Pronounced differences in inhibition potency of lactone and non-lactone compounds for mouse and human coumarin 7-hydroxylases (CYP2A5 and CYP2A6)

Xenobiotica

Volumn 30, Issue 1, 2000, Pages 81-92

  Juvonen, R O ^a   Gynther, J ^a   Pasanen, M ^b,c   Alhava, E ^a   Poso, A ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b UNIVERSITY OF OULU   (Finland)

^c NATIONAL AGENCY FOR MEDICINES   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZOXAZOLONE DERIVATIVE; 2 INDANONE; COUMARIN; COUMARIN 7 HYDROXYLASE; COUMARIN DERIVATIVE; GAMMA VALEROLACTONE; LACTONE; LACTONE DERIVATIVE; PYRAZOLE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; ENZYME ACTIVE SITE; ENZYME INHIBITION; FEMALE; HUMAN; HUMAN CELL; HYDROXYLATION; LIVER MICROSOME; MALE; MOUSE; NONHUMAN; SPECIES DIFFERENCE;

ANIMALIA;

EID: 0033968218     PISSN: 00498254     EISSN: None     Source Type: Journal    
DOI: 10.1080/004982500237848     Document Type: Article

References (28)

1. Aitio, A., 1978, A simple and sensitive assay of 7-ethoxycoumarin deethylation. Analytical Biochemistry, 85, 488-491.
2. Asikainen, J., Fasanen, M. and Juvonen, R. O., 1996, Inhibition of mice coumarin 7-hydroxylase bu undecanoic σ-lacton, benzoxazole and 2H-pyran-2-one. Experimental and Toxicologic Pathology, 48 (suppl. II), 13-17.
3. Chang, T. K. H. and Waxman, D. J., 1996, The CYP2A subfamily. In C. Ioannides (ed.), Cytochromes P450 : Metabolic and Toxicological Aspects (Boca Raton : CRC Press), pp. 99-134.
4. Ding, S., Lake, B. G., Friedberg, T. and Wolf, C. R., 1995, Expression and alternative splicing of the cytochrome P-450 CYP2A7. Biochemical Journal, 306, 161-166.
5. Draper, A. J., Madam, A. and Parkinson, A., 1997, Inhibition of coumarin 7-hydroxylase activity in human liver microsomes. Archives of Biochemistry and Biophysics, 341, 47-61.
6. Gotoh, O., 1992, Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. Journal of Biological Chemistry, 267, 83-90.
7. Halpert, J. R. and He, Y., 1993, Engineering of cytochrome P4502B1 specificity: conversion of an androgen 16β-hydroxylase to a 15α-hydroxylase. Journal of Biological Chemistry, 268, 4453-4457.
8. Honkakoski, P. and Negishi, M., 1997, The structure, function and regulation of cytochrome P4502A enzymes. Drug metabolism reviews, 29, 977-996.
9. Juvonen, R. O., Iwasaki, M. and Negishi, M., 1991, Structural function of residue-209 in coumarin 7-hydroxylase (P450coh). Enzyme-kinetic studies and site-directed mutagenesis. Journal of Biological Chemistry, 266, 16431-16435.
10. Juvonen, R. O., Kaipainen, P. K. and Lang, M. A., 1985, Selective induction of coumarin 7-hydroxylase by pyrazole in D2 mice. European Journal of Biochemistry, 152, 3-8.
11. Juvonen, R. O., Shkumatov, V. M. and Lang, M. A., 1988, Purification and characterization of a liver microsomal cytochrome P-450 isoenzyme with a high affinity and metabolic capacity for coumarin from pyrazole-treated D2 mice. European Journal of Biochemistry, 171, 205-211.
12. Kimonen, T., Juvonen, R. O., Alhava, E. and Pasanen, M., 1995, The inhibition of CYP enzymes in mouse and human liver by pilocarpine. British Journal of Pharmacology, 114, 832-836.
13. Kinonen, T., Pasanen, M., Gynther, J., Poso, A., Järvinen, T., Alhava, E. and Juvonen, R. O., 1995, Competitive inhibition of coumarin 7-hydroxylation by pilocrpine and its interaction with mouse CYP 2A5 and human CYP 2A6. British Journal of Pharmacology, 116, 2625-2630.
14. Lang, M. A., Juvonen, R. O., Järvinen, P., Honkakoski, P. and Raunio, H., 1989, Mouse liver P450coh: genetic regulation of the pyrazole-inducible enzyme and comparison with other P450 isoenzymes. Archives of Biochemistry and Biophysics, 271, 139-148.
15. Lang, M. A. and Nebert, D. W., 1981, Structural gene products of the Ah locus. Evidence for many unique P-450-mediated monooxygenase activities reconstituted from 3-methylcholantrene-treated C57BL/6N mouse liver microsomes. Journal of Biological Chemistry, 256, 12058-12067.
16. Lindberg, R. L. P. and Negishi, M., 1989, Alteration of mouse cytochrome P450coh substrate specificity by mutation of a single amino-acid residue. Nature, 339, 632-634.
17. Mäenpää, J., Sigusch, H., Raunio, H., Syngelmä, T., Vuorela, P., Vuorela, H. and Pelkonen, O., 1993, Differential inhibition of coumarin hydroxylase activity in mouse and human liver microsomes. Biochemical Pharmacology, 45, 1035-1042.
18. max of the enzyme for bufuralol but not debrisoquine hydroxylation. Journal of Biological Chemistry, 265, 17197-17201.
19. Messina, E. S., Tyndale, R. F. and Sellers, E. M., 1997, A major role for CYP2A6 in nicotine C-oxidation by human liver microsomes. Journal of Pharmacology and Experimental Therapeutics, 282, 1608-1614.
20. Miles, J. S., McLare, A. W., Forrester, L. M., Glancey, M. J., Lang, M. A. and Wolf, C. R., 1990, Identification of the human liver cytochrome P-450 responsible for coumarin 7-hydroxylase activity. Biochemical Journal, 267, 365-371.
21. Negishi, M., Lindberg, R., Burkhart, B., Ichikawa, T., Honkakoski, P. and Lang, M., 1989, Mouse Steroid 15alpha-hydroxylase gene family: identification of type II P-450(15)alpha as coumarin 7-hydroxylase. Biochemistry, 28, 4169-4172.
22. Pelkonen, O., Raunio, H., Rautio, A., Pasanen, M. and Lang, M. A., 1997, The metabolism of coumarin. In Coumarins: Biology, Applications and Mode of Action (Chichester: John Wiley), pp. 67-92.
23. Raunio, H., Juvonen, R., Pasanen, M., Pelkonen, O., Pääkkö, P. and Soini, Y., 1998, Cytochrome P4502A6 (CYP2A6) expression in human hepatocellular carcinoma. Hepatology, 27, 427-432.
24. Raunio, H., Valtonen, J., Honkakoski, P., Lang, M. A., Stahlberg, M., Kairaluoma, M.A., Rautio, A., Pasanen, M. and Pelkonen, O., 1990, Immunochemical detection of human liver cytochrome P450 forms related to phenobarbital-inducible forms in the mouse. Biochemical Pharmacology, 40, 2503-2509.
25. Smith, P. K., Krohn, R. I., Hermanson, G. T., Mallia, A. K., Gartner, F. H., Provenzano, M. D., Fujimoto, E. K., Goeke, N. M., Olson, B. J. and Klenk, D. C., 1985, Measurement of protein using bicinchonic acid. Analytical Biochemistry, 150, 76-85.
26. Sraub, P., Lloyd, M., Johnson, E. F. and Kemper, B., 1994, Differential effects of mutation in substrate recognition site 1 of cytochrome P450 2C2 on lauric acid and progesterone hydroxylation. Biochemistry, 33, 8029-8034.
27. Yamano, S., Tatsuno, J. and Gonzalez, F. J., 1990, The CYP2A3 gene product catalyzes coumarin 7-hydroxylation in human liver microsomes. Biochemistry, 29, 1322-1329.
28. Yun, C. H., Shimada, T. and Guengerich, F. P., 1991, Purification and characterization of human liver microsomal cytochrome P450 of the IIA subfamily from human liver microsomes. Molecular Pharmacology, 40, 679.