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Volumn 36, Issue 11, 2008, Pages 2234-2243

Differential inhibition of cytochromes P450 3A4 and 3A5 by the newly synthesized coumarin derivatives 7-coumarin propargyl ether and 7-(4-trifluoromethyl)coumarin propargyl ether

Author keywords

[No Author keywords available]

Indexed keywords

7 (4 TRIFLUOROMETHYL) COUMARIN PROPARGYL ETHER; 7 COUMARIN PROPARGYL ETHER; COUMARIN DERIVATIVE; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; DRUG METABOLITE; UNCLASSIFIED DRUG;

EID: 54349127112     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.108.021493     Document Type: Article
Times cited : (12)

References (37)
  • 1
    • 0024412071 scopus 로고
    • Cytochrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver: CDNA and deduced amino acid sequence and distinct specificities of cDNA-expressed hPCN1 and hPCN3 for the metabolism of steroid hormones and cyclosporine
    • Aoyama T, Yamano S, Waxman DJ, Lapenson DP, Meyer UA, Fischer V, Tyndale R, Inaba T, Kalow W, and Gelboin HV (1989) Cytochrome P-450 hPCN3, a novel cytochrome P-450 IIIA gene product that is differentially expressed in adult human liver: cDNA and deduced amino acid sequence and distinct specificities of cDNA-expressed hPCN1 and hPCN3 for the metabolism of steroid hormones and cyclosporine. J Biol Chem 264:10388-10395.
    • (1989) J Biol Chem , vol.264 , pp. 10388-10395
    • Aoyama, T.1    Yamano, S.2    Waxman, D.J.3    Lapenson, D.P.4    Meyer, U.A.5    Fischer, V.6    Tyndale, R.7    Inaba, T.8    Kalow, W.9    Gelboin, H.V.10
  • 2
    • 34447133553 scopus 로고    scopus 로고
    • Time-dependent inactivation of P450 3A4 by raloxifene: Identification of Cys239 as the site of apoprotein alkylation
    • Baer BR, Wienkers LC, and Rock DA (2007) Time-dependent inactivation of P450 3A4 by raloxifene: identification of Cys239 as the site of apoprotein alkylation. Chem Res Toxicol 20:954-964.
    • (2007) Chem Res Toxicol , vol.20 , pp. 954-964
    • Baer, B.R.1    Wienkers, L.C.2    Rock, D.A.3
  • 3
    • 0024408814 scopus 로고
    • Lidocaine metabolism in human liver microsomes by cytochrome P450IIIA4
    • Bargetzi MJ, Aoyama T, Gonzalez FJ, and Meyer UA (1989) Lidocaine metabolism in human liver microsomes by cytochrome P450IIIA4. Clin Pharmacol Ther 46:521-527.
    • (1989) Clin Pharmacol Ther , vol.46 , pp. 521-527
    • Bargetzi, M.J.1    Aoyama, T.2    Gonzalez, F.J.3    Meyer, U.A.4
  • 4
    • 0036918608 scopus 로고    scopus 로고
    • Mechanism-based inactivation of cytochromes P450 2E1 and 2E1 T303A by tert-butyl acetylenes: Characterization of reactive intermediate adducts to the heme and apoprotein
    • Blobaum AL, Kent UM, Alworth WL, and Hollenberg PF (2002) Mechanism-based inactivation of cytochromes P450 2E1 and 2E1 T303A by tert-butyl acetylenes: characterization of reactive intermediate adducts to the heme and apoprotein. Chem Res Toxicol 15:1561-1571.
    • (2002) Chem Res Toxicol , vol.15 , pp. 1561-1571
    • Blobaum, A.L.1    Kent, U.M.2    Alworth, W.L.3    Hollenberg, P.F.4
  • 5
    • 0031722367 scopus 로고    scopus 로고
    • Selective Clara cell injury in mouse lung following acute administration of coumarin
    • Born SL, Fix AS, Caudill D, and Lehman-McKeeman LD (1998) Selective Clara cell injury in mouse lung following acute administration of coumarin. Toxicol Appl Pharmacol 151:45-56.
    • (1998) Toxicol Appl Pharmacol , vol.151 , pp. 45-56
    • Born, S.L.1    Fix, A.S.2    Caudill, D.3    Lehman-McKeeman, L.D.4
  • 6
    • 0027374515 scopus 로고
    • A highly sensitive tool for the assay of cytochrome P450 enzyme activity in rat, dog and man: Direct fluorescence monitoring of the deethylation of 7-ethoxy-4- trifluoromethylcoumarin
    • Buters JT, Schiller CD, and Chou RC (1993) A highly sensitive tool for the assay of cytochrome P450 enzyme activity in rat, dog and man: direct fluorescence monitoring of the deethylation of 7-ethoxy-4- trifluoromethylcoumarin. Biochem Pharmacol 46:1577-1584.
    • (1993) Biochem Pharmacol , vol.46 , pp. 1577-1584
    • Buters, J.T.1    Schiller, C.D.2    Chou, R.C.3
  • 9
    • 0033569516 scopus 로고    scopus 로고
    • Pharmacogenomics: Translating functional genomics into rational therapeutics
    • Evans WE and Relling MV (1999) Pharmacogenomics: translating functional genomics into rational therapeutics. Science 286:487-491.
    • (1999) Science , vol.286 , pp. 487-491
    • Evans, W.E.1    Relling, M.V.2
  • 11
    • 0027223881 scopus 로고
    • Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme
    • Gillam EM, Baba T, Kim BR, Ohmori S, and Guengerich FP (1993) Expression of modified human cytochrome P450 3A4 in Escherichia coli and purification and reconstitution of the enzyme. Arch Biochem Biophys 305:123-131.
    • (1993) Arch Biochem Biophys , vol.305 , pp. 123-131
    • Gillam, E.M.1    Baba, T.2    Kim, B.R.3    Ohmori, S.4    Guengerich, F.P.5
  • 12
    • 0028912205 scopus 로고
    • Expression of cytochrome P450 3A5 in Escherichia coli: Effects of 5′ modification, purification, spectral characterization, reconstitution conditions, and catalytic activities
    • Gillam EM, Guo Z, Ueng YF, Yamazaki H, Cock I, Reilly PE, Hooper WD, and Guengerich FP (1995) Expression of cytochrome P450 3A5 in Escherichia coli: effects of 5′ modification, purification, spectral characterization, reconstitution conditions, and catalytic activities. Arch Biochem Biophys 317:374-384.
    • (1995) Arch Biochem Biophys , vol.317 , pp. 374-384
    • Gillam, E.M.1    Guo, Z.2    Ueng, Y.F.3    Yamazaki, H.4    Cock, I.5    Reilly, P.E.6    Hooper, W.D.7    Guengerich, F.P.8
  • 13
    • 0028234586 scopus 로고
    • Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily
    • Gorski JC, Hall SD, Jones DR, VandenBranden M, and Wrighton SA (1994) Regioselective biotransformation of midazolam by members of the human cytochrome P450 3A (CYP3A) subfamily. Biochem Pharmacol 47:1643-1653.
    • (1994) Biochem Pharmacol , vol.47 , pp. 1643-1653
    • Gorski, J.C.1    Hall, S.D.2    Jones, D.R.3    VandenBranden, M.4    Wrighton, S.A.5
  • 14
    • 0031822496 scopus 로고    scopus 로고
    • Role of the alanine at position 363 of cytochrome P450 2B2 in influencing the NADPH- and hydroperoxide-supported activities
    • Hanna IH, Teiber JF, Kokones KL, and Hollenberg PF (1998) Role of the alanine at position 363 of cytochrome P450 2B2 in influencing the NADPH- and hydroperoxide-supported activities. Arch Biochem Biophys 350:324-332.
    • (1998) Arch Biochem Biophys , vol.350 , pp. 324-332
    • Hanna, I.H.1    Teiber, J.F.2    Kokones, K.L.3    Hollenberg, P.F.4
  • 17
    • 0036707616 scopus 로고    scopus 로고
    • Differential oxidation of mifepristone by cytochromes P450 3A4 and 3A5: Selective inactivation of P450 3A4
    • Khan KK, He YQ, Correia MA, and Halpert JR (2002) Differential oxidation of mifepristone by cytochromes P450 3A4 and 3A5: selective inactivation of P450 3A4. Drug Metab Dispos 30:985-990.
    • (2002) Drug Metab Dispos , vol.30 , pp. 985-990
    • Khan, K.K.1    He, Y.Q.2    Correia, M.A.3    Halpert, J.R.4
  • 18
    • 0000574406 scopus 로고    scopus 로고
    • Evaluation of atypical cytochrome P450 kinetics with two-substrate models: Evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites
    • Korzekwa KR, Krishnamachary N, Shou M, Ogai A, Parise RA, Rettie AE, Gonzalez FJ, and Tracy TS (1998) Evaluation of atypical cytochrome P450 kinetics with two-substrate models: evidence that multiple substrates can simultaneously bind to cytochrome P450 active sites. Biochemistry 37:4137-4147.
    • (1998) Biochemistry , vol.37 , pp. 4137-4147
    • Korzekwa, K.R.1    Krishnamachary, N.2    Shou, M.3    Ogai, A.4    Parise, R.A.5    Rettie, A.E.6    Gonzalez, F.J.7    Tracy, T.S.8
  • 20
    • 0032767738 scopus 로고    scopus 로고
    • Coumarin metabolism, toxicity and carcinogenicity: Relevance for human risk assessment
    • Lake BG (1999) Coumarin metabolism, toxicity and carcinogenicity: relevance for human risk assessment. Food Chem Toxicol 37:423-453.
    • (1999) Food Chem Toxicol , vol.37 , pp. 423-453
    • Lake, B.G.1
  • 21
    • 30644472081 scopus 로고    scopus 로고
    • Metabolism of coumarin by human P450s: A molecular modelling study
    • Lewis DF, Ito Y, and Lake BG (2006) Metabolism of coumarin by human P450s: a molecular modelling study. Toxicol In Vitro 20:256-264.
    • (2006) Toxicol In Vitro , vol.20 , pp. 256-264
    • Lewis, D.F.1    Ito, Y.2    Lake, B.G.3
  • 22
    • 0036196318 scopus 로고    scopus 로고
    • Mechanism-based inactivation of cytochrome P345 3A4 by 17-alpha-ethynylestradiol: Evidence for heme destruction and covalent binding to protein
    • Lin HL, Kent UM, and Hollenberg PF (2002) Mechanism-based inactivation of cytochrome P345 3A4 by 17-alpha-ethynylestradiol: evidence for heme destruction and covalent binding to protein. J Pharmacol Exp Ther 301:160-167.
    • (2002) J Pharmacol Exp Ther , vol.301 , pp. 160-167
    • Lin, H.L.1    Kent, U.M.2    Hollenberg, P.F.3
  • 24
    • 0018937071 scopus 로고
    • Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates
    • Ortiz de Montellano PR and Kunze KL (1980) Self-catalyzed inactivation of hepatic cytochrome P-450 by ethynyl substrates. J Biol Chem 255:5578-5585.
    • (1980) J Biol Chem , vol.255 , pp. 5578-5585
    • Ortiz de Montellano, P.R.1    Kunze, K.L.2
  • 28
    • 84883846728 scopus 로고
    • Naturally occurring coumarins and related physiological activities
    • Soine TO (1964) Naturally occurring coumarins and related physiological activities. J Pharm Sci 53:231-264.
    • (1964) J Pharm Sci , vol.53 , pp. 231-264
    • Soine, T.O.1
  • 29
    • 0033010482 scopus 로고    scopus 로고
    • Identification of selective mechanism-based inactivators of cytochromes P-450 2B4 and 2B5, and determination of the molecular basis for differential susceptibility
    • Strobel SM, Szklarz GD, He Y, Foroozesh M, Alworth WL, Roberts ES, Hollenberg PF, and Halpert JR (1999) Identification of selective mechanism-based inactivators of cytochromes P-450 2B4 and 2B5, and determination of the molecular basis for differential susceptibility. J Pharmacol Exp Ther 290:445-451.
    • (1999) J Pharmacol Exp Ther , vol.290 , pp. 445-451
    • Strobel, S.M.1    Szklarz, G.D.2    He, Y.3    Foroozesh, M.4    Alworth, W.L.5    Roberts, E.S.6    Hollenberg, P.F.7    Halpert, J.R.8
  • 30
    • 0033859758 scopus 로고    scopus 로고
    • Identification of the human liver microsomal cytochrome P450s involved in the metabolism of N-nitrosodi- n-propylamine
    • Teiber JF and Hollenberg PF (2000) Identification of the human liver microsomal cytochrome P450s involved in the metabolism of N-nitrosodi- n-propylamine. Carcinogenesis 21:1559-1566.
    • (2000) Carcinogenesis , vol.21 , pp. 1559-1566
    • Teiber, J.F.1    Hollenberg, P.F.2
  • 31
    • 4644339625 scopus 로고    scopus 로고
    • Identification of amino acid residues involved in the inactivation of cytochrome P450 2B1 by two acetylenic compounds: The role of three residues in nonsubstrate recognition Sites
    • Von Weymarn LB, Sridar C, and Hollenberg PF (2004) Identification of amino acid residues involved in the inactivation of cytochrome P450 2B1 by two acetylenic compounds: the role of three residues in nonsubstrate recognition Sites. J Pharmacol Exp Ther 311:71-79.
    • (2004) J Pharmacol Exp Ther , vol.311 , pp. 71-79
    • Von Weymarn, L.B.1    Sridar, C.2    Hollenberg, P.F.3
  • 33
    • 0034093628 scopus 로고    scopus 로고
    • Human cytochrome P-450 3A4: In vitro drug-drug interaction patterns are substrate-dependent
    • Wang RW, Newton DJ, Liu N, Atkins WM, and Lu AY (2000) Human cytochrome P-450 3A4: in vitro drug-drug interaction patterns are substrate-dependent. Drug Metab Dispos 28:360-366.
    • (2000) Drug Metab Dispos , vol.28 , pp. 360-366
    • Wang, R.W.1    Newton, D.J.2    Liu, N.3    Atkins, W.M.4    Lu, A.Y.5
  • 34
    • 17844387084 scopus 로고    scopus 로고
    • Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil
    • Wang YH, Jones DR, and Hall SD (2005) Differential mechanism-based inhibition of CYP3A4 and CYP3A5 by verapamil. Drug Metab Dispos 33:664-671.
    • (2005) Drug Metab Dispos , vol.33 , pp. 664-671
    • Wang, Y.H.1    Jones, D.R.2    Hall, S.D.3
  • 37
    • 0026750647 scopus 로고
    • The human hepatic cytochromes P450 involved in drug metabolism
    • Wrighton SA and Stevens JC (1992) The human hepatic cytochromes P450 involved in drug metabolism. Crit Rev Toxicol 22:1-21.
    • (1992) Crit Rev Toxicol , vol.22 , pp. 1-21
    • Wrighton, S.A.1    Stevens, J.C.2


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