메뉴 건너뛰기




Volumn 10, Issue 9, 1997, Pages 1037-1044

Identification of enzymes involved in the metabolism of atrazine, terbuthylazine, ametryne, and terbutryne in human liver microsomes

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA NAPHTHOFLAVONE; AMETRYN; ATRAZINE; CYTOCHROME P450; DIETHYLDITHIOCARBAMIC ACID; FURAFYLLINE; GESTODENE; HERBICIDE; KETOCONAZOLE; MICROSOME ENZYME; QUINIDINE; SULFAPHENAZOLE; SULFOXIDE; TERBUTRYN; TERBUTYLAZINE; TRIAZINE DERIVATIVE; UNSPECIFIC MONOOXYGENASE;

EID: 0030773392     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx970081l     Document Type: Article
Times cited : (64)

References (43)
  • 1
    • 0000033768 scopus 로고
    • Herbicide resistance and crossresistance: Changes at three distinct sites in the herbicide binding protein
    • Erickson, J. M., Rahire, M., Rochaix, J.-D., and Mets, L. (1985) Herbicide resistance and crossresistance: changes at three distinct sites in the herbicide binding protein. Science 228, 204-207.
    • (1985) Science , vol.228 , pp. 204-207
    • Erickson, J.M.1    Rahire, M.2    Rochaix, J.-D.3    Mets, L.4
  • 3
    • 0342600829 scopus 로고
    • Depositionsmonitoring von Pflanzenschutzmitteln: Teil 2 Süddeutscher Raum
    • Gath, B., Jaeschke, W., Kubiak, R., Ricker, I., Schmider, F., and Zietz, E. (1993) Depositionsmonitoring von Pflanzenschutzmitteln: Teil 2 Süddeutscher Raum. (Monitoring of the disposition of pesticides: Part 2 southern part of Germany.) Nachrichtenbl. Dtsch. Pfanzenschutzdienst 45, 134-143.
    • (1993) Nachrichtenbl. Dtsch. Pfanzenschutzdienst , vol.45 , pp. 134-143
    • Gath, B.1    Jaeschke, W.2    Kubiak, R.3    Ricker, I.4    Schmider, F.5    Zietz, E.6
  • 4
    • 0001365104 scopus 로고
    • Herbicides
    • Hayes, W. J., and Lawas, E. R., Jr., Eds., Academic Press, New York
    • Stevens, J. T., and Summer, D. D. (1991) Herbicides. In Handbook of Pesticide Toxicology (Hayes, W. J., and Lawas, E. R., Jr., Eds.) pp 1381-1389, Academic Press, New York.
    • (1991) Handbook of Pesticide Toxicology , pp. 1381-1389
    • Stevens, J.T.1    Summer, D.D.2
  • 6
    • 0023676325 scopus 로고
    • Urinary metabolites as indicators for human exposure to atrazine
    • Ikonen, R., Kangas, J., and Savolainen, H. (1988) Urinary metabolites as indicators for human exposure to atrazine. Toxicol. Lett. 44, 109-112.
    • (1988) Toxicol. Lett. , vol.44 , pp. 109-112
    • Ikonen, R.1    Kangas, J.2    Savolainen, H.3
  • 8
    • 0024435936 scopus 로고
    • Testosterone metabolism in neuroendocrine organs in male rats under atrazine and deethylatrazine influence
    • Babic-Gojmerac, T., Kniewald, Z., and Kniewald, J. (1989) Testosterone metabolism in neuroendocrine organs in male rats under atrazine and deethylatrazine influence. J. Steroid Biochem. 33, 141-146.
    • (1989) J. Steroid Biochem. , vol.33 , pp. 141-146
    • Babic-Gojmerac, T.1    Kniewald, Z.2    Kniewald, J.3
  • 9
    • 0023635278 scopus 로고
    • Indirect influence of s-triazines on rat gonadotropic mechanism at early postnatal period
    • Kniewald, J., Peruzovic, M., Gojmerac, T., Milkovic, K., and Kniewald, Z. (1987) Indirect influence of s-triazines on rat gonadotropic mechanism at early postnatal period. J. Steroid Biochem. 27, 1095-1100.
    • (1987) J. Steroid Biochem. , vol.27 , pp. 1095-1100
    • Kniewald, J.1    Peruzovic, M.2    Gojmerac, T.3    Milkovic, K.4    Kniewald, Z.5
  • 10
    • 0029813484 scopus 로고    scopus 로고
    • In vitro metabolism of atrazine, terbuthylazine, ametryne and terbutryne in rats, pigs and humans
    • Lang, D., Criegee, D., Grothusen, A., Saalfrank, R. W., and Böcker, R. H. (1996) In vitro metabolism of atrazine, terbuthylazine, ametryne and terbutryne in rats, pigs and humans. Drug. Metab. Dispos. 24, 859-865.
    • (1996) Drug. Metab. Dispos. , vol.24 , pp. 859-865
    • Lang, D.1    Criegee, D.2    Grothusen, A.3    Saalfrank, R.W.4    Böcker, R.H.5
  • 11
    • 0022550688 scopus 로고
    • Oxidation of 4-aryl-and 4-alkyl-substituted 2,6-dimethyl-3,5-bis(alkoxycarbonyl)-1,4-dihydropyrídines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450
    • Böcker, R. H., and Guengerich, F. P. (1986) Oxidation of 4-aryl-and 4-alkyl-substituted 2,6-dimethyl-3,5-bis(alkoxycarbonyl)-1,4-dihydropyrídines by human liver microsomes and immunochemical evidence for the involvement of a form of cytochrome P-450. J. Med. Chem. 29, 1596-1603.
    • (1986) J. Med. Chem. , vol.29 , pp. 1596-1603
    • Böcker, R.H.1    Guengerich, F.P.2
  • 12
    • 0017385471 scopus 로고
    • Methoxyresorufin as a substrate for the fluorometric assay of insect microsomal O-dealkylases
    • Mayer, R. T., Jermyn, J. W., Burke, M. D., and Prough, R. A. (1977) Methoxyresorufin as a substrate for the fluorometric assay of insect microsomal O-dealkylases. Pestic. Biochem. Phys. 7, 349-354.
    • (1977) Pestic. Biochem. Phys. , vol.7 , pp. 349-354
    • Mayer, R.T.1    Jermyn, J.W.2    Burke, M.D.3    Prough, R.A.4
  • 13
    • 0021253492 scopus 로고
    • An alternative 7-ethoxyresorufin O-deethylase activity assay: A continuous visible spectrophotometric method for measurement of cytochrome P-450 monooxygenase activity
    • Klotz, A. V., Stegeman, J. J., and Walsh, C. (1984) An alternative 7-ethoxyresorufin O-deethylase activity assay: a continuous visible spectrophotometric method for measurement of cytochrome P-450 monooxygenase activity. Anal. Biochem. 140, 138-145.
    • (1984) Anal. Biochem. , vol.140 , pp. 138-145
    • Klotz, A.V.1    Stegeman, J.J.2    Walsh, C.3
  • 14
    • 4243278074 scopus 로고
    • Aminocarbonsäuren und deren Derivate
    • Georg Thieme Verlag, Stuttgart, New York
    • Krüger, G. (1985) Aminocarbonsäuren und deren Derivate. (Amino acids and their derivatives.) In Houben-Weyl, Bd E5, 4 Auflage, pp 538, Georg Thieme Verlag, Stuttgart, New York.
    • (1985) Houben-Weyl, Bd E5, 4 Auflage , vol.E5 , pp. 538
    • Krüger, G.1
  • 15
    • 0343490597 scopus 로고
    • Optically active 5,5′-disubstituted hydantoins
    • Sobotka, H., Holzman, F. M., and Kahn, J. (1932) Optically active 5,5′-disubstituted hydantoins. J. Am. Chem. Soc. 54, 4697-4702.
    • (1932) J. Am. Chem. Soc. , vol.54 , pp. 4697-4702
    • Sobotka, H.1    Holzman, F.M.2    Kahn, J.3
  • 16
    • 0000428146 scopus 로고
    • Analysis and characterization of enzymes
    • Hayes, A. W., Ed., Raven Press, New York
    • Guengerich, F. P. (1989) Analysis and characterization of enzymes. In Principles and Methods of Toxicology (Hayes, A. W., Ed.) pp 777-814, Raven Press, New York.
    • (1989) Principles and Methods of Toxicology , pp. 777-814
    • Guengerich, F.P.1
  • 17
    • 50449100139 scopus 로고
    • The carbon monoxid-binding pigment of liver microsomes
    • Omura, T., and Sato, R. (1964) The carbon monoxid-binding pigment of liver microsomes, J. Biol. Chem. 239, 2379-2385.
    • (1964) J. Biol. Chem. , vol.239 , pp. 2379-2385
    • Omura, T.1    Sato, R.2
  • 18
    • 0017184389 scopus 로고
    • A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding
    • Bradford, M. M. (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
  • 19
    • 0030854077 scopus 로고    scopus 로고
    • Baculovirus-mediated expression and purification of human FMO3: Catalytic, immunochemical and structural characterization
    • in press
    • Haining, R. L., Hunter, A. P., Sadeque, A. J. M., Philpot, R. M., and Rettie, A. E. (1997) Baculovirus-mediated expression and purification of human FMO3: catalytic, immunochemical and structural characterization. Drug Metab. Dispos. in press.
    • (1997) Drug Metab. Dispos.
    • Haining, R.L.1    Hunter, A.P.2    Sadeque, A.J.M.3    Philpot, R.M.4    Rettie, A.E.5
  • 20
    • 0022357068 scopus 로고
    • Ethoxy-, pentoxy-, and benzyloxyphenoxazones and homologues: A series of substrates to distinguish between different induced cytochromes P-450
    • Burke, M. D., Thompson, S., Elcombe, C. R., Halpert, J., Haaparanta, T., and Mayer, R. T. (1985) Ethoxy-, pentoxy-, and benzyloxyphenoxazones and homologues: A series of substrates to distinguish between different induced cytochromes P-450. Biochem. Pharmacol. 34, 3337-3345.
    • (1985) Biochem. Pharmacol. , vol.34 , pp. 3337-3345
    • Burke, M.D.1    Thompson, S.2    Elcombe, C.R.3    Halpert, J.4    Haaparanta, T.5    Mayer, R.T.6
  • 21
    • 0026066337 scopus 로고
    • Human embryonic cytochrome P450s: Phenoxazone ethers as probes for expression of functional isoforms during organogenesis
    • Lee, Q. P., Fantel, A. G., and Juchau, M. R. (1991) Human embryonic cytochrome P450s: Phenoxazone ethers as probes for expression of functional isoforms during organogenesis. Biochem. Pharmacol. 42, 2377-2385.
    • (1991) Biochem. Pharmacol. , vol.42 , pp. 2377-2385
    • Lee, Q.P.1    Fantel, A.G.2    Juchau, M.R.3
  • 22
    • 0025022689 scopus 로고
    • The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes
    • Yamano, S., Tatsuno, J., and Gonzalez, F. J. (1990) The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry 29, 1322-1329.
    • (1990) Biochemistry , vol.29 , pp. 1322-1329
    • Yamano, S.1    Tatsuno, J.2    Gonzalez, F.J.3
  • 23
    • 0021842439 scopus 로고
    • Catalytic and immunological comparison of coumarin 7-hydroxylation in different species
    • Kaipainen, P., Koivusaari, U., and Lang, M. (1985) Catalytic and immunological comparison of coumarin 7-hydroxylation in different species Comp. Biochem. Physiol. 81C, 293-296.
    • (1985) Comp. Biochem. Physiol. , vol.81 C , pp. 293-296
    • Kaipainen, P.1    Koivusaari, U.2    Lang, M.3
  • 25
    • 0028858604 scopus 로고
    • Highly sensitive and specific high-performance liquid chromatographic analysis of 7-hydroxywarfarin, a marker for human cytochrome P-4502C9 activity
    • Lang, D., and Böcker, R. (1995) Highly sensitive and specific high-performance liquid chromatographic analysis of 7-hydroxywarfarin, a marker for human cytochrome P-4502C9 activity. J. Chromatogr. B 672, 305-309.
    • (1995) J. Chromatogr. B , vol.672 , pp. 305-309
    • Lang, D.1    Böcker, R.2
  • 28
    • 0023258883 scopus 로고
    • High-performance liquid chromatographic assays for bufuralol 1′-hydroxylase, debrisoquine 4-hydroxylase, and dextromethorphan O-demethylase in microsomes and purified cytochrome P-450 isozymes of human liver
    • Kronbach, T., Mathys, D., Gut, M., Catin, T., and Meyer, U. A. (1987) High-performance liquid chromatographic assays for bufuralol 1′-hydroxylase, debrisoquine 4-hydroxylase, and dextromethorphan O-demethylase in microsomes and purified cytochrome P-450 isozymes of human liver. Anal. Biochem. 162, 24-32.
    • (1987) Anal. Biochem. , vol.162 , pp. 24-32
    • Kronbach, T.1    Mathys, D.2    Gut, M.3    Catin, T.4    Meyer, U.A.5
  • 30
    • 0022998708 scopus 로고
    • Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism
    • Guengerich, F. P., Martin, M. V., Beaune, P. H., Kremers, P., Wolff, T., and Waxman, D. J. (1986) Characterization of rat and human liver microsomal cytochrome P-450 forms involved in nifedipine oxidation, a prototype for genetic polymorphism in oxidative drug metabolism. J. Biol. Chem. 261, 5051-5060.
    • (1986) J. Biol. Chem. , vol.261 , pp. 5051-5060
    • Guengerich, F.P.1    Martin, M.V.2    Beaune, P.H.3    Kremers, P.4    Wolff, T.5    Waxman, D.J.6
  • 31
    • 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
  • 32
    • 0012109145 scopus 로고
    • Formation of an intermediate N-oxide in the oxidative demethylation of N,N-dimethylaniline catalyzed by liver microsomes
    • Ziegler, D. M., and Pettit, F. H. (1964) Formation of an intermediate N-oxide in the oxidative demethylation of N,N-dimethylaniline catalyzed by liver microsomes. Biochem. Biophys. Res. Commun. 15, 188-193.
    • (1964) Biochem. Biophys. Res. Commun. , vol.15 , pp. 188-193
    • Ziegler, D.M.1    Pettit, F.H.2
  • 33
    • 0029834386 scopus 로고    scopus 로고
    • A convenient method to discriminate between cytochrome P450 enzymes and flavin-containing monooxygenases in human liver microsomes
    • Grothusen, A., Hardt, J., Bräutigam, L., Lang, D., and Böcker, R. (1996) A convenient method to discriminate between cytochrome P450 enzymes and flavin-containing monooxygenases in human liver microsomes. Arch. Toxicol. 71, 64-71.
    • (1996) Arch. Toxicol. , vol.71 , pp. 64-71
    • Grothusen, A.1    Hardt, J.2    Bräutigam, L.3    Lang, D.4    Böcker, R.5
  • 34
    • 0028237729 scopus 로고
    • Interindividual variations in human liver cytychrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians
    • Shimada, T., Yamazaki, T., Mimura, M., Inui, Y., and Guengerich, F. P. (1994) Interindividual variations in human liver cytychrome P-450 enzymes involved in the oxidation of drugs, carcinogens and toxic chemicals: Studies with liver microsomes of 30 Japanese and 30 Caucasians. J. Pharmacol. Exp. Ther. 270, 414-423.
    • (1994) J. Pharmacol. Exp. Ther. , vol.270 , pp. 414-423
    • Shimada, T.1    Yamazaki, T.2    Mimura, M.3    Inui, Y.4    Guengerich, F.P.5
  • 36
    • 0029047732 scopus 로고
    • Roles of divalent metal ions in oxidations catalyzed by recombinant cytochrome P450 3A4 and replacement of NADPH-cytochrome P450 reductase with other flavoproteins, ferredoxins and oxygen surrogates
    • Yamazaki, H., Ueng, Y.-F., Shimada, T., and Guengerich, F. P. (1995) Roles of divalent metal ions in oxidations catalyzed by recombinant cytochrome P450 3A4 and replacement of NADPH-cytochrome P450 reductase with other flavoproteins, ferredoxins and oxygen surrogates. Biochemistry 34, 8380-8389.
    • (1995) Biochemistry , vol.34 , pp. 8380-8389
    • Yamazaki, H.1    Ueng, Y.-F.2    Shimada, T.3    Guengerich, F.P.4
  • 38
    • 0030454188 scopus 로고    scopus 로고
    • Stable expression and coexpression of human cytochrome P450 oxidoreductase and cytochrome P450 1A2 in V79 chinese hamster cells: Sensitivity to quinones and biotransformation of 7-alkoxyresorufins and triazines
    • Schmalix, W. A., Lang, D., Schneider, A., Böcker, R., Greim, H., and Doehmer, J. (1996) Stable expression and coexpression of human cytochrome P450 oxidoreductase and cytochrome P450 1A2 in V79 chinese hamster cells: Sensitivity to quinones and biotransformation of 7-alkoxyresorufins and triazines. Drug Metab. Dispos. 24, 1314-1319.
    • (1996) Drug Metab. Dispos. , vol.24 , pp. 1314-1319
    • Schmalix, W.A.1    Lang, D.2    Schneider, A.3    Böcker, R.4    Greim, H.5    Doehmer, J.6
  • 39
    • 0028864480 scopus 로고
    • The sulfoxidation of hexachlorobutadiene metabolite N-acetyl-S-(1,2,3,4,4-pentachlorobutadienyl)-L-cysteine is catalyzed by human cytochrome P450 3A enzymes
    • Werner, M., Guo, Z., Birner, G., Dekant, W., and Guengerich, F. P. (1995) The sulfoxidation of hexachlorobutadiene metabolite N-acetyl-S-(1,2,3,4,4-pentachlorobutadienyl)-L-cysteine is catalyzed by human cytochrome P450 3A enzymes. Chem. Res. Toxicol. 8, 917-923.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 917-923
    • Werner, M.1    Guo, Z.2    Birner, G.3    Dekant, W.4    Guengerich, F.P.5
  • 40
    • 0028945438 scopus 로고
    • Structural and catalytic properties of the mammalian flavin-containing monooxygenase
    • Cashman, J. R. (1995) Structural and catalytic properties of the mammalian flavin-containing monooxygenase. Chem. Res. Toxicol. 8, 165-181.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 165-181
    • Cashman, J.R.1
  • 41
    • 0027185830 scopus 로고
    • Expression in Escherichia coli of the flavin-containing monooxygenase D (form II) from adult human liver: Determination of the distinct tertiary amine substrate specificity
    • Lomri, N., Yang, Z., and Cashman, J. R. (1993) Expression in Escherichia coli of the flavin-containing monooxygenase D (form II) from adult human liver: Determination of the distinct tertiary amine substrate specificity. Chem. Res. Toxicol. 6, 425-429.
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 425-429
    • Lomri, N.1    Yang, Z.2    Cashman, J.R.3
  • 42
    • 0011320311 scopus 로고
    • Sulindac metabolism by human liver microsomes
    • Hamman, M. A., Wrighton, S. A., and Hall, S. D. (1994) Sulindac metabolism by human liver microsomes. ISSX Proc. 6, 251.
    • (1994) ISSX Proc. , vol.6 , pp. 251
    • Hamman, M.A.1    Wrighton, S.A.2    Hall, S.D.3
  • 43
    • 0028820801 scopus 로고
    • Role of cytochrome P4501A2 in chemical carcinogenesis: Implications for human variability in expression and enzyme activity
    • Eaton, D. L., Gallagher, E. P., Bammler, T. K., and Kunze, K. L. (1995) Role of cytochrome P4501A2 in chemical carcinogenesis: implications for human variability in expression and enzyme activity. Pharmocogenetics 5, 259-274.
    • (1995) Pharmocogenetics , vol.5 , pp. 259-274
    • Eaton, D.L.1    Gallagher, E.P.2    Bammler, T.K.3    Kunze, K.L.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.