. 72, 568-583.
20. Ito, A., and Sato, R. (1969) Proteolytic dissection of smoothsurfaced vesicles of liver microsomes. J. Cell Biol. 40, 179-189.
21. Freedman, R. (1989) Protein disulphide isomerase: multiple roles in the modification of nascent secretory proteins. Cell 57, 1069-1072.
22. DePierre, J. W., and Ernster, L. (1977) Enzyme topology of intracellular membranes. Annu. Rev. Biochem. 26, 1201-1262.
23. Kenna, J. G., Neuberger, J., and Williams, R. (1987) Identification by immunoblotting of three halothane-induced liver microsomal polypeptide antigens recognized by antibodies in sera from patients with halothane hepatitis. J. Pharmacol. Exp. Ther. 242, 733-741.
24. Wade, L. T., Kenna, J. G., and Caldwell, J. (1997) Immunochemical identification of mouse hepatic protein adducts derived from the nonsteroidal antiinflammatory drugs diclofenac, sulindac and ibuprofen. Chem. Res. Toxicol. 10, 546-555.
25. Anthony, A., Caldwell, J., Hutt, A. J., and Smith, R. L. (1987) Metabolism of estragole in rat and mouse and influence of dose size on excretion of the proximate carcinogen 1′-hydroxyestragole. Food Chem. Toxicol. 25, 799-806.
26. Falany, C. N. (1991) Molecular enzymology of human liver cytosolic sulfotransferases. Trends Pharmacol. Sci. 12, 255-259.
27. Weinshilboum, R. M., and Otterness, D. M. (1994) Sulfotransferase enzymes. In Conjugation-Deconjugation Reactions in Drug Metabolism and Toxicity (Kauffman, F. C., Ed.) Chapter 22, Vol. 112, pp 45-78, Springer-Verlag, Berlin, Heidelberg.
28. Kiehlbauch, C. C., Lam, Y. F., and Ringer, D. P. (1995) Homodimeric and heterodimeric aryl sulfotransferases catalyze the sulfuric acid esterification of N-hydroxy-2-acetylaminofluorene. J. Biol. Chem. 270, 18941-18947.
29. Weinshilboum, R. M., Otterness, D. M., Aksoy, I. A., Wood, T. C., Her, C., and Raftogianis, R. B. (1997) Sulfotransferase molecular biology: cDNAs and genes. FASEB J. 11, 3-14.
30. Howes, A. J., Chan, V. S. W., and Caldwell, J. (1990) Structurespecificity of the genotoxicity of some naturally occurring alkenylbenzenes determined by the unscheduled DNA synthesis assay in rat hepatocytes. Food. Chem. Toxicol. 28, 537-542.
31. Oude Elferinck, R. P. J., Meijer, D. K. F., Kuipers, F., Jansen, P. L. M., Groen, A. K., and Groothuis, G. M. M. (1995) Hepatobiliary secretion of organic compounds; molecular mechanisms of membrane transport. Biochim. Biophys. Acta 1241, 215-268.
32. Gautam, A., Ng, O.-C., and Boyer, J. L. (1987) Isolated rat hepatocyte couplets in short-term culture: structural characteristics and plasma membrane reorganization. Hepatology 7, 216-223.
33. Guillouzo, A. (1986) Use of isolated and cultured hepatocytes for xenobiotic metabolism and cytotoxicity studies. In Isolated and cultured hepatocytes (Guillouzo, A., and Guguen-Guillouzo, C., Eds.) Chapter 14, pp 313-332, John Libbey Eurotext Ltd./ INSERM, Paris.
34. Rubin, G. L., Sharp, S., Jones, A. L., Glatt, H., Mills, J. A., and Coughtrie, M. W. (1997) Design, production and characterization of antibodies discriminating between the phenol- and monoaminesulphating forms of human phenol sufltransferase. Xenobiotica 26, 1113-1119.