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Xenobiotica
the fate of foreign compounds in biological systems
Volume 34, 2004 - Issue 5
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Research Article

Influence of different recombinant systems on the cooperativity exhibited by cytochrome P4503A4

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Pages 473-486 | Received 15 Jan 2004, Published online: 22 Sep 2008

Reference

  • ATKINS, W. M., WANG, R. and Lu, A. Y.-H., 2001, Allosteric behavior in cytochrome P450-dependent in vitro drug—drug interactions: a prospective based on conformational dynamics. Chemical Research in Toxicology, 14, 338–347.
  • BUENING, M. K., CHANG, R. L., HUANG, M.-T., FORTNER, J. G., WOOD, A. W. and CONNEY, A. H., 1981, Activation and inhibition of benzo(a)pyrene and afiatoxin Bl metabolism in human liver microsomes by naturally occurring fiavonoids. Cancer Research, 41, 67–72.
  • CRESPI, C. and MILLER, V., 1999, The use of heterologously expressed drug metabolizing enzymes — state of the art and prospects for the future. Pharmacology and Therapeutics, 84, 121–131.
  • DOMANSKI, T. L., HE, Y. A., HARLOW, G. R. and HALPERT, J. R., 2000, Dual role of human cytochrome P450 3A4 residue Phe-304 in substrate specificity and cooperativity. Journal of Pharmacology and Experimental Therapeutics, 293, 585–591.
  • EGNELL, A.-C., HOUSTON, B. and BOYER, S., 2003, In vivo CYP3A4 heteroactivation is a possible mechanism for the drug interaction between felbamate and carbamazepine. Journal of Pharmacology and Experimental Therapeutics, 305, 1251–1262.
  • EMOTO, C., YAMAZAKI, H., IKETAKI, H., YAMASAKI, S., SATOH, T., SHIMIZU, R., SUZUKI, S., SHIMADA, N., NAKAJIMA, M. and YoKoi, T., 2001, Cooperativity of a-naphthofiavone in cytochrome P450 3A-dependent drug oxidation activities in hepatic and intestinal microsomes from mouse and human. Xenobiotica, 31, 265–275.
  • GALETIN, A., CLARKE, S. E. and HOUSTON, J. B., 2002, Quinidine and haloperidol as modifiers of CYP3A4 activity: multisite kinetic model approach. Drug Metabolism and Disposition, 30, 1512–1522.
  • GONZALEZ, F. J. and KORZEKWA, K. R., 1995, Cytochrome P450 expression systems. Annual Review in Pharmacology and Toxicology, 35, 369–390.
  • GUENGERICH, F. P., 1997, Role of cytochrome P450 enzymes in drug—drug interactions. Advances in Pharmacology, 43, 7–35.
  • HARLOW, G. R. and HALPERT, J. R., 1998, Analysis of human cytochrome P450 3A4 cooperativity: construction and characterization of a site-directed mutant that displays hyperbolic steroid hydroxylation kinetics. Proceedings of the National Academy of Sciences, USA, 95, 6636–6641.
  • HOSEA, N. A., MILLER, G. P. and GUENGERICH, F. P., 2000, Elucidation of distinct ligand binding sites for cytochrome P450 3A4. Biochemistry, 39, 5929–5939.
  • HUTZLER, J. M., HAUER, M. J. and TRACY, T. S., 2001, Dapsone activation of CYP2C9-mediated metabolism: evidence for activation of multiple substrates and a two-site model. Drug Metabolism and Disposition, 29, 1029–1034.
  • INGELMAN-SUNDBERG, M., 1986, Cytochrome P-450 organization and membrane interactions. In P. R. Ortiz de Montellano (ed.), Cytochrome P450. Structure, Mechanism, and Biochemistry (New York: Plenum), pp. 119–160.
  • JOHNSON, E. F., 2003, Deciphering substrate recognition by drug-metabolizing cytochrome P450. Drug Metabolism and Disposition, 31, 1532–1540.
  • KERR, B. M., THUMMEL, K. E., WURDEN, C. J., KLEIN, S. M., KROETZ, D. L., GONZALEZ, F. J. and LEVY, R. H., 1994, Human liver carbamazepine metabolism. Role of CYP3A4 and CYP2C8 in 10,11-epoxide formation. Biochemical Pharmacology, 47, 1969–1979.
  • KOLEY, A. P., BUTERS, J. T. M., ROBINSON, R. C., MARKOWITZ, A. and FRIEDMAN, F. K., 1997, Differential mechanism of cytochrome P450 inhibition and activation by a-naphthefiavone. Journal of Biological Chemistry, 272, 3149–3152.
  • KORZEKWA, K. R., KRISHNAMACHARY, N., SHOU, M., OGAI, A., PARISE, R. A., RETTIE, A. E., GONZALEZ, F. J. and TRACY, T. S., 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.
  • LE MAIRE, M., CHAMPEIL, P. and MOLLER, J. V., 2000, Interaction of membrane proteins and lipids with solubilizing detergents. Biochimica et Biophysica Acta, 1508, 86–111.
  • LOMBARDINO, J. G., 1981, Synthesis and antiinflammatory activity of metabolites of piroxicam. Journal of Medicinal Chemistry, 24, 39–42.
  • LUDWIG, E., SCHMID, J., BESCHKE, K. and EBNER, T., 1999, Activation of human cytochrome P-450 3A4-catalysed meloxicam 5'-methylhydroxylation by quinidine and hydroquinidine in vitro. Journal of Pharmacology and Experimental Therapeutics, 290, 1–8.
  • MARQUARDT, D. W., 1963, An algorithm for least-squares estimation of nonlinear parameters. Journal of the Society of Industrial and Applied Mathematics, 11, 431–441.
  • 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 Metabolism and Disposition, 23,154–158.
  • NGUI, J. S., CHEN, Q., SHOU, M., WANG, R., STEARNS, R. A., BAILLIE, T. A. and TANG, W., 2001, In vitro stimulation of warfarin metabolism by quinidine: Increases in the formation ofand10-hydroxywarfarin. Drug Metabolism and Disposition, 29, 877–886.
  • NGUI, J. S., TANG, W., STEARNS, R. A., SHOU, M., MILLER, R. R., ZHANG, Y., LIN, J. H. and BAILLIE, T. A., 2000, Cytochrome P450 3A4-mediated interactions of diclofenac and quinidine. Drug Metabolism and Disposition, 28, 1043–1050.
  • NIWA, T., SHIRAGA, T., YAMASAKI, S., ISHIBASHI, K., OHNO, Y. and KAGAYAM A., 2003, In vitro activation of 7-benzyloxyresorufin 0-debenzylation and nifedipine oxidation in human liver microsomes. Xenobiotica, 7, 717–729.
  • OMURA, T. and SATO, R. 1964, The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. Journal of Biological Chemistry, 239, 2370–2378.
  • RAUCY, J. L. and LASKER, J. M., 1991, Isolation of P450 enzymes from human liver. Methods in Enzymology, 206, 557–587.
  • SHOU, M., MEI, Q., ETTORE, M. W., JR, DAI, R., BAILLIE, T. A. and RUSHMORE, T. H., 1999, Sigmoidal kinetic model for two cooperative substrate-binding sites in a cytochrome P450 3A4 active site: an example for the metabolism of diazepam and its derivatives. Biochemical Journal, 340, 845–853.
  • TANG, W., STEARNS, R. A., BANDIERA, S. M., ZHANG, Y., RAAB, C., BRAUN, M. P., DEAN, D. C., PANG, J., LEUNG, K. H., Doss, G. A., STRAUSS, J. R., KWEI, G. Y., RUSHMORE, T. H., CHiu, S.-H. L. and BAILLIE, T. A., 1999b, Studies on hepatic cytochrome P450-mediated bioactivation of diclofenac in rats and in human hepatocytes: identification of glutathione conjugated metabolites. Drug Metabolism and Disposition, 27, 365–372.
  • TANG, W., STEARNS, R. A., KWEI, G. Y., ILIFF, S. A., MILLER, R. R., EGAN, M. A., Yu, N. X., DEAN, D. C., KUMAR, S., SHOU, M., LIN, J. H. and BAILLIE, T. A., 1999a, Interaction of diclofenac and quinidine in monkeys: stimulation of diclofenac metabolism. Journal of Pharmacology and Experimental Therapeutics, 291, 1068–1074.
  • TANG. W. and STEARNS, R. A., 2001, Heterotropic cooperativity in cytochrome P4503A4 and potential drug—drug interactions. Current Drug Metabolism, 2, 185–198.
  • UENG, Y.-F., KUWABARA, T., CHUN, Y.-J. and OUENGERICH, F. P., 1997, Cooperativity in oxidations catalysed by cytochrome P450 3A4. Biochemistry, 36, 370–381.
  • WANG, R. W., NEWTON, D. J., Liu, N., ATKINS, W. M. and Lu, A. Y.-H., 2000, Human cytochrome P-450 3A4: in vitro drug—drug interaction patterns are substrate-dependent. Drug Metabolism and Disposition, 28, 360–366.
  • WILLIAMS, P. A., COSME, J., WARD, A., ANGOVE, H. C., VINKOVIC, D. M. and Noll, H., 2003, Crystal structure of human cytochrome P450 2C9 with bound warfarin. Nature, 424, 464-468. WRIGHTON, S. A. and STEVENS, J. C., 1992, The human hepatic cytochrome P450 involved in drug metabolism. Critical Reviews in Toxicology, 22, 1–21.
  • XUE, J., WANG, H. F., WANG, Q., SZKLARZ, G. D., DOMANSKI, T. L., HALPERT, J. R. and CORREIA, M. A., 2001, Influence of P450 3A4 SRS-2 residues on cooperativity and/or regioselectivity of aflatoxin B1 oxidation. Chemical Research in Toxicology, 14, 483–491.
  • ZHAO, J., LEEMANN, T. and DAYER, P., 1992, In vitro oxidation of oxicam NSAIDS by a human liver cytochrome P450. Life Sciences, 51, 575–581.

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