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Xenobiotica
the fate of foreign compounds in biological systems
Volume 34, 2004 - Issue 8
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Research Article

Selectivity of 7-alkoxycoumarins as probe substrates for rat hepatic cytochrome P450 forms is influenced by the substitution pattern on the coumarin nucleus

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Pages 707-722 | Received 10 Apr 2004, Published online: 22 Sep 2008

Reference

  • ABDOU, W. M., MAHRAN, M. R., MAHMOUD, M. and WAMHOFF, H., 1988, Photochemistry of pesticides. 13. Some photoreactions of 0,0-diethyl-0-(4-methyl-2-oxo-2H-1-benzopyran-7-yl)phosphor-othioate (Potasan). Phosphorus and Sulfur, 39, 199–203.
  • AITIO, A., 1978, A simple and sensitive assay of 7-ethoxycoumarin deethylation. Analytical Biochemistry, 85, 488–491.
  • BALL, S. E., THIEL, V. E., TR), C. 0., Lim, H.-K., KAO, J., SISENWINE, S. F. and SCATINA, J., 1996, [14C]7-ethoxycoumarin metabolism in precision-cut rat hepatic slices. Drug Metabolism and Disposition, 24, 383–389.
  • BOOBIS, A. R., KAHN, G. C., WHYTE, C., BRODIE, M. J. and DAVIES, D. S., 1981, Biphasic 0-deethylation of phenacetin and 7-ethoxycoumarin by human and rat liver microsomal fractions. Biochemical Pharmacology, 17, 2451–2456.
  • CRESPI, C. L. and STRESSER, D. M., 2000, Fluorometric screening for metabolism-based drug—drug interactions. Journal of Pharmacological and Toxicological Methods, 44, 325–331.
  • DEAN, F. M. and PARTON, B., 1969, The structure and synthesis of (+)-obliquin. Journal of the Chemical Society C, 526–531.
  • DELucA, J. G., DYSART, G. R., RASNICK, D. and BRADLEY, M. 0., 1988, A direct, highly sensitive assay for cytochrome P-450 catalyzed 0-deethylation using a novel coumarin analog. Biochemical Pharmacology, 37, 1731–1739.
  • FERNYHOUGH, L., KELL, S. W., HAMMOND, A. H., THOMAS, N. W. and FRY, J. R., 1994, Comparison of in vivo and in vitro rat hepatic toxicity of coumarin and methyl analogues, and application of quantitative morphometry to toxicity in vivo. Toxicology, 88, 113–125.
  • FRY, J. R., CARLE, M. J. and LAL, K., 1992, Differentiation of cytochrome P450 inducers on the basis of 7-alkoxycoumarin 0-dealkylase activities. Xenobiotica, 22, 211–215.
  • FUKUTO, J. M., KUMAGAI, Y. and CH0, A. K., 1991, Determination of the mechanism of demethylenation of (methylenedioxy)phenyl compounds by cytochrome P450 using deuterium isotope effects. Journal of Medicinal Chemistry, 34, 2871–2876.
  • GIURNAZI, A. M., CARLE, M. J., LAL, K. and FRY, J. R., 1996, 7-Ethoxy-3,4-dimethylcoumarin: a substrate for a cytochrome P450-mediated mono-oxygenase activity that is highly induced by phenobarbitone and 0-naphthoflavone. Journal of Pharmacy and Pharmacology, 48, 729–733.
  • HAMMOND, A. H. and FRY, J. R., 1997, Involvement of cytochrome P4502E1 in the toxicity of dichloropropanol to rat hepatocyte cultures. Toxicology, 118, 171–179.
  • INDAHL, S. R. and SCHELINE, R. R., 1971, The metabolism of umbelliferone and herniarin in rats and by the intestinal microflora. Xenobiotica, 1, 13–24.
  • JUNG, B., GRAF, H. and ULLRICH, V., 1985, A new monooxygenase product from 7-ethoxycoumarin and its relation to the 0-dealkylation product. Bio-Chemische Hoppe-Seyler, 366, 23–31.
  • KAMATAKI, T., ANDO, M., YAMAZOE, Y., Ism', K. and KATO, R., 1980, Sex difference in the 0-dealkylation activity of 7-hydroxycoumarin 0-alkyl derivatives in liver microsomes of rats. Biochemical Pharmacology, 29, 1015–1022.
  • KNOEVENAGEL, E. and SCHRoTER, F., 1898, Ueber eine darstellungsweise der alkyliden-acetessigester. Bereich Deutsche Chemische Gesellschaft, 31, 730–737.
  • LEWIS, D. F. V., 2000, On the recognition of mammalian microsomal cytochrome P450 substrates and their characteristics. Biochemical Pharmacology, 60, 293–306.
  • LEWIS, D. F. V., IOANNIDES, C. and PARKE, D. V., 1986, Molecular dimensions of the substrate binding site of cytochrome P-448. Biochemical Pharmacology, 35, 2179–2185.
  • LEWIS, D. F. V. and LAKE, B. G., 1997, Molecular modelling of mammalian CYP2B isoforms and their interactions with substrates, inhibitors and redox partners. Xenobiotica, 27, 443–478.
  • LIN J. H and Lu A. Y. H., 2001, Interindividual variability in inhibition and induction of cytochrome P450 enzymes. Annual Reviews of Pharmacology and Toxicology, 41, 535–567.
  • Lu, A. Y. H., WANG, R. W. and LIN, J. H., 2003, Cytochrome P450 in vitro reaction phenotyping: a re-evaluation of approaches used for P450 isoform identification. Drug Metabolism and Disposition, 31, 345–350.
  • MANN, F. G. and SAUNDERS, B. C., 1960, Practical Organic Chemistry, 4th edn (London: Longman), pp. 305–306.
  • MATSUBARA, T., OTSUBO, S., YOSHIHARA, E. and TOUCHI, A., 1983, Biotransformation of coumarin derivatives (2) Oxidative metabolism of 7-alkoxycoumarins by microsomal enzymes and a simple assay procedure for 7-alkoxycoumarin 0-dealkylase. Japanese Journal of Pharmacology, 33, 41–56.
  • NAKAMURA, K., HANNA, I. H., CAI, H., NISHIMURA, Y., WILLIAMS, K. M. and GUENGERICH, F. P., 2001, Coumarin substrates for cytochrome P450 2D6 fluorescence assays. Analytical Biochemistry, 292, 280–286.
  • OKUYUMA, M., INOUE, C., AIJIMA, K., NAKAMURA, Y., KABURAGI, T. and SHIGEMATSU, A., 1997, In vitro method for assessing hepatic drug metabolism. Biological and Pharmaceutical Bulletin, 20, 1–5.
  • PATERSON, P., FRY, J. R. and HORNER, S. A., 1984, Influence of cytochrome P-450 type on the pattern of conjugation of 7-hydroxycoumarin generated from 7-alkoxycoumarins. Xenobiotica, 14, 849–859.
  • RAJANIBALA, K., PANDYA, K. and PANDYA, C., 1955, The condensation of aldehydes with b-oxo esters in the presence of organic bases. 1. Salicylaldehyde and its derivatives with ethyl acetoacetate. Agra University Journal of Research, 4, 305–315.
  • RANGASWAMI, SESHADRI and VENKATEswARLu, 1941, Proceedings of the Indian Academy of Sciences Section A, 13, 316–318. [identified through the MDL Crossfire Beilstein Commander program]
  • REEN, R. K., RAMAKANTH, S., WIEBEL, F. J., JAIN, M. P. and SINGH, J., 1991, Dealkylation of 7-methoxycoumarin as assay for measuring constitutive and phenobarbital-inducible cytochrome P450s. Analytical Biochemistry, 194, 243–249.
  • RENWICK, A. B., LAVIGNETTER, G., WORBOYS, P. D., WILLIAMS, B., SURRY, D., LEWIS, D. F. V., PRICE, R. J., LAKE, B. G. and EVANS, D. C., 2001, Evaluation of 7-benzyloxy-4-trifluoro-methylcoumarin, some other 7-hydroxy-4-trofluoromethylcoumarin derivatives as fluorescent derivatives as fluorescent substrates for rat hepatic cytochrome P450 enzymes. Xenobiotica, 31, 861–878.
  • ROSER, R. and THOMAS, H., 2000, A direct, highly sensitive fluorometric assay for a microsomal cytochrome P450-mediated 0-demethylation using a novel coumarin analog substrate. Zeitscrift far Naturforschung C, 55, 915–922.
  • SHAH, D. N. and SHAH, N. M., 1954, The Fries isomerization of acetyl and benzoyl esters of umbelliferones. Journal of Organic Chemistry, 19, 1681–1685.
  • SHARMA, U., ROBERTS, E. S. and HOLLENBERG, P. F., 1996, Inactivation of cytochrome P4502B1 by the monoamine oxidase inhibitors R-(—)-deprenyl and clorgyline. Drug Metabolism and Disposition, 24, 669–675.
  • THAKOR and SHAH, 1947, Journal of University of Bombay Science, 15/5A, 14. [identified through the MDL Crossfire Beilstein Commander program]
  • TSUJIHARA, K., HONGU, M., SAITO, K., KAWANISHI, H., KURIYAMA, K., MATSUMOTO, M., OKU, A., UETA, K., TSUDA, M. and SAITO, A., 1999, Natglucose cotransporter (SGLT) inhibitors as antidiabetic agents. 4. Synthesis and pharmacological properties of 4'-dehydroxyphlorizin derivatives substituted on the B ring. Journal of Medicinal Chemistry, 42, 5311–5324.
  • ULLRICH, V., FROMMER, U. and WEBER, P., 1973, Differenceas in the 0-dealkylation of 7-ethoxycoumarin after pretreatment with phenobarbital and 3-methylcholanthrene. Hoppe-Seyler Zeitschrift far Physiologische Chemie, 354, 514–520.
  • ULLRICH, V. and WEBER, P., 1972, The 0-dealkylation of 7-ethoxycoumarin by liver microsomes. Hoppe-Seyler Zeitschrift far Physiologische Chemie, 353, 1171–1177.
  • USGAONKAR, R. N., THAKOR, V. M. and JADHAv, G. V., 1953, Pechmann condensation. I. Condensation of 2,5-disubstituted phenols with ethyl acetoacetate. Journal of the Indian Chemical Society, 30, 535–538.
  • WALSH, J. S. and MIWA, G. T., 1984, The mechanism of the cytochrome P448-mediated 6-hydroxylation of 7-ethoxycoumarin. Biochemical and Biophysical Research Communications, 121, 960–966.
  • WHITE, I. N. H., 1988, A continuous fluorometric assay for cytochrome P-450-dependent mixed function oxidases using 3-cyano-7-ethoxycoumarin. Analytical Biochemistry, 172, 304–310.
  • YUAN, R., MADANI, S., WET, X.-X., REYNOLDS, K. and HUANG, S.-M., 2002, Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. Drug Metabolism and Disposition, 30, 1311–1139.

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