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Volumn 17, Issue 8, 2004, Pages 1151-1156

Identification of the main human cytochrome P450 enzymes involved in safrole 1′-hydroxylation

Author keywords

[No Author keywords available]

Indexed keywords

1' HYDROXYSAFROLE; 4 METHYLPYRAZOLE; CHLORZOXAZONE; CYTOCHROME P450; CYTOCHROME P450 2C9; CYTOCHROME P450 2E1; CYTOCHROME P450 INHIBITOR; DIETHYLDITHIOCARBAMIC ACID; ESSENTIAL OIL; SAFROLE; SULFAPHENAZOLE; SULFATE; TOLBUTAMIDE; UNCLASSIFIED DRUG;

EID: 4243125326     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx030055p     Document Type: Article
Times cited : (60)

References (40)
  • 1
    • 0036841322 scopus 로고    scopus 로고
    • Biological monitoring of environment exposure to safrole and the Taiwanese betel quid chewing
    • Chang, M. J. W., Ko, C. Y., Lin, R. F., and Hsieh, L. L. (2002) Biological monitoring of environment exposure to safrole and the Taiwanese betel quid chewing. Arch. Environ. Contam. Toxicol. 43, 432-437.
    • (2002) Arch. Environ. Contam. Toxicol. , vol.43 , pp. 432-437
    • Chang, M.J.W.1    Ko, C.Y.2    Lin, R.F.3    Hsieh, L.L.4
  • 2
    • 0036986985 scopus 로고    scopus 로고
    • Combined effects of chronic hepatitis virus infections and substance-use habits on chronic liver disease in Taiwanese aborigines
    • Lin, H.-H., Wang, L.-Y., Shaw, C.-K., Cheng, M.-L., Chung, W.-K., Chiang, H.-J., Lin, T.-Y., and Chen, C.-J. (2002) Combined effects of chronic hepatitis virus infections and substance-use habits on chronic liver disease in Taiwanese aborigines. J. Formosan Med. Assoc. 101, 826-834.
    • (2002) J. Formosan Med. Assoc. , vol.101 , pp. 826-834
    • Lin, H.-H.1    Wang, L.-Y.2    Shaw, C.-K.3    Cheng, M.-L.4    Chung, W.-K.5    Chiang, H.-J.6    Lin, T.-Y.7    Chen, C.-J.8
  • 3
    • 0019788152 scopus 로고
    • Safrole: Its metabolism, carcinogenicity and interactions with cytochrome P-450
    • Ioannides, C., Delaforge, M., and Parke, D. V. (1981) Safrole: Its metabolism, carcinogenicity and interactions with cytochrome P-450. Food, Cosmet. Toxicol. 19, 657-666.
    • (1981) Food, Cosmet. Toxicol. , vol.19 , pp. 657-666
    • Ioannides, C.1    Delaforge, M.2    Parke, D.V.3
  • 4
    • 0033377368 scopus 로고    scopus 로고
    • Safrole-like DNA adducts in oral tissue from oral cancer patients with a betel quid chewing history
    • Chen, C. L., Chi, C. W., Chang, K. W., and Liu, T. Y. (1999) Safrole-like DNA adducts in oral tissue from oral cancer patients with a betel quid chewing history. Carcinegenesis 20, 2331-2334.
    • (1999) Carcinegenesis , vol.20 , pp. 2331-2334
    • Chen, C.L.1    Chi, C.W.2    Chang, K.W.3    Liu, T.Y.4
  • 5
    • 0000153393 scopus 로고
    • Phenolic compounds of betel quid chewing juice
    • Wang, C. K., and Hwang, L. S. (1993) Phenolic compounds of betel quid chewing juice. Food Sci. 20, 458-471.
    • (1993) Food Sci. , vol.20 , pp. 458-471
    • Wang, C.K.1    Hwang, L.S.2
  • 6
    • 0034692551 scopus 로고    scopus 로고
    • Cytotoxicity and genotoxicity of methyleugenol and related congeners - A mechanism of activation for methyleugenol
    • Burkey, J. L., Sauer, J. M., McQueen, C. A., and Sipes, G. (2000) Cytotoxicity and genotoxicity of methyleugenol and related congeners-a mechanism of activation for methyleugenol. Mutat. Res. 453, 25-33.
    • (2000) Mutat. Res. , vol.453 , pp. 25-33
    • Burkey, J.L.1    Sauer, J.M.2    McQueen, C.A.3    Sipes, G.4
  • 7
    • 0015593170 scopus 로고
    • The metabolism of the naturally occurring hepatocarcinogen safrole to 1′-hydroxysafrole and the elctrophilic reactivity of 1′- acetoxysafrole
    • Borchert, P., Wislocki, P. G., Miller, J. A., and Miller, E. C. (1973) The metabolism of the naturally occurring hepatocarcinogen safrole to 1′-hydroxysafrole and the elctrophilic reactivity of 1′- acetoxysafrole. Cancer Res. 33, 575-589.
    • (1973) Cancer Res. , vol.33 , pp. 575-589
    • Borchert, P.1    Wislocki, P.G.2    Miller, J.A.3    Miller, E.C.4
  • 8
    • 0008527609 scopus 로고
    • Preparation of microsomal and cytosolic fractions
    • (Hayes, A. W., Ed.) 3rd ed., Raven Press, New York
    • Guengerich, F. P. (1994) Preparation of microsomal and cytosolic fractions. In Principles and Methods of Toxicology (Hayes, A. W., Ed.) 3rd ed., pp 1267-1268, Raven Press, New York.
    • (1994) Principles and Methods of Toxicology , pp. 1267-1268
    • Guengerich, F.P.1
  • 9
    • 0014791820 scopus 로고
    • Two substrate kinetics of drug-metabolizing enzyme systems of hepatic microsomes
    • Alvares, A. P., and Mannering, G. J. (1977) Two substrate kinetics of drug-metabolizing enzyme systems of hepatic microsomes. Mol. Pharmacol. 6, 206-212.
    • (1977) Mol. Pharmacol. , vol.6 , pp. 206-212
    • Alvares, A.P.1    Mannering, G.J.2
  • 10
    • 0030843652 scopus 로고    scopus 로고
    • Drug metabolism by Escherichia coli expressing human cytochrome P450
    • Parikh, A., Gillam, E. M. J., and Guengerich, F. P. (1997) Drug metabolism by Escherichia coli expressing human cytochrome P450. Nat. Biotechnol. 15, 784-788.
    • (1997) Nat. Biotechnol. , vol.15 , pp. 784-788
    • Parikh, A.1    Gillam, E.M.J.2    Guengerich, F.P.3
  • 11
    • 78651165715 scopus 로고
    • The carbonmonoxide-binding pigment of liver microsomes. 1. Evidence for its hemeprotein nature
    • Omura, T., and Sato, R. (1964) The carbonmonoxide-binding pigment of liver microsomes. 1. Evidence for its hemeprotein nature. J. Biol. Chem. 239, 2370-2379.
    • (1964) J. Biol. Chem. , vol.239 , pp. 2370-2379
    • Omura, T.1    Sato, R.2
  • 12
    • 0345493210 scopus 로고    scopus 로고
    • Novel sensitive high-performance liquid chromatographic method for assay of coumarin 7-hydroxylation
    • Souček, P. (1999) Novel sensitive high-performance liquid chromatographic method for assay of coumarin 7-hydroxylation. J. Chromatogr. B 734, 23-29.
    • (1999) J. Chromatogr. B , vol.734 , pp. 23-29
    • Souček, P.1
  • 13
    • 0031451433 scopus 로고    scopus 로고
    • Mechanism-based inactivation of human liver cytochrome P450 2A6 by 8-methoxysoralen
    • Koenigs, L. L., Peter, R. M., Thompson, S. J., Rettie, A. E., and Trager, W. F. (1997) Mechanism-based inactivation of human liver cytochrome P450 2A6 by 8-methoxysoralen. Drug Metab. Dispos. 25, 1407-1415.
    • (1997) Drug Metab. Dispos. , vol.25 , pp. 1407-1415
    • Koenigs, L.L.1    Peter, R.M.2    Thompson, S.J.3    Rettie, A.E.4    Trager, W.F.5
  • 14
    • 0019219257 scopus 로고
    • A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions
    • Pohl, R. J., and Fouts, J. R. (1980) A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions. Anal. Biochem. 107, 150-155.
    • (1980) Anal. Biochem. , vol.107 , pp. 150-155
    • Pohl, R.J.1    Fouts, J.R.2
  • 15
    • 0022350885 scopus 로고
    • Dealkylation of pentoxyresorufin: A rapid and sensitive assay for measuring induction of cytochrome(s) P-450 by phenobarbital and other xenobiotics in the rat
    • Lubet, R. A., Mayer, R. T., Cameron, J. W., Nims, R. W., Burke, M. D., Wolff, T., and Guengerich, F. P. (1985) Dealkylation of pentoxyresorufin: A rapid and sensitive assay for measuring induction of cytochrome(s) P-450 by phenobarbital and other xenobiotics in the rat. Arch. Biochem. Biophys. 238, 43-48.
    • (1985) Arch. Biochem. Biophys. , vol.238 , pp. 43-48
    • Lubet, R.A.1    Mayer, R.T.2    Cameron, J.W.3    Nims, R.W.4    Burke, M.D.5    Wolff, T.6    Guengerich, F.P.7
  • 16
    • 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. V. (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.V.6
  • 18
    • 0031912544 scopus 로고    scopus 로고
    • Roles of two allelic variants (Arg144Cys and Ile359Leu) of cytochrome P450 2C9 in the oxidation of tolbutamide and warfarin by human liver microsomes
    • Yamazaki, H., Inoue, K., and Shimada, T. (1998) Roles of two allelic variants (Arg144Cys and Ile359Leu) of cytochrome P450 2C9 in the oxidation of tolbutamide and warfarin by human liver microsomes. Xenobiotica 28, 103-115.
    • (1998) Xenobiotica , vol.28 , pp. 103-115
    • Yamazaki, H.1    Inoue, K.2    Shimada, T.3
  • 20
    • 0028858960 scopus 로고
    • Cytochrome P450 inhibitors: Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes
    • Newton, D. J., Wang, R. W., and Lu, A. Y. H. (1995) Cytochrome P450 inhibitors: Evaluation of specificities in the in vitro metabolism of therapeutic agents by human liver microsomes. Drug Metab. Dispos. 23, 154-158.
    • (1995) Drug Metab. Dispos. , vol.23 , pp. 154-158
    • Newton, D.J.1    Wang, R.W.2    Lu, A.Y.H.3
  • 21
    • 0025239050 scopus 로고
    • Oxidation of pyrazole by reconstituted systems containing cytochrome P-450 IIE1
    • Clejan, L. A., and Cederbaum, A. I. (1990) Oxidation of pyrazole by reconstituted systems containing cytochrome P-450 IIE1. Biochim. Biophys. Acta 1034, 233-237.
    • (1990) Biochim. Biophys. Acta , vol.1034 , pp. 233-237
    • Clejan, L.A.1    Cederbaum, A.I.2
  • 22
    • 0026035519 scopus 로고
    • Role of human cytochrome P450 2E1 in the oxidation of many low molecular weight cancer suspects
    • Guengerich, F. P., Kim, D. H., and Iwasaki, M. (1991) Role of human cytochrome P450 2E1 in the oxidation of many low molecular weight cancer suspects. Chem. Res. Toxicol. 4, 168-179.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 168-179
    • Guengerich, F.P.1    Kim, D.H.2    Iwasaki, M.3
  • 23
    • 0031845647 scopus 로고    scopus 로고
    • In vivo genotoxicity and DNA adduct levels in the liver of rats treated with safrole
    • Daimon, H., Sawada, S., Asakura, S., and Sagami, F. (1998) In vivo genotoxicity and DNA adduct levels in the liver of rats treated with safrole. Carcinogenesis 19, 141-146.
    • (1998) Carcinogenesis , vol.19 , pp. 141-146
    • Daimon, H.1    Sawada, S.2    Asakura, S.3    Sagami, F.4
  • 25
    • 0019798592 scopus 로고
    • The side-chain epoxidation and hydroxylation of the hepatocarcinogens safrole and estragole and some related compounds by rat and mouse liver microsomes
    • Swanson, A. B., Miller, E. C., and Miller, J. A. (1981) The side-chain epoxidation and hydroxylation of the hepatocarcinogens safrole and estragole and some related compounds by rat and mouse liver microsomes. Biochim. Biophys. Acta 673, 504-516.
    • (1981) Biochim. Biophys. Acta , vol.673 , pp. 504-516
    • Swanson, A.B.1    Miller, E.C.2    Miller, J.A.3
  • 26
    • 0031940804 scopus 로고    scopus 로고
    • Effect of common organic solvents on in vitro cytochrome P450-mediated metabolic activities in human liver microsomes
    • Chauret, N., Gauthier, A., and Nicoll-Griffith, D. A. (1998) Effect of common organic solvents on in vitro cytochrome P450-mediated metabolic activities in human liver microsomes. Drug Metab. Dispos. 26, 1-4.
    • (1998) Drug Metab. Dispos. , vol.26 , pp. 1-4
    • Chauret, N.1    Gauthier, A.2    Nicoll-Griffith, D.A.3
  • 27
    • 0031921010 scopus 로고    scopus 로고
    • Evaluation of the selectivity of in vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities
    • Hickman, D., Wang, J.-P., Wang, Y., and Unadkat, J. D. (1998) Evaluation of the selectivity of in vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities. Drug Metab. Dispos. 26, 207-215.
    • (1998) Drug Metab. Dispos. , vol.26 , pp. 207-215
    • Hickman, D.1    Wang, J.-P.2    Wang, Y.3    Unadkat, J.D.4
  • 29
    • 0036893593 scopus 로고    scopus 로고
    • Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions
    • Yuan, R., Madani, S., Wei, X.-X., Reynolds, K., and Huang, S.-M. (2002) Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. Drug Metab. Dispos. 30, 1311-1319.
    • (2002) Drug Metab. Dispos. , vol.30 , pp. 1311-1319
    • Yuan, R.1    Madani, S.2    Wei, X.-X.3    Reynolds, K.4    Huang, S.-M.5
  • 30
    • 0031856787 scopus 로고    scopus 로고
    • Characterization of CYP2C19 and CYP2C9 from human liver: Respective roles in microsomal tolbutamide, S-mephenytoin, and omeprazole hydroxylations
    • Lasker, J. M., Wester, M. R., Aramsombatdee, E., and Raucy, J. L. (1998) Characterization of CYP2C19 and CYP2C9 from human liver: respective roles in microsomal tolbutamide, S-mephenytoin, and omeprazole hydroxylations. Arch. Biochem. Biophys. 353, 16-28.
    • (1998) Arch. Biochem. Biophys. , vol.353 , pp. 16-28
    • Lasker, J.M.1    Wester, M.R.2    Aramsombatdee, E.3    Raucy, J.L.4
  • 31
    • 0028237729 scopus 로고
    • Interindividual variations in human liver cytochrome 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, H., Mimura, M., Inui, Y., and Guengerich, F. P. (1994) Interindividual variations in human liver cytochrome 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, H.2    Mimura, M.3    Inui, Y.4    Guengerich, F.P.5
  • 32
    • 0001113139 scopus 로고
    • The molecular biology of cytochrome P450s
    • Gonzalez, F. J. (1989) The molecular biology of cytochrome P450s. Pharmacol. Rev. 40, 244-276.
    • (1989) Pharmacol. Rev. , vol.40 , pp. 244-276
    • Gonzalez, F.J.1
  • 33
    • 0029832576 scopus 로고    scopus 로고
    • Regulation of constitutive rat hepatic cytochromes P450 by 3-methylcholanthrene
    • Jones, E. J., and Riddick, D. S. (1996) Regulation of constitutive rat hepatic cytochromes P450 by 3-methylcholanthrene. Xenobiotica 26, 995-1012.
    • (1996) Xenobiotica , vol.26 , pp. 995-1012
    • Jones, E.J.1    Riddick, D.S.2
  • 35
    • 0026512675 scopus 로고
    • Phenobarbital induction of cytochrome P-450 gene expression
    • Waxman, D. J., and Azaroff, L. (1992) Phenobarbital induction of cytochrome P-450 gene expression. Biochem. J. 281, 577-592.
    • (1992) Biochem. J. , vol.281 , pp. 577-592
    • Waxman, D.J.1    Azaroff, L.2
  • 36
    • 0029051278 scopus 로고
    • Differential induction of UDP-glucuronosyltransferase activity and gene expression in rat liver
    • Wong, B. K., Fei, P., and Kong, A.-N. T. (1995) Differential induction of UDP-glucuronosyltransferase activity and gene expression in rat liver. Pharm. Res. 12, 1105-1108.
    • (1995) Pharm. Res. , vol.12 , pp. 1105-1108
    • Wong, B.K.1    Fei, P.2    Kong, A.-N.T.3
  • 37
    • 0031933097 scopus 로고    scopus 로고
    • Effect of cigarette smoke on UDP-glucuronosyltransferase activity and cytochrome P450 content in liver, lung and kidney microsomes in mice
    • Villard, P. H., Herber, R., Sérée, E. M., Attolini, L., Magdalou, J., and Lacarelle, B. (1998) Effect of cigarette smoke on UDP-glucuronosyltransferase activity and cytochrome P450 content in liver, lung and kidney microsomes in mice. Pharmacol. Toxicol. 82, 74-79.
    • (1998) Pharmacol. Toxicol. , vol.82 , pp. 74-79
    • Villard, P.H.1    Herber, R.2    Sérée, E.M.3    Attolini, L.4    Magdalou, J.5    Lacarelle, B.6
  • 38
    • 0031437805 scopus 로고    scopus 로고
    • Human lymphocyte cytochrome P450 2E1, a putative marker for alcohol-mediated changes in hepatic chlorzoxazone activity
    • Raucy, J. L., Schultz, E. D., Wester, M. R., Arora, S., Johnston, D. E., Omdahl, J. L., and Carpenter, S. P. (1997) Human lymphocyte cytochrome P450 2E1, a putative marker for alcohol-mediated changes in hepatic chlorzoxazone activity. Drug Metab. Dispos. 25, 1429-1435.
    • (1997) Drug Metab. Dispos. , vol.25 , pp. 1429-1435
    • Raucy, J.L.1    Schultz, E.D.2    Wester, M.R.3    Arora, S.4    Johnston, D.E.5    Omdahl, J.L.6    Carpenter, S.P.7
  • 39
    • 0034874878 scopus 로고    scopus 로고
    • The effects of alcohol and diallyl sulphide on CYP2E1 activity in humans: A phenotyping study using chlorzoxazone
    • Loizou, G. D., and Cocker, J. (2001) The effects of alcohol and diallyl sulphide on CYP2E1 activity in humans: A phenotyping study using chlorzoxazone. Hum. Exp. Toxicol. 20, 321-327.
    • (2001) Hum. Exp. Toxicol. , vol.20 , pp. 321-327
    • Loizou, G.D.1    Cocker, J.2


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