Covalent binding of acetaminophen to N-10-formyl-tetrahydrofolate dehydrogenase in mice

Journal of Pharmacology and Experimental Therapeutics

Volumn 280, Issue 1, 1997, Pages 501-505

  Pumford, Neil R ^a   Halmes, N Christine ^a   Martin, Brian M ^b   Cook, Robert J ^c   Wagner, Conrad ^c,d   Hinson, Jack A ^a  

^a UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

^c VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d VETERANS AFFAIRS MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROFOLATE REDUCTASE; PARACETAMOL;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; COVALENT BOND; DRUG METABOLISM; ENZYME INACTIVATION; ENZYME SUBSTRATE COMPLEX; LIVER TOXICITY; MALE; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PRIORITY JOURNAL; TOXICOKINETICS;

ACETAMINOPHEN; ANALGESICS, NON-NARCOTIC; ANIMALS; LIVER; MALE; MICE; MOLECULAR WEIGHT; OXIDOREDUCTASES ACTING ON CH-NH GROUP DONORS; PROTEIN BINDING;

EID: 0030892030     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. BANSAL, M. P., MUKHOPADHYAY, T., SCOTT, J., COOK, R. G., MUKHOPADHYAY, R. AND MEDINA, D.: DNA sequencing of a mouse liver protein that binds selenium: Implications for selenium's mechanism of action in cancer prevention. Carcinogenesis. 11: 2071-2073, 1990.
2. BARTOLONE, J. B., SPARKS, K., COHEN, S. D. AND KHAIRALLAH, E. A.: Immuno-chemical detection of acetaminophen-bound liver proteins. Biochem. pharmacol, 36: 1193-1196, 1987.
3. BARTOLONE, J. B., BIRGE, R. B., BULERA, S. J., BRUNO, M. K., NISHANIAN, E. V., COHEN S. D. AND KHAIRALLAH, E. A.: Purification, antibody production, and partial amino acid sequence of the 58-kDa acetaminophen-binding liver proteins. Toxicol. Appl. Pharmacol. 113: 19-29, 1992.
4. BLACK M., CORNELL, J. F., RABIN, L. AND SHACHTER, N.: Late presentation of acetaminophen hepatotoxicity. Digest. Dis. Sci. 27: 370-374, 1982.
5. BRADFORD, M. M.: A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72: 248-254, 1976.
6. BULERA, S. J., BIRGE, R. B., COHEN, S. D. AND KHAIRALLAH, E. A.: Identification of the mouse liver 44-kDa acetaminophen-binding protein as a subunit of glutamine synthetase. Toxicol. Appl. Pharmacol. 134: 313-320, 1995.
7. BURCHAM, P. C. AND HARMAN, A. W.: Effect of acetaminophen hepatotoxicity on hepatic mitochondrial and microsomal calcium contents in mice. Tpxicol. Lett. 44: 91-9, 1988.
8. CHAMPION. K. M., COOK, R. J., TOLLAKSEN, S. L. AND GIOMETTI, C. S.: Identification of a heritable deficiency of the folate-dependcnt enzyme 10-formyltetrahydrofolate dehydrogenase in mice. Proc. Natl. Acad. Sci. U.S.A. 91: 11338-11342, 1994.
9. COOK, R. J. AND WAGNER, C: Purification of rat liver folate-binding protein: Cytosol I. Methods Enzymol. 122: 251-255, 1986.
10. COOK, R. J., LLOYD, R. S. AND WAGNER, C: Isolation and characterization of cDNA clones for rat liver 10-formyltetrahydrofolate dehydrogenase. J. Biol. Chem. 266: 4965-4973, 1991.
11. COOK, R. J. AND WAGNER, C: Enzymatic activities of rat liver cytosol 10-formyltetrahydrofolate dehydrogenase. Arch. Biochem. Biophys. 321: 336-344, 1995.
12. DEVEREUX, J., HAEBERLI, P. AND SMITHIES, O.: A comprehensive set of sequence analysis programs for the VAX. Nucleic Acids Res. 12: 387-395, 1984.
13. GUPTA, S,. ROGERS, L. K. AND SMITH, C. V.: Inhibition of carbamyl phosphate synthetase I (CPS I) by hepatotoxic doses of acetaminophen (AP) in mice. Fund. Appl. Toxicol. 15: 153, 1995.
14. HALMES, N. C., HINSON, J. A., MARTIN, B. M. AND PUMFORD, N. R.: Glutamate dehydrogenase covalently binds to a reactive metabolite of acetaminophen. Chem. Res. Toxicol. 9: 541-546, 1996.
15. HINSON, J. A.: Biochemical toxicology of acetaminophen. Rev. Biochem. Toxicol. 2: 103-129, 1980.
16. HINSON, J. A., PUMFORD, N. R. AND ROBERTS, D. W.: Mechanisms of acetaminophen toxicity: Immunochemical detection of drug-protein adducts. Drug Metab. Rev. 27: 72-92, 1995.
17. JOLLOW, D. J., MITCHELL, J. R., POTTER, W. Z., DAVIS, D. C., GILLETTE, J. R. AND BRODIE, B. B.: Acetaminophen-induced hepatic necrosis. II. Role of covalent binding in vivo. J. Pharmacol. Exp. Ther. 187: 195-202, 1973.
18. LANDIN, J. S., COHEN, S. D. AND KHAIRALLAH, E. A.: Redox and the covalent binding of acetaminophen (APAP) to mitochondrial aldehyde dehydrogenase. Toxicol. Appl. Pharmacol. 141: 299-307, 1996.
19. LANFEAR, J., FLEMING, J., WALKER, M. AND HARRISON, P.: Different patterns of regulation of the genes encoding the closely related 56 kDa selenium- and acetaminophen-binding proteins in normal tissues and during carcmogenesis. Carcinogenesis 14: 335-340, 1993.
20. MACKENZIE, R. E. AND TAN, L. U. L.: Methylenetetrahydrofolate dehydrogenase-methenyl-tetrahydrofolate cyclohydroloase-formyltetrahydrofolate synthetase: a multifunctional protein from porcine liver. Methods Enzymol. 68: 609-615, 1980.
21. MARTIN, B. M. AND ELIASON, W. K.: Glycopeptidase F Treatment and amino acid sequence determination of glycoproteins immobilized on PVDF and its derivatives. In Techniques in Protein Chemistry II, ed. by J. J. Villafranca, pp. 191-196, Academic Press, San Diego, CA, 1991.
22. MIN, H., SHANE, B. AND STOKSTAD, E. L. R.: Identification of 10-formyltetrahydrofolate dehydrogenase-hydrolase as a major folate binding protein in liver cytosol. Biochim. Biophys. Acta 967: 348-353, 1988.
23. MITCHELL, J. R., JOLLOW, D. J., POTTER, W. Z., DAVIS, D. C., GILLETTE, J. R. AND BRODIE, B. B.: Acetaminophen-induced hepatic necrosis. I. Role of drug metabolism. J. Pharmcol. Exp. Ther. 187: 185-194, 1973.
24. PUMFORD, N. R., HINSON, J. A., POTTER, D. W., ROWLAND, K. L., BENSON, R. W. AND ROBERTS, D. W.: Immunochemical quantitation of 3-(cystein-S-yl)acetaminophen adducts in serum and liver proteins of acetaminophen-treated mice. J. Pharmacol. Exp. Ther. 248: 190-196, 1989.
25. PUMFORD, N. R., HINSON, J. A., BENSON, R. W. AND ROBERTS, D. W.: Immunoblot analysis of protein containing 3-(cystein-S-yl)acetaminophen adducts in serum and subcellular liver fractions from acetaminophen-treated mice. Toxicol. Appl. Pharmacol. 104: 521-532, 1990.
26. PUMFORD, N. R., MARTIN, B. M. AND HINSON, J. A.: A metabolite of acetaminophen covalently binds to the 56 kDa selenium binding protein. Biochem. Biophys. Res. Commun. 182: 1348-1355, 1992.
27. ROBERTS, D. W., PUMFORD, N. R., POTTER, D. W., BENSON, R. W. AND HINSON, J. A.: A sensitive immunochemical assay for acetaminophen-protein adducts. J. Pharmacol Exp. Ther. 241: 527-533, 1987.