Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 31, 2001 - Issue 5
102
Views
22
CrossRef citations to date
0
Altmetric
Research Article

Cooperativity of α-naphthoflavone in cytochrome P450 3A-dependent drug oxidation activities in hepatic and intestinal microsomes from mouse and human

, , , , , , , , & show all
Pages 265-275 | Published online: 22 Sep 2008

References

  • CUPP-VICKERY, J., ANDERSON, R. and HATZIRIS, Z., 2000, Crystal structures of ligand complexes of P450eryF exhibiting homotropic cooperativity. Proceedings of National Academy of Sciences, USA, 97, 3050–3055.
  • 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.
  • DOMANSKI, T. L., Liu, J., HARLOW, G. R. and HALPERT, J. R., 1998, Analysis of four residues within substrate recognition site 4 of human cytochrome P450 3A4: Role in steroid hydroxylase activity and a-naphthofiavone stimulation. Archives of Biochemistry and Biophysics, 350, 223–232.
  • EDGAR, B., BAILEY, D. G., BERGS TRAND, R., JOHNSSON, G. and LuRjE, L., 1990, Formulation dependent interaction between felodipine and grapefruit juice. Clinical Pharmacology and Therapeutics, 47, 181.
  • EMOTO, C., YAMAZAKI, H., YAMASAKI, S., SHIMADA, N., NAKADMA, M. and YOKOI, T., 2000a, Use of everted sacs of mouse small intestine as enzyme sources for the study of drug oxidation activities in vitro. Xenobiotica, 30, 971–982.
  • EMOTO, C., YAMAZAKI, H., YAMASAKI, S., SHIMADA, N., NAKADMA, M. and YOKOI, T., 2000b, Characterization of cytochrome P450 enzymes involved in drug oxidations in mouse intestinal microsomes. Xenobiotica, 30, 943–953.
  • GIBBS, M. A., THUMMEL, K. E., SHEN, D. D. and KUNZE, K. L., 1999, Inhibition of cytochrome P-450 3A (CYP3A) in human intestinal and liver microsomes: comparison of K, values and impact of CYP3A5 expression. Drug Metabolism and Disposition, 27, 180–187.
  • GUENGERICH, F. P., 1991, Reactions and significance of cytochrome P-450 enzymes. Journal of Biological Chemistry, 266, 10019–10022.
  • GUENGERICH, F. P., 1995, Human cytochrome P450 enzymes. In P. R. Oritiz de Montellano (ed), Cytochrome P450 (New York: Plenum), pp. 473–535.
  • 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 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.
  • HOUSTON, J. B. and KENWORTHY, K. E., 2000, In vitro in vivo scaling of CYP kinetic data not consistent with the classical Michaelis-Menten model. Drug Metabolism and Disposition, 28, 246–254.
  • IATSIMIRSKAIA, E., TULEBAEV, S., STOROZHUK, E., UTKIN, I., SMITH, D., GERBER, N. and KOUDRIAKOVA, T., 1997, Metabolism of rifabutin in human enterocyte and liver microsomes: kinetic parameters, identification of enzyme systems, and drug interactions with macrolides and antifungal agents. Clinical Pharmacology and Therapeutics, 61, 554–562.
  • 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.
  • KORZEKWA, K. R., KRISHNAMACHARY, N., Suou, 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.
  • KRISHNA, D. R. and KLOTZ, U., 1994, Extrahepatic metabolism of drugs in humans. Clinical Pharmacokinetics, 26, 144–160.
  • LALONDE, R. L., LESSARD, D. and GAUDREAULT, J., 1996, Population pharmacokinetics of terfenadine. Pharmaceutical Research, 13, 832–838.
  • LOWN, K. S., Guosu, M. and WATKINS, P. B., 1998, Sequences of intestinal and hepatic cytochrome P450 3A4 cDNAs are identical. Drug Metabolism and Disposition, 26, 185–187.
  • LOWRY, O. 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.
  • MA, B., PRUEKSARITANONT, T. and LIN, J. H., 2000, Drug interactions with calcium channel blockers: possible involvement of metaboliteintermediate complexation with CYP3A. Drug Metabolism and Disposition, 28, 125–130.
  • MÁENPAW, J., HALL, S. D., RING, B. J., STROM, S. C. and WEIGH-roN, S. A., 1998, Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: the effect of assay conditions and regioselective stimulation by a-naphthofiavone, terfenadine and testosterone. Pharmacogenetics, 8, 137–155.
  • NAKAMURA, T., OKADA, K., NAGATA, K. and YAMAZOE, Y., 2000, Intestinal cytochrome P450 and response to rifampicin in rabbits. Japanese Journal of Pharmacology, 82, 232–239.
  • PAINE, M. F., KHALIctu, M., FISHER, J. M., SHEN, D. D., KUNZE, K. L., MARSH, C. L., PARKINS, J. D. and THUMMEL, K. E., 1997, Characterization of interintestinal and intraintestinal variations in human CYP3A-dependent metabolism. Journal of Pharmacology and Experimental Therapeutics, 283, 1552–1562.
  • PAINE, M. F., SHEN, D. D., KUNZE, K. L., PERKINS, J. D., MARSH, C. L., McVicAR, J. P., BARR, D. M., Gamm.s, B. S. and THUMMEL, K. E., 1996, First-pass metabolism of midazolam by the human intestine. Clinical Pharmacology and Therapeutics, 60, 14–24.
  • SHET, M. S., FISHER, C. W., HOLMANS, P. L. and ESTABROOK, R. W., 1993, Human cytochrome P450 3A4: enzymatic properties of a purified recombinant fusion protein containing NADPH-P450 reductase. Proceedings of National Academy of Sciences, USA, 90, 11748–11752.
  • 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.
  • Suou, M., GROGAN, J., MANCEWICW, J. A., KRAUSZ, K. W., GONZALEZ, F. J., GELBOIN, H. V. and KORZEKWA, K. R., 1994, Activation of CYP3A4: Evidence for the simultaneous binding of substrates in a cytochrome P450 active site. Biochemistry, 33, 6450–6455.
  • Smuni, M. T., EADIE, M. J. and BROPHY, T. O. R., 1981, The pharmacokinetics of midazolam in man. European Journal of Clinical Pharmacology, 19, 271–278.
  • SZKLARZ, G. D. and HALPERT, J. R., 1997, Molecular modeling of cytochrome P450 3A4. Journal of Computer-Aided Molecular Design, 11, 265–272.
  • 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.
  • WANG, H. F., DICK, R., YIN, H. Q., LICAD-COLES, E., KROETZ, D. L., SZKLARZ, G., HARLOW, G., HALPERT, J. R. and CORREIA, M. A., 1998, Structurefunction relationships of human liver cytochromes P450 3A: afiatoxin B1 metabolism as a probe. Biochemistry, 37, 12536–12545.
  • WANG, R. W., NEwroN, D. J., Lm, 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.
  • WATKINS, P. B., WEIorrroN, S. A., SCHUETZ, E. G., MOLOWA, D. T. and GUZELIAN, P. S., 1987, Identification of glucocorticoid-inducible cytochromes P-450 in the intestinal mucosa of rats and man. Journal of Clinical Investigation, 80, 1029–1036.
  • YAMAZAKI, H. and SHEMADA, T., 1997, Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Archives of Biochemistry and Biophysics, 346, 161–169.
  • YANAGIMOTO, T., Pron, S., SAWADA, M. and KAMATAKI, T., 1997, Mouse cytochrome P450 (Cyp3a11): predominant expression in liver and capacity to activate aflatoxin B1. Archives of Biochemistry and Biophysics, 340, 215–218.
  • ZHAO, X.-J. and Ismzmu, T., 1997, The in vitro hepatic metabolism of quinine in mice, rats and dogs: comparison with human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 283, 1168–1176.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.