Effect of conformational dynamics on substrate recognition and specificity as probed by the introduction of a de novo disulfide bond into cytochrome P450 2B1

Journal of Biological Chemistry

Volumn 284, Issue 38, 2009, Pages 25678-25686

  Zhang, Haoming ^a   Kenaan, Cesar ^a   Hamdane, Djemel ^b   Hoa, Gaston Hui Bon ^b   Hollenberg, Paul F ^a,c  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

^b INSERM   (France)

^c NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONAL DYNAMICS; CYTOCHROME P450; DEMETHYLATION; DISULFIDE BONDING; DISULFIDE BONDS; HIGH HYDROSTATIC PRESSURE; IN-SILICO; MOLECULAR DYNAMICS SIMULATIONS; PROTEIN DYNAMICS; SUBSTRATE RECOGNITION; SUBSTRATE SPECIFICITY; WILD TYPES;

HYDROSTATIC PRESSURE; MOLECULAR DYNAMICS; SUBSTRATES;

DYNAMICS;

7 ETHOXYTRIFLUOROMETHYLCOUMARIN; ANDROSTENEDIONE; BENZPHETAMINE; COUMARIN DERIVATIVE; CYSTEINE; CYTOCHROME P450 2B1; TESTOSTERONE; UNCLASSIFIED DRUG; ANDROSTERONE; DISULFIDE;

ARTICLE; CATALYSIS; COMPUTER MODEL; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DEMETHYLATION; DISULFIDE BOND; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HYDROSTATIC PRESSURE; MOLECULAR DYNAMICS; MOLECULAR PROBE; MOLECULAR RECOGNITION; NONHUMAN; PRIORITY JOURNAL; PROTEIN STRUCTURE; STEADY STATE; WILD TYPE; AMINO ACID SUBSTITUTION; CHEMISTRY; GENETICS; HUMAN; MISSENSE MUTATION; PROTEIN SECONDARY STRUCTURE;

AMINO ACID SUBSTITUTION; ANDROSTERONE; CYTOCHROME P-450 CYP2B1; DISULFIDES; HUMANS; MUTATION, MISSENSE; PROTEIN STRUCTURE, SECONDARY; SUBSTRATE SPECIFICITY; TESTOSTERONE;

EID: 70350028665     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M109.032748     Document Type: Article

References (47)

1. Hollenberg, P. F., Kent, U. M., and Bumpus, N. N. (2008) Chem. Res. Toxicol. 21, 189-205
2. Williams, P. A., Cosme, J., Sridhar, V., Johnson, E. F., and McRee, D. E. (2000) J. Inorg. Biochem. 81, 183-190
3. Scott, E. E., He, Y. A., Wester, M. R., White, M. A., Chin, C. C., Halpert, J. R., Johnson, E. F., and Stout, C. D. (2003) Proc. Natl. Acad. Sci. U.S.A. 100, 13196-13201
4. Schlichting, I., Berendzen, J., Chu, K., Stock, A. M., Maves, S. A., Benson, D. E., Sweet, R. M., Ringe, D., Petsko, G. A., and Sligar, S. G. (2000) Science 287, 1615-1622
5. Scott, E. E., White, M. A., He, Y. A., Johnson, E. F., Stout, C. D., and Halpert, J. R. (2004) J. Biol. Chem. 279, 27294-27301
6. Zhao, Y., White, M. A., Muralidhara, B. K., Sun, L., Halpert, J. R., and Stout, C. D. (2006) J. Biol. Chem. 281, 5973-5981
7. Ekroos, M., and Sjögren, T. (2006) Proc. Natl. Acad. Sci. U.S.A. 103, 13682-13687
8. Skopalík, J., Anzenbacher, P., and Otyepka, M. (2008) J. Phys. Chem. B. 112, 8165-8173
9. Smith, S. V., Koley, A. P., Dai, R., Robinson, R. C., Leong, H., Markowitz, A., and Friedman, F. K. (2000) Biochemistry 39, 5731-5737
10. Muralidhara, B. K., Negi, S., Chin, C. C., Braun, W., and Halpert, J. R. (2006) J. Biol. Chem. 281, 8051-8061
11. Hanna, I. H., Roberts, E. S., and Hollenberg, P. F. (1998) Biochemistry 37, 311-318
12. Kent, U. M., Mills, D. E., Rajnarayanan, R. V., Alworth, W. L., and Hollenberg, P. F. (2002) J. Pharmacol. Exp. Ther. 300, 549-558
13. Hamdane, D., Kiger, L., Hoa, G. H., Dewilde, S., Uzan, J., Burmester, T., Hankeln, T., Moens, L., and Marden, M. C. (2005) J. Biol. Chem. 280, 36809-36814
14. Hui Bon Hoa, G., Douzou, P., Dahan, N., and Balny, C. (1982) Anal. Biochem. 120, 125-135
15. Zhang, H., Im, S. C., and Waskell, L. (2007) J. Biol. Chem. 282, 29766-29776
16. Reed, J. R., and Hollenberg, P. F. (2003) J. Inorg. Biochem. 93, 152-160
17. Zhang, H., Hamdane, D., Im, S. C., and Waskell, L. (2008) J. Biol. Chem. 283, 5217-5225
18. Sali, A., and Blundell, T. L. (1993) J. Mol. Biol. 234, 779-815
19. Thompson, J. D., Higgins, D. G., and Gibson, T. J. (1994) Nucleic Acids Res. 22, 4673-4680
20. Laskowski, R. A., MacAthur, M. W., Moss, D. S., and Thornton, J. M. (1993) J. Appl. Crystallogr. 26, 283-291
21. Wallner, B., and Elofsson, A. (2003) Protein Sci. 12, 1073-1086
22. Dombkowski, A. A. (2003) Bioinformatics 19, 1852-1853
23. Phillips, J. C., Braun, R., Wang, W., Gumbart, J., Tajkhorshid, E., Villa, E., Chipot, C., Skeel, R. D., Kalé, L., and Schulten, K. (2005) J. Comput. Chem. 26, 1781-1802
24. Petrek, M., Otyepka, M., Banás, P., Kosinová, P., Koca, J., and Damborský, J. (2006) BMC Bioinformatics 7, 316
25. He, Y. Q., He, Y. A., and Halpert, J. R. (1994) Chem. Res. Toxicol. 8, 574-579
26. Luo, Z., He, Y. A., and Halpert, J. R. (1994) Arch. Biochem. Biophys. 309, 52-57
27. He, Y., Luo, Z., Klekotka, P. A., Burnett, V. L., and Halpert, J. R. (1994) Biochemistry 33, 4419-4424
28. Honma, W., Li, W., Liu, H., Scott, E. E., and Halpert, J. R. (2005) Arch. Biochem. Biophys. 435, 157-165
29. Gotoh, O. (1992) J. Biol. Chem. 267, 83-90
30. Seifert, A., and Pleiss, J. (2009) Proteins 74, 1028-1035
31. Tschirret-Guth, R. A., Hui Bon Hoa, G., and Ortiz de Montellano, P. (1998) J. Am. Chem. Soc. 120, 3590-3596
32. Ghosh, D., Griswold, J., Erman, M., and Pangborn, W. (2009) Nature 457, 219-223
33. Cojocaru, V., Winn, P. J., and Wade, R. C. (2007) Biochim. Biophys. Acta 1770, 390-401
34. Davydov, D. R., Deprez, E., Hoa, G. H., Knyushko, T. V., Kuznetsova, G. P., Koen, Y. M., and Archakov, A. I. (1995) Arch. Biochem. Biophys. 320, 330-344
35. Davydov, D. R., Halpert, J. R., Renaud, J. P., and Hui Bon Hoa, G. (2003) Biochem. Biophys. Res. Commun. 312, 121-130
36. Hui Bon Hoa, G., McLean, M. A., and Sligar, S. G. (2002) Biochim. Biophys. Acta 1595, 297-308
37. Von Weymarn, L. B., Sridar, C., and Hollenberg, P. F. (2004) J. Pharmacol. Exp. Ther. 311, 71-79
38. Porubsky, P. R., Meneely, K. M., and Scott, E. E. (2008) J. Biol. Chem. 283, 33698-33707
39. Li, W., Liu, H., Scott, E. E., Gräter, F., Halpert, J. R., Luo, X., Shen, J., and Jiang, H. (2005) Drug Metab. Dispos. 33, 910-919
40. Haines, D. C., Tomchick, D. R., Machius, M., and Peterson, J. A. (2001) Biochemistry 40, 13456-13465
41. Lin, H. L., Zhang, H., Waskell, L., and Hollenberg, P. F. (2003) J. Pharmacol. Exp. Ther. 306, 744-751
42. Lin, H. L., Kent, U. M., Zhang, H., Waskell, L., and Hollenberg, P. F. (2003) Chem. Res. Toxicol. 16, 129-136
43. He, Y. A., Balfour, C. A., Kedzie, K. M., and Halpert, J. R. (1992) Biochemistry 31, 9220-9226
44. Domanski, T. L., He, Y. Q., Scott, E. E., Wang, Q., and Halpert, J. R. (2001) Arch. Biochem. Biophys. 394, 21-28
45. Yao, H., McCullough, C. R., Costache, A. D., Pullela, P. K., and Sem, D. S. (2007) Proteins 69, 125-138
46. Nguyen, T. A., Tychopoulos, M., Bichat, F., Zimmermann, C., Flinois, J. P., Diry, M., Ahlberg, E., Delaforge, M., Corcos, L., Beaune, P., Dansette, P., André, F., and de Waziers, I. (2008) Mol. Pharmacol. 73, 1122-1133
47. Harris, D. L., Park, J. Y., Gruenke, L., and Waskell, L. (2004) Proteins 55, 895-914