Synthesis and characterization of diazomethylarachidonyl ketone: An irreversible inhibitor of N-arachidonylethanolamine amidohydrolase

Journal of Pharmacology and Experimental Therapeutics

Volumn 286, Issue 1, 1998, Pages 184-190

  Edgemond, William S ^a   Greenberg, Marcie J ^a   Mcginley, P J ^a   Muthian, Shanmugam ^a   Campbell, William B ^a   Hillard, Cecilia J ^a  

^a MEDICAL COLLEGE OF WISCONSIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDASE; ANANDAMIDE; DIAZOMETHYLARACHIDONYL KETONE; ENZYME INHIBITOR; N ARACHIDONYLETHANOLAMINE AMIDOHYDROLASE; N ARACHIDONYLETHANOLAMINE AMIDOHYDROLASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ANION EXCHANGE CHROMATOGRAPHY; ARTICLE; BINDING COMPETITION; DOSE RESPONSE; DRUG PROTEIN BINDING; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME INHIBITION; ENZYME MECHANISM; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

AMIDOHYDROLASES; ANIMALS; ARACHIDONIC ACIDS; CYCLOHEXANOLS; DIAZOMETHANE; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; MALE; RATS; RATS, SPRAGUE-DAWLEY; TUMOR CELLS, CULTURED;

EID: 0031847458     PISSN: 00223565     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. Arreaza G, Devane WA, Omeir RL, Sajnani G, Kunz J, Cravatt BF and Deutsch DG (1997) The cloned rat hydrolytic enzyme responsible for the breakdown of anandamide also catalyzes its formation via the condensation of arachidonic acid and ethanolamine. Neurosci Lett 234:59-62.
2. Beltramo M, di Tomaso E and Piomelli D (1997) Inhibition of anandamide hydrolysis in rat brain tissue by (E)-6-(bromomethylene) tetrahydro-3-(1-naphthalenyl)-2H-pyran-2-one. FEBS Lett 403:263-267.
3. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-252.
4. 50) of an enzymatic reaction. Biochem Pharmacol 22:3099-3110.
5. Cravatt BF, Giang DK, Mayfield SP, Boger DL, Lerner RA and Guila NB (1996) Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature 384:84-87.
6. DePetrocellis L, Melck D, Ueda N, Maurelli S, Kurahashi Y, Yamamoto S, Marino G and Di Marzo V (1997) Novel inhibitors of brain, neuronal, and basophilic anandamide amidohydrolase. Biochem Biophys Res Commun 231:82-88.
7. Desarnaud F, Cadas H and Piomelli D (1995) Anandamide amidohydrolase activity in rat brain microsomes. J Biol Chem 270:6030-6035.
8. Deutsch DG and Chin SA (1993) Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem Pharmacol 47:711-715.
9. Deutsch DG, Lin S, Hill WAG, Morse KL, Salehani D, Arreaza G, Omeir RL and Makriyannis A (1997) Fatty acid sulfonyl fluorides inhibit anandamide metabolism and bind to the cannabinoid receptor. Biochem Biophys Res Commun 231: 217-221.
10. Deutsch DG, Omeir R, Arreaza G, Salehani D, Prestwich GD, Huang Z and Howlett A (1997a) Methyl arachidonyl fluorophosphate: A potent irreversible inhibitor of anandamide amidase. Biochem Pharmacol 53:255-260.
11. Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, Gibson D, Mandelbaum A, Etinger A and Mechoulam R (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258:1946-1949.
12. Ermer A, Baumann H, Stuede G, Peters K, Fittkau S, Dolaschka P and Genov NC (1990) Peptide diazomethyl ketones are inhibitors of subtilisin-type serine proteases. J Enzym Inhib 4:35-42.
13. Felder CC, Briley EM, Axelrod J, Simpson JT, Mackie K and Devane WA (1993) Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA 90:7656-7660.
14. Fride E and Mechoulam R (1993) Pharmacological activity of the cannabinoid receptor agonist, anandamide, a brain constituent. Eur J Pharmacol 231:313-314.
15. Hillard CJ, Wilkison DM, Edgemond WS and Campbell WB (1995) Characterization of the kinetics and distribution of N-arachidonylethanolamine (anandamide) hydrolysis by rat brain. Biochim Biophys Acta 1257:249-256.
16. Hillard CJ, Edgemond WS and Campbell WB (1995a) Characterization of ligand binding to the cannabinoid receptor of rat brain membranes using a novel method: application to anandamide. J Neurochem 64:677-683.
17. Koutek B, Prestwich GD, Howlett AC, Chin SA, Salehan D, Akhavan N and Deutsch DG (1994) Inhibitors of arachidonyl ethanolamide hydrolysis. J Biol Chem 269: 22937-22940.
18. Kraut J (1977) Serine proteases: structure and mechanism of catalysis. Annu Rev Biochem 46:331-358.
19. Lang W, Qin C, Hill WAG, Lin S, Khanolkar AD and Makriyannis A (1996) High performance liquid Chromatographic determination of anandamide amidase activity in rat brain microsomes. Anal Biochem 238:40-45.
20. Mackie K, Devane WA and Hille B (1993) Anandamide, an endogenous cannabinoid, inhibits calcium currents as a partial agonist in N18 neuroblastoma cells. Mol Pharmacol 44:498-503.
21. Maurelli S, Bisogno T, De Petrocellis L, Di Luccia A, Marino G and Di Marzo V (1995) Two novel classes of neuroactive fatty acid amides are substrates for mouse neuroblastoma 'anandamide amidohydrolase.' FEBS Lett 377:82-86.
22. 14C] as a substrate for anandamide amidase. Life Sci 56:1999-2006.
23. Patterson JE, Ollmann IR, Cravatt BF, Boger DL, Wong C-H and Lerner RA (1996) Inhibition of oleamide hydrolase catalyzed hydrolysis of the endogenous sleep-inducing lipid cis-9-octadecenamide. J Am Chem Soc 118:5938-5945.
24. Rawlings ND and Barrett AJ (1994) Families of serine peptidases. Methods Enzymol 244:19-61.
25. Schmid PC, Zuzarte-Augustin ML and Schmid (1985) Properties of rat liver N-acylethanolamine amidohydrolase. J Biol Chem 260:14145-14149.
26. Shaw E (1994) Peptidyl diazomethanes as inhibitors of cysteine and serine proteinases. Methods Enzymol 244:649-656.
27. Stone SR, Rennex D, Wikstrom P, Shaw E and Hofsteenge J (1992) Peptidyldiazomethanes. A novel mechanism of interaction with prolyl endopeptidase. Biochem J 283:871-876.
28. Ueda N, Kurahashi Y, Yamamoto S and Tokunaga T (1995) Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. J Biol Chem 270:23823-23827.
29. Vogel Z, Barg J, Levy R, Saya D, Heldman E and Mechoulam R (1993) Anandamide, a brain endogenous compound, interacts specifically with cannabinoid receptors and inhibits adenylate cyclase. J Neurochem 61:352-355.
30. Watanabe H, Green GD and Shaw E (1979) A comparison of the behavior of chymotrypsin and cathepsin B towards peptidyl diazomethyl ketones. Biochem Biophys Res Commun 89:1354-1360.