Trifluoromethyl ketone inhibitors of fatty acid amide hydrolase: A probe of structural and conformational features contributing to inhibition

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 2, 1999, Pages 265-270

  Boger, Dale L ^a   Sato, Haruhiko ^a   Lerner, Aaron E ^a   Austin, Bryce J ^a   Patterson, Jean E ^a   Patricelli, Matthew P ^a   Cravatt, Benjamin F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FATTY ACID AMIDASE INHIBITOR; HYDROLASE INHIBITOR; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME CONFORMATION; ENZYME INHIBITOR INTERACTION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

AMIDOHYDROLASES; INHIBITORY CONCENTRATION 50; KETONES; OLEIC ACIDS; TEMPERATURE;

EID: 0033579908     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00734-3     Document Type: Article

References (53)

1. Review: Boger, D. L.; Henriksen, S. J.; Cravatt, B. F. Curr. Pharm. Design. 1998, 4, 303.
2. Cravatt, B. F.; Prospero-Garcia, O.; Siuzdak, G.; Gilula, N. B.; Henriksen, S. J.; Boger, D. L.; Lerner, R. A. Science 1995, 268, 1506.
3. Review: Di Marzo, V.; Fontana, A. Prostaglandins, Leukotrienes, Essen. Fatty Acids 1995, 53, 1.
4. Devane, W. A.; Hanus, L.; Breuer, A.; Pertwee, R. G.; Stevenson, L. A.; Griffin, G.; Gibson, D.; Mandelbaum, A.; Etinger, A.; Mechoulam, R. Science 1992, 258, 1946.
5. Arafat, E. S.; Trimble, J. W.; Andersen, R. N.; Dass, C.; Desiderio, D. M. Life Sci. 1989, 45, 1679.
6. Lerner, R. A.; Siuzdak, G.; Prospero-Garcia, O.; Henriksen, S. J.; Boger, D. L.; Cravatt, B. F. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 9505.
7. Cravatt, B. F.; Lerner, R. A.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 580.
8. Huidobro-Toro, J. P.; Harris, R. A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 8078.
9. Thomas, E. A.; Carson, M. J.; Neal, M. J.; Sutcliffe, J. G. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 14115.
10. Boger, D. L.; Patterson, J. E.; Jin, Q. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4102.
11. Yost, C. S.; Hampson, A. J.; Leonoudakis, D.; Koblin, D. D.; Bornheim, L. M.; Gray, A. T. Anesth. Analg. 1998, 86, 1294.
12. Guan, X.; Cravatt, B. F.; Ehring, G. R.; Hall, J. E.; Boger, D. L.; Lerner, R. A.; Gilula, N. B. J. Cell Biol. 1997, 139, 1785.
13. Boger, D. L.; Patterson, J. E.; Guan, X.; Cravatt, B. F.; Lerner, R. A.; Gilula, N. B. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4810.
14. Mechoulam, R.; Fride, E.; Hanus, L.; Sheskin, T.; Bisogno, T.; Di Marzo, V.; Bayewitch, M.; Vogel, Z. Nature 1997, 389, 25.
15. Di Marzo, V.; Fontana, A.; Cadas, H.; Schinelli, S.; Cimino, G.; Schwartz, J.-C.; Piomelli, D. Nature 1994, 372, 686.
16. Fan, P. J. Neurophysiol. 1995, 73, 907.
17. Kimura, T.; Ohta, T.; Watanabe, K.; Yoshimura, H.; Yamamoto, I. Biol. Pharm. Bull. 1998, 21, 224.
18. Wakamatsu, K.; Masaki, T.; Itoh, F.; Kondo, K.; Sudo, K. Biochem. Biophys. Res. Commun. 1990, 168, 423.
19. Review: Schmid, H. H. O.; Schmid, P. C.; Natarajan, V. Prog. Lipid Res. 1990, 29, 1.
20. Barg, J.; Fride, E.; Hanus, L.; Levy, R.; Matus-Leibovitch, N.; Heldman, E.; Bayewitch, M.; Mechoulam, R.; Vogel, Z. Eur. J. Pharmacol. 1995, 287, 145.
21. Skaper, S. D.; Buriani, A.; Dal Toso, R.; Petrelli, L.; Romanello, S.; Facci, L.; Leon, A. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 3984.
22. Cravatt, B. F.; Giang, D. K.; Mayfield, S. P.; Boger, D. L.; Lerner, R. A.; Gilula, N. B. Nature 1996, 384, 83.
23. Giang, D. K.; Cravatt, B. F. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 2238.
24. Deutsch, D. G.; Chin, S. A. Biochem. Pharmacol. 1993, 46, 791.
25. Desarnaud, F.; Cadas, H.; Piomelli, D. J. Biol. Chem. 1995, 270, 6030.
26. Hillard, C. J.; Wilkison, D. M.; Edgsmond, W. S.; Campbell, W. B. Biochim. Biophys. Acta 1995, 1257, 249.
27. Ueda, N.; Kurahashi, Y.; Yamamoto, S.; Tokunaga, T. J. Biol. Chem. 1995, 270, 23823.
28. Omeir, R. L.; Chin, S.; Hong, Y.; Ahern, D. G.; Deutsch, D. G. Life Sci. 1995, 56, 1999.
29. Maurelli, S.; Bisogno, T.; De Petrocellis, L.; Di Luccia, A.; Marino, G.; Di Marzo, V. FEBS Lett. 1995, 377, 82.
30. Thomas, E. A.; Cravatt, B. F.; Danielson, P. E.; Gilula, N. B.; Sutcliffe, J. G. J. Neurosci. Res. 1997, 50, 1047. See also refs 25 and 26.
31. Goparaju, S. K.; Ueda, N.; Yamaguchi, H.; Yamamoto, S. FEBS Lett. 1998, 442, 69.
32. Kurahashi, Y.; Ueda, N.; Suzuki, H.; Suzuki, M.; Yamamoto, S. Biochem. Biophys. Res. Commun. 1997, 257, 512.
33. Bisogno, T.; Sepe, N.; Melck, D.; Maurelli, S.; De Petrocellis, L.; Di Marzo, V. Biochem. J. 1997, 522, 671. Di Marzo, V.; Bisogno, T.; Sugiura, T.; Melck, D.; De Petrocellis, L. Biochem. J. 1998, 331, 15.
34. Bisogno, T.; Sepe, N.; Melck, D.; Maurelli, S.; De Petrocellis, L.; Di Marzo, V. Biochem. J. 1997, 522, 671. Di Marzo, V.; Bisogno, T.; Sugiura, T.; Melck, D.; De Petrocellis, L. Biochem. J. 1998, 331, 15.
35. Patricelli, M. P.; Patterson, J. E.; Boger, D. L.; Cravatt, B. F. Bioorg. Med. Chem. Lett. 1998, 8, 613.
36. Torii, S.; Mitsumori, K.; Inubushi, S.; Yanagisawa, I. Psychopharmacologia 1973, 29, 65.
37. Koutek, B.; Prestwich, G. D.; Howlett, A. C.; Chin, S. A.; Salehani, D.; Akhavan, N.; Deutsch, D. G. J. Biol. Chem. 1994, 269, 22937.
38. Patterson, J. E.; Ollmann, I. R.; Cravatt, B. F.; Boger, D. L.; Wong, C.-H.; Lerner, R. A. J. Am. Chem. Soc. 1996, 118, 5938.
39. Deutsch, D. G.; Omeir, R.; Arreaza, G.; Salehani, D.; Prestwich, G. D.; Huang, Z.; Howlett, A. Biochem. Pharmacol. 1997, 53, 255. Deutsch, D. G.; Lin, S.; Hill, W. A. G.; Morse, K. L.; Salehani, D.; Arreaza, G.; Omeir, R. L.; Makriyannis, A. Biochem. Biophys. Res. Commun. 1997, 231, 217.
40. Deutsch, D. G.; Omeir, R.; Arreaza, G.; Salehani, D.; Prestwich, G. D.; Huang, Z.; Howlett, A. Biochem. Pharmacol. 1997, 53, 255. Deutsch, D. G.; Lin, S.; Hill, W. A. G.; Morse, K. L.; Salehani, D.; Arreaza, G.; Omeir, R. L.; Makriyannis, A. Biochem. Biophys. Res. Commun. 1997, 231, 217.
41. De Petrocellis, L.; Melck, D.; Ueda, N.; Maurelli, S.; Kurahashi, Y.; Yamamoto, S.; Marino, G.; Di Marzo, V. Biochem. Biophys. Res. Commun. 1997, 231, 82.
42. 36,37 have been disclosed previously and have been included for direct comparison under the present assay conditions.
43. 3OH, 23 h, 25 °C) of 17 and 19. The carboxylic acids leading to 21-23 are commercially available.
44. 3OH, 23 h, 25 °C) of 17 and 19. The carboxylic acids leading to 21-23 are commercially available.
45. Boivin, J.; El Kaim, L.; Zard, S. Z. Tetrahedron Lett. 1992, 33, 1285.
46. For 1 and 3 (ref. 37); for 2 (Besterman, H. J.; Stansky, W.; Vostrowsky, O.; Range, P. Chem. Ber. 1975, 108, 3582; for -7 (Parrilla, A.; Villuendas I.; Guerrero, A. Bioorg. Med. Chem. 1994, 2, 243); for (Begue, J.-P.; Bonnet-Delpon, D.; Mesureur, D.; Nee, G.; Wu, S.-W. J. Org. Chem. 1992, 57, 3807); for (Dishart, K. T.; Levine, R. J. Am. Chem. Soc. 1956, 78, 2268); for (Barkley, L. B.; Levine, R. J. Am. Chem. Soc.1953, 75, 2059). Full characterization of 11-23 can be supplied upon request.
47. For 1 and 3 (ref. 37); for 2 (Besterman, H. J.; Stansky, W.; Vostrowsky, O.; Range, P. Chem. Ber. 1975, 108, 3582; for 4-7 (Parrilla, A.; Villuendas I.; Guerrero, A. Bioorg. Med. Chem. 1994, 2, 243); for (Begue, J.-P.; Bonnet-Delpon, D.; Mesureur, D.; Nee, G.; Wu, S.-W. J. Org. Chem. 1992, 57, 3807); for (Dishart, K. T.; Levine, R. J. Am. Chem. Soc. 1956, 78, 2268); for (Barkley, L. B.; Levine, R. J. Am. Chem. Soc.1953, 75, 2059). Full characterization of 11-23 can be supplied upon request.
48. For 1 and 3 (ref. 37); for 2 (Besterman, H. J.; Stansky, W.; Vostrowsky, O.; Range, P. Chem. Ber. 1975, 108, 3582; for -7 (Parrilla, A.; Villuendas I.; Guerrero, A. Bioorg. Med. Chem. 1994, 2, 243); for 8 (Begue, J.-P.; Bonnet-Delpon, D.; Mesureur, D.; Nee, G.; Wu, S.-W. J. Org. Chem. 1992, 57, 3807); for (Dishart, K. T.; Levine, R. J. Am. Chem. Soc. 1956, 78, 2268); for (Barkley, L. B.; Levine, R. J. Am. Chem. Soc.1953, 75, 2059). Full characterization of 11-23 can be supplied upon request.
49. For 1 and 3 (ref. 37); for 2 (Besterman, H. J.; Stansky, W.; Vostrowsky, O.; Range, P. Chem. Ber. 1975, 108, 3582; for -7 (Parrilla, A.; Villuendas I.; Guerrero, A. Bioorg. Med. Chem. 1994, 2, 243); for (Begue, J.-P.; Bonnet-Delpon, D.; Mesureur, D.; Nee, G.; Wu, S.-W. J. Org. Chem. 1992, 57, 3807); for 9 (Dishart, K. T.; Levine, R. J. Am. Chem. Soc. 1956, 78, 2268); for (Barkley, L. B.; Levine, R. J. Am. Chem. Soc.1953, 75, 2059). Full characterization of 11-23 can be supplied upon request.
50. For 1 and 3 (ref. 37); for 2 (Besterman, H. J.; Stansky, W.; Vostrowsky, O.; Range, P. Chem. Ber. 1975, 108, 3582; for -7 (Parrilla, A.; Villuendas I.; Guerrero, A. Bioorg. Med. Chem. 1994, 2, 243); for (Begue, J.-P.; Bonnet-Delpon, D.; Mesureur, D.; Nee, G.; Wu, S.-W. J. Org. Chem. 1992, 57, 3807); for (Dishart, K. T.; Levine, R. J. Am. Chem. Soc. 1956, 78, 2268); for 10 (Barkley, L. B.; Levine, R. J. Am. Chem. Soc. 1953, 75, 2059). Full characterization of 11-23 can be supplied upon request.
51. Linderman, R. J.; Graves, D. M. J. Org. Chem. 1989, 54, 661.
52. 2. The products were resuspended in 8 μL EtOH, spotted on thin layer chromatography plates and developed in 50% EtOAc-hexanes. The developed plates were placed on a phosphorimaging film (2-12 h) and the conversion of oleamide to oleic acid was determined via a phosphorimager (Packard brand phosphorimager, model A431201).
53. Conde-Frieboes, K.; Reynolds, L. J.; Lio, Y.-C.; Hale, M. R.; Wasserman, H. H.; Dennis, E. A. J. Am. Chem. Soc. 1996, 118, 5519.