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Volumn 9, Issue 3, 1996, Pages 659-666

Chemical and immunochemical comparison of protein adduct formation of four carboxylate drugs in rat liver and plasma

Author keywords

[No Author keywords available]

Indexed keywords

ANTICONVULSIVE AGENT; ANTILIPEMIC AGENT; CARBOXYLIC ACID DERIVATIVE; CLOFIBRATE; DIFLUNISAL; GLUCURONIDE; NONSTEROID ANTIINFLAMMATORY AGENT; VALPROIC ACID; ZOMEPIRAC;

EID: 0029863135     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx960017o     Document Type: Article
Times cited : (70)

References (49)
  • 1
    • 0021707968 scopus 로고
    • Properties of acyl glucuronides: Implications for studies of the pharmacokinetics and metabolism of acidic drugs
    • Faed, E. M. (1984) Properties of acyl glucuronides: Implications for studies of the pharmacokinetics and metabolism of acidic drugs. Drug Metab. Rev. 15, 1213-1249.
    • (1984) Drug Metab. Rev. , vol.15 , pp. 1213-1249
    • Faed, E.M.1
  • 2
    • 0026532030 scopus 로고
    • Acyl glucuronides revisited: Is the glucuronidation process a toxification as well as a detoxification mechanism?
    • Spahn-Langguth, H., and Benet, L. Z. (1992) Acyl glucuronides revisited: Is the glucuronidation process a toxification as well as a detoxification mechanism? Drug Metab. Rev. 24, 5-47.
    • (1992) Drug Metab. Rev. , vol.24 , pp. 5-47
    • Spahn-Langguth, H.1    Benet, L.Z.2
  • 3
    • 0027247569 scopus 로고
    • Acyl glucuronide conjugates: Reactive metabolites of nonsteroidal anti-inflammatory drugs
    • Dickinson, R. G. (1993) Acyl glucuronide conjugates: reactive metabolites of nonsteroidal anti-inflammatory drugs. Proc. Western Pharmacol. Soc. 36, 157-162.
    • (1993) Proc. Western Pharmacol. Soc. , vol.36 , pp. 157-162
    • Dickinson, R.G.1
  • 4
    • 0001590317 scopus 로고
    • Acyl glucuronides as chemically reactive intermediates
    • Fenselau, C. (1994) Acyl glucuronides as chemically reactive intermediates. Handb. Exp. Pharmacol. 112, 367-389.
    • (1994) Handb. Exp. Pharmacol. , vol.112 , pp. 367-389
    • Fenselau, C.1
  • 5
    • 0027154750 scopus 로고
    • Evidence for covalent binding of acyl glucuronides to serum albumin via an imine mechanism as revealed by tandem mass spectrometry
    • Ding, A., Ojingwa, J. C., McDonagh, A. F., Burlingame, A. L., and Benet, L. Z. (1993) Evidence for covalent binding of acyl glucuronides to serum albumin via an imine mechanism as revealed by tandem mass spectrometry. Proc. Natl. Acad. Sci. U.S.A. 90, 3797-3801.
    • (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 3797-3801
    • Ding, A.1    Ojingwa, J.C.2    McDonagh, A.F.3    Burlingame, A.L.4    Benet, L.Z.5
  • 6
    • 0028196565 scopus 로고
    • Studies on the reactivity of acyl glucuronides - VI. Modulation of reversible and covalent interaction of diflunisal acyl glucuronide and its isomers with human plasma protein in vitro
    • Williams, A. M., and Dickinson, R. G. (1994) Studies on the reactivity of acyl glucuronides - VI. Modulation of reversible and covalent interaction of diflunisal acyl glucuronide and its isomers with human plasma protein in vitro. Biochem. Pharmacol. 47, 457-467.
    • (1994) Biochem. Pharmacol. , vol.47 , pp. 457-467
    • Williams, A.M.1    Dickinson, R.G.2
  • 7
    • 0028968377 scopus 로고
    • Reactivity of tolmetin glucuronide with human serum albumin: Identification of binding sites and mechanisms of reaction by tandem mass spectrometry
    • Ding, A., Zia-Amirhosseini, P., McDonagh, A. F., Burlingame, A. L., and Benet, L. Z. (1995) Reactivity of tolmetin glucuronide with human serum albumin: Identification of binding sites and mechanisms of reaction by tandem mass spectrometry. Drug Metab. Dispos 23, 369-376.
    • (1995) Drug Metab. Dispos , vol.23 , pp. 369-376
    • Ding, A.1    Zia-Amirhosseini, P.2    McDonagh, A.F.3    Burlingame, A.L.4    Benet, L.Z.5
  • 8
    • 0022477143 scopus 로고
    • Irreversible binding of zomepirac to plasma protein in vitro and in vivo
    • Smith, P. C., McDonagh, A. F., and Benet, L. Z. (1986) Irreversible binding of zomepirac to plasma protein in vitro and in vivo. J. Clin. Invest. 77, 934-939.
    • (1986) J. Clin. Invest. , vol.77 , pp. 934-939
    • Smith, P.C.1    McDonagh, A.F.2    Benet, L.Z.3
  • 10
    • 0024851893 scopus 로고
    • Covalent binding of diflunisal and probenecid to plasma protein in humans: Persistence of the adducts in the circulation
    • McKinnon, G. E., and Dickinson, R. G. (1989) Covalent binding of diflunisal and probenecid to plasma protein in humans: persistence of the adducts in the circulation. Res. Commun. Chem. Pathol. Pharmacol. 66, 339-354.
    • (1989) Res. Commun. Chem. Pathol. Pharmacol. , vol.66 , pp. 339-354
    • McKinnon, G.E.1    Dickinson, R.G.2
  • 11
    • 0025095648 scopus 로고
    • Stereoselective binding of the glucuronide conjugates of carpofen enantiomers to human serum albumin
    • Iwakawa, S., Spahn, H., Benet, L. Z., and Lin, E. T. (1990) Stereoselective binding of the glucuronide conjugates of carpofen enantiomers to human serum albumin. Biochem. Pharmacol. 39, 949-953.
    • (1990) Biochem. Pharmacol. , vol.39 , pp. 949-953
    • Iwakawa, S.1    Spahn, H.2    Benet, L.Z.3    Lin, E.T.4
  • 12
    • 0025872002 scopus 로고
    • Stereoselective degradation of the fenoprofen acyl glucuronide enantiomers and irreversible binding to plasma protein
    • Volland, C., Sun, H., Dammeyer, J., and Benet, L. Z. (1991) Stereoselective degradation of the fenoprofen acyl glucuronide enantiomers and irreversible binding to plasma protein. Drug Metab. Dispos. 19, 1080-1086.
    • (1991) Drug Metab. Dispos. , vol.19 , pp. 1080-1086
    • Volland, C.1    Sun, H.2    Dammeyer, J.3    Benet, L.Z.4
  • 13
    • 0025916815 scopus 로고
    • In vivo covalent binding of clofibric acid to human plasma proteins and rat liver proteins
    • Sallustio, B. C., Knights, K. M., Roberts, B. J., and Zacest, R. (1991) In vivo covalent binding of clofibric acid to human plasma proteins and rat liver proteins. Biochem. Pharmacol. 42, 1421-1425.
    • (1991) Biochem. Pharmacol. , vol.42 , pp. 1421-1425
    • Sallustio, B.C.1    Knights, K.M.2    Roberts, B.J.3    Zacest, R.4
  • 14
    • 0026583192 scopus 로고
    • Studies on the reactivity of acyl glucuronides - III. Glucuronide-derived adducts of valproic acid and plasma protein and anti-adduct antibodies in humans
    • Williams, A. M., de Jersey, J., Worrall, S., and Dickinson, R. G. (1992) Studies on the reactivity of acyl glucuronides - III. Glucuronide-derived adducts of valproic acid and plasma protein and anti-adduct antibodies in humans. Biochem. Pharmacol. 43, 745-755.
    • (1992) Biochem. Pharmacol. , vol.43 , pp. 745-755
    • Williams, A.M.1    De Jersey, J.2    Worrall, S.3    Dickinson, R.G.4
  • 16
    • 0027502617 scopus 로고
    • Studies on the reactivity of acyl glucuronides - IV. Covalent binding of diflunisal to tissues of the rat
    • King, A. R., and Dickinson, R. G. (1993) Studies on the reactivity of acyl glucuronides - IV. Covalent binding of diflunisal to tissues of the rat. Biochem. Pharmacol. 45, 1043-1047.
    • (1993) Biochem. Pharmacol. , vol.45 , pp. 1043-1047
    • King, A.R.1    Dickinson, R.G.2
  • 17
    • 0027436783 scopus 로고
    • Studies on the reactivity of acyl glucuronides - V. Glucuronide-derived covalent binding of diflunisal to bladder tissue of rats and its modulation by urinary pH and β-glucuronidase
    • Dickinson, R. G., and King, A. R. (1993) Studies on the reactivity of acyl glucuronides - V. Glucuronide-derived covalent binding of diflunisal to bladder tissue of rats and its modulation by urinary pH and β-glucuronidase Biochem. Pharmacol. 46, 1175-1182.
    • (1993) Biochem. Pharmacol. , vol.46 , pp. 1175-1182
    • Dickinson, R.G.1    King, A.R.2
  • 18
    • 0027930364 scopus 로고
    • Metabolic activation and immunochemical localization of liver protein adducts of the nonsteroidal anti-inflammatory drug diclofenac
    • Hargus, S. J., Amouzedeh, H. R., Pumford, N. R., Myers, T. G., McCoy, S. C., and Pohl, L. R. (1994) Metabolic activation and immunochemical localization of liver protein adducts of the nonsteroidal anti-inflammatory drug diclofenac. Chem. Res. Toxicol. 7, 575-582.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 575-582
    • Hargus, S.J.1    Amouzedeh, H.R.2    Pumford, N.R.3    Myers, T.G.4    McCoy, S.C.5    Pohl, L.R.6
  • 19
    • 0028137859 scopus 로고
    • Selective protein adducts to membrane proteins in cultured rat hepatocytes exposed to diclofenac: Radiochemical and immunochemieal analysis
    • Kretz-Rommel, A., and Boelsterli, U. A. (1994) Selective protein adducts to membrane proteins in cultured rat hepatocytes exposed to diclofenac: Radiochemical and immunochemieal analysis. Mol. Pharmacol. 45, 237-244.
    • (1994) Mol. Pharmacol. , vol.45 , pp. 237-244
    • Kretz-Rommel, A.1    Boelsterli, U.A.2
  • 21
    • 0028951167 scopus 로고
    • Rat serum albumin modified by diflunisal acyl glucuronide is immunogenic in rats
    • Worrall, S., and Dickinson, R. G. (1995) Rat serum albumin modified by diflunisal acyl glucuronide is immunogenic in rats. Life Sci 56, 1921-1930.
    • (1995) Life Sci , vol.56 , pp. 1921-1930
    • Worrall, S.1    Dickinson, R.G.2
  • 22
    • 0023885175 scopus 로고
    • Three cases of diflunisal hypersensitivity
    • Cook, D. J., Achong, M. R., and Murphy, F. R. (1988) Three cases of diflunisal hypersensitivity. Can. Med. Assoc. J. 138, 1029-1030.
    • (1988) Can. Med. Assoc. J. , vol.138 , pp. 1029-1030
    • Cook, D.J.1    Achong, M.R.2    Murphy, F.R.3
  • 23
    • 0025604923 scopus 로고
    • Update of hepatotoxicity due to classes of drugs in common clinical use: Nonsteroidal drugs, anti-inflammatory drugs, antibiotics, antihypertensives, and cardiac and psychotropic agents
    • Zimmerman, H. J. (1990) Update of hepatotoxicity due to classes of drugs in common clinical use: nonsteroidal drugs, anti-inflammatory drugs, antibiotics, antihypertensives, and cardiac and psychotropic agents. Semin. Liver Dis. 10, 322-338.
    • (1990) Semin. Liver Dis. , vol.10 , pp. 322-338
    • Zimmerman, H.J.1
  • 24
    • 0023864274 scopus 로고
    • Valproate-associated hepatotoxicity and its biochemical mechanisms
    • Eadie, M J., Hooper, W. D., and Dickinson, R G. (1988) Valproate-associated hepatotoxicity and its biochemical mechanisms. Med. Toxicol 3, 85-106.
    • (1988) Med. Toxicol , vol.3 , pp. 85-106
    • Eadie, M.J.1    Hooper, W.D.2    Dickinson, R.G.3
  • 25
    • 0021961277 scopus 로고
    • Stability of acyl glucuronides in blood, plasma and urine: Studies with zomepirac
    • Smith, P. C , Hasegawa, J., Langendijk, P. N J., and Benet, L. Z. (1985) Stability of acyl glucuronides in blood, plasma and urine: studies with zomepirac. Drug Metab. Dispos. 13, 110-112.
    • (1985) Drug Metab. Dispos. , vol.13 , pp. 110-112
    • Smith, P.C.1    Hasegawa, J.2    Langendijk, P.N.J.3    Benet, L.Z.4
  • 26
    • 0025276462 scopus 로고
    • Reactivity of diflunisal acyl glucuronide in human and rat plasma and albumin solutions
    • Watt, J. A., and Dickinson, R G. (1990) Reactivity of diflunisal acyl glucuronide in human and rat plasma and albumin solutions. Biochem. Pharmacol. 39, 1067-1075.
    • (1990) Biochem. Pharmacol. , vol.39 , pp. 1067-1075
    • Watt, J.A.1    Dickinson, R.G.2
  • 27
    • 0024511940 scopus 로고
    • Aging of proteins: Immunological detection of a glucose-derived pyrrole formed during Maillard reaction in vivo
    • Hayase, F., Nagaraj, R. H., Miyata, S., Njoroge, F. G., and Monnier, V. M. (1989) Aging of proteins: Immunological detection of a glucose-derived pyrrole formed during Maillard reaction in vivo. J. Biol. Chem. 264, 3758-3764.
    • (1989) J. Biol. Chem. , vol.264 , pp. 3758-3764
    • Hayase, F.1    Nagaraj, R.H.2    Miyata, S.3    Njoroge, F.G.4    Monnier, V.M.5
  • 28
    • 0028893894 scopus 로고
    • Studies on the reactivity of acyl glucuronides - VIII. Generation of an antiserum for the detection of diflunisal-modified proteins in diflunisal-dosed rats
    • Williams, A. M., Worrall, S., De Jersey, J., and Dickinson, R. G. (1995) Studies on the reactivity of acyl glucuronides - VIII. Generation of an antiserum for the detection of diflunisal-modified proteins in diflunisal-dosed rats. Biochem. Pharmacol. 49, 209-217.
    • (1995) Biochem. Pharmacol. , vol.49 , pp. 209-217
    • Williams, A.M.1    Worrall, S.2    De Jersey, J.3    Dickinson, R.G.4
  • 29
    • 0018634361 scopus 로고
    • Disposition of valproic acid in the rat: Dose-dependent metabolism, distribution, enterohepatic recirculation and choleretic effect
    • Dickinson, R. G., Harland, R. C., Ilias, A. M., Rodgers, R. M., Kaufman, S. N., Lynn, R. K., and Gerber, N. (1979) Disposition of valproic acid in the rat: dose-dependent metabolism, distribution, enterohepatic recirculation and choleretic effect. J. Pharmacol. Exp. Ther. 211, 583-595.
    • (1979) J. Pharmacol. Exp. Ther. , vol.211 , pp. 583-595
    • Dickinson, R.G.1    Harland, R.C.2    Ilias, A.M.3    Rodgers, R.M.4    Kaufman, S.N.5    Lynn, R.K.6    Gerber, N.7
  • 30
    • 0024450037 scopus 로고
    • Reactivity considerations in the analysis of glucuronide and sulfate conjugates of diflunisal
    • Dickinson, R. G., and King, A. R. (1989) Reactivity considerations in the analysis of glucuronide and sulfate conjugates of diflunisal. Ther. Drug Monit. 11, 712-720.
    • (1989) Ther. Drug Monit. , vol.11 , pp. 712-720
    • Dickinson, R.G.1    King, A.R.2
  • 31
    • 0024495739 scopus 로고
    • Urinary excretion of valproate and some metabolites in chronically treated patients
    • Dickinson, R. G., Hooper, W. D., Dunstan, P. R., and Eadie, M. J. (1989) Urinary excretion of valproate and some metabolites in chronically treated patients. Ther. Drug Monit. 11, 127-133.
    • (1989) Ther. Drug Monit. , vol.11 , pp. 127-133
    • Dickinson, R.G.1    Hooper, W.D.2    Dunstan, P.R.3    Eadie, M.J.4
  • 32
    • 0020971356 scopus 로고
    • Enzyme-linked immunotransfer blot techniques (EITB) for studying the specificities of antigens and antibodies
    • Tsang, V. C., Peralta, J. M., and Simons, A. R. (1983) Enzyme-linked immunotransfer blot techniques (EITB) for studying the specificities of antigens and antibodies. Methods Enzymol. 92, 377-391.
    • (1983) Methods Enzymol. , vol.92 , pp. 377-391
    • Tsang, V.C.1    Peralta, J.M.2    Simons, A.R.3
  • 33
    • 0016915142 scopus 로고
    • Bile and urine as complementary pathways for the excretion of foreign organic compounds
    • Hirom, P. C., Millburn, P., and Smith, R. L. (1976) Bile and urine as complementary pathways for the excretion of foreign organic compounds. Xenobiotica 6, 55-64.
    • (1976) Xenobiotica , vol.6 , pp. 55-64
    • Hirom, P.C.1    Millburn, P.2    Smith, R.L.3
  • 34
    • 0021233529 scopus 로고
    • Mechanisms of bile formation, hepatic uptake and biliary excretion
    • Klaassen, C. D., and Watkins, J. B. (1984) Mechanisms of bile formation, hepatic uptake and biliary excretion. Pharmacol. Rev. 36, 1-67.
    • (1984) Pharmacol. Rev. , vol.36 , pp. 1-67
    • Klaassen, C.D.1    Watkins, J.B.2
  • 35
    • 0024818098 scopus 로고
    • Elimination of diflunisal as its acyl glucuronide, phenolic glucuronide and sulfate conjugates in bile-exteriorized and intact rats
    • Dickinson, R. G., King, A. R., and Verbeeck, R. K. (1989) Elimination of diflunisal as its acyl glucuronide, phenolic glucuronide and sulfate conjugates in bile-exteriorized and intact rats. Clin. Exp. Pharmacol. Physiol. 16, 913-924.
    • (1989) Clin. Exp. Pharmacol. Physiol. , vol.16 , pp. 913-924
    • Dickinson, R.G.1    King, A.R.2    Verbeeck, R.K.3
  • 36
    • 0020539448 scopus 로고
    • Species differences in the metabolic conjugation of clofibric acid and clofibrate in laboratory animals and man
    • Emudianughe, T. S., Caldwell, J., Sinclair, K. A., and Smith, R. L. (1983) Species differences in the metabolic conjugation of clofibric acid and clofibrate in laboratory animals and man. Drug Metab. Dispos. 11, 97-102.
    • (1983) Drug Metab. Dispos. , vol.11 , pp. 97-102
    • Emudianughe, T.S.1    Caldwell, J.2    Sinclair, K.A.3    Smith, R.L.4
  • 38
    • 0018942998 scopus 로고
    • The metabolism of zomepirac sodium II. Isolation and identification of the urinary metabolites in rat, mouse, rhesus monkey and man
    • Wu, W. N., Weaner, L. E., Kalbron, J., O'Neill, P. J., and Grindel, J. M. (1980). The metabolism of zomepirac sodium II. Isolation and identification of the urinary metabolites in rat, mouse, rhesus monkey and man. Drug Metab. Dispos. 8, 349-352.
    • (1980) Drug Metab. Dispos. , vol.8 , pp. 349-352
    • Wu, W.N.1    Weaner, L.E.2    Kalbron, J.3    O'Neill, P.J.4    Grindel, J.M.5
  • 39
    • 0021847237 scopus 로고
    • Acylation of albumin by 1-O-acyl glucuronides
    • Van Breeman, R. B., and Fenselau, C. (1985) Acylation of albumin by 1-O-acyl glucuronides. Drug Metab. Dispos. 13, 318-320
    • (1985) Drug Metab. Dispos. , vol.13 , pp. 318-320
    • Van Breeman, R.B.1    Fenselau, C.2
  • 40
    • 0023773044 scopus 로고
    • The acylation of proteins by xenobiotic amphipathic carboxylic acids in cultured rat hepatocytes
    • Hertz, R., and Bar-Tana, J. (1988) The acylation of proteins by xenobiotic amphipathic carboxylic acids in cultured rat hepatocytes. Biochem. J. 254, 39-44.
    • (1988) Biochem. J. , vol.254 , pp. 39-44
    • Hertz, R.1    Bar-Tana, J.2
  • 41
    • 0021932043 scopus 로고
    • Oxidation and glucuronidation of valproic acid in male rats - Influence of phenobarbital, 3-methylchloranthrane, β-naptholflavone and clofibrate
    • Heinemeyer, G , Nau, H., Hildebrandt, A. G., and Roots, I. (1985) Oxidation and glucuronidation of valproic acid in male rats - Influence of phenobarbital, 3-methylchloranthrane, β-naptholflavone and clofibrate. Biochem. Pharmacol. 34, 133-139.
    • (1985) Biochem. Pharmacol. , vol.34 , pp. 133-139
    • Heinemeyer, G.1    Nau, H.2    Hildebrandt, A.G.3    Roots, I.4
  • 42
    • 0024563425 scopus 로고
    • The covalent binding to protein of valproic acid and its hepatotoxic metabolite, 2-n-propyl-4-pentenoic acid, in rats and in isolated rat hepatocytes
    • Porubek, D. J., Grillo, M P., and Baillie, T. A. (1989) The covalent binding to protein of valproic acid and its hepatotoxic metabolite, 2-n-propyl-4-pentenoic acid, in rats and in isolated rat hepatocytes. Drug Metab. Dispos. 17, 123-130.
    • (1989) Drug Metab. Dispos. , vol.17 , pp. 123-130
    • Porubek, D.J.1    Grillo, M.P.2    Baillie, T.A.3
  • 43
    • 0028289068 scopus 로고
    • Metabolic activation of unsaturated derivatives of valproic acid. Identification of novel glutathione adducts formed through coenzyme A-dependent and -independent processes
    • Kassahun, K., Hu, P., Grillo, M. P., Davis, M. R., Jin, L., and Baillie, T. A. (1994) Metabolic activation of unsaturated derivatives of valproic acid. Identification of novel glutathione adducts formed through coenzyme A-dependent and -independent processes. Chem.-Biol Interact. 90, 253-275.
    • (1994) Chem.-Biol Interact. , vol.90 , pp. 253-275
    • Kassahun, K.1    Hu, P.2    Grillo, M.P.3    Davis, M.R.4    Jin, L.5    Baillie, T.A.6
  • 44
    • 0029026474 scopus 로고
    • Fluorinated analogues as mechanistic probes in valproic acid hepatotoxicity: Hepatic microvesicular steatosis and glutathione status
    • Tang, W., Borel, A. G., Fujimiya, T., and Abbott, F. S. (1995) Fluorinated analogues as mechanistic probes in valproic acid hepatotoxicity: hepatic microvesicular steatosis and glutathione status. Chem. Res. Toxicol. 8, 671-682.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 671-682
    • Tang, W.1    Borel, A.G.2    Fujimiya, T.3    Abbott, F.S.4
  • 45
    • 0027477180 scopus 로고
    • Immunochemical detection of liver protein adducts of the nonsteroidal anti-inflammatory drug diclofenac
    • Pumford, N. R., Myers, T. G., Davila, J. C., Highet, R. J., and Pohl, L. R. (1993) Immunochemical detection of liver protein adducts of the nonsteroidal anti-inflammatory drug diclofenac. Chem. Res. Toxicol. 6, 147-150.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 147-150
    • Pumford, N.R.1    Myers, T.G.2    Davila, J.C.3    Highet, R.J.4    Pohl, L.R.5
  • 46
    • 0028815559 scopus 로고
    • Covalent modification of rat Liver dipeptidyl peptidase IV (CD26) by the nonsteroidal anti-inflammatory drug diclofenac
    • Hargus, S. J., Martin, B. M., George, J. W., and Pohl, L. R. (1995) Covalent modification of rat Liver dipeptidyl peptidase IV (CD26) by the nonsteroidal anti-inflammatory drug diclofenac. Chem. Res. Toxicol. 8, 993-996.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 993-996
    • Hargus, S.J.1    Martin, B.M.2    George, J.W.3    Pohl, L.R.4
  • 47
    • 0027269444 scopus 로고
    • Diclofenac covalent protein binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes
    • Kretz-Rommel, A., and Boelsterli, U. A. (1993) Diclofenac covalent protein binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes. Toxicol. Appl. Pharmacol. 120, 155-161.
    • (1993) Toxicol. Appl. Pharmacol. , vol.120 , pp. 155-161
    • Kretz-Rommel, A.1    Boelsterli, U.A.2
  • 48
    • 0028143028 scopus 로고
    • Mechanism of covalent adduct formation of diclofenac to rat hepatic microsomal proteins. Retention of the glucuronic acid moiety in the adduct
    • Kretz-Rommel, A., and Boelsterli, U. A. (1994) Mechanism of covalent adduct formation of diclofenac to rat hepatic microsomal proteins. Retention of the glucuronic acid moiety in the adduct. Drug Metab. Dispos. 22, 956-961.
    • (1994) Drug Metab. Dispos. , vol.22 , pp. 956-961
    • Kretz-Rommel, A.1    Boelsterli, U.A.2
  • 49
    • 0023664739 scopus 로고
    • Molecular cloning and nucleotide sequence of cDNA encoding the entire precursor of rat liver medium chain acyl coenzyme A dehydrogenase
    • Matsubara, Y., Kraus, J. P., Ozasa, H., Glassberg, R., Finocchiaro, G., Ikeda, Y., Mole, J., Rosenberg, L. E., and Tanaka, K. (1987) Molecular cloning and nucleotide sequence of cDNA encoding the entire precursor of rat liver medium chain acyl coenzyme A dehydrogenase. J. Biol. Chem. 262, 10104-10108.
    • (1987) J. Biol. Chem. , vol.262 , pp. 10104-10108
    • Matsubara, Y.1    Kraus, J.P.2    Ozasa, H.3    Glassberg, R.4    Finocchiaro, G.5    Ikeda, Y.6    Mole, J.7    Rosenberg, L.E.8    Tanaka, K.9


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