메뉴 건너뛰기




Volumn 94, Issue 1, 1998, Pages 65-71

The acetaminophen regioisomer 3'-hydroxyacetanilide inhibits and covalently binds to cytochrome P450 2E1

Author keywords

3' Hydroxyacetanilide; Acetaminophen; Cytochrome P450 2E1; Protein covalent binding

Indexed keywords

CYTOCHROME P450; LIVER PROTEIN; METACETAMOL; PARACETAMOL DERIVATIVE;

EID: 0032536073     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0378-4274(97)00100-8     Document Type: Article
Times cited : (13)

References (29)
  • 3
    • 0023854490 scopus 로고
    • Ligand-dependent maintenance of ethanol-inducible cytochrome P-450 in primary rat hepatocyte cell cultures
    • Eliasson E., Johansson I., Ingelman-Sundberg M. Ligand-dependent maintenance of ethanol-inducible cytochrome P-450 in primary rat hepatocyte cell cultures. Biochem. Biophys. Res. Commun. 150:1988;436-443.
    • (1988) Biochem. Biophys. Res. Commun. , vol.150 , pp. 436-443
    • Eliasson, E.1    Johansson, I.2    Ingelman-Sundberg, M.3
  • 4
    • 0029996390 scopus 로고    scopus 로고
    • Immunochemical detection of protein adducts in mice treated with trichloroethylene
    • Halmes N.C., McMillan D.C., Oatis J.E. Jr, Pumford N.R. Immunochemical detection of protein adducts in mice treated with trichloroethylene. Chem. Res. Toxicol. 9:1996;451-456.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 451-456
    • Halmes, N.C.1    McMillan, D.C.2    Oatis J.E., Jr.3    Pumford, N.R.4
  • 5
    • 0029935673 scopus 로고    scopus 로고
    • Glutamate dehydrogenase covalently binds to a reactive metabolite of acetaminophen
    • Halmes N.C., Hinson J.A., Martin B.M., Pumford N.R. Glutamate dehydrogenase covalently binds to a reactive metabolite of acetaminophen. Chem. Res. Toxicol. 9:1996;541-546.
    • (1996) Chem. Res. Toxicol. , vol.9 , pp. 541-546
    • Halmes, N.C.1    Hinson, J.A.2    Martin, B.M.3    Pumford, N.R.4
  • 6
    • 0022589360 scopus 로고
    • The metabolism of 2- And 3-hydroxyacetanilide
    • Hamilton M., Kissinger P.T. The metabolism of 2- and 3-hydroxyacetanilide. Drug Metab. Dispos. 14:1986;5-12.
    • (1986) Drug Metab. Dispos. , vol.14 , pp. 5-12
    • Hamilton, M.1    Kissinger, P.T.2
  • 7
    • 0000855767 scopus 로고
    • Biochemical toxicology of acetaminophen
    • Hinson J.A. Biochemical toxicology of acetaminophen. Rev. Biochem. Toxicol. 2:1980;103-129.
    • (1980) Rev. Biochem. Toxicol. , vol.2 , pp. 103-129
    • Hinson, J.A.1
  • 8
    • 0023900010 scopus 로고
    • Ethanol-, fasting-, and acetone-inducible cytochromes P-450 in rat liver: Regulation and characteristics of enzymes belonging to the IIB and IIE gene subfamilies
    • Johansson I., Ekstrom G., Scholte B., Puzycki D., Jornvall H., Ingelman-Sundberg M. Ethanol-, fasting-, and acetone-inducible cytochromes P-450 in rat liver: regulation and characteristics of enzymes belonging to the IIB and IIE gene subfamilies. Biochemistry. 27:1988;1925-1934.
    • (1988) Biochemistry , vol.27 , pp. 1925-1934
    • Johansson, I.1    Ekstrom, G.2    Scholte, B.3    Puzycki, D.4    Jornvall, H.5    Ingelman-Sundberg, M.6
  • 9
    • 0001435384 scopus 로고
    • Metabolic reactions: Role of cytochrome P450 in the formation of reactive oxygen species
    • J.B. Schenkman, Greim H. Berlin: Springer
    • Kappas H. Metabolic reactions: role of cytochrome P450 in the formation of reactive oxygen species. Schenkman J.B., Greim H. Cytochrome P450. 105:1993;145-154 Springer, Berlin.
    • (1993) Cytochrome P450 , vol.105 , pp. 145-154
    • Kappas, H.1
  • 10
    • 0021806780 scopus 로고
    • Immunochemical evidence for induction of the alcohol-oxidizing cytochrome P-450 of rabbit liver microsomes by diverse agents: Ethanol, imidazole, trichloroethylene, acetone, pyrazole, and isoniazid
    • Koop D.R., Crump B.L., Nordblom G.D., Coon M.J. Immunochemical evidence for induction of the alcohol-oxidizing cytochrome P-450 of rabbit liver microsomes by diverse agents: ethanol, imidazole, trichloroethylene, acetone, pyrazole, and isoniazid. Proc. Natl. Acad. Sci. USA. 82:1985;4065-4069.
    • (1985) Proc. Natl. Acad. Sci. USA , vol.82 , pp. 4065-4069
    • Koop, D.R.1    Crump, B.L.2    Nordblom, G.D.3    Coon, M.J.4
  • 11
    • 0022494453 scopus 로고
    • Hydroxylation of p-nitrophenol by rabbit ethanol-inducible chrochrome P-450 isozyme 3a
    • Koop D.R. Hydroxylation of p-nitrophenol by rabbit ethanol-inducible chrochrome P-450 isozyme 3a. Mol. Pharmacol. 29:1986;399-404.
    • (1986) Mol. Pharmacol. , vol.29 , pp. 399-404
    • Koop, D.R.1
  • 13
    • 0030459693 scopus 로고    scopus 로고
    • Acetaminophen-induced hepatotoxicity: Analysis of total covalent binding versus specific binding to cysteine
    • Matthews A.M., Roberts D.W., Hinson J.A., Pumford N.R. Acetaminophen-induced hepatotoxicity: analysis of total covalent binding versus specific binding to cysteine. Drug Metab. Dispos. 24:1996;1192-1196.
    • (1996) Drug Metab. Dispos. , vol.24 , pp. 1192-1196
    • Matthews, A.M.1    Roberts, D.W.2    Hinson, J.A.3    Pumford, N.R.4
  • 14
    • 0031013960 scopus 로고    scopus 로고
    • Comparison of covalent binding of acetaminophen and the regioisomer 3'-hydroxyacetanilide to mouse liver protein
    • Matthews A.M., Hinson J.A., Roberts D.W., Pumford N.R. Comparison of covalent binding of acetaminophen and the regioisomer 3'-hydroxyacetanilide to mouse liver protein. Toxicol. Lett. 90:1997;77-82.
    • (1997) Toxicol. Lett. , vol.90 , pp. 77-82
    • Matthews, A.M.1    Hinson, J.A.2    Roberts, D.W.3    Pumford, N.R.4
  • 16
    • 0028950762 scopus 로고
    • A comparative study of mouse liver proteins arylated by reactive metabolites of acetaminophen and its nonhepatotoxic regioisomer, 3′-hydroxyacetanilide
    • Myers T.G., Dietz E.C., Anderson N.L., Khairallah E.A., Cohen S.D., Nelson S.D. A comparative study of mouse liver proteins arylated by reactive metabolites of acetaminophen and its nonhepatotoxic regioisomer, 3′-hydroxyacetanilide. Chem. Res. Toxicol. 8:1995;403-413.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 403-413
    • Myers, T.G.1    Dietz, E.C.2    Anderson, N.L.3    Khairallah, E.A.4    Cohen, S.D.5    Nelson, S.D.6
  • 17
    • 0018904278 scopus 로고
    • The pharmacology and toxicology of meta-substituted acetanilide: I. Acute toxicity of 3HAA in mice
    • Nelson E.B. The pharmacology and toxicology of meta-substituted acetanilide: I. Acute toxicity of 3HAA in mice. Res. Commun. Chem. Pathol. Pharmacol. 28:1980;447-456.
    • (1980) Res. Commun. Chem. Pathol. Pharmacol. , vol.28 , pp. 447-456
    • Nelson, E.B.1
  • 20
    • 0030927213 scopus 로고    scopus 로고
    • Protein targets of reactive intermediates of xenobiotics
    • Pumford N.R., Halmes N.C. Protein targets of reactive intermediates of xenobiotics. Annu. Rev. Pharmacol. Toxicol. 37:1997;91-117.
    • (1997) Annu. Rev. Pharmacol. Toxicol. , vol.37 , pp. 91-117
    • Pumford, N.R.1    Halmes, N.C.2
  • 21
    • 0025075052 scopus 로고
    • Immunoblot analysis of protein containing 3-(cystein-S-yl)acetaminophen adducts in serum and subcellular liver fractions from acetaminophen-treated mice
    • Pumford N.R., Hinson J.A., Benson R.W., 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. 104:1990;521-532.
    • (1990) Toxicol. Appl. Pharmacol. , vol.104 , pp. 521-532
    • Pumford, N.R.1    Hinson, J.A.2    Benson, R.W.3    Roberts, D.W.4
  • 22
    • 0030788713 scopus 로고    scopus 로고
    • Covalent binding of xenobiotics to specific proteins in the liver
    • Pumford N.R., Halmes N.C., Hinson J.A. Covalent binding of xenobiotics to specific proteins in the liver. Drug Metab. Rev. 29:1997;39-57.
    • (1997) Drug Metab. Rev. , vol.29 , pp. 39-57
    • Pumford, N.R.1    Halmes, N.C.2    Hinson, J.A.3
  • 23
    • 0024381948 scopus 로고
    • Investigations of the N-hydroxylation of 3'-hydroxyacetanilide, a non-hepatotoxic positional isomer of acetaminophen
    • Rashed M.S., Streeter A.J., Nelson S.D. Investigations of the N-hydroxylation of 3'-hydroxyacetanilide, a non-hepatotoxic positional isomer of acetaminophen. Drug Metab. Dispos. 17:1989;355-359.
    • (1989) Drug Metab. Dispos. , vol.17 , pp. 355-359
    • Rashed, M.S.1    Streeter, A.J.2    Nelson, S.D.3
  • 24
    • 0025113960 scopus 로고
    • Hepatic protein arylation, glutathione depletion, and metabolite profiles of acetaminophen and a non-hepatotoxic regioisomer, 3′-hydroxyacetanilide, in the mouse
    • Rashed M.S., Myers T.G., Nelson S.D. Hepatic protein arylation, glutathione depletion, and metabolite profiles of acetaminophen and a non-hepatotoxic regioisomer, 3′-hydroxyacetanilide, in the mouse. Drug Metab. Dispos. 18:1990;765-770.
    • (1990) Drug Metab. Dispos. , vol.18 , pp. 765-770
    • Rashed, M.S.1    Myers, T.G.2    Nelson, S.D.3
  • 25
    • 84863966825 scopus 로고
    • Acetaminophen structure-toxicity relationships: Why is 3HAA not hepatotoxic?
    • Roberts S.A., Jollow D.J. Acetaminophen structure-toxicity relationships: Why is 3HAA not hepatotoxic? Pharmacologist. 21:1979;259.
    • (1979) Pharmacologist , vol.21 , pp. 259
    • Roberts, S.A.1    Jollow, D.J.2
  • 26
    • 0018380382 scopus 로고
    • Acetaminophen structure-toxicity studies: In vivo covalent binding of a non-hepatotoxic analog, 3-hydroxyacetanilide
    • Roberts S.A., Jollow D.J. Acetaminophen structure-toxicity studies: In vivo covalent binding of a non-hepatotoxic analog, 3-hydroxyacetanilide. Fed. Proc. 38:1980;426.
    • (1980) Fed. Proc. , vol.38 , pp. 426
    • Roberts, S.A.1    Jollow, D.J.2
  • 27
    • 0025009272 scopus 로고
    • Acetaminophen structure-toxicity studies: In vivo covalent binding of a nonhepatotoxic analog, 3′-hydroxyacetanilide
    • Roberts S.A., Price V.F., Jollow D.J. Acetaminophen structure-toxicity studies: in vivo covalent binding of a nonhepatotoxic analog, 3′-hydroxyacetanilide. Toxicol. Appl. Pharmacol. 105:1990;195-208.
    • (1990) Toxicol. Appl. Pharmacol. , vol.105 , pp. 195-208
    • Roberts, S.A.1    Price, V.F.2    Jollow, D.J.3
  • 28
    • 0026546019 scopus 로고
    • Degradation of cytochrome P450 2E1: Selective loss after labilization of the enzyme
    • Tierney D.J., Haas A.L., Koop D.R. Degradation of cytochrome P450 2E1: selective loss after labilization of the enzyme. Arch. Biochem. Biophys. 293:1992;9-16.
    • (1992) Arch. Biochem. Biophys. , vol.293 , pp. 9-16
    • Tierney, D.J.1    Haas, A.L.2    Koop, D.R.3
  • 29
    • 0021192474 scopus 로고
    • Suicide substrates, mechanism-based enzyme inactivators: Recent developments
    • Walsh C.T. Suicide substrates, mechanism-based enzyme inactivators: recent developments. Annu. Rev. Biochem. 53:1984;493-535.
    • (1984) Annu. Rev. Biochem. , vol.53 , pp. 493-535
    • Walsh, C.T.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.