Synthesis and evaluation of N-[11C]methylated analogues of epibatidine as tracers for positron emission tomographic studies of nicotinic acetylcholine receptors

Journal of Medicinal Chemistry

Volumn 41, Issue 22, 1998, Pages 4199-4206

  Horti, Andrew G ^a,b   Scheffel, Ursula ^b   Kimes, Alane S ^a   Musachio, John L ^b   Ravert, Hayden T ^b   Mathews, William B ^b   Zhan, Yougen ^b   Finley, Paige A ^b   London, Edythe D ^a   Dannals, Robert F ^b  

^a NATIONAL INSTITUTE ON DRUG ABUSE   (United States)

^b DEPARTMENT OF PATHOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 11; EPIBATIDINE; FLUORINE 18; HALOGEN; METHYL GROUP; METHYL IODIDE; NICOTINIC RECEPTOR; TRACER; TRITIUM;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CEREBELLUM; CONTROLLED STUDY; DRUG DISTRIBUTION; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SYNTHESIS; DRUG UPTAKE; INTRAVENOUS DRUG ADMINISTRATION; ISOTOPE LABELING; LD 50; LIPOPHILICITY; MALE; METHYLATION; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RECEPTOR AFFINITY; SUPERIOR COLLICULUS; THALAMUS;

ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; BRAIN; CARBON RADIOISOTOPES; INJECTIONS, INTRAVENOUS; LETHAL DOSE 50; MALE; MICE; PYRIDINES; RADIOPHARMACEUTICALS; RECEPTORS, NICOTINIC; TISSUE DISTRIBUTION; TOMOGRAPHY, EMISSION-COMPUTED;

EID: 14444267817     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980233p     Document Type: Article

References (42)

1. Decker, M. W.; Brioni, J. D.; Bannon, A. W.; Arneric, S. P. Diversity Of Neuronal Nicotinic Acetylcholine Receptors; Lessons from Behavior and Implications for CNS Therapeutics. Life Sci. 1995, 56, 545-570.
2. Flicker, C.; Dean, R. L.; Watkins, D. L.; Fisher, S. K.; Bartus, R. T. Behavioral and Neurochemical Effects Following Neurotoxic Lesions of a Major Cholinergic Input to the Cerebral Cortex in the Rat. Pharmacol. Biochem. Behav. 1983, 18, 973-981.
3. Irle, E.; Markowitsch, H. J. Basal Forebrain-Lesioned Monkeys are Severely Impaired in Tasks of Association and Recognition Memory. Ann. Neurol. 1987, 22, 735-743.
4. Levin, E. D.; Rose, J. E. Acute and Chronic Nicotinic Interactions with Dopamine Systems and Working Memory Performance. Ann. N. Y. Acad. Sci. 1995, 757, 245-252.
5. Pert, A. Cholinergic and Catecholaminergic Modulation of Nociceptive Reactions. Interactions with Opiates. In Pain and Headache, Neurotransmitters and Pain Control; Akil, H., Lewis, J. W., Eds.; Karger: Basel, 1987; pp 1-63.
6. Whitehouse, P. J.; Martino, A. M.; Antuono, P. G.; Lowenstein, P. R.; Coyle, J. T.; Price, D. L.; Kellar, K. J. Nicotinic Acetylcholine Binding Sites in Alzheimer's Disease. Brain Res. 1986, 377, 146-151.
7. London, E. D.; Ball, M. J.; Waller, S. B. Nicotinic Binding Sites in Cerebral Cortex and Hippocampus in Alzheimer's Dementia. Neurochem. Res. 1989, 14, 745-750.
8. 3H]Nicotine Binding Sites in Human Brain. J. Neurochem. 1988, 50, 1243-1247.
9. Nybäck, H.; Nordberg, A.; Långström, B.; Halldin, C.; Hartvig, P.; Åhlin, A.; Swahn, C. G.; Sedvall, G. Attempts to Visualize Nicotinic Receptors in the Brain of Monkey and Man by Positron Emission Tomography. Prog. Brain Res. 1989, 79, 313-319.
10. Mazière, M.; Berger, G.; Masse, R.; Plummer, D.; Comar, D. The "In Vivo" Distribution of Carbon 11 Labeled (-) Nicotine in Animals: A Method Suitable for Use in Man. In Electrophysiological Effects of Nicotine; Redmond, A., Izard, C., Eds.; Elsevier: Amsterdam, 1979; pp 31-47.
11. Spande, T. F.; Garrafffo, H. M.; Edwards, M. W.; Yeh, H.; Pannell, L.; Daly, J. W. Epibatidine: A Novel (Chloropyridyl)Azabicycloheptane with Potent Analgesic Activity from an Ecuadoran Poison Frog. J. Am. Chem. Soc. 1992, 114, 3475-3478.
12. London, E. D.; Scheffel, U.; Kimes, A. S.; Kellar, K. J. In Vivo Labeling of Nicotinic Acetylcholine Receptors in Brain with [3H]-Epibatidine. Eur. J. Pharmacol 1995, 278, R1-R2.
13. Badio, B.; Daly, J. W. Epibatidine, A Potent Analgetic and Nicotinic Agonist. Mol. Pharmacol. 1994, 45, 563-569.
14. Sullivan, J. P.; Decker, M. W.; Brioni, J. D.; Donnelly-Roberts, D.; Anderson, D. J.; Bannon, A. W.; Kang, C. H.; Adams, P.; Piattoni-Kaplan, M.; Buckley, M. J. (±)-Epibatidine Elicits a Diversity of In Vitro and In Vivo Effects Mediated by Nicotinic Acetylcholine Receptors. J. Pharmacol. Exp. Ther. 1994, 271, 624-631.
15. Badio, B.; Shi, D.; Garraffo, H. M.; Daly, J. W. Antinociceptive Effect of the Alkaloid Epibatidine: Further Studies on Involvement of Nicotinic Receptors. Drug Dev. Res. 1995, 36, 45-59.
16. 3H]Epibatidine Binding to Nicotinic Cholinergic Receptors in Rat and Human Brain. Mol. Pharmacol. 1995, 48, 280-287.
17. Scheffel, U.; Taylor, G. F.; Kepler, J. A.; Carroll, F. I.; Kuhar, M. J. In Vivo Labeling of Neuronal Nicotinic Acetylcholine Receptors with Radiolabeled Isomers of Norchloroepibatidine. NeuroReport 1995, 6, 2483-2488.
18. Horti, A.; Ravert, H. T.; London, E. D.; Dannals, R. F. Synthesis of a Radiotracer for Studying Nicotinic Acetylcholine Receptors: (±)-exo-2-(2-[18F]fluoro-5-pyridyl-7-azabicyclo[2.21]heptane. J. Labeled Compd. Radiopharm. 1996, 38, 355-366.
19. Horti, A.; Scheffel, U.; Stathis, M.; Finley, P.; Ravert, H. T.; London, E. D.; Dannals, R. F. Fluorine-18-FPH for PET Imaging of Nicotinic Acetylcholine Receptors. J. Nucl. Med. 1997, 38, 1260-1265.
20. Horti, A.; Scheffel, U.; Dannals, R. F.; Stathis, M.; Finley, P.; Ravert, H. T.; London, E. D. [18F]-(+)-Exo-2-(2-fluoro-5-pyridyl)-7-azabicyclo[2.2.1]heptane. A Radioligand for In Vivo Labeling and Imaging of Central Nicotinic Acetylcholine Receptors. J. Nucl. Med. 1998, 37, 11P.
21. Ding, Y.; Gatley, J.; Fowler, J. S.; Volkow, N. D.; Aggarwal, D.; Logan, J.; Dewey, S. L.; Liang, F.; Carroll, F. L; Kuhar, M. Mapping Nicotinic Acetylcholine Receptors with PET. Synapse 1996, 24, 403-407.
22. Villemagne, V. L.; Horti, A.; Scheffel, U.; Ravert, H. T.; Finley, P.; London, E. D.; Dannals, R. F. Imaging Nicotinic Acetylcholine Receptors in Baboon Brain by PET. J. Nucl. Med. 1996, 37, 11P.
23. Villemagne, V. L.; Horti, A.; Scheffel, U.; Ravert, H. T.; Finley, P.; Clough, D. J.; London, E. D.; Wagner, H. N., Jr.; Dannals, R. F. Imaging Nicotinic Acetylcholine Receptors with Fluorine-18-FPH, an Epibatidine Analogue. J. Nucl. Med. 1997, 38, 1737-1741.
24. +123I]IPH: A Radioiodinated Analogue of Epibatidine for In Vivo Studies of Nicotinic Acetylcholine Receptors. Synapse 1997, 26, 392-399.
25. Fisher, M.; Huangfu, D.; Shen, T. Y.; Guyenet, P. G. Epibatidine, an Alkaloid from the Poison Frog Epipedobates tricolor, is a Powerful Ganglionic Depolarizing Agent. J. Pharmacol. Exp. Ther. 1994, 270, 702-707.
26. 18F]Norchlorofluoroepibatidine (NFEP): Preclinical Toxicological Studies. J. Nucl. Med. 1997, 38, 287P.
27. Horti, A.; Ravert, H. T.; Mathews, W. B.; Kimes, A. S.; London, E. D.; Dannals, R. F. Synthesis of High Specific Activity Carbon11 N-methylated Analogues of Epibatidine for Imaging nAChRs. J. Nucl. Med. 1996, 37, 192P.
28. Liang, F.; Navarro, H. A.; Abraham, P.; Kotian, P.; Ding, Y. S.; Fowler, J.; Volkow, N.; Kuhar, M. J.; Carroll, F. I. Synthesis and Nicotinic Acetylcholine Receptor Binding Properties of exo2-(2′-fluoro-5′-pyridinyl)-7-azabicyclo-[2.2.1]heptane: A New Positron Emission Tomography Ligand for Nicotinic Receptors. J. Med. Chem. 1997, 40, 2293-2295.
29. 50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
30. 3H]l-Nicotine in the Mouse Brain. Life Sci. 1989, 44, 1123-1132.
31. 3H]Nicotine Binding Sites in the Rat Brain. Neurosci. Lett. 1985, 53, 179-184.
32. Rekker, R. F. The Hydrophobic Fragmental Constant: Its Derivation and Application. A Means of Characterizing Membrane Systems; Elsevier Scientific Publishing Co.: Amsterdam, 1977.
33. Martin, Y. C. Studies of Relationships Between Structural Properties and Biological Activity by Hansch Analysis. In Structure-Activity Correlation as a Predictive Tool in Toxicology; Goldberg, L., Ed.; Hemisphere Publishing Co.; Washington, 1983; pp 77-92.
34. Broka, C. A. Synthetic Approaches to Epibatidine. Med. Chem. Res. 1994, 4, 449-460.
35. Dehmlow, E. V. The Epibatidine Competition: Synthetic Work on a Novel Natural Analgetic. J. Prakt. Chem. 1995, 337, 167-174.
36. Clayton, S. C.; Regan, A. C. A total Synthesis of (±)-Epibatidine. Tetrahedron Lett. 1993, 34, 7493-7496.
37. 18F]fluoroethylepibatidine: Ligands for the Neuronal Nicotinic Receptor. J. Labeled Compd. Radio-pharm. 1995, 37, 355-356.
38. Gerzanich, V.; Peng, X.; Wang, F.; Wells, G.; Anand, R.; Fletcher, S.; Lindstrom, J. Comparative Pharmacology of Epibatidine: A Potent Agonist for Neuronal Nicotinic Acetylcholine Receptors. Mol. Pharmacol. 1995, 48, 774-782.
39. Xiao, Y.; Meyer, E. L.; Houghtling, R. A; Thompson, J. M.; Kellar, K. J. Stable Expression of Rat Nicotinic Acetylcholine Receptor Subtypes in Mammalian Cells. Soc. Neurosci. Abstr. 1996, 22, 1034.
40. Scheffel, U.; Ricaurte, G. A. Paroxetine as an In Vivo Indicator of 3,4-Methylenedioxymethamphetamine Neurotoxicity: A Presynaptic Serotonergic Positron Emission Tomography Ligand. Brain Res. 1990, 527, 89-95.
41. 2subunits and is up-regulated by chronic nicotine treatment. Mol. Pharmacol. 1992, 41, 31-37.
42. Marks, M. J.; Smith, K. W.; Colline, A. C. Differential agonist inhibition identifies multiple epibatidine binding sites in mouse brain. J. Pharmacol. Exp. Ther. 1998, 285, 377-386.