Computational redesign of human butyrylcholinesterase for anticocaine medication

Proceedings of the National Academy of Sciences of the United States of America

Volumn 102, Issue 46, 2005, Pages 16656-16661

  Pan, Yongmei ^a   Gao, Daquan ^a   Yang, Wenchao ^a   Cho, Hoon ^a   Yang, Guangfu ^a   Tai, Hsin Hsiung ^a   Zhan, Chang Guo ^a  

^a University of Kentucky   (United States)

Author keywords

Cocaine; Enzyme substrate binding; Molecular dynamics; Rational design; Transition state stabilization

Indexed keywords

CARBONYL DERIVATIVE; CHOLINESTERASE; COCAINE; OXYGEN;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG DESIGN; ENERGY; ENZYME STRUCTURE; HYDROGEN BOND; HYDROLYSIS; MOLECULAR DYNAMICS; PRIORITY JOURNAL; SIMULATION;

BUTYRYLCHOLINESTERASE; CATALYSIS; COCAINE; COCAINE-RELATED DISORDERS; DRUG DESIGN; HUMANS; HYDROGEN BONDING; MUTAGENESIS, SITE-DIRECTED; MUTATION;

EID: 28044458963     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0507332102     Document Type: Article

References (52)

1. Mendelson, J. H. & Mello, N. K. (1996) N. Engl. J. Med. 334, 965-972.
2. Singh, S. (2000) Chem. Rev. 100, 925-1024.
3. Paula, S., Tabet, M. R., Farr, C. D., Norman, A. B. & Ball, W. J., Jr. (2004) J. Med. Chem. 47, 133-142.
4. Sparenborg, S., Vocci, F. & Zukin, S. (1997) Drug Alcohol Depend. 48, 149-151.
5. Gorelick, D. A. (1997) Drug Alcohol Depend. 48, 159-165.
6. Redish, A. D. (2004) Science 306, 1944-1947.
7. Landry, D. W., Zhao, K., Yang, G. X.-Q., Glickman, M. & Georgiadis, T. M. (1993) Science 259, 1899-1901.
8. Carrera, M. R. A., Ashley, J. A., Parsons, L. H., Wirsching, P., Koob, G. F. & Janda, K. D. (1995) Nature 378, 727-730.
9. Baird, T. J., Deng, S.-X., Landry, D. W., Winger, G. & Woods, J. H. (2000) J. Pharmacol. Exp. Ther. 295, 1127-1134.
10. Carrera, M. R. A., Ashley, J. A., Wirsching, P., Koob, G. F. & Janda, K. D. (2001) Proc. Natl. Acad. Sci. USA 98, 1988-1992.
11. Deng, S.-X., de Prada, P. & Landry, D. W. (2002) J. Immunol. Methods 269, 299-310.
12. Kantak, J. M. (2003) Expert Opin. Pharmacother. 4, 213-218.
13. Gorelick, D. A., Gardner, E. L. & Xi, Z.-X. (2004) Drugs 64, 1547-1573.
14. Carrera, M. R. A., Kaufmann, G. F., Mee, J. M., Meijler, M. M., Koob, G. F. & Janda, K. D. (2004) Proc. Natl. Acad. Sci. USA 101, 10416-10421.
15. Dickerson, T. J., Kaufmann, G. F. & Janda, K. D. (2005) Expert Opin. Biol. Ther. 5, 773-781.
16. Meijler, M. M., Kaufmann, G. F., Qi, L. W., Mee, J. M., Coyle, A. R., Moss, J. A., Wirsching, P., Matsushita, M. & Janda, K. D. (2005) J. Am. Chem. Soc. 127, 2477-2484.
17. Zhan, C.-G., Deng, S.-X., Skiba, J. G., Hayes, B. A., Tschampel, S. M., Shields, G. C. & Landry, D. W. (2005) J. Comput. Chem. 26, 980-986.
18. Kamendulis, L. M., Brzezinski, M. R., Pindel, E. V., Bosron, W. F. & Dean, R. A. (1996) J. Pharmacol. Exp. Ther. 279, 713-717.
19. Gateley, S. J. (1991) Biochem. Pharmacol. 41, 1249-1254.
20. Gatley, S. J., MacGregor, R. R., Fowler, J. S., Wolf, A. P., Dewey, S. L. & Schlyer, D. J. (1990) J. Neurochem. 54, 720-723.
21. Darvesh, S., Hopkins, D. A. & Geula, C. (2003) Nat. Rev. Neurosci. 4, 131-138.
22. Giacobini, E., ed. (2003) Butyrylcholinesterase: Its Function and Inhibitors (Martin Dunitz, London).
23. Sun, H., Yazal, J. E., Lockridge, O., Schopfer, L. M., Brimijoin, S. & Pang, Y. P. (2001) J. Biol. Chem. 276, 9330-9336.
24. Sun, H., Shen, M. L., Pang, Y. P., Lockridge, O. & Brimijoin, S. (2002) J. Pharmacol. Exp. Ther. 302, 710-716.
25. Sun, H., Pang, Y. P., Lockridge, O. & Brimijoin, S. (2002) Mol. Pharmacol. 62, 220-224.
26. Zhan, C.-G., Zheng, F. & Landry, D. W. (2003) J. Am. Chem. Soc. 125, 2462-2474.
27. Hamza, A., Cho, H., Tai, H.-H. & Zhan, C.-G. (2005) J. Phys. Chem. B 109, 4776-4782.
28. Gao, Y., Atanasova, E., Sui, N., Pancook, J. D., Watkins, J. D. & Brimijoin, S. (2005) Mol. Pharmacol. 67, 204-211.
29. Eksterowicz, J. E. & Houk, K. N. (1993) Chem. Rev. 93, 2439-2461.
30. Case, D. A., Pearlman, D. A., Caldwell, J. W., Cheatham, T. E., III, Wang, J., Ross, W. S., Simmerling, C. L., Darden, T. A., Merz, K. M., Stanton, R. V., et al. (2002) AMBER 7 (Univ. of California, San Francisco).
31. Nicolet, Y., Lockridge, O., Masson, P., Fontecilla-Camps, J. C. & Nachon, F. (2003) J. Biol. Chem. 278, 41141-41147.
32. Bernstein, F. C., Koetzle, T. F., Williams, G. J. B., Meyer, E. E., Jr., Brice, M. D., Rodgers, J. R., Kennard, O., Shimanouchi, T. & Tasumi, M. (1977) J. Mol. Biol. 112, 535-542.
33. Gao, D. & Zhan, C.-G. (2005) Proteins, in press.
34. Zhan, C.-G. & Gao, D. (2005) Biophys. J., in press.
35. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., et al. (2003) GAUSSIAN 03, Revision A.1 (Gaussian, Pittsburgh).
36. Zhan, C.-G., Norberto de Souza, O., Rittenhouse, R. & Ornstein, R. L. (1999) J. Am. Chem. Soc. 121, 7279-7282.
37. Koca, J., Zhan, C.-G., Rittenhouse, R. & Ornstein, R. L. (2001) J. Am. Chem. Soc. 123, 817-826.
38. Koca, J., Zhan, C.-G., Rittenhouse, R. C. & Ornstein, R. L. (2003) J. Comput. Chem. 24, 368-378.
39. Hamza, A., Cho, K, Tai, H.-H. & Zhan, C.-G. (2005) Bioorg. Med. Chem. 13, 4544-4551.
40. Jorgensen, W. L., Chandrasekhar, J., Madura, J. D. & Klein, M. L. (1983) J. Chem. Phys. 79, 926-935.
41. Berendsen, H. J. C., Postma, J. P. M., van Gunsteren, W. F., DiNola, A. & Haak, J. R. (1984) J. Chem. Phys. 81, 3684-3690.
42. Ryckaert, J. P., Ciccotti, G. & Berendsen, H. J. C. (1977) J. Comp. Phys. 23, 327-341.
43. Essmann, U., Perera, L., Berkowitz, M. L., Darden, T., Lee, H. & Pedersen, L. G. (1995) J. Chem. Phys. 103, 8577-8593.
44. Braman, J., Papworth, C. & Greener, A. (1996) Methods Mol. Biol. 57, 31-44.
45. Masson, P., Legrand, P., Bartels, C. F., Froment, M.-T., Schopfer, L. M. & Lockridge, O. (1997) Biochemistry 36, 2266-2277.
46. Masson, P., Xie, W., Froment, M.-T., Levitsky, V., Fortier, P.-L., Albaret, C. & Lockridge, O. (1999) Biochim. Biophys. Acta 1433, 281-293.
47. Xie, W., Altamirano, C. V., Bartels, C. F., Speirs, R. J., Cashman, J. R. & Lockridge, O. (1999) Mol. Pharmacol. 55, 83-91.
48. Duysen, E. G., Bartels, C. F. & Lockridge, O. (2002) J. Pharmacol. Exp. Ther. 302, 751-758.
49. Nachon, F., Nicolet, Y., Viguie, N., Masson, P., Fontecilla-Camps, J. C. & Lockridge, O. (2002) Eur. J. Biochem. 269, 630-637. ;
50. Brock, A., Mortensen, V., Loft, A. G. R. & Nørgaard-Pedersen, B. (1990) J. Clin. Chem. Clin. Biochem. 28, 221-224.
51. Khattab, A. D., Walker, C. H., Johnston, G., Siddiqui, M. K. & Saphier, P. W. (1994) Environ. Toxicol. Chem. 13, 1661-1667.
52. Morris, G. M., Goodsell, D. S., Halliday, R. S., Huey, R., Hart, W. E., Belew, R. K. & Olson, A. J. (1998) J. Comput. Chem. 19, 1639-1662.