Novel analogues of arachidonylethanolamide (anandamide): Affinities for the CB1 and CB2 cannabinoid receptors and metabolic stability

Journal of Medicinal Chemistry

Volumn 41, Issue 27, 1998, Pages 5353-5361

  Lin, Sonyuan ^a   Khanolkar, Atmaram D ^a   Fan, Pusheng ^b   Goutopoulos, Andreas ^a   Qin, Ce ^a   Papahadjis, Demetris ^b   Makriyannis, Alexandras ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b INSTITUTE OF BIOLOGY   (Greece)

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; ANANDAMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID RECEPTOR; CANNABINOID RECEPTOR AGONIST; N PROPARGYLARACHIDONAMIDE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; DRUG BRAIN LEVEL; DRUG RECEPTOR BINDING; DRUG STABILITY; ENZYME STABILITY; MOLECULAR INTERACTION; MOUSE; NONHUMAN; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

AMIDOHYDROLASES; ANIMALS; ARACHIDONIC ACIDS; BRAIN; CANNABINOIDS; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); MICE; POLYUNSATURATED ALKAMIDES; RADIOLIGAND ASSAY; RATS; RECEPTOR, CANNABINOID, CB2; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; SERINE PROTEINASE INHIBITORS; SPLEEN; STRUCTURE-ACTIVITY RELATIONSHIP; TOSYL COMPOUNDS;

EID: 0032585499     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970257g     Document Type: Article

References (40)

1. Devane, W. A.; Dysarz, F. A.; Johnson, R. M.; Melvin, L. S.; Howlett, A. C. Détermination and Characterization of a Cannabinoid Receptor in Rat Brain. Mol. Pharmacol. 1988, 34, 605-613.
2. Howlett, A. C.; Qualy, J. M.; Khachatrian, L. L. Involvement of G; in thé Inhibition of Adenylate Cyclase by Cannabimimetic Drugs. Mol. Pharmacol. 1986, 29, 307-313.
3. Herkenham, M.; Lynn, A. B.; Johnson, M. R.; Melvin, L. S.; Decosta, B. R.; Rice, K. C. Characterization and Localization of Cannabinoid Receptors in Rat Brain: a Quantitative in vitro Autoradiographic Study. J. Neurosci. 1991, 11, 563-583.
4. Munro, S.; Thomas, K. L.; Abu-Shaar, M. Molecular Characterization of a Peripheral Receptor for Cannabinoids. Nature 1993, 365, 61-65.
5. Matsudà, L. A.; Lolait, S. J.; Brownstein, M. J.; Young, A. C.; Bonner, T. I. Structure of a Cannabinoid Receptor and Functional Expression of the Cloned cDNA. Nature 1990, 346, 561-564.
6. Lynn, A. B.; Herkenham, M. Localization of Cannabinoid Receptors and Nonsaturable High-Density Cannabinoid Binding Sites in Peripheral Tissues of the Rat: Implications for ReceptorMediated Immune Modulation by Cannabinoids. J. Pharmacol. Exp. Ther. 1994, 268, 1612-1623.
7. Devane, W. A.; Hanus, L.; Breuer, A.; Pertwee, R. G.; Stevenson, L. A.; Griffin, G.; Gibson, D.; Mandèlbaum, A.; Etinger, A.; Mechoulam, R. Isolation and Structure of a Brain Constituent That Binds to the Cannabinoid Receptor. Science 1992, 258, 1946-1949.
8. 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.
9. Fride, E.; Mechoulam, R. Pharmacological Activity of the Cannabinoid Receptor Agonist, Anandamide, a Brain Constituent. Ear. J. Pharmacol. 1993, 231, 313-314.
10. 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.
11. Mackie, K.; Devane, W. A.; Hille, B. Anandamide, an Endogenous Cannabinoid, Inhibits Calcium Currents as a Partial Agonist in N18 Neuroblastoma Cells. Mol. Pharmacol. 1993, 44, 498-503.
12. Pertwee, R. G.; Stevenson, L. A.; Elrick, D. B.; Mechoulam, R.; Corbett, A. D. Inhibitory Effects of Certain Enantiomeric Cannabinoids in the Mouse Vas Deferens and the Myenteric Plexus Preparation of Guinea-pig Small Intestine. Br. J. Pharmacol. 1992, 705, 980-984.
13. Pertwee, R. G.; Fernando, S. R.; Griffin, G.; Abadji, V.; Makriyannis, A. Effect of Phenylmethylsulfonyl Fluoride on the Potency of Anandamide as an Inhibitor of Electrically Evoked Contractions in Two Isolated Tissue Preparations. Eur. J. Pharmacol. 1995, 272, 73-78.
14. Crawley, J. N.; Corwin, R. L.; Robinson, J.; 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.
15. 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.
16. Pertwee, R. G.; Stevenson, L. A. Effect of Pretreatment with Delta-9-Tetrahydro-Cannabinol on the Ability of Certain Cannabimimetic Agents to Induce Hypothermia in Mice. In Temperature Regulation. Recent Physiological and Pharmacological Advances; Milton, A. S., Ed.; Birkhäuser: Basal, 1994; pp 177-182.
17. Welch, S. P.; Dunlow, L. D.; Patrick, G. S.; Razdan, R. K. Characterization of Anandamide- and FluoroanandamideInduced Antinociception and Cross-Tolerance to A9-THC after Intrathecal Administration to Mice: Blockade of A9-THCInduced Antinociception. J. Pharmacol. Exp. Ther. 1995, 273, 1235-1244.
18. Romero, J.; Garcia-Palomero, E.; Lin, S.; Ramos, J. A.; Makriyannis, A.; Fernandez-Ruiz, J. J. Extrapyramidal Effects of Methanandamide, an Analogue of Anadamide, the Endogenous CB1 Receptor Ligand. Life Sci. 1996, 58, 1249-1257.
19. Jarbe, T. U. C.; Sheppard, R.; Lamb, R. J.; Lin, S.; Goutopolos, A.; Makriyannis, A. Effects of Delta-9-THC and (fl)-Methanandamide on Open-Field Behaviors in Rats. Behav. Pharmacol. 1997, in press.
20. Deutsch, D. G.; Chin, S. A. Enzymatic Synthesis and Degradation of Anandamide, a Cannabinoid Receptor Agonist. Biochem, Pharmacol. 1993, 46, 791-796.
21. Desarnaud, F.; Cadas, H.; Piomelli, D. Anandamide Amidohydrolase Activity in Rat Brain Microsomes: Identification and Partial Characterization. J. Biol. Chem. 1995, 270, 6030-6035.
22. 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. FEES Lett. 1995, 377, 82-86.
23. Lang, W.; Qin, C.; Hill, W. A. G.; Lin, S.; Khanolkar, A. D.; Makriyannis, A. High-Performance Liquid Chromatographie Determination of Anandamide Amidase Activity in Rat Brain Microsomes. Anal. Biochem. 1996, 238, 40-45.
24. 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.
25. 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.
26. Pinto, J. C.; Potie, F.; Rice, K. C.; Boring, D.; Johnson, M. R.; Evans, D. M.; Wilken, G. H.; Cantrell, C. H.; Howlett, A. C. Cannabinoid Receptor Binding and Agonist Activity of Amides and Esters of Arachidonic Acid. Mol. Pharmacol. 1994, 46, 516-522.
27. 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.
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, the Endogenous Cannabinoid Ligand. J. Med. Chem. 1996, 39, 4515-4519.
29. Abadji, V.; Lin, S.; Taha, G.; Griffin, G.; Stevenson, L. A.; Pertwee, R. G.; Makriyannis, A. (fl)-Methanandamide: A Chiral Novel Anandamide Possessing Higher Potency and Metabolic Stability. J. Med. Chem. 1994, 37, 1889-1893.
30. Hill, W. A. G.; Morse, K. L.; Colasanto, J.; Khanolkar, A. D.; Makriyannis, A. Structure Activity Relationships between Classical Cannabinoids on the Central (CB1) and the Peripheral (CB2) Cannabinoid Receptors. Unpublished results.
31. Corey, E. J.; Cashman, J. R.; Kantner, S. S.; Wright, S. W. Rationally Designed, Potent Competitive Inhibitors of Leukotriene Biosynthesis. J. Am. Chem. Soc. 1984, 106, 1503-1504.
32. Shimizu, M.; Nakahara, Y.; Yoshioka, H. Chemoselective Fluorination for Primary Alcohols. Tetrahedron Lett. 1985, 26, 4207-4210.
33. Charalambous, A.; Guo, Y.; Houston, D. B.; Howlett, A. C.; Compton, D. R.; Martin, B. R.; Makriyannis, A. 5'-azido-A8THC: A Novel Photoaffmity Label for the Cannabinoid Receptor. J. Med. Chem. 1992, 35, 3076-3079.
34. Cheng, Y. C.; Prusoff, W. H. Relationship Between the Inhibition Constant CKi) and the Concentration of Inhibitor Which Causes 50% Inhibition (ICso) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3102.
35. Thomas, B. F.; Adam, I. B.; Mascarella, S. W.; Martin, B. R.; Razdan, R. K. Structure-Activity Analysis of Anandamide Analogues: Relationship to a Cannabinoid Pharmacophore. J. 'Med. Chem. 1996, 39, 471-479.
36. Sheskin, T.; Hanus, L.; Slager, J.; Vogel, Z.; Mechoulam, R. Structural Requirements for Binding of Anandamide-Type Compounds to the Brain Cannabinoid Receptor. J. Med. Chem. 1997, 40, 659-667.
37. Dodd, P. R.; Hardy, J. A.; Oakley, A. E.; Edwardson, J. A.; Perry, E. K.; Delaunoy, J.-P. A Rapid Method for Preparing Synaptosomes: Comparison with Alternative Procedures. Brain Res. 1981, 226, 107-118.
38. Selley, D. E.; Stark, S.; Sim, L. J.; Childers, S. R. Cannabinoid Receptor Stimulation of Guanosine-S'-O-O-pSJthkOtriphosphate Binding in Rat Brain Membranes. Life Sci. 1996, 59, 659-668.
39. Hoshohata, K.; Quock, R. M.; Hoshohata, Y.; Burkey, T. H.; Makriyannis, A.; Consroe, P.; Roeske, W. R.; Yamamura, H. I. AM630 is a Competitive Cannabinoid Receptor Antagonist in the Guinea Pig Brain. Life Sci. 1997, 61, 115-118.
40. Markwell, M. A. K; Haas, S. M.; Beiher, 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.