Metabolism of 2,5-bis(trifluoromethyl)-7-benzyloxy-4-trifluoromethylcoumarin by human hepatic CYP isoforms: evidence for selectivity towards CYP3A4

References

• BURKE, M. D., THOMFSON, S., WEAVER, R. J., WOLF, C. R. and MAYER, R. T., 1994, Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human liver microsomes. Biochemical Pharmacology, 48, 923–936.
   PubMed Web of Science ®Google Scholar
• BUSBY, W. F., JR, ACKERMANN, J. M. and CRFSPI, C. L., 1999, Effect of methanol, ethanol, dirnethyl sulphoxide, and acetonitrile on in vitro activities of cDNA-expressed human cytochromes P-450. Drug Metabolism and Disposition, 27, 246–249.
   Google Scholar
• BUTERS, J. T. M., SCHILLER, C. D. and Cuou, R. C., 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. Biochemical Pharmacology, 46, 1577–1584.
   Google Scholar
• CHANG, T. K. H., GONZALEZ, F. J. and WAXMAN, D. J., 1994, Evaluation of triacetyloleandomycin, a-naphthofiavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Archives of Biochemistry and Biophysics, 311, 437–442.
   Google Scholar
• 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 Metabolism and Disposition, 26, 1–4.
   PubMed Web of Science ®Google Scholar
• CHAURET, N., TREMBLAY, N., LACKMAN, R. L., GAUTHIER, J.Y., SILVA, J. M., MAROIS, J., YERGEY, J. Y. and NICOLL-GRIFFITH, D. A., 1999, Description of a 96-well plate assay to measure cytochrome P4503A inhibition in human liver microsomes using a selective fluorescent probe. Analytical Biochemistry, 276, 215–226.
   Google Scholar
• CLARKE, S. E., 1998, In vitro assessment of human cytochrome P450. Xenobiotica, 28, 1167–1202.
   Google Scholar
• CODE, E. L., CRESPI, C. L., PENMAN, B. W., GONZALEZ, F. J., CHANG, T. K. H. and WAXMAN, D. J., 1997, Human cytochrome P4502B6. Interindividual hepatic expression, substrate specificity, and role in precarcinogen activation. Drug Metabolism and Disposition, 25, 985–993.
   Google Scholar
• CRESPI, C. L., MILLER, V. P., ACKERMANN, J. M., STRESSER, D. M. and BUSBY, W. F., JR, 1999, Novel high throughput fluorescent cytochrome P450 assays. Toxicological Sciences, 48(1-S), 69.
   Google Scholar
• CRESPI, C. L., MILLER, V. P. and PENMAN, B. W., 1997, Microtiter plate assays for inhibition of human, drug-metabolizing cytochromes P450. Analytical Biochemistry, 248, 188–190.
   PubMed Web of Science ®Google Scholar
• CRESPI, C. L., MILLER, V. P. and PENMAN, B. W., 1998, High throughput screening for inhibition of cytochrome P450 metabolism. Medical Chemistry Research, 8, 457–471.
   Web of Science ®Google Scholar
• FORRESTER, L. M., HENDERSON, C. J., GLANCEY, M. J., BACK, D. J., PARK, B. K., BALL, S. E., KITTERINGHAM, M. R., MCCLAREN, A. W., MILES, J. S., SKETT, P. and WOLF, C. R., 1992, Relative expression of cytochrome P450 isoenzymes in human liver and association with the metabolism of drugs and xenobiotics. Biochemical Journal, 281, 359–368.
   PubMed Web of Science ®Google Scholar
• GORSKI, J. C., JoNER, D. R., WRiciutoN, S. A. and HALL, S. D., 1994, Characterization of dextromethorphan N-demethylation by human liver microsomes. Contribution of the cytochrome P450 3A (CYP3A) subfamily. Biochemical Pharmacology, 48, 173–182.
   PubMed Web of Science ®Google Scholar
• GOTOH, 0., 1992, Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. Journal of Biological Chemistry, 267, 83–90.
   Google Scholar
• KENWORTHY, K. E., BLOOMER, J. C., CLARICE, S. E. and HOUSTON, J. B., 1999, CYP3A4 drug interactions: correlation of 10 in vitro probe substrates. British Journal of Clinical Pharmacology, 48, 716–727.
   PubMed Web of Science ®Google Scholar
• LAKE, B. G., 1987, Preparation and characterisation of microsomal fractions for studies of xenobiotic metabolism. In K. Snell and B. Mullock (eds), Biochemical Toxicology: A Practical Approach (Oxford: IRL Press), pp. 183–215.
   Google Scholar
• LEWIS, D. F. V., DICKINS, M., EDDERSHAW, P. J., TARBIT, M. H. and GOLDFARB, P. S., 1999b, Cytochrome P450 substrate specificities, substrate structural templates and enzyme active site geometries. Drug Metabolism and Drug Interactions, 15, 1–49.
   Google Scholar
• LEWIS, D. F. V., EDDERSHAW, P. J., GOLDFARB, P. S. and TARBIT, M. H., 1996, Molecular modelling of CYP3A4 from an alignment with CYP102: identification of key interactions between putative active site residues and CYP3A-specific chemicals. Xenobiotica, 26, 1067–1086.
   Google Scholar
• LEWIS, D. F. V., LAKE, B. G., DICKINS, M., EDDERSHAW, P. J., TARBIT, M. H. and GOLDFARB, P. S., 1999a, Molecular modelling of CYP2B6, the human CYP2B isoform, by homology with the substrate-bound CYP102 crystal structure: evaluation of CYP2B6 substrate characteristics, the cytochrome b5 binding site and comparisons with CYP2B1 and CYP2B4. Xenobiotica, 29, 361–393.
   Google Scholar
• Li, H. and PouLos, T. L., 1997, The structure of the cytochrome P450Bm3 haem domain complexed with the fatty acid substrate, palmitoleic acid. Nature Structural Biology, 4, 140–146.
   PubMedGoogle Scholar
• LOWRY, 0. H., ROSEBROUGH, N. J., FARR, A. L. and RANDALL, R. J. 1951, Protein measurement with the Folin phenol reagent. Journal of Biological Chemistry, 193, 265–275.
   Google Scholar
• MEI, Q., TANG, C., ASSANG, C., LIN, Y., SLAUGHTER, D., RODRIGUES, A. D., BAILLIE, T. A., RUSHMORE, T. H. and Stiou, M., 1999, Role of a potent inhibitory monoclonal antibody to cytochrome P-450 3A4 in assessment of human drug metabolism. Journal of Pharmacology and Experimental Therapeutics, 291, 749–759.
   PubMed Web of Science ®Google Scholar
• NELSON, D. R., KOYMANS, L., KAMATAKI, T., STEGEMAN, J. J., FEYEREISEN, R., WAXMAN, D. J., WATERMAN, M. R., GOTOH, 0., COON, M. J., ESTABROOK, R. W., GUNSALUS, I. C. and NEBERT, D. W., 1996, P450 superfamily: update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics, 6, 1–42.
   Google Scholar
• NEwroN, 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 Metabolism and Disposition, 23, 154–158.
   PubMed Web of Science ®Google Scholar
• ONO, S., HATANAKA, T., HOTTA, H., SATOH, T., GONZALEZ, F. J. and TSUTSUI, M., 1996, Specificity of substrate and inhibitor probes for cytochrome P450s: evaluation of in vitro metabolism using cDNA-expressed human P450s and human liver microsomes. Xenobiotica, 26, 681–693.
   PubMed Web of Science ®Google Scholar
• PARKINSON, A., 1996, Biotransformation of xenobiotics. In C. D. Klaassen (ed.), Casarett and DoulPs Toxicology: The Basic Science of Poisons, 5th edn (New York: McGraw-Hill), pp. 113–186.
   Google Scholar
• PELKONEN, 0., MAENPAÀ, J., TAAVITSAINEN, P., RAUTIO, A. and RAUNIO, H., 1998, Inhibition and induction of human cytochrome P450 (CYP) enzymes. Xenobiotica, 28, 1203–1253.
   Google Scholar
• RENWICK, A. B., MISTRY, H., BALL, S. E., WALTERS, D. G., KAO, J. and LAKE, B. G., 1998, Metabolism of zaleplon by human hepatic cytochrome P450 isoforms. Xenobiotica, 28, 337–348.
   PubMed Web of Science ®Google Scholar
• RENWICK, A. B., SURRY, D., PRICE, R. J., LAKE, B. G. and EVANS, D. C., 2000, Metabolism of 7-benzyloxy-4-trifluoromethylcoumarin by human hepatic cytochrome P450 isoforms. Xenobio-tica, 30, 955–969.
   PubMed Web of Science ®Google Scholar
• RODRIGUES, A. D., 1999, Integrated cytochrome P450 reaction phenotyping. Attempting to bridge the gap between cDNA-expressed cytochromes P450 and native human liver microsomes. Biochemical Pharmacology, 57, 465–480.
   PubMed Web of Science ®Google Scholar
• 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. Journal of Pharmacology and Experimental Therapeutics, 270, 414–423.
   PubMed Web of Science ®Google Scholar
• STRESSER, D. M., MILLER, V. P., BLANCHARD, A., ACKERMANN, J. M., DANDENEAU, A. and CRESPI, C. L., 2000, Cytochrome P450 inhibition assays - the challenges in interpreting data for CYP3A4. Toxicological Sciences, 54(1-S), 101.
   Google Scholar
• TASSANEEYAKUL, W BIRKETT, D. J., McMANus, M. E., TASSANEEYAKUL, W., VERONESE, M. E., ANDERSSON, T., TUKEY, R. H. and MINERS, J. 0., 1994, Caffeine metabolism by human hepatic cytochromes P450: contributions of 1A2, 2E1 and 3A isoforms. Biochemical Pharmacology, 47, 1767–1776.
   Google Scholar
• UENG, Y.-F., KUWABARA, T., CHUN, Y.-J. and GUENGERICH, F. P., 1997, Cooperativity in oxidations catalysed by cytochrome P450 3A4. Biochemistry, 36, 370–381.
   PubMed Web of Science ®Google Scholar
• WAXMAN, D. J., LAPENS ON, D. P., AOYAMA, T., GELBOIN, H. V., GONZALEZ, F. J. and KORZEKWA, K., 1991, Steroid hormone hydroxylase specificities of eleven cDNA-expressed human cytochrome P450s. Archives of Biochemistry and Biophysics, 290, 160–166.
   PubMed Web of Science ®Google Scholar
• WRIGHToN, S. A., VANDENBRANDEN, M., STEVENS, J. C., SHIPLEY, LA., RING, B. J., RETTIE, A. E. and CAS1LVIAN, J. R., 1993, In vitro methods for assessing human hepatic drug metabolism: their use in drug development. Drug Metabolism Reviews, 25, 453–484.
   Google Scholar
• YANG, T. J., KRAUSZ, K. W., SAI, Y., GONZALEZ, F. J. and GELBOIN, H. V., 1999, Eight inhibitory monoclonal antibodies define the role of individual P-450s in human liver microsomal diazepam, 7-ethoxycoumarin and imipramine metabolism. Drug Metabolism and Disposition, 27, 102–109.
   PubMed Web of Science ®Google Scholar