Spectroscopic analysis of benzylidene anabaseine complexes with acetylcholine binding proteins as models for ligand-nicotinic receptor interactions

Biochemistry

Volumn 45, Issue 29, 2006, Pages 8894-8902

  Talley, Todd T ^a   Yalda, Samar ^a   Ho, Kwok Yiu ^a   Tor, Yitzhak ^a   Soti, Ferene S ^b   Kem, William R ^b   Taylor, Palmer ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF FLORIDA COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CRYSTAL STRUCTURE; FLUORESCENCE; PERMITTIVITY MEASUREMENT; POLARIZATION; QUANTUM THEORY;

ACETYLCHOLINE BINDING PROTEINS (ACHBPS); ANABASEINES; LIGAND; LIGAND-NICOTINIC RECEPTOR INTERACTIONS;

PROTEINS;

ACETYLCHOLINE; ACETYLCHOLINE BINDING PROTEIN; BENZYLIDENE ANABASEINE DERIVATIVE; BENZYLIDENE DERIVATIVE; LIGAND; NICOTINIC RECEPTOR; UNCLASSIFIED DRUG;

APLYSIA; ARTICLE; BULINUS; COMPLEX FORMATION; CORRELATION ANALYSIS; CRYSTAL STRUCTURE; DIELECTRIC CONSTANT; FLUORESCENCE; LIGAND BINDING; LYMNAEA; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN FAMILY; PROTEIN INTERACTION; PROTEIN PURIFICATION; QUANTUM CHEMISTRY; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

ANABASINE; ANIMALS; APLYSIA; BENZYLIDENE COMPOUNDS; BULINUS; CARRIER PROTEINS; HYDROGEN-ION CONCENTRATION; LIGANDS; LYMNAEA; RECEPTORS, NICOTINIC; SPECTROMETRY, FLUORESCENCE;

APLYSIA; BULINUS; LYMNAEA;

EID: 33646822242     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi060534y     Document Type: Article

References (26)

1. Brejc, K., van Dijk, W. J., Klaassen, R. V., Schuurmans, M., van Der Oost, J., Smit, A. B., and Sixma, T. K. (2001) Crystal structure of an ACh-binding protein reveals the ligand-binding domain of nicotinic receptors, Nature 411, 269-276.
2. Smit, A. B., Syed, N. I., Schaap, D., van Minnen, J., Klumperman, J., Kits, K. S., Lodder, H., van der Schors, R. C., van Elk, R., Sorgedrager, B., Brejc, K., Sixma, T. K., and Geraerts, W. P. (2001) A glia-derived acetylcholine-binding protein that modulates synaptic transmission, Nature 411, 261-268.
3. Celie, P. H., Klaassen, R. V., van Rossum-Fikkert, S. E., van Elk, R., van Nierop, P., Smit, A. B., and Sixma, T. K. (2005) Crystal structure of acetylcholine-binding protein from Bulinus truncatus reveals the conserved structural scaffold and sites of variation in nicotinic acetylcholine receptors, J. Biol. Chem. 280, 26457-26466.
4. Hansen, S. B., Talley, T. T., Radic, Z., and Taylor, P. (2004) Structural and ligand recognition characteristics of an acetylcholine-binding protein from Aplysia californica, J. Biol. Chem. 279, 24197-24202.
5. Celie, P. H., van Rossum-Fikkert, S. E., van Dijk, W. J., Brejc, K., Smit, A. B., and Sixma, T. K. (2004) Nicotine and carbamylcholine binding to nicotinic acetylcholine receptors as studied in AChBP crystal structures, Neuron 41, 907-914.
6. Hansen, S. B., Sulzenbacher, G., Huxford, T., Marchot, P., Taylor, P., and Bourne, Y. (2005) Structures of Aplysia AChBP complexes with nicotinic agonists and antagonists reveal distinctive binding interfaces and conformations, EMBO J. 24, 3635-3646.
7. Celie, P. H., Kasheverov, I. E., Mordvintsev, D. Y., Hogg, R. C., van Nierop, P., van Elk, R., van Rossum-Fikkert, S. E., Zhmak, M. N., Bertrand, D., Tsetlin, V., Sixma, T. K., and Smit, A. B. (2005) Crystal structure of nicotinic acetylcholine receptor homolog AChBP in complex with an alpha-conotoxin PnIA variant, Nat. Struct. Mol. Biol. 12, 582-588.
8. Bourne, Y., Talley, T. T., Hansen, S. B., Taylor, P., and Marchot, P. (2005) Crystal structure of a Cbtx-AChBP complex reveals essential interactions between snake alpha-neurotoxins and nicotinic receptors, EMBO J. 24, 1512-1522.
9. Papke, R. L., Meyer, E. M., Lavieri, S., Bollampally, S. R., Papke, T. A., Horenstein, N. A., Itoh, Y., and Porter Papke, J. K. (2004) Effects at a distance in alpha 7 nAChR selective agonists: benzylidene substitutions that regulate potency and efficacy, Neuropharmacology 46, 1023-1038.
10. Kern, W. R., Mahnir, V. M., Prokai, L., Papke, R. L., Cao, X., LeFrancois, S., Wildeboer, K., Prokai-Tatrai, K., Porter-Papke, J., and Soti, F. (2004) Hydroxy metabolites of the Alzheimer's drug candidate 3-[(2,4-dimethoxy)benzylidene]-anabaseine dihydrochloride (GTS-21): their molecular properties, interactions with brain nicotinic receptors, and brain penetration, Mol. Pharmacol. 65, 56-67.
11. Kem, W. R. (1971) A study of the occurrence of anabaseine in Paranemertes and other nemertines, Toxicon 9, 23-32.
12. Kem, W. R., Mahnir, V. M., Papke, R. L., and Lingle, C. J. (1997) Anabaseine is a potent agonist on muscle and neuronal alpha-bungarotoxin- sensitive nicotinic receptors, J. Pharmacol. Exp. Ther. 283, 979-992.
13. Stokes, C., Papke, J. K., Horenstein, N. A., Kem, W. R., McCormack, T. J., and Papke, R. L. (2004) The structural basis for GTS-21 selectivity between human and rat nicotinic alpha7 receptors, Mol. Pharmacol. 66, 14-24.
14. Machu, T. K., Hamilton, M. E., Frye, T. P., Shanklin, C. L., Harris, M. C., Sun, H., Tenner, T. E., Jr., Soti, F. S., and Kem, W. R. (2001) Benzylidene analogs of anabaseine display partial agonist and antagonist properties at the mouse 5-hydroxytryptamine(3A) receptor, J. Pharmacol. Exp. Ther. 299, 1112-11129.
15. Stevens, K. E., Kern, W. R., Mahnir, V. M., and Freedman, R. (1998) Selective alpha7-nicotinic agonists normalize inhibition of auditory response in DBA mice, Psychopharmacology (Berlin) 136, 320-327.
16. O'Neill, H. C., Rieger, K., Kem, W. R., and Stevens, K. E. (2003) DMXB, an alpha7 nicotinic agonist, normalizes auditory gating in isolation-reared rats, Psychopharmacology (Berlin) 169, 332-339.
17. Kitagawa, H., Takenouchi, T., Azuma, R., Wesnes, K. A., Kramer, W. G., Clody, D. E., and Burnett, A. L. (2003) Safety, pharmacokinetics, and effects on cognitive function of multiple doses of GTS-21 in healthy, male volunteers. Neuropsychopharmacology 28, 542-551.
18. Olincy, A., Harris, J. G., Johnson, L. L., Pender, V., Kongs, S., Allensworth, D., Ellis, J., Zerbe, G. O., Leonard, S., Stevens, K. E., Stevens, J. O., Martin, L. F., Adler, L. E., Soti, F., Kem, W. R., and Freedman, R. (2006) Proof-of-concept trial of an α7 nicotinic agonist in schizophrenia, Arch. Gen. Psychiatry 63, 630-638.
19. Hansen, S. B., Radic, Z., Talley, T. T., Molles, B. E., Deerinck, T., Tsigelny, I., and Taylor, P. (2002) Tryptophan fluorescence reveals conformational changes in the acetylcholine binding protein, J. Biol. Chem. 277, 41299-41302.
20. Hibbs, R. E., Talley, T. T., and Taylor, P. (2004) Acrylodan-conjugated cysteine side chains reveal conformational state and ligand site locations of the acetylcholine-binding protein, J. Biol. Chem. 279, 28483-28491.
21. Cheng, Y., and Prusoff, W. H. (1973) Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50% inhibition (I50) of an enzymatic reaction, Biochem. Pharmacol. 22, 3099-108.
22. Hansch, C., Leo, A., and Taft, R. W. (1991) A survey of Hammett substituent constants and resonance and field parameters, Chem. Rev. 91, 165-195.
23. Reichard, C. (1994) Solvatochromic dyes as solvent polarity indicators, Chem. Rev. 94, 2319-2358.
24. Lakowicz, J. R. (1999) Principles of Fluorescence Spectroscopy, 2nd ed., Kluwer Academic Publishers and Plenum Publishing Corp., New York.
25. Bouzat, C., Gumilar, F., Spitzmaul, G., Wang, H. L., Rayes, D., Hansen, S. B., Taylor, P., and Sine, S. M. (2004) Coupling of agonist binding to channel gating in an ACh-binding protein linked to an ion channel, Nature 430, 896-900.
26. Le Francois, S. E., Prokai, L., Soti, P., and Kern, W. R. (2004), 2004 Abstract Viewer/Itinerary Planner, Society for Neuroscience, 2004, Washington, D.C.