Alanine-scanning mutagenesis of a putative substrate recognition site in human cytochrome P450 3A4. Role of residues 210 and 211 in flavonoid activation and substrate specificity

Journal of Biological Chemistry

Volumn 272, Issue 9, 1997, Pages 5396-5402

  Harlow, Greg R ^a   Halpert, James R ^a  

^a UNIVERSITY OF ARIZONA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHROMANONE DERIVATIVE; ALANINE; ALPHA NAPHTHOFLAVONE; BETA NAPHTHOFLAVONE; CYTOCHROME P450; FLAVONE; FLAVONOID; TESTOSTERONE;

AEROBIC METABOLISM; AMINO ACID SUBSTITUTION; ARTICLE; BINDING SITE; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME SUBSTRATE; GENE MUTATION; LIVER METABOLISM; PRIORITY JOURNAL; SITE DIRECTED MUTAGENESIS;

ALANINE; ARYL HYDROCARBON HYDROXYLASES; AUTORADIOGRAPHY; BENZOFLAVONES; BETA-NAPHTHOFLAVONE; CHROMATOGRAPHY, THIN LAYER; CHROMONES; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME ACTIVATION; FLAVONOIDS; HUMANS; KINETICS; MIXED FUNCTION OXYGENASES; MUTAGENESIS, SITE-DIRECTED; PROGESTERONE; SOLUBILITY; STEROID 17-ALPHA-HYDROXYLASE; STEROID HYDROXYLASES; SUBSTRATE SPECIFICITY;

EID: 0031041652     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.272.9.5396     Document Type: Article

References (49)

1. Guengerich, F. P. (1992) FASEB J. 6, 745-748
2. Guengerich, F. P. (1995) in Cytochrome P450: Structure, Mechanism, and Biochemistry (Ortiz de Montellano, P. R., ed) pp. 473-535, Plenum Press, New York
3. Guengerich, F. P. (1990) Chem. Res. Toxicol. 3, 363-371
4. Waxman, D. J., Lapenson, D. P., Aoyama, T., Gelboin, H. V., Gonzales, F. J., and Korzekwa, K. (1991) Arch. Biochem. Biophys. 290, 160-166
5. Kronbach, T., Mathys, D., Umeno, M., Gonzalez, F. J., and Meyer, U. A. (1989) Mol. Pharmacol. 36, 89-96
6. Aoyama, T., Yamano, S., Waxman, D. J., Lapenson, D. P., Meyer, U. A., Fischer, V., Tyndale, R., Inaba, T., Kalow, W., Gelboin, H. V., and Gonzalez, F. J. (1989) J. Biol. Chem. 264, 10388-10395
7. Yun, C.-H., Okerholm, R. A., and Guengerich, F. P. (1993) Drug Metab. Dispos. 21, 403-409
8. Shimada, T., and Guengerich, F. P. (1989) Proc. Natl. Acad. Sci. U. S. A. 86, 462-465
9. Raney, K. D., Shimada, T., Kim, D., Groopman, J. D., Harris, T. M., and Guengerich, F. P. (1992) Chem. Res. Toxicol. 5, 202-210
10. Huang, M.-T., Johnson, E. F., Muller-Eberhard, U., Koop, D. R., Coon, M. J., and Conney, A. H. (1981) J. Biol. Chem. 256, 10897-10901
11. Korzekwa, K. R., and Jones, J. P. (1993) Pharmacogenetics 3, 1-18
12. Schwab, G. E., Raucy, J. L., and Johnson, E. F. (1988) Mol. Pharmacol. 33, 493-499
13. Shou, M., Grogan, J., Mancewicz, J. A., Krausz, K. W., Gonzalez, F. J., Gelboin, H. V., and Korzekwa, K. R. (1994) Biochemistry 33, 6450-6455
14. Ueng, Y., Shimada, T., Yamazaki, H., and Guengerich, F. P. (1995) Chem. Res. Toxicol. 8, 218-225
15. Gotoh, O. (1992) J. Biol. Chem. 267, 83-90
16. Liu, J., He, Y. A., and Halpert, J. R. (1996) Arch. Biochem. Biophys. 327, 167-173
17. Luo, Z., He, Y., and Halpert, J. R. (1994) Arch. Biochem. Biophys. 309, 52-57
18. Kedzie, K. M., Balfour, C. A., Escobar, G. Y., Grimm, S. W., He, Y., Pepperl, D. J., Regan, J. W., Stevens, J. C., and Halpert, J. R. (1991) J. Biol. Chem. 266, 22515-22521
19. He, Y., Luo, Z., Klekotka, P. A., Burnett, V. L., and Halpert, J. R. (1994) Biochemistry 33, 4419-4424
20. He, Y. A., Balfour, C. A., Kedzie, K. M., and Halpert, J. R. (1992) Biochemistry 31, 9220-9226
21. Hasler, J. A., Harlow, G. R., Szklarz, G. D., John, G. H., Kedzie, K. M., Burnett, V. L., He, Y.-A., Kaminsky, L. S., and Halpert, J. R. (1994) Mol. Pharmacol. 46, 338-345
22. Harlow, G. R., and Halpert, J. R. (1996) Arch. Biochem. Biophys. 326, 85-92
23. Halpert, J. R., and He, Y. (1993) J Biol. Chem. 268, 4453-4457
24. Iwasaki, M., Darden, T. A., Pedersen, L. G., Davis, D. G., Juvonen, R. O., Sueyoshi, T., and Negishi, M. (1993) J. Biol. Chem. 268, 759-762
25. Juvonen, R. O., Iwasaki, M., and Negishi, M. (1991) J. Biol. Chem. 266, 16431-16435
26. Lindberg, R. L. P., and Negishi, M. (1989) Nature 339, 632-634
27. Hsu, M.-H., Griffin, K. J., Wang, Y., Kemper, B., and Johnson, E. F. (1993) J. Biol. Chem. 268, 6939-6944
28. Imai, Y., and Nakamura, M. (1989) Biochem. Biophys. Res. Commun. 158, 717-722
29. Kronbach, T., Kemper, B., and Johnson, E. F. (1991) Biochemistry 30, 6097-6102
30. Kronbach, T., and Johnson, E. F. (1991) Biochemistry 266, 6215-6220
31. Kaminsky, L. S., de Morais, S. M. F., Faletto, M. B., Dunbar, D. A., and Goldstein, J. A. (1992) Mol. Pharmacol. 43, 234-239
32. Straub, P., Lloyd, M., Johnson, E. F., and Kemper, B. (1993) J. Biol. Chem. 268, 21997-22003
33. Hasemann, C. A., Kurumbail, R. G., Boddupalli, S. S., Peterson, J. A., and Deisenhofer, J. (1995) Curr. Biol. 2, 41-62
34. Iwasaki, M., Juvonen, R., Lindberg, R., and Negishi, M. (1991) J. Biol. Chem. 266, 3380-3382
35. Beaune, P. H., Umbenhauer, D. R., Bork, R. W., Lloyd, R. S., and Guengerich, F. P. (1986) Proc. Natl. Acad. Sci. U. S. A. 83, 8064-8068
36. Gillam, E. M., Baba, T., Kim, B., Ohmori, S., and Guengerich, F. P. (1993) Arch. Biochem. Biophys. 305, 123-131
37. Gonzalez, F. J., Schmid, B. J., Umeno, M., McBride, O. W., Hardwick, J. P., Meyer, U. A., Gelboin, H. V., and Idle, J. R. (1988) DNA 7, 79-86
38. John, G. H., Hasler, J. A., He, Y., and Halpert, J. R. (1994) ArcA. Biochem. Biophys. 314, 367-375
39. Shen, A. L., Porter, T. D., Wilson, T. E., and Kasper, C. B. (1989) J. Biol. Chem. 264, 7584-7589
40. Waxman, D. J. (1991) Methods Enzymol. 206, 462-476
41. Cunningham, B. C., and Wells, J. A. (1989) Science 244, 1081-1085
42. Imaoka, S., Imai, Y., Shimada, T., and Funae, Y. (1992) Biochemistry 31, 6063-6069
43. Von Wachenfeldt, C., and Johnson, E. F. (1995) in Cytochrome P450: Structure, Mechanism, and Biochemistry (Ortiz de Montellano, P. R., ed) pp. 183-223, Plenum Press, New York
44. Iwasaki, M., Lindberg, R. L. P., Juvonen, R. O., and Negishi, M. (1993) Biochem. J. 291, 569-573
45. White, R. E., McCarthy, M. B., Egeberg, K. D., and Sligar, S. G. (1984) Arch. Biochem. Biophys. 228, 493-502
46. Szklarz, G. D., He, Y. A., and Halpert, J. R. (1995) Biochemistry 34, 14312-14322
47. Loida, P. J., and Sligar, S. G. (1993) Biochemistry 32, 11530-11538
48. Yeom, H., Sligar, S. G., Li, H., Poulos, T. L., and Fulco, A. J. (1995) Biochemistry 34, 14733-14740
49. Juvonen, R. O., Iwasaki, M., and Negishi, M. (1992) Biochemistry 31, 11519-11523