Substrate specificity and stereoselectivity of rat brain microsomal anandamide amidohydrolase

Journal of Medicinal Chemistry

Volumn 42, Issue 5, 1999, Pages 896-902

  Lang, Wensheng ^a   Qin, Ce ^a   Lin, Sonyuan ^a   Khanolkar, Atmaram D ^a   Goutopoulos, Andreas ^a   Fan, Pusheng ^a   Abouzid, Khaled ^a   Meng, Zhaoxing ^a   Biegel, Diane ^b   Makriyannis, Alexandras ^a,b  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b UNIVERSITY OF CONNECTICUT HEALTH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; 5 (1,1 DIMETHYLHEPTYL) 2 (3 HYDROXY 7 HYDROXYMETHYLDECAHYDRO 1 NAPHTHYL)PHENOL; AMIDASE; ANANDAMIDE; RIMONABANT; TETRAHYDROCANNABINOL;

ANIMAL TISSUE; ARTICLE; DRUG EFFECT; DRUG HYDROLYSIS; DRUG MECHANISM; DRUG METABOLISM; DRUG STABILITY; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME SPECIFICITY; KINETICS; NEUROTRANSMISSION; NONHUMAN; RAT; RECEPTOR AFFINITY; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

AMIDOHYDROLASES; ANIMALS; ARACHIDONIC ACIDS; BRAIN; CANNABINOIDS; HYDROLYSIS; KINETICS; LIGANDS; MICROSOMES; POLYUNSATURATED ALKAMIDES; RATS; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 0033545637     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980461j     Document Type: Article

References (40)

1. Devane, W. A.; Hanus, L.; Breuer, A.; Pertwee, R. G.; Stevenson, L. A.; Griffin, G.; Gibson, D.; Mandelbaum, A.; Etinger, A.; Mechoulam, R. Isolation and Structure of a Brain Constituent That Binds to the Brain Cannabinoid Receptor. Science 1992, 258, 1946-1949.
2. Johnson, D. E.; Heald, S. L.; Dally, R. D.; Janis, R. A. Isolation, Identification, and Synthesis of an Endogenous Arachidonic Amide that Inhibits Calcium Channel Antagonist 1,4-Dihydropyridine Binding. Prostaglandins, Leukotrienes, Essent. Fatty Acids 1993, 48, 429-437.
3. Felder, C. C.; Briley, E. M.; Axelrod, J.; Simpson, J. T.; Mackie, K.; Devane, W. A. Anandamide, an Endogenous Cannabimimetic Eicosanoid, Binds to the Cloned Human Cannabinoid Receptor and Stimulates Receptor-Mediated Signal Transduction. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 7656-7660.
4. Childers, S. R.; Sexton, T.; Roy, M. B. Effects of Anandamide on Cannabinoid Receptors in Rat Brain Microsomes. Biochem. Pharmacol. 1994, 47, 711-715.
5. Vogel, Z.; Barg, J.; Levy, R.; Saya, D.; Heldman, E.; Mechoulam, R. Anandamide, a Brain Endogenous Compound Interacts Specifically with Cannabinoid Receptors and Inhibits Adenylate Cyclase. J. Neurochem. 1993, 61, 352-355.
6. Mackie, K.; Devane, W. A.; Hille, B. Anandamide, an Endogenous Cannabinoid Inhibits Calcium Currents as Partial Agonist in N18 Neuroblastoma Cells. Mol. Pharmacol. 1993, 44, 498-503.
7. Fride, E.; Mechoulam, R. Pharmacological Activity of the Cannabinoid Receptor Agonist, Anandamide, a Brain Constituent. Eur. J. Pharmacol. 1993, 231, 313-314.
8. Crawley, J. N.; Corwin, R. L.; Robinson, J. K.; Felder, C. C.; Devane, W. A.; Axelrod, J. Anandamide, an Endogenous Ligand of the Cannabinoid Receptor, Induces Hypomotility and Hypothermia In Vivo in Rodents. Pharmacol. Biochem. Behav. 1993, 46, 967-972.
9. Smith, P. B.; Compton, D. R.; Welch, S. P.; Razdan, R. K.; Mechoulam, R.; Martin, B. R. The Pharmacological Activity of Anandamide, a Putative Endogenous Cannabinoid, in Mice. J. Pharmacol. Exp. Ther. 1994, 270, 219-227.
10. (a) Adams, I. B.; Ryan, W.; Singer, M.; Thomas, B. F.; Compton, D. R.; Razdan, R. K.; Martin, B. R. Evaluation of Cannabinoid Receptor Binding and In Vivo Activities for Anandamide Analogues. J. Pharmacol. Exp. Ther. 1995, 273, 1172-1181.
11. (b) Adams, I. B.; Ryan, W.; Singer, M.; Razdan, R. K.; Compton, D. R.; Martin, B. R. Pharmacological and Behavioral Evaluation of Alkylated Anandamide Analogues. Life Sci. 1995, 56, 2041-2048.
12. Hanus, L.; Gopher, A.; Almog, S.; Mechoulam, R. Two New Unsaturated Fatty Acid Ethanolamides in Brain That Bind to the Cannabinoid Receptor. J. Med. Chem. 1993, 36, 3032-3034.
13. Deutsch, D. G.; Chin, S. A. Enzymatic Synthesis and Degradation of Anandamide, a Cannabinoid Receptor Agonist. Biochem. Pharmacol. 1993, 46, 791-796.
14. (a) Di Marzo, P.; Fontana, A.; Cadas, H.; Schinelli, S.; Cimino, G.; Schwartz, J.; Piomelli, D. Formation and Inactivation of Endogenous Cannabinoid Anandamide in Central Neurons Nature 1994, 372, 686-691.
15. (b) Desarnaud, F.; Cadas, H.; Piomelli, D. Anandamide Amidohydrolase Activity in Rat Brain Microsomes. Identification and Partial Characterization. J. Biol. Chem. 1995, 270, 6030-6035.
16. Qin, C.; Hill, W. A. G.; Goutopoulos, A.; Lin, S.; Makriyannis, A. Purification of Anandamide Amidase by Affinity Chromatography. Proceeding of 1997 ICRS Meeting, Stone Mountain, GA.
17. Ueda, N.; Kurahashi, Y.; Yamamoto, S.; Tokunaga, T. Partial Purification and Characterization of the Porcine Brain Enzyme Hydrolyzing and Synthesizing Anandamide. J. Biol. Chem. 1995, 270, 23823-23827.
18. Maurelli, S.; Bisogno, T.; De Petrocellis, L.; Di Luccia, A.; Marino, G.; Di Marzo, V. Two Novel Classes of Neuroactive Fatty Acid Amides are Substrates for Mouse Neuroblastoma 'Anandamide Amidohydrolase'. FEBS Lett. 1995, 377, 82-86.
19. Deutsch, D. G.; Lin, S.; Hill, W. A. G.; Morse, K. L.; Salehani, D.; Arreaza, G.; Omeir, R. L.; Makriyannis, A. Fatty Acid Sulfonylfluorides Inhibit Anandamide Metabolism and Bind to the Cannabinoid Receptor. Biochem. Biophys. Res. Commun. 1997, 231, 217-221.
20. (a) Koutek, B.; Prestwich, G. D.; Hewlett, A. C.; Chin, S. A.; Salehani, D.; Akhavan, N.; Deutsch, D. G. Inhibitors of Arachidonylethanolamide Hydrolysis. J. Biol. Chem. 1994, 269, 22937-22940.
21. (b) Deutsch, D. G.; Omeir, R.; Arreaza, G.; Salehani, D.; Prestwich, G. D.; Huang, Z.; Howlett, A. Methyl Arachidonyl Fluorophosphonate: A Potent Irreversible Inhibitor of Anandamide Amidase. Biochem. Pharmacol. 1997, 53, 255-260.
22. Beltramo, M.; DiTomaso, E.; Piomelli, D. Inhibition of Anandamide Hydrolysis in Rat Brain Tissue by (E)-6-(Bromomethylene)-tetrahydro-3-(1-naphthalenyl)-2H-pyran-2-one. FEBS Lett. 1997, 403, 263-267.
23. De Petrocellis, L.; Melck, D.; Ueda, N.; Maurelli, S.; Kurahashi, Y.; Yamamoto, S.; Marino, G.; Di Marzo, V. Novel Inhibitors of Brain, Neuronal, and Basophilic Anandamide Amidohydrolase. Biochem. Biophys. Res. Commun. 1997, 231, 82-88.
24. Deutsch, D. G.; Makriyannis, A. Inhibitors of Anandamide Breakdown. NIDA Res. Monogr. 173 1997, 65-84.
25. Cravatt, B. F.; Giang, D. K.; Mayfield, S. P.; Boger, D. L.; Lerner, R. A.; Gilula, N. B. Molecular Characterization of an Enzyme that Degrades Neuromodulatory Fatty-Acid Amides. Nature 1996, 384, 83-87.
26. Beltramo, M.; Stella, N.; Calignano, A.; Lin, S.; Makriyannis, A.; Piomelli, D. Functional Role of High-Affinity Anandamide Transport, as Revealed by Selective Inhibition. Science 1997, 277, 1094-1097.
27. Abadji, V.; Lin, S.; Taha, G.; Griffin, G.; Stevenson, L. A.; Pertwee, R. G.; Makriyannis, A. (R)-Methanandamide: A Chiral Novel Anandamide Possessing Higher Potency and Metabolic Stability. J. Med. Chem. 1994, 37, 1889-1893.
28. Khanolkar, A. D.; Abadji, V.; Lin, S.; Hill, W. A. G.; Taha, G.; Abouzid, K.; Meng, Z.; Fan, P.; Makriyannis, A. Headgroup Analogues of Arachidonylethanolamide, an Endogenous Cannabinoid Ligand. J. Med. Chem. 1996, 39, 4515-4519.
29. Lin, S.; Khanolkar, A. D.; Fan, P.; Goutopoulos, A.; Qin, C.; Papahadjis, D.; Makriyannis, A. Novel Anandamide Analogues. Affinities for the CB1 and CB2 Cannabinoid Receptors and Biochemical Stability. J. Med. Chem. 1998, 41, 5353-5361.
30. Lang, W.; Qin, C.; Hill, W. A. G.; Lin, S.; Khanolkar, A.; Makriyannis, A. High-Performance Liquid Chromatographic Determination of Anandamide Amidase Activity in Rat Brain Microsomes. Anal. Biochem. 1996, 238, 40-45.
31. Qin, C.; Lin, S.; Lang, W.; Goutopoulos, A.; Pavlopoulos, S.; Mauri, F.; Makriyannis, A. Determination of Anandamide Amidase Activity Using UV Active Amine Derivatives and Reverse-Phase High-Performance Liquid Chromatography. Anal. Biochem. 1998, 261, 8-15.
32. Takakuwa, Y.; Nishino, H.; Ishibe, Y.; Ishibashi, T. Properties and Kinetics of Membrane-Bound Enzymes When Both the Enzyme and Substrates are Components of the same Microsomal Membrane. Studies on Lathosterol 5-Desaturase. J. Biol. Chem. 1994, 269, 27889-27893.
33. Hillard, C. J.; Wilkison, D. M.; Edgemond, W. S.; Campbell, W. B. Characterization of the Kinetics and Distribution of N-Arachidonylethanolamine (Anandamide) Hydrolysis by Rat Brain. Biochim. Biophys. Acta 1995, 1257, 249-256.
34. Edgemond, W. S.; Campbell, W. B.; Hillard, C. J. The Binding of Novel Phenolic Derivatives of Anandamide to Rat Brain Cannabinoid Receptors. Prostaglandins Leukotrienes Essent. Fatty Acids 1995, 52, 83-86.
35. (a) Stella, N.; Schweitzer, P.; Piomelli, D. A Second Endogenous Cannabinoid That Modulates Long-Term Potentiation. Nature 1997, 388, 773-778.
36. (b) Mechoulam, R.; Ben-Shabat, S.; Hanus, L.; Ligumsky, M.; Kaminski, N. E.; Schatz, A. R.; Gopher, A.; Almog, S.; Martin, B. R.; Compton, D. R.; Pertwee, R. G.; Griffin, G.; Bayewitch, M.; Barg, J.; Vogel, Z. Identification of an Endogenous 2-Monoglyceride, Present in Canine Gut, That Binds to Cannabinoid Receptors. Biochem. Pharmacol. 1995, 50, 83-90.
37. Goparaju, S. K.; Ueda, N.; Yamamguchi, H.; Yamamoto, S. Anandamide Amidohydrolase Reacting with 2-Arachidonylglycerol, Another Cannabinoid Receptor Ligand. FEBS Lett. 1998, 422, 69-73.
38. Watanabe, K.; Kayano, Y.; Matsunaga, T.; Yamamoto, I.; Yoshimura, H. Inhibition of Anandamide Amidase Activity in Mouse Brain Microsomes by Cannabinoids. Biol. Pharm. Bull. 1996, 19, 1109-1111.
39. Rich, M. R. Conformational Analysis of Arachidonic and Related Fatty Acids Using Molecular Dynamics Simulations. Biochim. Biophys. Acta 1993, 1178, 87-96.
40. Markwell, M. A. K.; Haas, S. M.; Bieber, L. L.; Tolbert, N. E. A Modification of the Lowry Procedure to Simplify Protein Determination in Membrane and Lipoprotein Samples. Anal. Biochem. 1978, 87, 206-210.