Inhibition of oleamide hydrolase catalyzed hydrolysis of the endogenous sleep-inducing lipid cis-9-octadecenamide

Journal of the American Chemical Society

Volumn 118, Issue 25, 1996, Pages 5938-5945

  Patterson, Jean E ^a   Ollmann, Ian R ^a   Cravatt, Benjamin F ^a   Boger, Dale L ^a   Wong, Chi Huey ^a   Lerner, Richard A ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

9 OCTADECENAMIDE; ENZYME INHIBITOR; FATTY ACID DERIVATIVE; HYDROLASE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; DRUG SYNTHESIS; ENZYME INHIBITION; LIVER; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; RAT; SLEEP; STRUCTURE ACTIVITY RELATION;

EID: 0030037917     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja954064z     Document Type: Article

References (53)

1. Cravatt, B. F.; Prospero-Garcia, O.; Siuzdak, G.; Gilula, N. B.; Henriksen, S. J.; Boger, D. L.; Lerner, R. A. Science 1995, 268, 1506-1509.
2. Lerner, R. A.; Siuzdak, G.; Prospero-Garcia, O.; Henriksen, S. J.; Boger, D. L.; Gravait, B. F. Proc. Natl. Acad. Sci. U.S.A 1994, 91, 9505-9508.
3. Cravatt, B. F.; Lerner, R. A.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 580-590.
4. Kettner, C.; Shaw, E. Biochemistry 1978, 17, 4778-4784.
5. Kettner, C.; Shaw, E. Thromb. Res. 1979, 14, 969-973.
6. Giordano, C.; Gallina, C.; Ottaviano, V.; Consalvi, V.; Scandurra, R. Eur. J. Med. Chem. 1992, 27, 865-873.
7. Rauber, P.; Angliker, H.; Walker, B.; Shaw, E. Biochem. J. 1986, 239, 633-640.
8. Angliker, H.; Wikstrom, P.; Rauber, P.; Shaw, E. Biochem. J. 1987, 247, 871-875.
9. Hanzlik, R. P.; Thompson, S. A. J. Med. Chem. 1984, 27, 711-712.
10. Parkes, C.; Kembhavi, A. A.; Barret, A. J. Biochem. J. 1985, 230, 509-516.
11. Brömme, D.; Schierhorn, A.; Kirschke, H.; Wiederanders, B.; Barth, A.; Fittkau, S.; Demuth, H.-U. Biochem. J. 1989, 263, 861-866.
12. Green, G. D. J.; Shaw, E. J. Biol. Chem. 1981, 256, 1923-1928.
13. Mehdi, S. Bioorg. Chem. 1993, 21, 249-259.
14. Brömme, D.; Bartels, B.; Kirschke, H.; Fittkau, S. J. Enzyme Inhib. 1989, 3, 13-21.
15. Westerik, J. O.; Wolfenden, R. J. Biol. Chem. 1972, 247, 8195-8197.
16. Ando, R.; Morinaka, Y.; Tokuyama, H.; Isaka, M.; Nakamura, E. J. Am. Chem. Soc. 1993, 115, 1174-1175.
17. Wolfenden, R. Annu. Rev. Biophys. Bioeng. 1976, 5, 271.
18. Gelb, M. H.; Svaren, J. P.; Abeles, R. H. Biochemistry 1985, 24, 1813-1817.
19. Imperiali, B.; Abeles, R. H. Biochemistry 1986, 25, 3760-3767.
20. Koutek, B.; Prestwich, G. D.; Howlett, A. C.; Chin, S. A.; Salehani, D.; Akhavan, N.; Deutsch, D. G. J. Biol. Chem. 1994, 269, 22937-22940.
21. Li, Z.; Patil, G. S.; Golubski, Z. E.; Hori, H.; Tehrani, K.; Foreman, J. E.; Eveleth, D. D.; Bartus, R. T.; Powers, J. C. J. Med. Chem. 1993, 36, 3472-3480.
22. Harbeson, S. L.; Abelleira, S. M.; Akiyama, A.; Barrett, R.; Carroll, R. M.; Straub, J. A.; Tkacz, J. N.; Wu, C.; Musso, G. F. J. Med. Chem. 1994, 37, 2918-2929.
23. Peet, N. P.; Burkhart, J. P.; Angelastro, M. R.; Giroux, E. L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schirlin, D. J. Med. Chem. 1990, 33, 394-407.
24. Angelastro, M. R.; Mehdi, S.; Burkhart, J. P.; Peet, N. P.; Bey, P. J. Med. Chem. 1990, 33, 11-13.
25. Ocain, T. D.; Rich, D. H. J. Med. Chem. 1992, 35, 451-456.
26. Yuan, W.; Wong, C.-H.; Haeggström, J. Z.; Wetterholm, A.; Samuelsson, B. J. Am. Chem. Soc. 1992, 114, 6552-6553.
27. Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Smith, S. A.; Petrillo, E. W. J. Med. Chem. 1993, 36, 2431-2447.
28. Muñoz, B.; Giam, C.-Z.; Wong, C.-H. Bioorg. Med. Chem. 1994, 2, 1085-1090.
29. Wasserman, H. H.; Ennis, D. S.; Power, P. L.; Ross, M. J.; Gomes, B. J. Org. Chem. 1993, 58, 4785-4787.
30. Maurelli, S.; Bisogno, T.; De Petrocellis, L.; Di Luccia, A.; Marino, G.; Di Marzo, V. FEBS Lett. 1995, 377, 82-86.
31. Mackenzie, N. E.; Grant, S. K.; Scott, A. I.; Malthouse, J. P. G. Biochemistry 1986, 25, 2293-2298.
32. Desarnaud, F.; Cadas, H.; Piomelli, D. J. Biol. Chem. 1995, 270, 6030-6035.
33. Linderman, R. J.; Jamois, E. A.; Roe, R. M. Rev. Pestic. Toxicol. 1991, 1, 261-9.
34. Takahasi, L. H.; Radhakrishnan, R.; Rosenfeld, R. E.; Meyer, E. F.; Trainer, D. A.; Stein, M. J. Mol. Biol 1988, 201, 423-428.
35. Liang, T.-C.; Abeles, R. H. Biochemistry 1987, 26, 7603-7608.
36. Schultz, R. M.; Cheerva, A. C. FEBS Lett. 1975, 50, 47-49.
37. Bell, R. P. Adv. Phys. Org. Chem. 1966, 4, 1-29 and references therein.
38. Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
39. Marx, M. H.; Wiley, R. A.; Satchell, D. G.; Maguire, M. H. J. Med. Chem. 1989, 32, 1319-1322.
40. Snider, B. B.; Kulkarni, Y. S. J. Org. Chem. 1987, 52, 307-310.
41. Konen, D. A.; Silben, L. S.; Pfeffer, P. E. J. Org. Chem. 1975, 40, 3253-3258.
42. Buchanan, G. L. Chem. Soc. Rev. 1988, 17, 91-109.
43. Boivin, J.; El Kaim, L.; Zard, S. Z. Tetrahedron Lett. 1992, 33, 1285-1288.
44. Wasserman, H. H.; Ennis, D. S.; Blum, C. A.; Rotello, V. M. Tetrahedron Lett. 1992, 33, 6003-6006.
45. Cooke, M. P.; Burman, D. L. J. Org. Chem. 1982, 47, 4955-4963.
46. Doleshall, G. Tetrahedron Lett. 1977, 381-382.
47. Kemp, T. R. J. Am. Oil Chem. Soc. 1975, 52, 300-302.
48. Doleshall, G. Tetrahedron Lett. 1980, 21, 4183-4186.
49. Mirallès, J.; Barnathan, G.; Galonnier, R.; Sall, T.; Samb, A.; Gaydou, E. M.; Kornprobst, J.-M. Lipids 1995, 30, 459-466.
50. Couderc, F. Lipids 1995, 30, 691-699.
51. Fersht, A. Enzyme Structure and Mechanism; W. H. Freeman and Co.: New York, 1985; pp 157.
52. Connors, K. A. Binding Constants; Wiley: New York, 1987; pp 385-395.
53. O'Leary, M. H.; Urberg, M.; Young, A. P. Biochemistry 1974, 13, 2077-2081.