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Volumn 326, Issue 2, 2008, Pages 657-671

Identification of the thiophene ring of methapyrilene as a novel bioactivation-dependent hepatic toxicophore

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOBENZOTRIAZOLE; ALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; CYTOCHROME P450 INHIBITOR; DRUG METABOLITE; GLUTATHIONE DERIVATIVE; METHAPYRILENE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SULFIDE; THIOL DERIVATIVE; THIOPHENE DERIVATIVE;

EID: 47949133634     PISSN: 00223565     EISSN: 15210103     Source Type: Journal    
DOI: 10.1124/jpet.107.135483     Document Type: Article
Times cited : (35)

References (40)
  • 1
    • 30344446981 scopus 로고    scopus 로고
    • Gene expression analysis of the hepatotoxicant methapyrilene in primary rat hepatocytes: An interlaboratory study
    • Beekman JM, Boess F, Hildebrand H, Kalkuhl A, and Suter L (2006) Gene expression analysis of the hepatotoxicant methapyrilene in primary rat hepatocytes: an interlaboratory study. Environ Health Perspect 114:92-99.
    • (2006) Environ Health Perspect , vol.114 , pp. 92-99
    • Beekman, J.M.1    Boess, F.2    Hildebrand, H.3    Kalkuhl, A.4    Suter, L.5
  • 2
    • 0035702199 scopus 로고    scopus 로고
    • Use of isotopes and LC-MS-ESI-TOF for mechanistic studies of tienilic acid metabolic activation
    • Belghazi M, Jean P, Poli S, Schmitter JM, Mansuy D, and Dansette PM (2001) Use of isotopes and LC-MS-ESI-TOF for mechanistic studies of tienilic acid metabolic activation. Adv Exp Med Biol 500:139-144.
    • (2001) Adv Exp Med Biol , vol.500 , pp. 139-144
    • Belghazi, M.1    Jean, P.2    Poli, S.3    Schmitter, J.M.4    Mansuy, D.5    Dansette, P.M.6
  • 3
    • 0032978204 scopus 로고    scopus 로고
    • Opposite behaviors of reactive metabolites of tienilic acid and its isomer toward liver proteins: Use of specific anti-tienilic acid-protein adduct antibodies and the possible relationship with different hepatotoxic effects of the two compounds
    • Bonierbale E, Valadon P, Pons C, Desfosses B, Dansette PM, and Mansuy D (1999) Opposite behaviors of reactive metabolites of tienilic acid and its isomer toward liver proteins: use of specific anti-tienilic acid-protein adduct antibodies and the possible relationship with different hepatotoxic effects of the two compounds. Chem Res Toxicol 12:286-296.
    • (1999) Chem Res Toxicol , vol.12 , pp. 286-296
    • Bonierbale, E.1    Valadon, P.2    Pons, C.3    Desfosses, B.4    Dansette, P.M.5    Mansuy, D.6
  • 4
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford MM (1976) 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) Anal Biochem , vol.72 , pp. 248-254
    • Bradford, M.M.1
  • 5
    • 34548188505 scopus 로고    scopus 로고
    • Hydrogen isotope exchange at alkyl positions using Crabtree's catalyst and its application to the tritiation of methapyrilene
    • Bushby N and Killick DA (2007) Hydrogen isotope exchange at alkyl positions using Crabtree's catalyst and its application to the tritiation of methapyrilene. J Label Compd Radiopharm 50:519-520.
    • (2007) J Label Compd Radiopharm , vol.50 , pp. 519-520
    • Bushby, N.1    Killick, D.A.2
  • 6
    • 0023848551 scopus 로고
    • Fungal transformations of antihistamines: Metabolism of methapyrilene, thenyldiamine and tripelennamine to N-oxide and N-demethylated derivatives
    • Cerniglia CE, Hansen EB, Lambert KJ, Korfmacher WA, and Miller DW (1988) Fungal transformations of antihistamines: metabolism of methapyrilene, thenyldiamine and tripelennamine to N-oxide and N-demethylated derivatives. Xenobiotica 18:301-312.
    • (1988) Xenobiotica , vol.18 , pp. 301-312
    • Cerniglia, C.E.1    Hansen, E.B.2    Lambert, K.J.3    Korfmacher, W.A.4    Miller, D.W.5
  • 8
    • 27544482086 scopus 로고    scopus 로고
    • First evidence that cytochrome P450 may catalyze both S-oxidation and epoxidation of thiophene derivatives
    • Dansette PM, Bertho G, and Mansuy D (2005) First evidence that cytochrome P450 may catalyze both S-oxidation and epoxidation of thiophene derivatives. Biochem Biophys Res Commun 338:450-455.
    • (2005) Biochem Biophys Res Commun , vol.338 , pp. 450-455
    • Dansette, P.M.1    Bertho, G.2    Mansuy, D.3
  • 9
    • 0026989166 scopus 로고
    • Evidence for thiophene-S-oxide as a primary reactive metabolite of thiophene in vivo: Formation of a dihydrothiophene sulfoxide mercapturic acid
    • Dansette PM, Thang DC, el Amri H, and Mansuy D (1992) Evidence for thiophene-S-oxide as a primary reactive metabolite of thiophene in vivo: formation of a dihydrothiophene sulfoxide mercapturic acid. Biochem Biophys Res Commun 186:1624-1630.
    • (1992) Biochem Biophys Res Commun , vol.186 , pp. 1624-1630
    • Dansette, P.M.1    Thang, D.C.2    el Amri, H.3    Mansuy, D.4
  • 10
    • 0015350818 scopus 로고
    • Optimal conditions for the kinetic assay of serum glutamate dehydrogenase activity at 37 degrees C
    • Ellis G and Goldberg DM (1972) Optimal conditions for the kinetic assay of serum glutamate dehydrogenase activity at 37 degrees C. Clin Chem 18:523-527.
    • (1972) Clin Chem , vol.18 , pp. 523-527
    • Ellis, G.1    Goldberg, D.M.2
  • 11
    • 33644665098 scopus 로고    scopus 로고
    • In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations in human liver microsomes: A comparison with SKF-525A
    • Emoto C, Murase S, Sawada Y, and Iwasaki K (2005) In vitro inhibitory effect of 1-aminobenzotriazole on drug oxidations in human liver microsomes: a comparison with SKF-525A. Drug Metab Pharmacokinet 20:351-357.
    • (2005) Drug Metab Pharmacokinet , vol.20 , pp. 351-357
    • Emoto, C.1    Murase, S.2    Sawada, Y.3    Iwasaki, K.4
  • 12
    • 1942486343 scopus 로고    scopus 로고
    • Characterization of glutathione conjugates of the remoxipride hydroquinone metabolite NCQ-344 formed in vitro and detection following oxidation by human neutrophils
    • Erve JC, Svensson MA, von Euler-Chelpin H, and Klasson-Wehler E (2004) Characterization of glutathione conjugates of the remoxipride hydroquinone metabolite NCQ-344 formed in vitro and detection following oxidation by human neutrophils. Chem Res Toxicol 17:564-571.
    • (2004) Chem Res Toxicol , vol.17 , pp. 564-571
    • Erve, J.C.1    Svensson, M.A.2    von Euler-Chelpin, H.3    Klasson-Wehler, E.4
  • 13
    • 77957179440 scopus 로고
    • Effects of methapyrilene on rat hepatic xenobiotic metabolizing enzymes and liver morphology
    • Graichen ME, Neptun DA, Dent JG, Popp JA, and Leonard TB (1985) Effects of methapyrilene on rat hepatic xenobiotic metabolizing enzymes and liver morphology. Fundam Appl Toxicol 5:165-174.
    • (1985) Fundam Appl Toxicol , vol.5 , pp. 165-174
    • Graichen, M.E.1    Neptun, D.A.2    Dent, J.G.3    Popp, J.A.4    Leonard, T.B.5
  • 14
    • 0024505639 scopus 로고
    • Glutathione and lipid peroxide levels in rat liver following administration of methapyrilene and analogs
    • and LijinskyW
    • Hernandez L and LijinskyW(1989) Glutathione and lipid peroxide levels in rat liver following administration of methapyrilene and analogs. Chem Biol Interact 69:217-224.
    • (1989) Chem Biol Interact , vol.69 , pp. 217-224
    • Hernandez, L.1
  • 15
    • 0024472909 scopus 로고
    • Chemical structure and toxicity of diuretics in isolated hepatocytes
    • Higaki J, Harada H, Tonda K, and Hirata M (1989) Chemical structure and toxicity of diuretics in isolated hepatocytes. Pharmacol Toxicol 65:21-24.
    • (1989) Pharmacol Toxicol , vol.65 , pp. 21-24
    • Higaki, J.1    Harada, H.2    Tonda, K.3    Hirata, M.4
  • 18
    • 0022590781 scopus 로고
    • Metabolism of methapyrilene by rat-liver homogenate
    • Kammerer RC and Schmitz DA (1986) Metabolism of methapyrilene by rat-liver homogenate. Xenobiotica 16:671-680.
    • (1986) Xenobiotica , vol.16 , pp. 671-680
    • Kammerer, R.C.1    Schmitz, D.A.2
  • 19
    • 0023712146 scopus 로고
    • A comparative in vitro metabolic study of methaphenilene and pyribenzamine
    • Kammerer RC and Schmitz DA (1988) A comparative in vitro metabolic study of methaphenilene and pyribenzamine. Xenobiotica 18:1085-1096.
    • (1988) Xenobiotica , vol.18 , pp. 1085-1096
    • Kammerer, R.C.1    Schmitz, D.A.2
  • 20
    • 0023799991 scopus 로고
    • The in vivo metabolism of methapyrilene, a hepatocarcinogen, in the rat
    • Kammerer RC, Schmitz DA, Lampe MA, and Kloc K (1988) The in vivo metabolism of methapyrilene, a hepatocarcinogen, in the rat. Xenobiotica 18:869-881.
    • (1988) Xenobiotica , vol.18 , pp. 869-881
    • Kammerer, R.C.1    Schmitz, D.A.2    Lampe, M.A.3    Kloc, K.4
  • 22
    • 0023231656 scopus 로고
    • The metabolism and elimination of pyrilamine maleate in the rat
    • Kelly DW and Slikker W Jr (1987) The metabolism and elimination of pyrilamine maleate in the rat. Drug Metab Dispos 15:460-465.
    • (1987) Drug Metab Dispos , vol.15 , pp. 460-465
    • Kelly, D.W.1    Slikker Jr, W.2
  • 23
    • 0023571426 scopus 로고
    • Cytochrome P-450 dependent binding of methapyrilene to DNA in vitro
    • Lampe MA and Kammerer RC (1987) Cytochrome P-450 dependent binding of methapyrilene to DNA in vitro. Carcinogenesis 8:1525-1529.
    • (1987) Carcinogenesis , vol.8 , pp. 1525-1529
    • Lampe, M.A.1    Kammerer, R.C.2
  • 24
    • 0025184982 scopus 로고
    • Species differences in the metabolism and macromolecular binding of methapyrilene: A comparison of rat, mouse and hamster
    • Lampe MA and Kammerer RC (1990) Species differences in the metabolism and macromolecular binding of methapyrilene: a comparison of rat, mouse and hamster. Xenobiotica 20:1269-1280.
    • (1990) Xenobiotica , vol.20 , pp. 1269-1280
    • Lampe, M.A.1    Kammerer, R.C.2
  • 25
    • 0020051222 scopus 로고
    • Distribution of the liver carcinogen methapyrilene in Fischer rats and its interaction with macromolecules
    • Lijinsky W and Muschik GM (1982) Distribution of the liver carcinogen methapyrilene in Fischer rats and its interaction with macromolecules. J Cancer Res Clin Oncol 103:69-73.
    • (1982) J Cancer Res Clin Oncol , vol.103 , pp. 69-73
    • Lijinsky, W.1    Muschik, G.M.2
  • 26
    • 27744510766 scopus 로고    scopus 로고
    • Kinetics of tienilic acid bioactivation and functional generation of drug-protein adducts in intact rat hepatocytes
    • López-García MP, Dansette PM, and Coloma J (2005) Kinetics of tienilic acid bioactivation and functional generation of drug-protein adducts in intact rat hepatocytes. Biochem Pharmacol 70:1870-1882.
    • (2005) Biochem Pharmacol , vol.70 , pp. 1870-1882
    • López-García, M.P.1    Dansette, P.M.2    Coloma, J.3
  • 27
    • 0032464529 scopus 로고    scopus 로고
    • Structural requirements for hepatotoxicity of nonsteroidal anti-inflammatory drugs in isolated rat hepatocytes
    • Masubuchi Y, Saito H, and Horie T (1998) Structural requirements for hepatotoxicity of nonsteroidal anti-inflammatory drugs in isolated rat hepatocytes. J Pharmacol Exp Ther 287:208-213.
    • (1998) J Pharmacol Exp Ther , vol.287 , pp. 208-213
    • Masubuchi, Y.1    Saito, H.2    Horie, T.3
  • 28
    • 77957183013 scopus 로고
    • Cytotoxicity of xenobiotics in adult rat hepatocytes in primary culture
    • McQueen CA and Williams GM (1982) Cytotoxicity of xenobiotics in adult rat hepatocytes in primary culture. Fundam Appl Toxicol 2:139-144.
    • (1982) Fundam Appl Toxicol , vol.2 , pp. 139-144
    • McQueen, C.A.1    Williams, G.M.2
  • 29
    • 77957186623 scopus 로고
    • 1-Aminobenzotriazole-induced destruction of hepatic and renal cytochromes P450 in male Sprague-Dawley rats
    • Mugford CA, Mortillo M, Mico BA, and Tarloff JB (1992) 1-Aminobenzotriazole-induced destruction of hepatic and renal cytochromes P450 in male Sprague-Dawley rats. Fundam Appl Toxicol 19:43-49.
    • (1992) Fundam Appl Toxicol , vol.19 , pp. 43-49
    • Mugford, C.A.1    Mortillo, M.2    Mico, B.A.3    Tarloff, J.B.4
  • 30
    • 0142150012 scopus 로고    scopus 로고
    • Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen
    • O'Donnell JP, Dalvie DK, Kalgutkar AS, and Obach RS (2003) Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen. Drug Metab Dispos 31:1369-1377.
    • (2003) Drug Metab Dispos , vol.31 , pp. 1369-1377
    • O'Donnell, J.P.1    Dalvie, D.K.2    Kalgutkar, A.S.3    Obach, R.S.4
  • 31
    • 0032425968 scopus 로고    scopus 로고
    • Effects of induction and inhibition of cytochromes P450 on the hepatotoxicity of methapyrilene
    • Ratra GS, Cottrell S, and Powell CJ (1998a) Effects of induction and inhibition of cytochromes P450 on the hepatotoxicity of methapyrilene. Toxicol Sci 46:185-196.
    • (1998) Toxicol Sci , vol.46 , pp. 185-196
    • Ratra, G.S.1    Cottrell, S.2    Powell, C.J.3
  • 33
    • 0034671877 scopus 로고    scopus 로고
    • Methapyrilene hepatotoxicity is associated with increased hepatic glutathione, the formation of glucuronide conjugates, and enterohepatic recirculation
    • Ratra GS, Powell CJ, Park BK, Maggs JL, and Cottrell S (2000) Methapyrilene hepatotoxicity is associated with increased hepatic glutathione, the formation of glucuronide conjugates, and enterohepatic recirculation. Chem Biol Interact 129:279-295.
    • (2000) Chem Biol Interact , vol.129 , pp. 279-295
    • Ratra, G.S.1    Powell, C.J.2    Park, B.K.3    Maggs, J.L.4    Cottrell, S.5
  • 34
    • 0019792469 scopus 로고
    • Morphology of early changes in liver carcinogenesis induced by methapyrilene
    • Reznik-SchüllerHM and Lijinsky W (1981) Morphology of early changes in liver carcinogenesis induced by methapyrilene. Arch Toxicol 49:79-83.
    • (1981) Arch Toxicol , vol.49 , pp. 79-83
    • SchüllerHM, R.1    Lijinsky, W.2
  • 35
    • 0023636022 scopus 로고
    • A comparison of in vivo and in vitro metabolites of the H1-antagonist N,N-dimethyl-N′-2-pyridyl-N′-(2-thienylmethyl)-1,2-ethanediamine (methapyrilene) in the rat
    • Singer SS, Lijinsky W, Kratz LE, Castagnoli N, and Rose JE (1987) A comparison of in vivo and in vitro metabolites of the H1-antagonist N,N-dimethyl-N′-2-pyridyl-N′-(2-thienylmethyl)-1,2-ethanediamine (methapyrilene) in the rat. Xenobiotica 17:1279-1291.
    • (1987) Xenobiotica , vol.17 , pp. 1279-1291
    • Singer, S.S.1    Lijinsky, W.2    Kratz, L.E.3    Castagnoli, N.4    Rose, J.E.5
  • 36
    • 0029852501 scopus 로고    scopus 로고
    • Thiophene sulfoxides as reactive metabolites: Formation upon microsomal oxidation of a 3-aroylthiophene and fate in the presence of nucleophiles in vitro and in vivo
    • Valadon P, Dansette PM, Girault JP, Amar C, and Mansuy D (1996) Thiophene sulfoxides as reactive metabolites: formation upon microsomal oxidation of a 3-aroylthiophene and fate in the presence of nucleophiles in vitro and in vivo. Chem Res Toxicol 9:1403-1413.
    • (1996) Chem Res Toxicol , vol.9 , pp. 1403-1413
    • Valadon, P.1    Dansette, P.M.2    Girault, J.P.3    Amar, C.4    Mansuy, D.5
  • 37
    • 0027946067 scopus 로고
    • A microtiter plate assay for total glutathione and glutathione disulfide contents in cultured/isolated cells: Performance study of a new miniaturized protocol
    • Vandeputte C, Guizon I, Genestie-Denis I, Vannier B, and Lorenzon G (1994) A microtiter plate assay for total glutathione and glutathione disulfide contents in cultured/isolated cells: performance study of a new miniaturized protocol. Cell Biol Toxicol 10:415-421.
    • (1994) Cell Biol Toxicol , vol.10 , pp. 415-421
    • Vandeputte, C.1    Guizon, I.2    Genestie-Denis, I.3    Vannier, B.4    Lorenzon, G.5
  • 40
    • 0019813113 scopus 로고
    • Trapping of metabolically generated electrophilic species with cyanide ion: Metabolism of methapyrilene
    • Ziegler R, Ho B, and Castagnoli N (1981) Trapping of metabolically generated electrophilic species with cyanide ion: metabolism of methapyrilene. J Med Chem 24:1133-1138.
    • (1981) J Med Chem , vol.24 , pp. 1133-1138
    • Ziegler, R.1    Ho, B.2    Castagnoli, N.3


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