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Xenobiotica
the fate of foreign compounds in biological systems
Volume 29, 1999 - Issue 3
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Research Article

Effects of arachidonic acid, prostaglandins, retinol, retinoic acid and cholecalciferol on xenobiotic oxidations catalysed by human cytochrome P450 enzymes

Pages 231-241 | Published online: 22 Sep 2008

References

  • CRESTEIL, T., MONSARRAT, B., ALVINERIE, P., TRELUYER, J. M., VIEIRA, I. and WRIGHT, M., 1994, Taxol metabolism by human liver microsomes: identification of cytochrome P450 isozymes involved in its biotransformation. Cancer Research, 54, 386–392.
  • DAIKH, B. E., LASKER, J. M., RAUCY, J. L. and KOOP, D. R.,1994,Regio- and stereoselectiveepoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C9. Journal of Pharmacology and Experimental Therapeutics, 271, 1427–1433.
  • DIRVEN, H., PETERS, J., GIBSON, G. G., PETERS, W. and JoNGENEELEN, F. J., 1991, Lauric acid hydroxylase activity and cytochrome P450IV family proteins in human liver microsomes. Biochemical Pharmacology, 42, 1841–1844.
  • GIBALDI, M., 1993, Stereoselective and isozyme-selective drug interactions. Chirality, 5, 407-413. GONZALEZ, F. J., 1990, Molecular genetics of the P-450 superfamily. Pharmacology and Therapeutics, 45, 1–38.
  • GUENGERICH, F. P., 1994, Analysis and characterization of enzymes. In: Principles and Methods of Toxicology, edited by A. W. Hayes (New York: Raven), pp. 1259–1313.
  • GUENGERICH, F. P., 1995, Human cytochrome P450 enzymes. In: Cytochrome P450, edited by P. R. Oritiz de Montellano (New York: Plenum), pp. 473–535.
  • GUENGERICH, F. P., 1997, Role of cytochrome P450 enzymes in drug-drug interactions. Advance in Pharmacology, 43, 7–35.
  • GUENGERICH, F. P. and SHIMADA, T., 1991, Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chemical Research in Toxicology, 4, 391–407.
  • HALPERT, J. R., 1995, Structural basis of selective cytochrome P450 inhibition. Annual Reviews of Pharmacology and Toxicology, 35, 29–53.
  • HALPERT, J. R., GUENGERICH, F. P., BEND, J. R. and CORREIA, M. A., 1994, Selective inhibitors of cytochromes P450. Toxicology and Applied Pharmacology, 125, 163–175.
  • HAYASHI, S., OMURA, T., WATANABE, T. and OKUDA, K., 1988a, Immunochemical evidence for the catalysis of vitamin D 25-hydroxylation and testosterone 16a-hydroxylation by homologous forms of cytochrome P-450 in rat liver microsomes. Journal of Biochemistry, 103, 853–857.
  • HAYASHI, S., USUI, E. and OKUDA, K., 1988b, Sex-related difference in vitamin D 25 -hydroxylase of rat liver microsomes. Journal of Biochemistry, 103, 863–866.
  • JAPANESE BIOCHEMICAL SOCIETY, 1979, Biochemistry Data Book, edited by T. Yamagawa (Tokyo: Kagaku Dojin).
  • KAKU, M., ICHIHARA, K., KUSUNOSE, E., OGITA, K., YAMAMOTO, S., YANO, I. and KUSUNOSE, M., 1984, Purification and characterization of cytochrome P-450 specific for prostaglandin and fatty acid hydroxylase activities from the microsomes of rabbit small intestinal mucosa. Journal of Biochemistry, 96, 1883–1891.
  • KARARA, A., MAKITA, K., JACOBSON, H. R., FALCK, J. R., GUENGERICH, F. P., DuBois, R. N. and CAPDEVILA, J. H., 1993, Molecular cloning expression and enzymatic characterization of the rat kidney cytochrome P-450 arachidonic acid epoxygenase. Journal of Biological Chemistry, 268, 13565–13570.
  • KITADA, M., KAMATAKI, T., ITAHASHI, K., RIKIHISA, T. and KANAKUBO, Y., 1987, P-450 HFLa, a form of cytochrome P-450 purified from human fetal livers, is the 16a-hydroxylase of dehydro-epiandrosterone 3-sulfate. Journal of Biological Chemistry, 262, 13534–13537.
  • KUMAR, G. N., WALLE, U. K. and WALLE, T., 1994, Cytochrome P450 3A-mediated human liver microsomal taxol 6a-hydroxylation. Journal of Pharmacology and Experimental Therapeutics, 268, 1160–1165.
  • LAETHEM, R. M. and KOOP, D. R., 1992, Identification of rabbit cytochromes P450 2C1 and 2C2 as arachidonic acid epoxygenases. Molecular Pharmacology, 42, 958–963.
  • Li, A. P., MAUREL, P., GOMEZ -LECHON, M. J., CHENG, L. C. and JuRimA -RomET, M., 1997, Preclinical evaluation of drug-drug interaction potential: present status of the application of primary human hepatocytes in the evaluation of cytochrome P450 induction. Chemico-Biologkal Interactions, 107, 5–16.
  • 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.
  • MIYATA, M., NAGATA, K., SHIVIADA, M., YAMAZOE, Y. and KATO, R., 1994, Structure of a gene and cDNA of a major constitutive form of testosterone 6/3-hydroxylase (P450/6/3) encoding CYP3A2: comparison of the cDNA with P450PCN2. Archives of Biochemistry and Biophysics, 314, 351–359.
  • NEBERT, D. W., NELSON, D. R., ADESNIK, M., COON, M. J., ESTABROOK, R. W., GONZALEZ, F. J., GUENGERICH, F. P., GUNSALUS, I. C., JOHNSON, E. F., KEMPER, B., LEVIN, W., PHILLIPS, I. R., SATO, R. and WATERMAN, M., 1989, The P450 superfamily : update listing of all genes and recommended nomenclature for the chromosomal loci. DNA, 8, 1–13.
  • 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. Pharmaco genetics, 6, 1–42.
  • 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.
  • PERITI, P., MAZZEI, T., MINI, E. and NOWLLI, A., 1992, Pharmacokinetic drug interactions of macrolides. Clinical Pharmacokinetics, 23, 106–131.
  • RAHMAN, A., KORZEKWA, K. R., GROGAN, J., GONZALEZ, F. J. and HARRIS, J. W., 1994, Selective biotransformation of taxol to 6a-hydroxytaxol by human cytochrome P450 2C8. Cancer Research, 54, 5543–5546.
  • R1FKIND, A. B., LEE, C., CHANG, T. K. H. and WAXMAN, D. J., 1995, Arachidonic acid metabolism by human cytochrome P450s 2C8, 2C9, 2E1 and 1A2: regioselective oxygenation and evidence for a role for CYP2C enzymes in arachidonic acid epoxygenation in human liver microsomes. Archives of Biochemistry and Biophysics, 320, 380–389.
  • ROYER, I., MONSARRAT, B., SONN1ER, M., WRIGHT, M. and CRESTEIL, T., 1996, Metabolism of docetaxel by human cytochromes P450: interactions with paclitaxel and other antineoplastic drugs. Cancer Research, 56, 58–65.
  • RYAN, D. E. and LEVIN, W., 1990, Purification and characterization of hepatic microsomal cytochrome P-450. Pharmacology and Therapeutics, 45, 153–239.
  • SHAW, P. M., HOSEA, N. A., THOMPSON, D. V., LENIUS, J. M. and GUENGERICH, F. P., 1997, Reconstitution premixes for assays using purified recombinant human cytochrome P450, NADPH-cytochrome P450 reductase and cytochrome b. Archives of Biochemistry and Biophysics, 348, 107–115.
  • SHIMADA, T., GILLAM, E. M. J., SUTTER, T. R., STRICKLAND, P. T., GUENGERICH, F. P. and YAMAZAKI, H., 1997, Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metabolism and Disposition, 25, 617–622.
  • SHIMADA, T., YAMAZAKI, H., MDAURA, 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.
  • SONNICHSEN, D. S., Liu, Q., SCHUETZ, E. G., SCHUETZ J. D., PAPPO, A. and RELLING, M. V., 1995, Variability in human cytochrome P450 paclitaxel metabolism. Journal of Pharmacology and Experimental Therapeutics, 275, 566–575.
  • TANAKA, S., IMAOKA, S., KUSUNOSE, E., KUSUNOSE, M., MAEKAWA, M. and FUNAE, Y., 1990, co- and (co-1)-hydroxylation of arachidonic acid, lauric acid and prostaglandin A by multiple forms of cytochrome P-450 purified from rat hepatic microsomes. Biochimica et Biophyska Acta, 1043, 177–181.
  • THEOHARIDES, A. D. and KUPFER, D., 1981, Evidence for different hepatic microsomal monooxygenases catalyzing co- and (co-1)-hydroxylations of prostaglandins E and E. Journal of Biological Chemistry, 256, 2168–2175.
  • TJIA, J. F., COLBERT, J. and BACK, D. J., 1996, Theophylline metabolism in human liver microsomes: inhibition studies. Journal of Pharmacology and Experimental Therapeutics, 276, 912–917.
  • VATSIS, K. P., THEOHARIDES, A. D., KUPFER, D. and COON, M. J., 1982, Hydroxylation of prostaglandins by inducible isozymes of rabbit liver microsomal cytochrome P-450. Journal of Biological Chemistry, 257, 11221–11229.
  • YAMAMOTO, S., KUSUNOSE, E., OGITA, K., KAKU, M., ICHIHARA, K. and KUSUNOSE, M., 1984, Isolation of cytochrome P-450 highly active in prostaglandin co-hydroxylation from lung microsomes of rabbits treated with progesterone. Journal of Biochemistry, 96, 593–603.
  • YAMAZAKI, H., INouE, K., SHAW, P. M., CHECOVICH W. J., GUENGERICH, F. P. and SHIMADA, T., 1997, Different contributions of cytochrome P450 2C19 and 3A4 in the oxidation of omeprazole by human liver microsomes: effects of contents of these two forms in individual human samples. Journal of Pharmacology and Experimental Therapeutics, 283, 434–442.
  • YAMAZAKI, H., SHAW, P. M., GUENGERICH, F. P. and SHIMADA, T., 1998, Roles of cytochrome P450 1A2 and 3A4 in the oxidation of estradiol and estrone in human liver microsomes. Chemical Research in Toxicology, 11, 659–665.
  • YAMAZAKI, H. and SHIMADA, T., 1997a, Human liver cytochrome P450 enzymes involved in the 7-hydroxylation of R- and S-warfarin enantiomers. Biochemical Pharmacology, 54, 1195–1203.
  • YAMAZAKI, H. and SHIMADA, T., 1997b, Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9 and 3A4 in human liver microsomes. Archives of Biochemistry and Biophysics, 346, 161–169.
  • ZELDIN, D. C., DuBois, R. N., FALCK, J. R. and CAPDEVILA, J. H., 1995, Molecular cloning, Expression and characterization of an endogenous human cytochrome P450 arachidonic acid epoxygenase iso form. Archives of Biochemistry and Biophysics, 322, 76–86.
  • ZELDIN, D. C., FoLEv, J., MA, J., BOYLE, J. E., PASCUAL, J. M. S., MOOMAW, C. R., TOMER, K. B., STEENBERGEN, C. and Wu, S., 1996a, CYP2J subfamily P450s in the lung: expression, localization, and potential functional significance. Molecular Pharmacology, 50, 1111–1117.
  • ZELDIN, D. C., FOLEY, J., GOLDSWORTHY, S. M., COOK, M. E., BOYLE, J. E., MA, J., MOOMAW, C. R., TOMER, K. B., STEENBERGEN, C. and Wu, S., 1997, CYP2J subfamily cytochrome P450s in the gastrointestinal tract: expression, localization, and potential functional significance. Molecular Pharmacology, 51, 931–943.
  • ZELDIN, D. C., MOOMAW C. R., JESSE, N., TOMER, K. B., BEETHAM J., HAMMOCK, B. D. and Wu, S., 1996b, Biochemical characterization of the human liver cytochrome P450 arachidonic acid epoxygenase pathway. Archives of Biochemistry and Biophysics, 330, 87–96.

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