Cytochrome P4501A(CYP1A) induction in rat and man by the benzodioxino derivative, fluparoxan

References

• ADAMS, N. H., LEVI, P. E. and H ODGSON, E., 1983, Regulation of cytochrome P-450 isozymes by methylenedioxyp henyl compounds. Chemico-Biological Interactions, 86, 255–274.
   Google Scholar
• AYRTON, D. A., M CFARLANE, M., WALKER, R., NEVILLE, S. and I OANNIDES, C., 1990, The induction of P450 I proteins by aromatic amines may be related to their carcinogenic potential. Carcino genesis, 11, 803–809.
   PubMed Web of Science ®Google Scholar
• BERESFORD, A. P., 1993, Cypl Al : friend or foe? Drug Metabolism Reviews, 25, 503–517.
   PubMed Web of Science ®Google Scholar
• BERESFORD, A. P., CASWELL, K., CHAMBERS, R. and KIRK, I. P., 1992, Advantages of achiral hplc as a preparative step for chiral analysis in biological samples and its use in toxicokinetic studies. Xenobiotica, 22, 789–798.
   PubMed Web of Science ®Google Scholar
• BERESFORD, A. P., TAYLOR, R. J., ASHCROFT, J.-A., AYRTON, J., T UCKER, G. T. and ELus, S. W., 1996, Expression of human cytochrome P450 1A1 (CYP1A1) in Saccharomyces cerevisiae inhibits cell division. Xenobiotica, 26, 1013–1023.
   Google Scholar
• BRADFORD, M M., 1976, A rapid and sensitive method for the quantitation of microgram quantities of protein utilising the principle of protein—dye binding. Annals of Biochemistry, 72, 248–254.
   Web of Science ®Google Scholar
• BURKE, M D. and MEYER, R. T., 1974, Ethoxyresorufin : direct fluorometric assay of a microsomal o-dealkylation which is preferentially inducible by 3-methylcholanthrene. Drug Metabolism and Disposition, 2, 583–588.
   PubMed Web of Science ®Google Scholar
• BURKE, M D., THOMPSON, S., WEAVER, R. J., WOLF, C. R. and M AYER, R. T., 1994, Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochemical Pharmacology, 48, 923–936.
   PubMed Web of Science ®Google Scholar
• CHALOUPKA, K., SANTOSTEFANO M., GOLDFARB, I. S., Liu, G., M YEAS M J., T SYROLV, I. B., GELBOIN H. V., KRISHNAN, V. and SAFE, S., 1994, Aryl hydrocarbon (Ah) receptor- independent induction of Cypla2 gene expression by acenaphthylene and related compounds in B6C3F1 mice. Carcino genesis, 15, 2835–2840.
   Google Scholar
• CONNEY, A. H., 1967, Pharmacological implications of microsomal enzyme induction. Pharmacological Reviews, 19, 317–366.
   PubMed Web of Science ®Google Scholar
• CONNEY, A. H., PANTUCK, E. J., H MAO, K.- C., GARLAND, W A., ANDERSON, K. E., ALVARES, A. P. and KAPPAS, A., 1976, Enhanced phenacetin metabolism in human subjects fed charcoal-broiled beef. Clinical Pharmacology and Therapeutics, 20, 633–642.
   Google Scholar
• COOK, J. C. and H ODGSON, E., 1985, The induction of cytochrome P-450 by isosafrole and related methylenedioxyp henol compounds, Chemico-Biological Interactions, 54, 299–315.
   Google Scholar
• DIAMOND, L. and GELBOIN, H. V., 1969, Alpha-naphthoflavone: an inhibitor of hydrocarbon cytotoxicity and microsomal hydroxylase. Science, 166, 1023–1025.
   PubMed Web of Science ®Google Scholar
• EDWARDS, R. J., MURRAY, B. P., SINGLETON, A. M., MURRAY, S., DAVIES, D. S. and Booms, A. R., 1993, Identification of the epitope of an anti-peptide antibody which binds to CYP1A2 in many species including man. Biochemical Pharmacology, 46, 213–220.
   PubMed Web of Science ®Google Scholar
• FUJII-KURIYAMA, Y., I MATAKA, H., SOGAWA, K., YASUMOTO K.-I. and K ncucta, Y., 1992, Regulation ofCYP1A1 expression. FASEB Journal, 6, 706–710.
   Google Scholar
• GRISTWOOD W E., 1990, Determination of fluparoxan (GR50360) in plasma by gas chromatography. Journal of Chromatography, 527, 436–440.
   Google Scholar
• HALLIDAY, C. A., JONES, B. J., STRAUGHAN, D. W., T YEAS, M. B., W ALSH, D. M., W ALSH, H. and WISE, H., 1988, GR50360, a novel and highly selective a2-adrenoceptor antagonist. British Journal of Pharmacology, 95, 751P.
   Web of Science ®Google Scholar
• HANIKINSON, O., 1995, The aryl hydrocarbon receptor complex. Annual Review of Pharmacology and Toxicology, 35, 307–340.
   Google Scholar
• IOANNIDES, C., L EWIS, D. F. V. and PARKE, D. V., 1994, The use of computers in the safety evaluation of drugs and other chemicals. European Journal of Drug Metabolism and Pharmacokinetics, 3, 225–233.
   Google Scholar
• IOANNIDES, C. and P ARKE, D. V., 1993, Induction of cytochrome P4501 as an indicator of potential chemical carcinogenesis. Drug Metabolism Reviews, 25, 485–501.
   PubMed Web of Science ®Google Scholar
• JOHNSON, M. A., BLACKWELL, C. P. and SMITH, J., 1995, Antagonism of the effects of clonidine by the a2-adrenoceptor antagonist, fluparoxan. British Journal of Clinical Pharmacology, 36, 477–483.
   Google Scholar
• JORGENSEN, E. C. B. and AUTRUP, H., 1996, Autoregulation of human CYP1A1 gene promoter activity in HepG2 and MCF- 7 cells. Carcinogenesis, 17, 435–441.
   Google Scholar
• KIMURA, S., GONZALEZ, F. J. and NEBERT, D. W., 1984, The murine Ah locus. Comparison of the complete cytochrome P1-450 and P3-450 cDNA nucleotide and amino acid sequences. Journal of Biological Chemistry, 259, 10 705–10 713.
   Google Scholar
• KOCH, G. G., 1972, The use of non-parametric methods in the statistical analysis of the two-period change-over design. Biometrics, 28, 577–584.
   PubMed Web of Science ®Google Scholar
• LAEMMLI, U. K., 1970, Change of structural proteins during the assembly of the head of bacteriophage T4. Nature, 227, 680–685.
   PubMed Web of Science ®Google Scholar
• LEWIS, D. F. V., 1996, Quantitative structure- activity relationships in substrates, inducers and inhibitors of cytochrome P4501 (CYP1). Drug Metabolism Reviews (in press).
   Google Scholar
• LEWIS, D. F. V., M OEREELS, H., LA, B. G., I OANNIDES, C. and P ARKE, D. V., 1994, Molecular modeling of enzymes and receptors involved in carcinogenesis : QSARs and COMPACT- 3D. Drug Metabolism Reviews, 26, 261–285.
   Google Scholar
• LUCAS, D., BERTHOU, F., DRANO, Y., LozAc'o, P., V OLANT, A. and M E.NEZ, J.-F., 1993, Comparison of levels of cytochrome P-450, CYP1A2, CYP2E1, and their related monooxygenase activities in human surgical liver samples. Alcoholism: Clinical and Experimental Research, 17, 900–905.
   Google Scholar
• MINESHITA, S., EGGERS, R., KITTERINGHAM, N. R. and O HNHAUS E. E., 1986, Determination Of phenacetin and its major metabolites in human plasma and urine by high performance liquid chromatography. Journal of Chromatography, 380, 407–413.
   Google Scholar
• NASH, T., 1953, The colorimetric estimation of formaldehyde by means of the Hantzsch reaction. Biochemical Journal, 55, 416–421.
   PubMed Web of Science ®Google Scholar
• NEBERT, D. W. and G ONZALEZ, F. J., 1987, P450 genes: structure, evolution, and regulation. Annual Review of Biochemistry, 45, 945–993.
   Google Scholar
• NEBERT, D. W. and Jos, J. E., 1989, Regulation of the mammalian cytochrome P1-450 (CYP1A1) gene. International Journal of Biochemistry, 21, 243–252.
   PubMedGoogle Scholar
• NEBERT, D. W., NELSON, D. R., ADESNIK, M., C OON, M. J., ESTABROOK, R. W., GONZALEZ, F. J., G UENGERICH, F. P., G UNSALUS, I. C., JOHNSON, E. F., KEMPER, B., L EVIN W., PHILLIPS, I. R., S ATO, R. and W ATERMAN, M. R., 1989, The P450 superfamily : updated listing of all genes and recommended nomenclature for the chromasomal loci. DNA, 8, 1–13.
   Google Scholar
• NEBERT, D. W., P UGA, A. and V ASILIOU, V., 1993, Role of the Ah receptor and the dioxin-inducible [Ali] gene battery in toxicity, cancer, and signal transduction. Annals of the New York Acadamy of Science, 685, 624–640.
   PubMed Web of Science ®Google Scholar
• NEDELCHEVA, V. and GUT, I., 1994, P450 in the rat and man: methods of investigation, substrate specificities and relevance to cancer. Xenobiotica, 24, 1151–1175.
   PubMed Web of Science ®Google Scholar
• NELSON, D. R., KOYMANS, L., KAMATAKI, T., STEGEMAN, J. J., FEYEREISEN, R., W AXMAN D. J., W ATERMAN, M. R., G OTOH, O., COON, M. J., ESTABROOK, R. W., G UNSALAS, I. C. and N EBERT, D. W., 1996, P450 superfamily : update on new sequences, gene mapping, accession numbers and nomenclature. Pharmacogenetics, 6, 1–42.
   Google Scholar
• NELSON, D. R. and S TROBEL, H. W., 1987, Evolution of cytochrome P-450 proteins. Molecular Biology and Evolution, 4, 572–593.
   PubMed Web of Science ®Google Scholar
• OKEY, A. B., 1990, Enzyme induction in the cytochrome P-450 system. Pharmacology and Therapeutics, 45, 241–298.
   PubMed Web of Science ®Google Scholar
• OMURA, T. and S ATO, R., 1964, The carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. Journal of Biological Chemistry, 239, 2370–2378.
   PubMed Web of Science ®Google Scholar
• PANTUCK E. J., PANTUCK, C. B., GARLAND, W. A., M IN, B. H., WATTENBERG, L. W., ANDERSON, K. E., KAPPAS, A. and Coy, A. H., Stimulatory effect of brussels sprouts and cabbage on human drug metabolism. Clinical Pharmacology and Therapeutics, 25, 88–95.
   Google Scholar
• PARKE, D. V., 1990, Induction of cytochromes P-450—general principles and biological consequences. In Frontiers of Biotransformation, vol. 2, edited by K. Ruckpaul and H. Rein (London: Taylor & Francis), pp. 1–34.
   Google Scholar
• PASCO, D. S., BOYUM, K. W., MERCHANT, S N., C HALBERG, S. C. and FAGAN, J. B., 1988, Trans-criptional and post-transcriptional regulation of the genes encoding cytochromes P-450c and P-450d in vivo and in primary hepatocyte cultures. Journal of Biological Chemistry, 263, 8671–8676.
   PubMed Web of Science ®Google Scholar
• PETERSEN, K.-U., 1995, Review article: omeprazole and the cytochrome P450 system. Alimentary Pharmacology and Therapeutics, 9, 1–9.
   PubMed Web of Science ®Google Scholar
• PUGA, A., RAYCHAUDHURI, B., S ALATA, K., Z HANG, Y. H. and NEBERT, D. W., 1990, Stable expression of mouse Cypla 1 and human CYP1A2 cDNAs transfected into mouse hepatoma cells lacking detectable P450 enzyme activity. DNA and Cell Biology, 9, 425–436.
   PubMedGoogle Scholar
• RAAFLAUB, J. and DUBACH U. C., 1975, On the pharmacokinetics of phenacetin in man. European Journal of Clinical Pharmacology, 8, 261–265.
   Google Scholar
• RAYCHAUDHURI, B., NEBERT, D. W. and PUG A., 1990, The murine Gyp/a-1 gene negatively regulates its own transcription and that of other members of the aromatic hydrocarbon-responsive [Ah] gene battery. Molecular Endocrinology, 4, 1773–1781.
   Google Scholar
• REIK M., ROBERTSON, R. W., PASCO, D. S. and FAGAN, J. B., 1994, Down-regulation of nuclear aryl hydrocarbon receptor DNA- binding and transactivation functions: requirement for a labile or inducible factor. Molecular Cell Biology, 14, 5653–5660.
   Google Scholar
• REKKER, R. F., TER L AAK, A. M. and M ANNHOLD, R., 1993, On the reliability of calculated logP-values : Rekker, Hansch/Leo and Suzuki approach. Quantitative Structure—Activ ity Relationships, 12, 152–157.
   Google Scholar
• RYAN, D. E., THOMAS, P. E. and L EVIN, W., 1980, Hepatic microsomal cytochrome P-450 from rats treated with isosafrole. Journal of Biological Chemistry, 255, 7941–7955.
   PubMed Web of Science ®Google Scholar
• RYU, D.-Y., LEVI, P. E., and H ODGSON, E., 1995, Regulation of cytochrome P-450 isozymes CYPIA1, CYP1A2 and CYP2B10 by three benzodioxole compounds. Chemico-Biological Interactions, 96, 235–247.
   PubMed Web of Science ®Google Scholar
• SESARDIC, D., B °OBIS, A. R., EDWARDS, R. J. and D AVIES, D. S., 1988, A form of cytochrome P-450 in man, orthologous to form d in the rat, catalyses the O-deethylation of phenacetin and is inducible by cigarette smoking. British Journal of Clinical Pharmacology, 26, 363–372.
   Google Scholar
• SESARDIC, D., BOOBIS, A. R., MURRAY, B. P., MURRAY, S., S EGURA, J., DE LA T ORRE, R. and DAVIES, D. S., 1990a, Furafylline is a potent and selective inhibitor of cytochrome P450IA2 in man. British Journal of Clinical Pharmacology, 29, 651–663.
   Google Scholar
• SESARDIC, D., PASANEN M PELKONEN, O. and BOOBIS, A. R., 1990b, Differential expression and regulation of the cytochrome P450IA gene subfamily in human tissues. Carcinogenesis, 11, 1183–1188.
   PubMed Web of Science ®Google Scholar
• SHIMADA, T., YAMAZAKI, H., M IMURA M I NUI, 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.
   Google Scholar
• TARRUS, E., CI, J., ROBERTS, D. J., S PICKETT, R. G. W., CELDRAN, E. and SEGURA, J., 1987a, Accumulation of caffeine in healthy volunteers treated with furafylline. British Journal of Clinical Pharmacology, 23, 9–18.
   Google Scholar
• TARRUS, E., G ARCIA, I., ROBERTS, D. J. and S MURA, J., 1987b, Animal model for the detection of drug-induced inhibition of caffeine metabolism. Methods and Findings in Experimental Clinical Pharmacology, 9, 311–316.
   Google Scholar
• THOMAS, P. E., REIK, L. M., RYAN, D. E. and L EVIN, W., 1983, Induction of two immunochemicall y related rat liver cytochrome P-450 isozymes, cytochromes P-450c and P-450d, by structurally diverse xenobiotics. Journal of Biological Chemistry, 258, 4590–4598.
   PubMed Web of Science ®Google Scholar