메뉴 건너뛰기




Volumn 9, Issue 1, 1996, Pages 291-297

Mechanistic studies on the cytochrome P450-catalyzed dehydrogenation of 3-methylindole

Author keywords

[No Author keywords available]

Indexed keywords

CAPRA HIRCUS;

EID: 0030050265     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx9501187     Document Type: Article
Times cited : (84)

References (38)
  • 1
    • 0022340154 scopus 로고
    • Structure of the glutathione adduct of activated 3-methylindole indicates that an imine methide is the electrophilic intermediate
    • Nocerini, M. R., Yost, G. S., Carlson, J. R., Liberate, D. J , and Breeze, R. G. (1985) Structure of the glutathione adduct of activated 3-methylindole indicates that an imine methide is the electrophilic intermediate. Drug Metab. Dispos. 13, 690-694.
    • (1985) Drug Metab. Dispos. , vol.13 , pp. 690-694
    • Nocerini, M.R.1    Yost, G.S.2    Carlson, J.R.3    Liberate, D.J.4    Breeze, R.G.5
  • 2
    • 0022405156 scopus 로고
    • Glutathione adduct formation with microsomally activated metabolites of the pulmonary alkylating and cytotoxic agent, 3-methylindole
    • Nocerini, M. R., Carlson, J. R., and Yost, G. S. (1985) Glutathione adduct formation with microsomally activated metabolites of the pulmonary alkylating and cytotoxic agent, 3-methylindole. Toxicol. Appl. Pharmacol. 81, 75-84.
    • (1985) Toxicol. Appl. Pharmacol. , vol.81 , pp. 75-84
    • Nocerini, M.R.1    Carlson, J.R.2    Yost, G.S.3
  • 3
    • 0020694129 scopus 로고
    • Effect of glutathione status on covalent binding and pneumotoxicity of 3-methylindole in goats
    • Nocerini, M. R., Carlson, J. R., and Breeze, R. G. (1983) Effect of glutathione status on covalent binding and pneumotoxicity of 3-methylindole in goats. Life Sci. 32, 449-458.
    • (1983) Life Sci. , vol.32 , pp. 449-458
    • Nocerini, M.R.1    Carlson, J.R.2    Breeze, R.G.3
  • 5
    • 0025910664 scopus 로고
    • Isolation of a mercapturate adduct produced subsequent to glutathione conjugation of bioactivated 3-methylindole
    • Skiles, G. L., Smith, D. J., Appleton, M. L., Carlson, J. R., and Yost, G. S. (1991) Isolation of a mercapturate adduct produced subsequent to glutathione conjugation of bioactivated 3-methylindole. Toxicol. Appl. Pharmacol. 108, 531-537.
    • (1991) Toxicol. Appl. Pharmacol. , vol.108 , pp. 531-537
    • Skiles, G.L.1    Smith, D.J.2    Appleton, M.L.3    Carlson, J.R.4    Yost, G.S.5
  • 6
    • 0026668007 scopus 로고
    • Identification of a cystinyl adduct of oxidized 3-methylindole isolated from goat lung and human liver microsomal proteins
    • Ruangyuttikarn, W., Skiles, G. L., and Yost, G. S. (1992) Identification of a cystinyl adduct of oxidized 3-methylindole isolated from goat lung and human liver microsomal proteins. Chem. Res. Toxicol. 5, 713-719.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 713-719
    • Ruangyuttikarn, W.1    Skiles, G.L.2    Yost, G.S.3
  • 7
    • 0029875880 scopus 로고    scopus 로고
    • Metabolism of 3-methylindole by vaccinia-expressed cytochrome P450 enzymes: Correlation of 3-methyleneindolenine formation and protein-binding
    • in press
    • Thornton-Manning, J. R., Appleton, M. L., Gonzalez, F. J., and Yost, G. S. (1996) Metabolism of 3-methylindole by vaccinia-expressed cytochrome P450 enzymes: correlation of 3-methyleneindolenine formation and protein-binding. J. Pharmacol. Exp. Ther. (in press).
    • (1996) J. Pharmacol. Exp. Ther.
    • Thornton-Manning, J.R.1    Appleton, M.L.2    Gonzalez, F.J.3    Yost, G.S.4
  • 8
    • 0027484078 scopus 로고
    • Metabolism and bioactivation of 3-methylindole by Clara cells, alveolar macrophages and subcellular fractions from rabbit lungs
    • Thornton-Manning, J. R., Nichols, W. K., Manning, B. W., Skiles, G. L., and Yost, G. S. (1993) Metabolism and bioactivation of 3-methylindole by Clara cells, alveolar macrophages and subcellular fractions from rabbit lungs. Toxicol. Appl. Pharmacol. 122, 182-190.
    • (1993) Toxicol. Appl. Pharmacol. , vol.122 , pp. 182-190
    • Thornton-Manning, J.R.1    Nichols, W.K.2    Manning, B.W.3    Skiles, G.L.4    Yost, G.S.5
  • 9
    • 0024416367 scopus 로고
    • Mechanisms of 3-methylindole pneumotoxicity
    • Yost, G. S. (1989) Mechanisms of 3-methylindole pneumotoxicity. Chem. Res. Toxicol. 2, 273-279.
    • (1989) Chem. Res. Toxicol. , vol.2 , pp. 273-279
    • Yost, G.S.1
  • 10
    • 0024762304 scopus 로고
    • Contemporary issues in toxicology: Mechanisms of lung injury by systemicaily administered chemicals
    • Yost, G. S., Buckpitt, A. R., Roth, R. A., and McLemore, T. L. (1989) Contemporary issues in toxicology: Mechanisms of lung injury by systemicaily administered chemicals. Toxicol. Appl. Pharmacol. 101, 179-185.
    • (1989) Toxicol. Appl. Pharmacol. , vol.101 , pp. 179-185
    • Yost, G.S.1    Buckpitt, A.R.2    Roth, R.A.3    McLemore, T.L.4
  • 11
    • 0026591316 scopus 로고
    • Oligomerization of indole-3-carbinol in aqueous acid
    • Gross, K R., and Bjeldanes, L. F. (1992) Oligomerization of indole-3-carbinol in aqueous acid. Chem. Res. Toxicol. 5, 188-193.
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 188-193
    • Gross, K.R.1    Bjeldanes, L.F.2
  • 14
    • 0024429854 scopus 로고
    • Cytochrome P-450 catalysis: Radical intermediates and dehydrogenation reactions
    • Ortiz de Montellano, P. R. (1989) Cytochrome P-450 catalysis: radical intermediates and dehydrogenation reactions. Trends Pharmacol Sci. 10, 354-359.
    • (1989) Trends Pharmacol Sci. , vol.10 , pp. 354-359
    • Ortiz De Montellano, P.R.1
  • 15
    • 0027470428 scopus 로고
    • Evidence for specific base catalysis in N-dealkylation reactions catalyzed by cytochrome P-450 and chloroperosidase
    • Okazaki, O., and Guengerich, F. P. (1993) Evidence for specific base catalysis in N-dealkylation reactions catalyzed by cytochrome P-450 and chloroperosidase. J. Biol. Chem. 268, 1546-1552.
    • (1993) J. Biol. Chem. , vol.268 , pp. 1546-1552
    • Okazaki, O.1    Guengerich, F.P.2
  • 16
    • 0000311595 scopus 로고
    • The hydrogenolysis of 3-hydroxymethylindole and other indole derivatives with lithium aluminum hydride
    • Leete, E., and Marion, L. (1953) The hydrogenolysis of 3-hydroxymethylindole and other indole derivatives with lithium aluminum hydride. Can. J. Chem. 31, 775-784.
    • (1953) Can. J. Chem. , vol.31 , pp. 775-784
    • Leete, E.1    Marion, L.2
  • 18
    • 0018081845 scopus 로고
    • Measurement of cytochrome P-450 in the presence of large amounts of contaminating hemoglobin and methemoglobin
    • Johannesen, K. A. M., and DePierre, J. W. (1978) Measurement of cytochrome P-450 in the presence of large amounts of contaminating hemoglobin and methemoglobin. Anal. Biochem. 86, 725-732.
    • (1978) Anal. Biochem. , vol.86 , pp. 725-732
    • Johannesen, K.A.M.1    Depierre, J.W.2
  • 20
    • 0000837057 scopus 로고
    • Least squares analysis and simplification of multi-isotope mass spectra
    • Brauman, J. I. (1966) Least squares analysis and simplification of multi-isotope mass spectra. Anal. Chem. 38, 607-610.
    • (1966) Anal. Chem. , vol.38 , pp. 607-610
    • Brauman, J.I.1
  • 21
    • 0025257457 scopus 로고
    • The use of Brauman's least squares approach for the quantification of deuterated chlorophenols
    • Korzekwa, K., Howald, W. N., and Trager, W. F. (1990) The use of Brauman's least squares approach for the quantification of deuterated chlorophenols. Biomed. Mass. Spectrom. 19, 211-217.
    • (1990) Biomed. Mass. Spectrom. , vol.19 , pp. 211-217
    • Korzekwa, K.1    Howald, W.N.2    Trager, W.F.3
  • 22
    • 0025677739 scopus 로고
    • Preparation of labeled molecules by exchange with oxygen-18 water
    • Murphy, R. C., and Clay, K. L. (1990) Preparation of labeled molecules by exchange with oxygen-18 water. Methods Enzymol. 193, 338-348.
    • (1990) Methods Enzymol. , vol.193 , pp. 338-348
    • Murphy, R.C.1    Clay, K.L.2
  • 23
    • 3142639857 scopus 로고
    • Insights into deuterium isotope effects on the metabolism of steroid hormones and foreign compounds by cytochrome P-450 enzymes
    • Gillette, J. R. (1990) Insights into deuterium isotope effects on the metabolism of steroid hormones and foreign compounds by cytochrome P-450 enzymes. Life Sci. 48, 1-14.
    • (1990) Life Sci. , vol.48 , pp. 1-14
    • Gillette, J.R.1
  • 24
    • 0020345922 scopus 로고
    • Deuterium and tritium kinetic isotope effects on initial rates
    • Northrop, D. B. (1982) Deuterium and tritium kinetic isotope effects on initial rates. Methods Enzymol. 87, 607-625.
    • (1982) Methods Enzymol. , vol.87 , pp. 607-625
    • Northrop, D.B.1
  • 25
    • 0000497670 scopus 로고
    • Isotopically sensitive branching and its effect on the observed intramolecular isotope effects in cytochrome P-450 catalyzed reactions: A new method for the estimation of intrinsic isotope effects
    • Jones, J. P., Korzekwa, K. R., Rettie, A. E., and Trager, W. F. (1986) Isotopically sensitive branching and its effect on the observed intramolecular isotope effects in cytochrome P-450 catalyzed reactions: A new method for the estimation of intrinsic isotope effects. J. Am. Chem. Soc. 108, 7074-7078.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7074-7078
    • Jones, J.P.1    Korzekwa, K.R.2    Rettie, A.E.3    Trager, W.F.4
  • 26
    • 0024451771 scopus 로고
    • Theory for the observed isotope effects from enzymatic systems that form multiple products via branched reaction pathways: Cytochrome P-450
    • Korzekwa, K. R., Trager, W. F., and Gillette, J. R. (1989) Theory for the observed isotope effects from enzymatic systems that form multiple products via branched reaction pathways: Cytochrome P-450. Biochemistry 28, 9012-9018.
    • (1989) Biochemistry , vol.28 , pp. 9012-9018
    • Korzekwa, K.R.1    Trager, W.F.2    Gillette, J.R.3
  • 28
    • 0027412659 scopus 로고
    • Cytochrome P-450-mediated dehydrogenation of 2-n-propyl-2(E)-pentenoic acid, a pharmacologically-active metabolite of valproic acid, in rat liver microsomal preparations
    • Kassahun, K., and Baillie, T. A. (1993) Cytochrome P-450-mediated dehydrogenation of 2-n-propyl-2(E)-pentenoic acid, a pharmacologically-active metabolite of valproic acid, in rat liver microsomal preparations. Drug Metab. Dispos. 21, 242-248.
    • (1993) Drug Metab. Dispos. , vol.21 , pp. 242-248
    • Kassahun, K.1    Baillie, T.A.2
  • 30
    • 0025972135 scopus 로고
    • Oxidation of butylated hydroxytoluene to toxic metabolites, factors influencing hydroxylation and quinone methide formation by hepatic and pulmonary microsomes
    • Bolton, J. L., and Thompson, J. A. (1991) Oxidation of butylated hydroxytoluene to toxic metabolites, factors influencing hydroxylation and quinone methide formation by hepatic and pulmonary microsomes. Drug Metab. Dispos. 19, 467-472.
    • (1991) Drug Metab. Dispos. , vol.19 , pp. 467-472
    • Bolton, J.L.1    Thompson, J.A.2
  • 32
    • 0023928052 scopus 로고
    • Cytochrome P-450-catalyzed dehydrogenation of 1,4-dihydropyridines
    • Guengerich, F. P., and Böcker, R. H. (1988) Cytochrome P-450-catalyzed dehydrogenation of 1,4-dihydropyridines. J. Biol. Chem. 263, 8168-8175.
    • (1988) J. Biol. Chem. , vol.263 , pp. 8168-8175
    • Guengerich, F.P.1    Böcker, R.H.2
  • 33
    • 0026691008 scopus 로고
    • Molecular aspects of paracetamol-induced hepatotoxicity and its mechanism-based prevention
    • Vermeulen, N. P. E., Bessems, J. G. M., and Van de Straat, R. (1992) Molecular aspects of paracetamol-induced hepatotoxicity and its mechanism-based prevention. Drug Metab. Rev. 24, 367-407.
    • (1992) Drug Metab. Rev. , vol.24 , pp. 367-407
    • Vermeulen, N.P.E.1    Bessems, J.G.M.2    Van De Straat, R.3
  • 35
    • 0025248279 scopus 로고
    • Biotransformation of lovastatin II. in vitro metabolism by rat and mouse liver microsomes and involvement of cytochrome P-450 in dehydrogenation of lovastatin
    • Vyas, K. P., Kari, P. H., Prakash, S. R., and Duggan, D. E. (1990) Biotransformation of lovastatin II. In vitro metabolism by rat and mouse liver microsomes and involvement of cytochrome P-450 in dehydrogenation of lovastatin. Drug Metab. Dispos. 18, 218-222.
    • (1990) Drug Metab. Dispos. , vol.18 , pp. 218-222
    • Vyas, K.P.1    Kari, P.H.2    Prakash, S.R.3    Duggan, D.E.4
  • 36
    • 0024843596 scopus 로고
    • Deprotonation of tertiary amine cation radicals. A direct experimental approach
    • Dinnocenzo, J. P., and Banach, T. E. (1989) Deprotonation of tertiary amine cation radicals. A direct experimental approach. J. Am. Chem. Soc. 111, 8646-8653.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8646-8653
    • Dinnocenzo, J.P.1    Banach, T.E.2
  • 37
    • 0029091593 scopus 로고
    • Radical cation intermediates in N-dealkylation reactions
    • Guengerich, F. P., Okazaki, O , Seto, Y., and Macdonald, T. L. (1995) Radical cation intermediates in N-dealkylation reactions. Xenobiotica 25, 689-709.
    • (1995) Xenobiotica , vol.25 , pp. 689-709
    • Guengerich, F.P.1    Okazaki, O.2    Seto, Y.3    Macdonald, T.L.4
  • 38
    • 0028947612 scopus 로고
    • Mechanism of oxidative amine dealkylation of substituted N,N-dimethylanilines by cytochrome P-450: Application of isotope effect profiles
    • Karki, S. B., Dinnocenzo, J. P., Jones, J. P., and Korzekwa, K. R. (1995) Mechanism of oxidative amine dealkylation of substituted N,N-dimethylanilines by cytochrome P-450: application of isotope effect profiles. J. Am. Chem. Soc. 117, 3657-3664.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 3657-3664
    • Karki, S.B.1    Dinnocenzo, J.P.2    Jones, J.P.3    Korzekwa, K.R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.