메뉴 건너뛰기




Volumn 28, Issue 3, 2013, Pages 229-238

Mechanism-based inhibition of CYP1A1 and CYP3A4 by the furanocoumarin chalepensin

Author keywords

Chalepensin; Cytochrome P450; Epoxidation; Hydroxylation; Mechanism based inhibition

Indexed keywords

CHALEPENSIN; CYTOCHROME P450 1A1; CYTOCHROME P450 1A2; CYTOCHROME P450 2A13; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; FUROCOUMARIN DERIVATIVE; GLUTATHIONE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; UNCLASSIFIED DRUG;

EID: 84879339923     PISSN: 13474367     EISSN: 18800920     Source Type: Journal    
DOI: 10.2133/dmpk.DMPK-12-RG-113     Document Type: Article
Times cited : (20)

References (42)
  • 1
    • 0002888510 scopus 로고
    • Human cytochrome P450 enzymes
    • Ortiz de Montellano PR, (ed.), New York, Plenum Press
    • Guengerich, F. P.: Human cytochrome P450 enzymes. In: Ortiz de Montellano PR, (ed.): Cytochrome P450. New York, Plenum Press, 1995, pp. 473-535.
    • (1995) Cytochrome P450 , pp. 473-535
    • Guengerich, F.P.1
  • 2
    • 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.: 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).
    • (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
  • 3
    • 27644596457 scopus 로고    scopus 로고
    • Predicting in vivo drug interactions from in vitro drug discovery data
    • Wienkers, L. C. and Health, T. G.: Predicting in vivo drug interactions from in vitro drug discovery data. Nat. Rev. Drug Discov., 4: 825-833 (2005).
    • (2005) Nat. Rev. Drug Discov. , vol.4 , pp. 825-833
    • Wienkers, L.C.1    Health, T.G.2
  • 4
    • 0034665139 scopus 로고    scopus 로고
    • Human cytochrome P450 CYP2A13: Predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobaccospecific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone
    • Su, T., Bao, Z., Zhang, Q.-Y., Smith, T. J., Hong, J.-Y. and Ding, X.: Human cytochrome P450 CYP2A13: predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobaccospecific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res., 60: 5074-5079 (2000).
    • (2000) Cancer Res. , vol.60 , pp. 5074-5079
    • Su, T.1    Bao, Z.2    Zhang, Q.-Y.3    Smith, T.J.4    Hong, J.-Y.5    Ding, X.6
  • 5
    • 2142695286 scopus 로고    scopus 로고
    • Oral exposure to benzo[a]pyrene in the mouse: Detoxication by inducible cytochrome P450 is more important than metabolic activation
    • Uno, S., Dalton, T. P., Derkenne, S., Curran, C. P., Miller, M. L., Shertzer, H. G. and Nebert, D. W.: Oral exposure to benzo[a]pyrene in the mouse: detoxication by inducible cytochrome P450 is more important than metabolic activation. Mol. Pharmacol., 65: 1225-1237 (2004).
    • (2004) Mol. Pharmacol. , vol.65 , pp. 1225-1237
    • Uno, S.1    Dalton, T.P.2    Derkenne, S.3    Curran, C.P.4    Miller, M.L.5    Shertzer, H.G.6    Nebert, D.W.7
  • 6
    • 72949119129 scopus 로고    scopus 로고
    • Structure, function, regulation and polymorphism of human cytochrome P450 2A6
    • Di, Y. M., Chow, V. D.-W., Yang, L.-P. and Zhou, S.-F.: Structure, function, regulation and polymorphism of human cytochrome P450 2A6. Curr. Drug Metab., 10: 754-780 (2009).
    • (2009) Curr. Drug Metab. , vol.10 , pp. 754-780
    • Di, Y.M.1    Chow, V.D.-W.2    Yang, L.-P.3    Zhou, S.-F.4
  • 7
    • 33847387556 scopus 로고    scopus 로고
    • CYP2A13 metabolizes the substrates of human CYP1A2, phenacetin and theophylline
    • Fukami, T., Nakajima, M., Sakai, H., Katoh, M. and Yokoi, T.: CYP2A13 metabolizes the substrates of human CYP1A2, phenacetin and theophylline. Drug Metab. Dispos., 35: 335-339 (2007).
    • (2007) Drug Metab. Dispos. , vol.35 , pp. 335-339
    • Fukami, T.1    Nakajima, M.2    Sakai, H.3    Katoh, M.4    Yokoi, T.5
  • 8
    • 41849093006 scopus 로고    scopus 로고
    • Human cytochrome P450 2A13 efficiently metabolizes chemicals in air pollutants: Naphthalene, styrene, and toluene
    • Fukami, T., Katoh, M., Yamazaki, H., Yokoi, T. and Nakajima, M.: Human cytochrome P450 2A13 efficiently metabolizes chemicals in air pollutants: naphthalene, styrene, and toluene. Chem. Res. Toxicol., 21: 720-725 (2008).
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 720-725
    • Fukami, T.1    Katoh, M.2    Yamazaki, H.3    Yokoi, T.4    Nakajima, M.5
  • 9
    • 35148815019 scopus 로고    scopus 로고
    • Effects of eleven isothiocyanates on P450 2A6-and 2A13-catalyzed coumarin 7-hydroxylation
    • von Weymarn, L. B., Chun, J. A., Knudsen, G. A. and Hollenberg, P. F.: Effects of eleven isothiocyanates on P450 2A6-and 2A13-catalyzed coumarin 7-hydroxylation. Chem. Res. Toxicol., 20: 1252-1259 (2007).
    • (2007) Chem. Res. Toxicol. , vol.20 , pp. 1252-1259
    • von Weymarn, L.B.1    Chun, J.A.2    Knudsen, G.A.3    Hollenberg, P.F.4
  • 10
    • 0034060357 scopus 로고    scopus 로고
    • Inhibitory effect of natural furanocoumarins on human microsomal cytochrome P450 3A activity
    • Guo, L.-Q., Taniguchi, M., Xiao, Y.-Q., Baba, K., Ohta, T. and Yamazoe, Y.: Inhibitory effect of natural furanocoumarins on human microsomal cytochrome P450 3A activity. Jpn. J. Pharmacol., 82: 122-129 (2000).
    • (2000) Jpn. J. Pharmacol. , vol.82 , pp. 122-129
    • Guo, L.-Q.1    Taniguchi, M.2    Xiao, Y.-Q.3    Baba, K.4    Ohta, T.5    Yamazoe, Y.6
  • 11
    • 0342868292 scopus 로고    scopus 로고
    • Role of furanocoumarin derivatives on grapefruit juice-mediated inhibition of human CYP3A activity
    • Guo, L.-Q., Fukuda, K., Ohta, T. and Yamazoe, Y.: Role of furanocoumarin derivatives on grapefruit juice-mediated inhibition of human CYP3A activity. Drug Metab. Dispos., 28: 766-771 (2000).
    • (2000) Drug Metab. Dispos. , vol.28 , pp. 766-771
    • Guo, L.-Q.1    Fukuda, K.2    Ohta, T.3    Yamazoe, Y.4
  • 12
    • 73349103803 scopus 로고    scopus 로고
    • Prediction of drug-drug interactions based on time-dependent inhibition from high throughput screening of cytochrome P450 3A4 inhibition
    • Sekiguchi, N., Higashida, A., Kato, M., Nabuchi, Y., Mitsui, T., Takanashi, K., Aso, Y. and Ishiga, M.: Prediction of drug-drug interactions based on time-dependent inhibition from high throughput screening of cytochrome P450 3A4 inhibition. Drug Metab. Pharmacokinet., 24: 500-510 (2009).
    • (2009) Drug Metab. Pharmacokinet. , vol.24 , pp. 500-510
    • Sekiguchi, N.1    Higashida, A.2    Kato, M.3    Nabuchi, Y.4    Mitsui, T.5    Takanashi, K.6    Aso, Y.7    Ishiga, M.8
  • 13
    • 0033831197 scopus 로고    scopus 로고
    • An in vivo model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation
    • Mayhew, B. S., Jones, D. R. and Hall, S. D.: An in vivo model for predicting in vivo inhibition of cytochrome P450 3A4 by metabolic intermediate complex formation. Drug Metab. Dispos., 28: 1031-1037 (2000).
    • (2000) Drug Metab. Dispos. , vol.28 , pp. 1031-1037
    • Mayhew, B.S.1    Jones, D.R.2    Hall, S.D.3
  • 15
    • 0034608997 scopus 로고    scopus 로고
    • High-resolution gaschromatographic analysis of the secondary metabolites obtained by subcritical-fluid extraction from Colombian rue (Ruta graveolens L.)
    • Stashenko, E. E., Acosta, R. and Martinez, R.: High-resolution gaschromatographic analysis of the secondary metabolites obtained by subcritical-fluid extraction from Colombian rue (Ruta graveolens L.). J. Biochem. Biophys. Methods, 43: 379-390 (2000).
    • (2000) J. Biochem. Biophys. Methods , vol.43 , pp. 379-390
    • Stashenko, E.E.1    Acosta, R.2    Martinez, R.3
  • 16
  • 19
    • 0030843652 scopus 로고    scopus 로고
    • Drug metabolism by Escherichia coli expressing human cytochrome P450
    • Parikh, A., Gillam, E. M. J. and Guengerich, F. P.: Drug metabolism by Escherichia coli expressing human cytochrome P450. Nat. Biotechnol., 15: 784-788 (1997).
    • (1997) Nat. Biotechnol. , vol.15 , pp. 784-788
    • Parikh, A.1    Gillam, E.M.J.2    Guengerich, F.P.3
  • 20
    • 28144450359 scopus 로고    scopus 로고
    • CYP2A6 and CYP2B6 are involved in nornicotine formation from nicotine in humans: Interindividual differences in these contributions
    • Yamanaka, H., Nakajima, M., Fukami, T., Sakai, H., Nakamura, A., Katoh, M., Takamiya, M., Aoki, Y. and Yokoi, T.: CYP2A6 and CYP2B6 are involved in nornicotine formation from nicotine in humans: interindividual differences in these contributions. Drug Metab. Dispos., 33: 1811-1818 (2005).
    • (2005) Drug Metab. Dispos. , vol.33 , pp. 1811-1818
    • Yamanaka, H.1    Nakajima, M.2    Fukami, T.3    Sakai, H.4    Nakamura, A.5    Katoh, M.6    Takamiya, M.7    Aoki, Y.8    Yokoi, T.9
  • 22
    • 0014791820 scopus 로고
    • Two-substrate kinetics of drugmetabolizing enzyme systems of hepatic microsomes
    • Alvares, A. P. and Mannering, G. J.: Two-substrate kinetics of drugmetabolizing enzyme systems of hepatic microsomes. Mol. Pharmacol., 6: 206-212 (1970).
    • (1970) Mol. Pharmacol. , vol.6 , pp. 206-212
    • Alvares, A.P.1    Mannering, G.J.2
  • 23
    • 73849173955 scopus 로고
    • Hepatic triphosphopyridine nucleotide-cytochrome c reductase: Isolation, characterization, and kinetic studies
    • Phillips, A. H. and Langdon, R. G.: Hepatic triphosphopyridine nucleotide-cytochrome c reductase: isolation, characterization, and kinetic studies. J. Biol. Chem., 237: 2652-2660 (1962).
    • (1962) J. Biol. Chem. , vol.237 , pp. 2652-2660
    • Phillips, A.H.1    Langdon, R.G.2
  • 24
    • 0019219257 scopus 로고
    • A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions
    • Pohl, R. J. and Fouts, J. R.: A rapid method for assaying the metabolism of 7-ethoxyresorufin by microsomal subcellular fractions. Anal. Biochem., 107: 150-155 (1980).
    • (1980) Anal. Biochem. , vol.107 , pp. 150-155
    • Pohl, R.J.1    Fouts, J.R.2
  • 25
    • 0017847465 scopus 로고
    • An improved assay of 7-ethoxycoumarin O-deethylase activity: Induction of hepatic enzyme activity in C57BL/6J and DBA/2J mice by phenobarbital, 3-methylcholanthrene and 2,3,7,8-tetrachlorodibenzo-p-dioxin
    • Greenlee, W. F. and Poland, A.: An improved assay of 7-ethoxycoumarin O-deethylase activity: induction of hepatic enzyme activity in C57BL/6J and DBA/2J mice by phenobarbital, 3-methylcholanthrene and 2,3,7,8-tetrachlorodibenzo-p-dioxin. J. Pharmacol. Exp. Ther., 205: 596-605 (1978).
    • (1978) J. Pharmacol. Exp. Ther. , vol.205 , pp. 596-605
    • Greenlee, W.F.1    Poland, A.2
  • 26
    • 0345493210 scopus 로고    scopus 로고
    • Novel sensitive high-performance liquid chromatographic method for assay of coumarin 7-hydroxylation
    • Souček, P.: Novel sensitive high-performance liquid chromatographic method for assay of coumarin 7-hydroxylation. J. Chromatogr. B Biomed. Sci. Appl., 734: 23-29 (1999).
    • (1999) J. Chromatogr. B Biomed. Sci. Appl. , vol.734 , pp. 23-29
    • Souček, P.1
  • 27
    • 0031451433 scopus 로고    scopus 로고
    • Mechanism-based inactivation of human liver cytochrome P450 2A6 by 8-methoxypsoralen
    • Koenigs, L. L., Peter, R. M., Thompson, S. J., Rettie, A. E. and Trager, W. F.: Mechanism-based inactivation of human liver cytochrome P450 2A6 by 8-methoxypsoralen. Drug Metab. Dispos., 25: 1407-1415 (1997).
    • (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
  • 28
    • 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.: 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).
    • (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
  • 30
    • 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.: 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).
    • (1998) Xenobiotica , vol.28 , pp. 103-115
    • Yamazaki, H.1    Inoue, K.2    Shimada, T.3
  • 31
    • 0016275313 scopus 로고
    • Glutathione S-transferase: The first enzymatic step in mercapturic acid formation
    • Habig, W. H., Pabst, M. J. and Jascoby, W. B.: Glutathione S-transferase: the first enzymatic step in mercapturic acid formation. J. Biol. Chem., 249: 7130-7139 (1974).
    • (1974) J. Biol. Chem. , vol.249 , pp. 7130-7139
    • Habig, W.H.1    Pabst, M.J.2    Jascoby, W.B.3
  • 33
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes. l. Evidence for its hemeprotein nature
    • Omura, T. and Sato, R.: The carbon monoxide-binding pigment of liver microsomes. l. Evidence for its hemeprotein nature. J. Biol. Chem., 239: 2370-2378 (1964).
    • (1964) J. Biol. Chem. , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 34
    • 0028930481 scopus 로고
    • Mechanism-based enzyme inactivators
    • Silverman, R. B.: Mechanism-based enzyme inactivators. Methods Enzymol., 249: 240-283 (1995).
    • (1995) Methods Enzymol. , vol.249 , pp. 240-283
    • Silverman, R.B.1
  • 35
    • 0032849028 scopus 로고    scopus 로고
    • Duration of cytochrome P-450 2E1 (CYP2E1) inhibition and estimation of functional CYP2E1 enzyme half-life after single-dose disulfiram administration in humans
    • Emery, M. G., Jubert, C., Thummel, K. E. and Kharasch, E. D.: Duration of cytochrome P-450 2E1 (CYP2E1) inhibition and estimation of functional CYP2E1 enzyme half-life after single-dose disulfiram administration in humans. J. Pharmacol. Exp. Ther., 291: 213-219 (1999).
    • (1999) J. Pharmacol. Exp. Ther. , vol.291 , pp. 213-219
    • Emery, M.G.1    Jubert, C.2    Thummel, K.E.3    Kharasch, E.D.4
  • 37
    • 48549110345 scopus 로고
    • Cytosol-mediated reduction of resorufin: A method for measuring quinone oxidoreductase
    • Nims, R. W., Prough, R. A. and Lubet, R. A.: Cytosol-mediated reduction of resorufin: a method for measuring quinone oxidoreductase. Arch. Biochem. Biophys., 229: 459-465 (1984).
    • (1984) Arch. Biochem. Biophys. , vol.229 , pp. 459-465
    • Nims, R.W.1    Prough, R.A.2    Lubet, R.A.3
  • 38
    • 0027380074 scopus 로고
    • Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline
    • Kunze, K. L. and Trager, W. F.: Isoform-selective mechanism-based inhibition of human cytochrome P450 1A2 by furafylline. Chem. Res. Toxicol., 6: 649-656 (1993).
    • (1993) Chem. Res. Toxicol. , vol.6 , pp. 649-656
    • Kunze, K.L.1    Trager, W.F.2
  • 39
    • 0033960956 scopus 로고    scopus 로고
    • Single-dose methoxsalen effects on human cytochrome P-450 2A6 activity
    • Kharasch, E. D., Hankins, D. C. and Taraday, J. K.: Single-dose methoxsalen effects on human cytochrome P-450 2A6 activity. Drug Metab. Dispos., 28: 28-33 (2000).
    • (2000) Drug Metab. Dispos. , vol.28 , pp. 28-33
    • Kharasch, E.D.1    Hankins, D.C.2    Taraday, J.K.3
  • 40
    • 0022642182 scopus 로고
    • Clinical pharmacokinetics of methoxsalen and other psoralens
    • de Wolff, F. A. and Thomas, T. V.: Clinical pharmacokinetics of methoxsalen and other psoralens. Clin. Pharmacokinet., 11: 62-75 (1986).
    • (1986) Clin. Pharmacokinet. , vol.11 , pp. 62-75
    • de Wolff, F.A.1    Thomas, T.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.