Mechanism of carbamate inactivation of FAAH: Implications for the design of covalent inhibitors and in vivo functional probes for enzymes

Chemistry and Biology

Volumn 12, Issue 11, 2005, Pages 1179-1187

  Alexander, Jessica P ^a   Cravatt, Benjamin F ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDASE; CARBAMIC ACID DERIVATIVE; ENZYME INHIBITOR; FATTY ACID AMIDASE; FATTY-ACID AMIDE HYDROLASE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; MALE; METABOLISM; MOLECULAR PROBE; MOUSE; PROTEOMICS;

AMIDOHYDROLASES; ANIMALS; CARBAMATES; DRUG DESIGN; ENZYME INHIBITORS; MALE; MICE; MODELS, MOLECULAR; MOLECULAR PROBES; MOLECULAR STRUCTURE; PROTEOMICS;

RODENTIA;

EID: 27744466783     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2005.08.011     Document Type: Article

References (47)

1. C.L. Bos, D.J. Richel, T. Ritsema, M.P. Peppelenbosch, and H.H. Versteeg Prostanoids and prostanoid receptors in signal transduction Int. J. Biochem. Cell Biol. 36 2004 1187 1205
2. N. Fukushima, I. Ishii, J.J. Contos, J.A. Weiner, and J. Chun Lysophospholipid receptors Annu. Rev. Pharmacol. Toxicol. 41 2001 507 534
3. M. Maccarrone, and A. Finazzi-Agro Endocannabinoids and their actions Vitam. Horm. 65 2002 225 255
4. C.J. Fowler, S. Holt, O. Nilsson, K.O. Jonsson, G. Tiger, and S.O. Jacobsson The endocannabinoid signaling system: pharmacological and therapeutic aspects Pharmacol. Biochem. Behav. 81 2005 248 262
5. B.F. Cravatt, K. Demarest, M.P. Patricelli, M.H. Bracey, D.K. Giang, B.R. Martin, and A.H. Lichtman Supersensitivity to anandamide and enhanced endogenous cannabinoid signaling in mice lacking fatty acid amide hydrolase Proc. Natl. Acad. Sci. USA 98 2001 9371 9376
6. F. Rodriguez de Fonseca, M. Navarro, R. Gomez, L. Escuredo, F. Nava, J. Fu, E. Murillo-Rodriguez, A. Giuffrida, J. LoVerme, and S. Gaetani An anorexic lipid mediator regulated by feeding Nature 414 2001 209 212
7. B.F. Cravatt, O. Prospero-Garcia, G. Siuzdak, N.B. Gilula, S.J. Henriksen, D.L. Boger, and R.A. Lerner Chemical characterization of a family of brain lipids that induce sleep Science 268 1995 1506 1509
8. W.A. Devane, L. Hanus, A. Breuer, R.G. Pertwee, L.A. Stevenson, G. Griffin, D. Gibson, A. Mandelbaum, A. Etinger, and R. Mechoulam Isolation and structure of a brain constituent that binds to the cannabinoid receptor Science 258 1992 1946 1949
9. D.M. Lambert, S. Vandevoorde, K.O. Jonsson, and C.J. Fowler The palmitoylethanolamide family: a new class of anti-inflammatory agents? Curr. Med. Chem. 9 2002 663 674
10. H. Cadas, S. Gaillet, M. Beltramo, L. Venance, and D. Piomelli Biosynthesis of an endogenous cannabinoid precursor in neurons and its control by calcium and cAMP J. Neurosci. 16 1996 3934 3942
11. H. Cadas, E. di Tomaso, and D. Piomelli Occurence and biosynthesis of endogenous cannabinoid precursor, N-arachidonyl phosphatidylethanolamine, in rat brain J. Neurosci. 17 1997 1226 1242
12. B.F. Cravatt, D.K. Giang, S.P. Mayfield, D.L. Boger, R.A. Lerner, and N.B. Gilula Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides Nature 384 1996 83 87
13. B.F. Cravatt, A. Saghatelian, E.G. Hawkins, A.B. Clement, M.H. Bracey, and A.H. Lichtman Functional disassociation of the central and peripheral fatty acid amide signaling systems Proc. Natl. Acad. Sci. USA 101 2004 10821 10826
14. A.H. Lichtman, C.C. Shelton, T. Advani, and B.F. Cravatt Mice lacking fatty acid amide hydrolase exhibit a cannabinoid receptor-mediated phenotypic hypoalgesia Pain 109 2004 319 327
15. F. Massa, G. Marsicano, H. Hermann, A. Cannich, K. Monory, B.F. Cravatt, G.-L. Ferri, A. Sibaev, M. Storr, and B. Lutz The endogenous cannabinoid system protects against colonic inflammation J. Clin. Invest. 113 2004 1202 1209
16. B.F. Cravatt, and A.H. Lichtman Fatty acid amide hydrolase: an emerging therapeutic target in the endocannabinoid system Curr. Opin. Chem. Biol. 7 2003 469 475
17. S. Gaetani, V. Cuomo, and D. Piomelli Anandamide hydrolysis: a new target for anti-anxiety drugs? Trends Mol. Med. 9 2003 474 478
18. A.H. Lichtman, D. Leung, C. Shelton, A. Saghatelian, C. Hardouin, D. Boger, and B.F. Cravatt Reversible inhibitors of fatty acid amide hydrolase that promote analgesia: evidence for an unprecedented combination of potency and selectivity J. Pharmacol. Exp. Ther. 311 2004 441 448
19. A.G. Hohmann, R.L. Suplita, N.M. Bolton, M.H. Neely, D. Fegley, R. Mangieri, J.F. Krey, J.M. Walker, P.V. Holmes, and J.D. Crystal An endocannabinoid mechanism for stress-induced analgesia Nature 435 2005 1108 1112
20. S. Kathuria, S. Gaetani, D. Fegley, F. Valino, A. Duranti, A. Tontini, M. Mor, G. Tarzia, G. La Rana, and A. Calignano Modulation of anxiety through blockade of anandamide hydrolysis Nat. Med. 9 2003 76 81
21. M.H. Bracey, M.A. Hanson, K.R. Masuda, R.C. Stevens, and B.F. Cravatt Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling Science 298 2002 1793 1796
22. M.K. McKinney, and B.F. Cravatt Structure and function of Fatty Acid amide hydrolase Annu. Rev. Biochem. 74 2005 411 432
23. D.G. Deutsch, R. Omeir, G. Arreaza, D. Salehani, G.D. Prestwich, Z. Huang, and A. Howlett Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase Biochem. Pharmacol. 53 1997 255 260
24. B. Koutek, G.D. Prestwich, A.C. Howlett, S.A. Chin, D. Salehani, N. Akhavan, and D.G. Deutsch Inhibitors of arachidonyl ethanolamide hydrolysis J. Biol. Chem. 269 1994 22937 22940
25. D.L. Boger, H. Sato, A.E. Lerner, B.J. Austin, J.E. Patterson, M.P. Patricelli, and B.F. Cravatt Trifluoromethyl ketone inhibitors of fatty acid amide hydrolase: a probe of structural and conformational features contributing to inhibition Bioorg. Med. Chem. Lett. 9 1999 265 270
26. D.L. Boger, H. Sato, A.E. Lerner, M.P. Hedrick, R.A. Fecik, H. Miyauchi, G.D. Wilkie, B.J. Austin, M.P. Patricelli, and B.F. Cravatt Exceptionally potent inhibitors of fatty acid amide hydrolase: the enzyme responsible for degradation of endogenous oleamide and anandamide Proc. Natl. Acad. Sci. USA 97 2000 5044 5049
27. B. Ibach, and E. Haen Acetylcholinesterase inhibition in Alzheimer's Disease Curr. Pharm. Des. 10 2004 231 251
28. M. Mor, S. Rivara, A. Lodola, P.V. Plazzi, G. Tarzia, A. Duranti, A. Tontini, G. Piersanti, S. Kathuria, and D. Piomelli Cyclohexylcarbamic acid 3′- or 4′-substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: synthesis, quantitative structure-activity relationships, and molecular modeling studies J. Med. Chem. 47 2004 4998 5008
29. Sit, S.-Y., and Xie, K. December 2002. U.S. patent W0 02/087569.
30. P. Bar-On, C.B. Millard, M. Harel, H. Dvir, A. Enz, J.L. Sussman, and I. Silman Kinetic and structural studies on the interaction of cholinesterases with the anti-Alzheimer drug rivastigmine Biochemistry 41 2002 3555 3564
31. E. Basso, A. Duranti, M. Mor, D. Piomelli, A. Tontini, G. Tarzia, and P. Traldi Tandem mass spectrometric data-FAAH inhibitory activity relationships of some carbamic acid O-aryl esters J. Mass Spectrom. 39 2004 1450 1455
32. M.P. Patricelli, M.A. Lovato, and B.F. Cravatt Chemical and mutagenic investigations of fatty acid amide hydrolase: evidence for a family of serine hydrolase with distinct catalytic properties Biochemistry 38 1999 9804 9812
33. M.K. McKinney, and B.F. Cravatt Evidence for distinct roles in catalysis for residues of the serine-serine-lysine catalytic triad of fatty acid amide hydrolase J. Biol. Chem. 278 2003 37393 37399
34. S. Sirois, G. Hatzakis, D. Wei, Q. Du, and K.C. Chou Assessment of chemical libraries for their druggability Comput. Biol. Chem. 29 2005 55 67
35. A.E. Speers, G.C. Adam, and B.F. Cravatt Activity-based protein profiling in vivo using a copper(I)-catalyzed azide-alkyne [3 + 2] cycloaddition J. Am. Chem. Soc. 125 2003 4686 4687
36. A.E. Speers, and B.F. Cravatt Profiling enzyme activities in vivo using click chemistry methods Chem. Biol. 11 2004 535 546
37. M.P. Patricelli, D.K. Giang, L.M. Stamp, and J.J. Burbaum Direct visualization of serine hydrolase activities in complex proteome using fluorescent active site-directed probes Proteomics 1 2001 1067 1071
38. N. Jessani, Y. Liu, M. Humphrey, and B.F. Cravatt Enzyme activity profiles of the secreted and membrane proteome that depict cancer cell invasiveness Proc. Natl. Acad. Sci. USA 99 2002 10335 10340
39. D. Leung, C. Hardouin, D.L. Boger, and B.F. Cravatt Discovering potent and selective inhibitors of enzymes in complex proteomes Nat. Biotechnol. 21 2003 687 691
40. J.G. Robertson Mechanistic basis of enzyme-targeted drugs Biochemistry 44 2005 5561 5571
41. D.C. Greenbaum, W.D. Arnold, F. Lu, L. Hayrapetian, A. Baruch, J. Krumrine, S. Toba, K. Chehade, D. Bromme, and I.D. Kuntz Small molecule affinity fingerprinting. A tool for enzyme family subclassification, target identification, and inhibitor design Chem. Biol. 9 2002 1085 1094
42. E.S. Okerberg, J. Wu, B. Zhang, B. Samii, K. Blackford, D.T. Winn, K.R. Shreder, J.J. Burbaum, and M.P. Patricelli High-resolution functional proteomics by active-site peptide profiling Proc. Natl. Acad. Sci. USA 102 2005 4996 5001
43. A.E. Speers, and B.F. Cravatt A tandem orthogonal proteolysis strategy for high-content chemical proteomics J. Am. Chem. Soc. 127 2005 10018 10019
44. D.W. Fry, A.J. Bridges, W.A. Denny, A. Doherty, K.D. Greis, J.L. Hicks, K.E. Hook, P.R. Keller, W.R. Leopold, and J.A. Loo Specific, irreversible inactivation of the epidermal growth factor receptor and erbB2, by a new class of tyrosine kinase inhibitor Proc. Natl. Acad. Sci. USA 95 1998 12022 12027
45. M.P. Patricelli, H.A. Lashuel, D.K. Giang, J.W. Kelly, and B.F. Cravatt Comparative characterization of a wild type and transmembrane domain-deleted fatty acid amide hydrolase: identification of the transmembrane domain as a site for oligomerization Biochemistry 37 1998 15177 15187
46. M.P. Patricelli, and B.F. Cravatt Characterization and manipulation of the acyl chain selectivity of fatty acid amide hydrolase Biochemistry 40 2001 6107 6115
47. D.L. Tabb, W.H. McDonald, and J.R. Yates III DTASelect and Contrast: tools for assembling and comparing protein identifications from shotgun proteomics J. Proteome Res. 1 2002 21 26