Molecular basis for the differences in lidocaine binding and regioselectivity of oxidation by cytochromes P450 2B1 and 2B2

Biochemistry

Volumn 37, Issue 1, 1998, Pages 311-318

  Hanna, Imad H ^a   Roberts, Elizabeth S ^b   Hollenberg, Paul F ^a,b,c  

^a WAYNE STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

^c 2301 Med Sci Research Building III ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETANILIDE DERIVATIVE; ALANINE; ALPHA DIETHYLAMINO 2 HYDROXYMETHYL 6 METHYLACETANILIDE; CHIMERIC PROTEIN; CYTOCHROME B5; CYTOCHROME P450; DEETHYLLIDOCAINE; GLYCINE; LIDOCAINE; MUTANT PROTEIN; SERINE; UNCLASSIFIED DRUG; VALINE;

ARTICLE; CONTROLLED STUDY; DRUG BINDING; DRUG OXIDATION; ENZYME KINETICS; POINT MUTATION; PRIORITY JOURNAL; STEREOCHEMISTRY;

ANIMALS; ARYL HYDROCARBON HYDROXYLASES; BINDING SITES; CHEMICAL FRACTIONATION; CYTOCHROME P-450 CYP2B1; CYTOCHROME P-450 ENZYME SYSTEM; ESCHERICHIA COLI; KINETICS; LIDOCAINE; MUTAGENESIS, SITE-DIRECTED; OXIDATION-REDUCTION; RATS; RECOMBINANT FUSION PROTEINS; RECOMBINANT PROTEINS; SPECTROPHOTOMETRY; STEREOISOMERISM; STEROID HYDROXYLASES;

EID: 0032488655     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi971528s     Document Type: Article

References (34)

1. Nelson, D. R., Koymans, L., Kamataki, T., Stegeman, J. J., Feyereisen, R., Waxman, D. J., Waterman, M. R., Gotoh, O., Coon, M. J., Estabrook, R. W., Gunsalus, I. R., and Nebert, D. W. (1996) Pharmacogenetics 6, 1-42.
2. Boyes, R. N., Adams, H. J., and Duce, B. R. (1970) J. Pharmacol. Exp. Ther. 174, 1-8.
3. Keenaghan J. B., and Boyes R. N. (1972) J. Pharmacol. Exp. Ther. 180, 454-463.
4. Parker, R. J., Collins, J. M., and Strong, J. M. (1995) Drug Metab. Disp. 24, 1167-1173.
5. Imaoka, S., Enomoto, K., Oda, Y., Asaka, A., Fujimori, M., Shimada, T., Fujita, S., Guengerich, F. P., and Funae, Y. (1990) J. Pharmacol. Exp. Ther. 255, 1385-1391.
6. Haseman, J. K., Crawford, D. D., Huff, J. E., Boorman, G. A., and McConnell, E. E. (1984) J. Toxicol. Environ. Health 14, 621-640.
7. Kawai, R., Fujita, S., and Suzuki, T. (1986) Drug Metab. Dispos. 14, 277-279.
8. Oda, Y., Imaoka, S., Nakahira, Y., Asada, A., Fujimori, M., Fujita, S., and Funae, Y. (1989) Biochem. Pharmacol. 38, 4439-4444.
9. Ryan, D. E., Thomas, P. E., and Levin, W. (1982) Arch. Biochem. Biophys. 216, 272-288.
10. Guengerich, F. P., Dannan, G. A., Wright, S. T., Martin, M. V., and Kaminsky, L. S. (1982) Biochemistry 21, 6019-6030.
11. Waxman, D. J., and Walsh, C. (1982) J. Biol. Chem. 257, 10446-10457.
12. Wolf, C. R., Miles, J. S., Seilman, S., Burke, M. D., Rospendowski, B. N., Kelly, K., and Smith, W. E. (1988) Biochemistry 27, 1597-1603.
13. Gotoh, O. (1992) J. Biol. Chem. 267, 83-90
14. He, Y.-A, Balfour, C. A., Kedzie, K. M., and Halpert, J. R. (1992) Biochemistry 31, 9220-9226.
15. He, Y.-A, Luo, Z., Klekotka, P. A., Burnett, V. L., and Halpert, J. R. (1994) Biochemistry 33, 4419-4424.
16. Barnes, H. J. (1996) Methods Enzymol. 272, 3-14.
17. Higuchi, R. (1990) in PCR Protocols: A Guide to Methods and Applications (Innis, M. A., Gelfand, D. H., Sninsky, J. J., and White, T. J., Eds.) pp 177-183, Academic Press, San Diego.
18. Sandhu, P., Guo, Z., Baba, T., Martin, M. V., Tukey, R. H., and Guengerich, F. P. (1994) Arch. Biochem. Biophys. 309, 168-177.
19. Guengerich, F. P., Martin, M. V., Guo, Z., and Chun, Y. (1996) Methods Enzymol. 272, 35-43.
20. Schenkman, J. B., Sugar, S. G., and Cinti, D. L. (1981) Pharmacol. Ther. 12, 43-71.
21. Guengerich F. P.. (1983) Biochemistry 22, 2811-2820.
22. Shen, A. L., Porter, T. D., Wilson, T. E., and Kasper, C. B. (1989) J. Biol. Chem. 264, 7584-7589.
23. Dawson, J. H. (1988) Science 240, 433-439.
24. Raag, R., and Poulos, T. L. (1989) Biochemistry 28, 917-922.
25. Raag, R., and Poulos, T. L. (1991) Biochemistry 30, 2674-2684.
26. Poulos, T. L., Cupp-Vickery, J., and Huiying, L. (1995) in Cytochrome P450 Structure, Mechanism, and Biochemistry, 2nd ed. (Ortiz de Montellano, P. R., Ed.) pp 125-150, Plenum Press, New York.
27. Korzekwa, K. R., and Jones, J. P. (1993) Pharmacogenetics 3, 1-18.
28. Miwa, G. T., Walsh, J. S., Kedderis, G. L., and Hollenberg, P. F. (1983) J. Biol. Chem. 258, 14445-14449.
29. Macdonald, T. L., Gutheim, W. G., Martin, R. B., and Guengerich, F. P. (1989) Biochemistry 28, 2071-2077.
30. Grace, J. M., Kinter, M. T., and Macdonald, T. L. (1994) Chem. Res. Toxicol. 7, 286-290.
31. Ellis, S. W., Hayhurst, G. P., Smith, G., Lightfoot, T., Wong, M. M. S., Simula, A. P., Ackland, M. J., Sternberg, M. J. E., Lennard, M. S., Tucker, G. T., and Wolf, C. R. (1995) J. Biol. Chem. 270, 29055-29058.
32. de Groot, M. J., Bijloo, G. J., Martens, B. J., van Acker, F. A. A., and Vermeulen, N. P. E. (1997) Chem. Res. Toxicol. 10, 41-48.
33. Fersht, A. (1977) Enzyme Structure and Mechanism, pp 244-273, W. H. Freeman and Company, San Francisco.
34. Gruenke, L. D., Konopka, K., Cadieu, M., and Waskell, L. (1995) J. Biol. Chem. 270, 24707-24718.