Exploration of biologically relevant conformations of anandamide, 2- arachidonylglycerol, and their analogues using conformational memories

Journal of Medicinal Chemistry

Volumn 41, Issue 24, 1998, Pages 4861-4872

  Barnett Norris, Judy ^a   Guarnieri, Frank ^b   Hurst, Dow P ^a   Reggio, Patricia H ^a  

^a KENNESAW STATE UNIVERSITY   (United States)

^b MOUNT SINAI SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ARACHIDONOYLGLYCEROL; ANANDAMIDE; ARACHIDONIC ACID; CANNABINOID; CANNABINOID RECEPTOR; N (2 HYDROXYETHYL)PROSTAGLANDIN BETA2 ETHANOLAMIDE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; DRUG CONFORMATION; DRUG STRUCTURE; ENTHALPY; MOLECULAR DYNAMICS; RECEPTOR AFFINITY; SOLVATION; X RAY ANALYSIS; X RAY CRYSTALLOGRAPHY;

ARACHIDONIC ACIDS; CANNABINOIDS; CHLOROFORM; GLYCERIDES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; POLYUNSATURATED ALKAMIDES; RECEPTORS, CANNABINOID; RECEPTORS, DRUG; VACUUM; WATER;

EID: 0032548089     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9803471     Document Type: Article

References (35)

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 Cannabinoid Receptor. Science 1992, 258, 1946-1949.
2. 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.
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. Showalter, V. M.; Compton, D. R.; Martin, B. R.; Abood, M. E. Evaluation of Binding in a Transfected Cell Line Expressing a Peripheral Cannabinoid Receptor (CB2): Identification of Cannabinoid Receptor Subtype Selective Ligands. J. Pharmacol. Exp. Ther. 1996, 278, 989-999.
5. Hillard, C. J.; Edgemond, W. S.; Jarrahian, A.; Campbell, W. B. Accumulation of N-Arachidonylethanolamide (Anandamide) into Cerebellar Granule Cells Occurs via Facilitated Diffusion. J. Neurochem. 1997, 69, 631-638.
6. Beltramo, M.; Stella, N.; Calignano, A.; Lin, S. Y.; Makriyannis, A.; Piomelli, D. Functional Role of High-Affinity Anandamide Transport, as Revealed by Selective Inhibition. Science 1997, 277, 1094-1097.
7. Desarnaud, F.; Cadas, H.; Piomelli, D. Anandamide Amidohydrolase Activity in Rat Brain Microsomes. J. Biol. Chem. 1995, 270, 6030-6035.
8. 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.
9. Karplus, M.; Petsko, G. A. Molecular Dynamics Simulations in Biology. Nature 1990, 347, 631-639.
10. Thomas, B. F.; Adams, 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.
11. Guarnieri, F.; Weinstein, H. Conformational Memories and the Exploration of Biologically Relevant Peptide Conformations: An Illustration for the Gonadotropin-Releasing Hormone. J. Am. Chem. Soc. 1996, 118, 5580-5589.
12. 4. J. Comput. Chem. 1995, 16, 648-653.
13. Metropolis, N.; Rosenbluth, A. W.; Rosenbluth, M. N.; Teller, A. H.; Teller, E. Equation of State Calculations by Fast Computing Machines. J. Chem. Phys. 1953, 21, 1087-1092.
14. Kirkpatrick, S.; Gelatt, C. D.; Veechi, M. P. Optimization by Simulated Annealing. Science 1983, 220, 671-680.
15. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caulfield, C.; Chang, G.; Hendrickson, T.; Still, W. C. MacroModel-An Integrated Software System for Modeling Organic and Biorganic Molecules Using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440-467.
16. Rich, M. R. Conformational Analysis of Arachidonic and Related Fatty Acids Using Molecular Dynamics Simulations. Biochim. Biophys. Acta 1993, 1178, 87-96.
17. Ernst, J.; Sheldrick, W. S.; Fuhrhop, J.-H. The Structures of the Essential Unsaturated Fatty Acids. Crystal Structure of Linoleic Acid and Evidence for the Crystal Structures of α-Linolenic and Arachidonic Acid. Z. Naturforsch. 1979, 34b, 706-711.
18. Shenkin, P. S.; McDonald, D. Q. Cluster Analysis of Molecular Conformations. J. Comput. Chem. 1994, 15, 899-916.
19. Applegate, K. R.; Glomset, J. A. Computer-based Modeling of the Conformation and Packing Properties of Docosahexaenoic Acid. J. Lipid Res. 1986, 27, 658-680.
20. Corey, E. J.; Iguchi, S.; Albright, J. O.; De, B. Studies on the Con formational Mobility of Arachidonic Acid. Facile Macrolactonization of 20-Hydroxyarachidonic Acid. Tetrahedron Lett. 1983, 24, 37-40.
21. Corey, E. J.; Niwa, H.; Falck, J. R. Selective Epoxidation of Eicosa-cis-5,8,11,14-tetraenoic (Arachidonic) Acid and Eicosacis-8,11,14-trienoic Acid. J. Am. Chem. Soc. 1979, 101, 1586-1587.
22. LaLonde, J. M.; Levenson, M. A.; Roe, J. J.; Bernlohr, D. A.; Banaszak, L. J. Adipocyte Lipid-binding Protein Complexed with Arachidonic Acid. J. Biol. Chem. 1994, 269, 25339-25347.
23. Rabinovich, A. L.; Ripatti, P. O. On the Conformational, Physical Properties and Functions of Polyunsaturated Acyl Chains. Biochim. Biophys. Acta 1991, 1085, 53-56.
24. Leach, A. R.; Prout, K. Automated Conformational Analysis: Directed Conformational Search Using the A* Algorithim. J. Comput. Chem. 1990, 11, 1193-1205.
25. Wilson, S. R.; Cui, W.; Moskowitz, J. W.; Schmidt, K. E. Conformational Analysis of Flexible Molecules: Location of the Global Minimum Conformation by the Simulated Annealing Methodology. Tetrahedron Lett. 1988, 29, 4373-4376.
26. Bonzom, P. M.; Zloh, M.; Reid, R. E.; Gibbons, W. A. Lipid Mimetics: The Design and Properties of Conformationally-Restricted Arachidonic Acid Lipidic and Peptidic Analogues. Biochem. Soc. Trans. 1997, 25, 26S.
27. Lopez, M.; Lozano, J. J.; Ruiz, J.; Pouplana, R. Conformational Search and Transitional States Study of Arachidonic Acid Using Molecular Dynamics and AM1 Semiempirical Calculations. In Trends in QSAR and Molecular Modeling 92: Proceedings of the 9th European Symposium on Structure-Activity Relationships: QSAR and Molecular Modeling; Leiden, The Netherlands, 1993; pp 429-430.
28. Stella, N.; Schweitzer, P.; Piomelli, D. A Second Endogenous Cannabinoid that Modulates Long-term Potentiation. Nature 1997, 388, 773-778.
29. Goparaju, S. K.; Ueda, N.; Yamaguchi, H.; Yamamoto, S. Anandamide Amidohydrolase Reacting with 2-Arachidonoylglycerol, Another Cannabinoid Receptor Ligand. FEBS Lett. 1998, 422, 69-73.
30. 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.
31. 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.
32. Seltzman, H. H.; Fleming, D. N.; Thomas, B. F.; Gilliam, A. F.; McCallion, D. S.; Pertwee, R. G.; Compton, D. R.; Martin, B. R. Synthesis and Pharmacological Comparison of Dimethylheptyl and Pentyl Analogues of Anandamide. J. Med. Chem. 1997, 40, 3626-3634.
33. Ryan, W. J.; Banner, W. K.; Wiley, J. L.; Martin, B. R.; Razdan, R. K. Potent Anandamide Analogues: The Effect of Changing the Length and Branching of the End Pentyl Chain. J. Med. Chem. 1997, 40, 3617-3625.
34. Compton, D. R.; Rice, K. C.; De Costa, B. K.; Razdan, R. K.; Melvin, L. S.; Johnson, M. R.; Martin, B. R. Cannabinoid Structure-Activity Relationships: Correlation of Receptor Binding and in Vivo Activities. J. Pharmacol. Exp. Ther. 1993, 265, 218-226.
35. 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.