메뉴 건너뛰기




Volumn 152, Issue 1, 2005, Pages 25-36

In vitro metabolic fate of a novel structural class: Evidence for the formation of a reactive intermediate on a benzothiophene moiety

Author keywords

Arene oxide; Exact mass mass spectrometry; Hepatocytes; In vitro metabolism

Indexed keywords

BENZOTHIOPHENE DERIVATIVE; GLUTATHIONE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

EID: 17644374794     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbi.2005.01.005     Document Type: Conference Paper
Times cited : (7)

References (34)
  • 1
    • 4544295323 scopus 로고    scopus 로고
    • The use of radiolabeled compounds for ADME studies in discovery and exploratory development
    • P.H. Marathe, W.C. Shyu, and W.G. Humphreys The use of radiolabeled compounds for ADME studies in discovery and exploratory development Curr. Pharm. Des. 1 2004 2991 3008
    • (2004) Curr. Pharm. Des. , vol.1 , pp. 2991-3008
    • Marathe, P.H.1    Shyu, W.C.2    Humphreys, W.G.3
  • 2
    • 0041918439 scopus 로고    scopus 로고
    • Rapid liquid chromatography with tandem mass spectrometry-based screening procedures for studies on the biotransformation of drug candidates
    • C.L. Fernández-Metzler, K.G. Owens, T.A. Baillie, and R.C. King Rapid liquid chromatography with tandem mass spectrometry-based screening procedures for studies on the biotransformation of drug candidates Drug Metab. Dispos. 27 1999 32 40
    • (1999) Drug Metab. Dispos. , vol.27 , pp. 32-40
    • Fernández-Metzler, C.L.1    Owens, K.G.2    Baillie, T.A.3    King, R.C.4
  • 3
  • 4
    • 1642281756 scopus 로고    scopus 로고
    • Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development
    • D.C. Evans, A.P. Watt, D.A. Nicoll-Griffith, and T.A. Baillie Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development Chem. Res. Toxicol. 17 2004 3 16
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 3-16
    • Evans, D.C.1    Watt, A.P.2    Nicoll-Griffith, D.A.3    Baillie, T.A.4
  • 5
    • 0042831348 scopus 로고    scopus 로고
    • Screening for the potential of a drug candidate to cause idiosyncratic drug reactions
    • J. Uetrecht Screening for the potential of a drug candidate to cause idiosyncratic drug reactions Drug Discov. Today 8 2003 832 837
    • (2003) Drug Discov. Today , vol.8 , pp. 832-837
    • Uetrecht, J.1
  • 6
    • 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
    • A. Kretzrommel, and U.A. Boelsterli 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 1993 155 161
    • (1993) Toxicol. Appl. Pharmacol. , vol.120 , pp. 155-161
    • Kretzrommel, A.1    Boelsterli, U.A.2
  • 7
    • 0030938658 scopus 로고    scopus 로고
    • Covalent binding of a reactive metabolite derived from propranolol and its active metabolite 4-hydroxypropranolol to hepatic microsomal proteins of the rat
    • S. Narimatsu, T. Arai, T. Watanabe, Y. Masubuchi, T. Horie, T. Suzuki, T. Ishikawa, M. Tsutsui, Y. Kumagai, and A.K. Cho Covalent binding of a reactive metabolite derived from propranolol and its active metabolite 4-hydroxypropranolol to hepatic microsomal proteins of the rat Chem. Res. Toxicol. 10 1997 289 295
    • (1997) Chem. Res. Toxicol. , vol.10 , pp. 289-295
    • Narimatsu, S.1    Arai, T.2    Watanabe, T.3    Masubuchi, Y.4    Horie, T.5    Suzuki, T.6    Ishikawa, T.7    Tsutsui, M.8    Kumagai, Y.9    Cho, A.K.10
  • 8
    • 0033048697 scopus 로고    scopus 로고
    • Metabolic activation of diclofenac by human cytochrome P4503A4: Role of 5-hydroxydiclofenac
    • S. Shen, M.R. Marchick, M.R. Davis, G.A. Doss, and L.R. Pohl Metabolic activation of diclofenac by human cytochrome P4503A4: Role of 5-hydroxydiclofenac Chem. Res. Toxicol. 12 1999 214 222
    • (1999) Chem. Res. Toxicol. , vol.12 , pp. 214-222
    • Shen, S.1    Marchick, M.R.2    Davis, M.R.3    Doss, G.A.4    Pohl, L.R.5
  • 9
    • 0036784480 scopus 로고    scopus 로고
    • In vitro metabolism of R(+)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl] pyrrolo[1,2,3-de]1,4-benzoxazinyl]-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist
    • Q. Zhang, P. Ma, M. Iszard, R.B. Cole, W. Wang, and G. Wang In vitro metabolism of R(+)-[2,3-dihydro-5-methyl-3-[(morpholinyl)methyl]pyrrolo[1,2,3- de]1,4-benzoxazinyl]-(1-naphthalenyl) methanone mesylate, a cannabinoid receptor agonist Drug Metab. Dispos. 30 2002 1077 1086
    • (2002) Drug Metab. Dispos. , vol.30 , pp. 1077-1086
    • Zhang, Q.1    Ma, P.2    Iszard, M.3    Cole, R.B.4    Wang, W.5    Wang, G.6
  • 10
    • 0026503611 scopus 로고
    • An investigation of the formation of cytotoxic, protein-reactive and stable metabolites from carbamazepine in vitro
    • M. Pirmohamed, N.R. Kitteringham, T.M. Guenthner, A.M. Breckenridge, and B.K. Park An investigation of the formation of cytotoxic, protein-reactive and stable metabolites from carbamazepine in vitro Biochem. Pharm. 43 1992 1675 1682
    • (1992) Biochem. Pharm. , vol.43 , pp. 1675-1682
    • Pirmohamed, M.1    Kitteringham, N.R.2    Guenthner, T.M.3    Breckenridge, A.M.4    Park, B.K.5
  • 11
    • 0034605712 scopus 로고    scopus 로고
    • Idiosyncratic drug reactions: The reactive metabolite syndromes
    • S.R. Knowles, J. Uetrecht, and N.H. Shear Idiosyncratic drug reactions: the reactive metabolite syndromes Lancet 356 2000 1587 1591
    • (2000) Lancet , vol.356 , pp. 1587-1591
    • Knowles, S.R.1    Uetrecht, J.2    Shear, N.H.3
  • 12
    • 0026989166 scopus 로고
    • Evidence for thiophene-S-oxide as a primary reactive metabolite of thiophene in vivo: Formation of a dihydrothiophene sulfoxide mercapturic acid
    • P.M. Dansette, D.C. Thang, H. el Amri, and D. Mansuy Evidence for thiophene-S-oxide as a primary reactive metabolite of thiophene in vivo: formation of a dihydrothiophene sulfoxide mercapturic acid Biochem. Biophys. Res. Comm. 186 1992 1624 1630
    • (1992) Biochem. Biophys. Res. Comm. , vol.186 , pp. 1624-1630
    • Dansette, P.M.1    Thang, D.C.2    El Amri, H.3    Mansuy, D.4
  • 13
    • 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
    • P. Valadon, P.M. Dansette, J.P. Girault, C. Amar, and D. Mansuy 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 1996 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
  • 14
    • 0015510826 scopus 로고
    • Arene oxides and the NIH shift, toxictiy and carcinogenicity of aromatic compounds
    • J.W. Daly, D.M. Jerina, and B. Witkop Arene oxides and the NIH shift, toxictiy and carcinogenicity of aromatic compounds Experientia 28 1972 1129 1149
    • (1972) Experientia , vol.28 , pp. 1129-1149
    • Daly, J.W.1    Jerina, D.M.2    Witkop, B.3
  • 15
    • 0022796435 scopus 로고
    • The enzymatic conjugation of glutathione with bay-region diol-epoxides of benzo[a]pyrene, benz[a]anthracene and chrysene
    • I. Robertson, and B. Jernstrom The enzymatic conjugation of glutathione with bay-region diol-epoxides of benzo[a]pyrene, benz[a]anthracene and chrysene Carcinogenesis 7 1986 1633 1636
    • (1986) Carcinogenesis , vol.7 , pp. 1633-1636
    • Robertson, I.1    Jernstrom, B.2
  • 17
    • 0029926719 scopus 로고    scopus 로고
    • Bioactivation of carbamazepine in the rat in vivo; Evidence for the formation of reactive arene oxide(s)
    • S. Madden, J.L. Maggs, and B.K. Park Bioactivation of carbamazepine in the rat in vivo; Evidence for the formation of reactive arene oxide(s) Drug Metab. Dispos. 24 1996 469 479
    • (1996) Drug Metab. Dispos. , vol.24 , pp. 469-479
    • Madden, S.1    Maggs, J.L.2    Park, B.K.3
  • 20
    • 0030911121 scopus 로고    scopus 로고
    • Molecular structure and hepatotoxicity: Compared data about two closely related thiophene compounds
    • D. Mansuy Molecular structure and hepatotoxicity: compared data about two closely related thiophene compounds J. Hepatol. 26 Suppl. 2 1997 22 25
    • (1997) J. Hepatol. , vol.26 , Issue.2 SUPPL. , pp. 22-25
    • Mansuy, D.1
  • 22
    • 1342310597 scopus 로고    scopus 로고
    • In vitro metabolism of 2-acetylbenzothiophene: Relevance to zileuton hepatotoxicity
    • E.M. Joshi, B.H. Heasley, M.D. Chordia, and T.L. Macdonald In vitro metabolism of 2-acetylbenzothiophene: relevance to zileuton hepatotoxicity Chem. Res. Toxicol. 17 2004 137 143
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 137-143
    • Joshi, E.M.1    Heasley, B.H.2    Chordia, M.D.3    MacDonald, T.L.4
  • 24
    • 0022971080 scopus 로고
    • Pathways involved in the metabolism and activation of polycyclic hydrocarbons
    • P.L. Grover Pathways involved in the metabolism and activation of polycyclic hydrocarbons Xenobiotica 16 1986 915 931
    • (1986) Xenobiotica , vol.16 , pp. 915-931
    • Grover, P.L.1
  • 26
    • 0023756891 scopus 로고
    • Protective role of glutathione and glutathione transferases in mutagenesis and carcinogenesis
    • B. Ketterer Protective role of glutathione and glutathione transferases in mutagenesis and carcinogenesis Mutat. Res. 202 1988 343 361
    • (1988) Mutat. Res. , vol.202 , pp. 343-361
    • Ketterer, B.1
  • 27
  • 28
    • 0142232002 scopus 로고    scopus 로고
    • Detoxication pathways involving glutathione and epoxide hydrolase in the in vitro metabolism of chloroprene
    • T. Munter, L. Cottrell, B.T. Golding, and W.P. Watson Detoxication pathways involving glutathione and epoxide hydrolase in the in vitro metabolism of chloroprene Chem. Res. Toxicol. 16 2003 1287 1297
    • (2003) Chem. Res. Toxicol. , vol.16 , pp. 1287-1297
    • Munter, T.1    Cottrell, L.2    Golding, B.T.3    Watson, W.P.4
  • 29
    • 0034953219 scopus 로고    scopus 로고
    • Glutathione depletion in rat hepatocytes: A mixture toxicity study with α,β-unsaturated esters
    • A. Freidig, M. Hofhuis, I. van Holstijn, and J. Hermens Glutathione depletion in rat hepatocytes: a mixture toxicity study with α,β- unsaturated esters Xenobiotica 31 2001 295 307
    • (2001) Xenobiotica , vol.31 , pp. 295-307
    • Freidig, A.1    Hofhuis, M.2    Van Holstijn, I.3    Hermens, J.4
  • 30
    • 0030991141 scopus 로고    scopus 로고
    • Chemical and biological oxidation of thiophene: Preparation and complete characterization of thiophene S-oxide dimers and evidence for thiophene S-oxide as an intermediate in thiophene metabolism in vivo and in vitro
    • A. Treiber, P.M. Dansette, H. el Amri, J-P. Girault, D. Ginderow, J-P. Mornon, and D. Mansuy Chemical and biological oxidation of thiophene: Preparation and complete characterization of thiophene S-oxide dimers and evidence for thiophene S-oxide as an intermediate in thiophene metabolism in vivo and in vitro J. Am. Chem. Soc. 119 1997 1565 1571
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1565-1571
    • Treiber, A.1    Dansette, P.M.2    El Amri, H.3    Girault, J.-P.4    Ginderow, D.5    Mornon, J.-P.6    Mansuy, D.7
  • 31
    • 0000167768 scopus 로고
    • Thiophene S-oxides as new reactive metabolites: Formation by cytochrome P450 dependent oxidation and reaction with nucleophiles
    • D. Mansuy, P. Valadon, I. Erdelmeier, P. Lopez-Garcia, C. Amar, J.P. Girault, and P.M. Dansette Thiophene S-oxides as new reactive metabolites: Formation by cytochrome P450 dependent oxidation and reaction with nucleophiles J. Am. Chem. Soc. 113 1991 7825 7826
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7825-7826
    • Mansuy, D.1    Valadon, P.2    Erdelmeier, I.3    Lopez-Garcia, P.4    Amar, C.5    Girault, J.P.6    Dansette, P.M.7
  • 32
    • 0032481052 scopus 로고    scopus 로고
    • 4-benzo[b]thien- 2-yl)methanone and study of its reactivity towards sulfur- and oxygen-containing nucleophiles
    • 4-benzo[b]thien-2-yl)methanone and study of its reactivity towards sulfur- and oxygen-containing nucleophiles Tetrahedron 54 1998 14811 14824
    • (1998) Tetrahedron , vol.54 , pp. 14811-14824
    • Pouzet, P.1    Erdelmeier, I.2    Dansette, P.M.3    Mansuy, D.4
  • 33
    • 0028785979 scopus 로고
    • Identification of the human liver cytochrome P450 enzymes involved in the metabolism of zileuton (ABT-077) and its N-dehydroxylated metabolite
    • J.M. Machinist, M.D. Mayer, M.S. Shet, J.L. Ferrero, and A.D. Rodrigues Identification of the human liver cytochrome P450 enzymes involved in the metabolism of zileuton (ABT-077) and its N-dehydroxylated metabolite Drug Metab. Dispos. 23 1995 1163 1174
    • (1995) Drug Metab. Dispos. , vol.23 , pp. 1163-1174
    • MacHinist, J.M.1    Mayer, M.D.2    Shet, M.S.3    Ferrero, J.L.4    Rodrigues, A.D.5
  • 34
    • 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
    • E. Bonierbale, P. Valadon, C. Pons, B. Desfosses, P.M. Dansette, and D. Mansuy 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 1999 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


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.