Synthesis and Electrophysiological Studies of a Novel Epibatidine Analogue

References

• Deneris E. S., Conolly J., Rogers S. W., Duvoisin R. Pharmacological and functional diversity of neuronal of nicotinic acetylcholine receptors. Trends Pharmacol. Sci. 1991; 12: 34–40
   PubMed Web of Science ®Google Scholar
• Luetje C. W., Patrick J. Both α- and β-subunits contribute to the agonist sensitivity of neuronal nicotinic acetylcholine receptor. J. Neurosci. 1991; 11: 837–845
   PubMed Web of Science ®Google Scholar
• Karlin A., Akabas M. H. Toward a structural basis for the function of nicotinic acetylcholine receptors and their cousins. Neuron 1995; 15: 1231–1244
   PubMed Web of Science ®Google Scholar
• Elogoyhen A. B., Johnsen D., Boulter J., Vetter D., Heineman S. F. α9: An acetylcholine receptor with novel pharmacological properties expressed in rat cochlear hair cells. Cell 1994; 79: 705–715
   PubMed Web of Science ®Google Scholar
• Sargent P. B. The diversity of neuronal nicotinic acetylcholine receptors. Annu. Rev. Neurosci. 1993; 16: 403–443
   PubMed Web of Science ®Google Scholar
• Galzi J.-L., Changeux J.-P. Neuronal nicotinic receptors: Molecular organisation and regulations. Neuropharmacology 1995; 34: 563–582
   PubMed Web of Science ®Google Scholar
• Hucho F., Tsetlin V. I., Machold J. The emerging three-dimensional structure of a receptor. The nicotinic acetylcholine receptor. Eur. J. Biochem. 1996; 239: 539–557
   PubMedGoogle Scholar
• Bertrand D., Bertrand S., Ballivet M. Pharmacological properties of the homomeric α7 receptor. Neurosci. Lett. 1992; 146: 87–90
   PubMed Web of Science ®Google Scholar
• Gotti C., Hanke W., Maury K., Moretti M., Ballivet M., Clementi F., Bertrand D. Pharmacology and biophysical properties of α7 and α7- α8 α-bungarotoxin receptor subtypes immunopurified from the chick optic lobe. Eur. J. Neurosci. 1994; 6: 1281–1291
   PubMed Web of Science ®Google Scholar
• Brioni J. D., Decker M. W., Sullivan J. P., Arneric S. P. The pharmacology of (-)-nicotine and novel cholinergic channel modulators. Adv. Pharmacol. 1997; 37: 153–214
   PubMedGoogle Scholar
• Colquhoun L. M., Patrick J. W. Pharmacology of neuronal nicotinic acetylcholine receptor subtypes. Adv. Pharmacol. 1997; 39: 191–220
   PubMedGoogle Scholar
• Badio B., Garraffo M. H., Spande T. F., Daly J. W. Epibatidine: Discovery and definition as a potent analgesic and nicotinic agonist. Med. Chem. Res. 1994; 4: 440–448
   Google Scholar
• Sullivan J. P., Bannon A. W. Epibatidine: Pharmacological properties of a novel nicotinic acetylcholine receptor agonist and analgesic agent. CNS Drug Rev. 1996; 2: 21–39
   Google Scholar
• Warpman U., Nordberg A. Epibatidine and ABT 418 reveal selective losses of α4β2 nicotinic receptors in Alzheimer brains. Neuroreport 1995; 6: 2419–2423
   PubMed Web of Science ®Google Scholar
• Badio B., Garraffo H. M., Plummer C. V., Padgett W. L., Daly J. W. Synthesis and nicotinic activity of epiboxidine: an isoxazole analogue of epibatidine. Eur. J. Pharmacol. 1997; 321: 189–194
   PubMed Web of Science ®Google Scholar
• Davila Garcia M. I., Musachio J. L., Perry D. C., Xiao Y., Horti A., London E. D., Dannals R. F., Kellar K. J. [125I]IPH, an epibatidine analog, binds with high affinity to neuronal nicotinic cholinergic receptors. J. Pharmacol. Exp. Ther. 1997; 282: 445–451
   PubMed Web of Science ®Google Scholar
• Ding Y. S., Liang F., Fowler J. S., Kuhar M. J., Carrol F. I. Synthesis of [18F]norchlorofluoroepibatidine and its N-methyl derivative: New PET ligands for mapping nicotinic acetylcholine receptors. J. Label. Comp. Radiopharm. 1997; 39: 827–832
   Web of Science ®Google Scholar
• 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[2,2.1]heptane. J. Label. Comp. Radiopharm. 1996; 38: 355–365
   Web of Science ®Google Scholar
• 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 exo-2-(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
   PubMed Web of Science ®Google Scholar
• Musachio J. L., Villemagne V. L., Scheffel U., Stathis M., Finley P., Horti A., London E. D., Dannals R. F. [125/123I]IPH: A radioiodinated analog of epibatidine for in vivo studies of nicotinic acetylcholine receptors. Synapse 1997; 26: 392–399
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Glennon R. A., Herndon J. L., Dukat M. Epibatidine-aided studies toward definition of a nicotine receptor pharmacophore. Med. Chem. Res. 1994; 4: 461–473
   Google Scholar
• Holladay M. W., Wasicak J. T., Lin N. H., He Y., Ryther K. B., Bannon A. W., Buckley M. J., Kim D. J. B., Decker M. W., Anderson D. J., Campbell J. E., Kuntzweiler T. A., Donnelly-Roberts D. L., Piattoni-Kaplan M., Briggs C. A., Williams M., Arneric S. P. Identification and initial structure-activity relationships of (R)-5-(2-azetidinylmethoxy)-2-chloropyridine(ABT-594), a potent, orally active, non-opiate analgesic agent acting via neuronal nicotinic acetylcholine receptors. J. Med. Chem. 1998; 41: 407–412
   PubMed Web of Science ®Google Scholar
• Kim K. H., Lin N. H., Anderson D. J. Quantitative structure-activity relationships of nicotine analogues as neuronal nicotinic acetylcholine receptor ligands. Bioorg. Med. Chem. 1996; 4: 2211–2217
   PubMed Web of Science ®Google Scholar
• Badio B., Daly J. W. Epibatidine, a potent analgetic and nicotinic agonist. Mol. Pharmacol. 1994; 45: 563–569
   PubMed Web of Science ®Google Scholar
• Clayton S. C., Regan A. C. A total synthesis of (±)-epibatidine. Tetrahedron Lett. 1993; 34: 7493–7496
   Web of Science ®Google Scholar
• Regan A. C. Improved synthesis of epibatidine, Personal communication
   Google Scholar
• Bertrand D., Cooper E., Valera S. Electrophysiology of neuronal nicotinic receptors expressed in Xenopus oocytes, following nuclear injection of genes or cDNAs. Academic Press Inc, New York 1991
   Google Scholar
• Bertrand D., Buisson B., Krause R. M., Hu H.-Y., Bertrand S. Electrophysiology: A method to investigate the functional properties of ligand-gated channels. J. Recept. Signal. Tr. R. 1997; 17: 227–242
   PubMed Web of Science ®Google Scholar
• Couturier S., Bertrand D., Matter J. M., Hernandez M. C., Bertrand S., Millar N., Valera S., Barkas T., Ballivet M. A neuronal nicotinic acetylcholine receptor subunit (α7) is developmentally regulated and forms a homo-oligomeric channel blocked by α-BTX. Neuron 1990; 5: 847–856
   PubMed Web of Science ®Google Scholar
• Papke R. L., de Fiebre C. M., Moulton B. A., Thinschmidt J. S., Quintana R., Meyer E. M. Activation and inhibition of neuronal nACHRs by potential therapeutic agents. Soc. Neurosci. 1995; 21
   Google Scholar
• Papke R. L., Bencherif M., Lippiello P. An evaluation of neuronal nicotinic acetylcholine receptor activation by quaternary nitrogen compounds indicates that choline is selective for the α7 subtype. Neurosci. Lett. 1996; 213: 201–4
   PubMed Web of Science ®Google Scholar