Regiospecificity of human cytochrome p450 1a1-mediated oxidations: The role of steric effects

Journal of Biomolecular Structure and Dynamics

Volumn 23, Issue 3, 2005, Pages 243-256

  Ericksen, Spencer S ^a   Szklarz, Grazyna D ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARACHIDONIC ACID; BENZO[A]PYRENE; CYTOCHROME P450 1A1; FATTY ACID; ICOSAPENTAENOIC ACID; PROSTAGLANDIN; XENOBIOTIC AGENT;

ARTICLE; ENZYME STRUCTURE; ENZYME SUBSTRATE COMPLEX; HUMAN; MOLECULAR DYNAMICS; MOLECULAR MODEL; OXIDATION; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 27844481046     PISSN: 07391102     EISSN: 15380254     Source Type: Journal    
DOI: 10.1080/07391102.2005.10507063     Document Type: Article

References (44)

1. Rendic, S., and Di Carlo, F. J., 1997. Drug Metab. Rev., 29:413–580.
2. Schwarz, D., Kisselev, P., Cascorbi, I., Schunck, W. H., and Roots, I., 2001. Carcinogenesis, 22:453–459.
3. Capdevila, J. H., and Falck, J. R., 2001. Biochem. Biophys. Res. Commun., 285:571–576.
4. Kroetz, D. L., and Zeldin, D. C., 2002. Curr. Opin. Lipidol., 13:273–283.
5. Jones, J. P., Shou, M., and Korzekwa, K. R., 1996. Adv. Exp. Med. Biol., 387:355–360.
6. Jones, J. P., Mysinger, M., and Korzekwa, K. R., 2002. Drug Metab. Dispos., 30:7–12.
7. Korzekwa, K. R., Grogan, J., DeVito, S., and Jones, J. P., 1996. Adv. Exp. Med. Biol., 387:361–369.
8. Korzekwa, K. R., and Jones, J. P., 1993. Pharmacogenetics, 3:1–18.
9. Singh, S. B., Shen, L. Q., Walker, M. J., and Sheridan, R. P., 2003. J. Med. Chem., 46:1330–1336.
10. Dowers, T. S., Rock, D. A., Rock, D. A., Perkins, B. N., and Jones, J. P., 2004. Drug Metab Dispos., 32:328–332.
11. Higgins, L., Korzekwa, K. R., Rao, S., Shou, M., and Jones, J. P., 2001. Arch. Biochem. Biophys., 385:220–230.
12. Iyer, K. R., Jones, J. P., Darbyshire, J. F., and Trager, W. F., 1997. Biochemistry, 36:7136–7143.
13. Hoch, U., Falck, J. R., and de Montellano, P. R., 2000. J. Biol. Chem., 275:26952–26958.
14. Paine, M. J., McLaughlin, L. A., Flanagan, J. U., Kemp, C. A., Sutcliffe, M. J., Roberts, G. C., and Wolf, C. R., 2003. J. Biol. Chem., 278:4021–4027.
15. Zamora, I., Afzelius, L., and Crociani, G., 2003. J. Med. Chem., 46:2313–2324.
16. Paulsen, M. D., Manchester, J. I., and Ornstein, R. L., 1996. Methods Enzymol., 272:347–357.
17. Keserü, G. M., Kolossváry, I., and Bertók, B., 1997. J. Am. Chem. Soc., 119:5126–5131.
18. Harris, D., and Loew, G. L., 1995. J. Am. Chem. Soc., 117:2738–2746.
19. Kuhn, B., Jacobsen, W., Christians, U., Benet, L. Z., and Kollman, P. A., 2001. J. Med. Chem., 44:2027–2034.
20. Vermeulen, N. P., 2003. Curr. Top. Med. Chem., 3:1227–1239.
21. Jones, J. P., Shou, M., and Korzekwa, K. R., 1995. Biochemistry, 34:6956–6961.
22. Schwarz, D., Kisselev, P., Ericksen, S. S., Szklarz, G. D., Chernogolov, A., Honeck, H., Schunck, W. H., and Roots, I., 2004. Biochem. Pharmacol., 67:1445–1457.
23. Szklarz, G. D., and Paulsen, M. D., 2002. J. Biomol. Struct. Dyn., 20:155–162.
24. Haines, D. C., Tomchick, D. R., Machius, M., and Peterson, J. A., 2001. Biochemistry, 40:13456–13465.
25. Schoneboom, J. C., Cohen, S., Lin, H., Shaik, S., and Thiel, W., 2004. J. Am. Chem. Soc., 126:4017–4034.
26. Meunier, B., de Visser, S. P., and Shaik, S., 2004. Chem. Rev., 104:3947–3980.
27. de Visser, S. P., Ogliaro, F., Harris, N., and Shaik, S., 2001. J. Am. Chem. Soc., 123:3037–3047.
28. Kim, J. H., Stansbury, K. H., Walker, N. J., Trash, M. A., Strickland, P. T., and Sutter, T. R., 1998. Carcinogenesis, 19:1847–1853.
29. Shaik, S., de Visser, S. P., and Kumar, D., 2004. J. Am. Chem. Soc., 126:11746–11749.
30. Ogliaro, F., de Visser, S. P., and Shaik, S., 2002. J. Inorg. Biochem., 91:554–567.
31. de Visser, S. P., Ogliaro, F., Sharma, P. K., and Shaik, S., 2002. J. Am. Chem. Soc., 124:11809–11826.
32. Szklarz, G. D., He, Y. A., and Halpert, J. R., 1995. Biochemistry, 34:14312–14322.
33. Paulsen, M. D., and Ornstein, R. L., 1992. J. Comput. Aided Mol. Des., 6:449–460.
34. Li, H., and Poulos, T. L., 1999. Biochim. Biophys. Acta., 1441:141–149.
35. Ludemann, S. K., Lounnas, V., and Wade, R. C., 2000. J. Mol. Biol., 303:797–811.
36. Winn, P. J., Ludemann, S. K., Gauges, R., Lounnas, V., and Wade, R. C., 2002. Proc. Natl. Acad. Sci. USA, 99:5361–5366.
37. Sturane, N., Sui, Z., Peterson, J. A., and Ortiz de Montellano, P. R., 1993. Biochemistry, 32:13732–13741.
38. Chuang, S. S., Helvig, C., Taimi, M., Ramshaw, H. A., Collop, A. H., Amad, M., White, J. A., Petkovich, M., Jones, G., and Korczak, B., 2004. J. Biol. Chem., 279:6305–6314.
39. Kahn, R. A., Le Bouquin, R., Pinot, F., Benveniste, I., and Durst, F., 2001. Arch. Biochem. Biophys., 391:180–187.
40. Jones, J. P., and Korzekwa, K. R., 1996. Methods Enzymol., 272:326–335.
41. Guengerich, F. P., 2002. Nat. Rev. Drug Discov., 1:359–366.
42. Rooseboom, M., Commandeur, J. N., and Vermeulen, N. P., 2004. Pharmacol. Rev., 56:53–102.
43. Harayama, S., 1997. Curr. Opin. Biotechnol., 8:268–273.
44. Kellner, D. G., Maves, S. A., and Sligar, S. G., 1997. Curr. Opin. Biotechnol., 8:274–278.