Further exploration of M1 allosteric agonists: Subtle structural changes abolish M1 allosteric agonism and result in pan-mAChR orthosteric antagonism

Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 1, 2013, Pages 223-227

  Sheffler, Douglas J ^a,b   Sevel, Christian ^a   Le, Uyen ^a,b   Lovell, Kimberly M ^a,b   Tarr, James C ^a,b   Carrington, Sheridan J S ^a   Cho, Hyekyung P ^a,b   Digby, Gregory J ^a   Niswender, Colleen M ^a,b   Conn, P Jeffrey ^a,b   Hopkins, Corey R ^a,b,c   Wood, Michael R ^a,b,c   Lindsley, Craig W ^a,b,c  

^a VANDERBILT UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b VANDERBILT UNIVERSITY MEDICAL CENTER   (United States)

^c VANDERBILT UNIVERSITY   (United States)

Author keywords

Allosteric agonist; M1; Muscarinic receptor; TBPB

Indexed keywords

MUSCARINIC M1 RECEPTOR AGONIST; PIPERIDINE; TRANSFERRIN BINDING PROTEIN B; UNCLASSIFIED DRUG; VU 0357017;

ALLOSTERISM; ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL MODIFICATION; DRUG ACTIVITY; DRUG STRUCTURE; IC 50; RECEPTOR BLOCKING;

ACETYLCHOLINE; ALLOSTERIC REGULATION; ALLOSTERIC SITE; ANIMALS; BENZAMIDES; BENZIMIDAZOLES; CALCIUM; CHO CELLS; CRICETINAE; CRICETULUS; HUMANS; PIPERIDINES; RATS; RECEPTOR, MUSCARINIC M1; RECEPTORS, MUSCARINIC; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSFECTION;

EID: 84871005904     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.10.132     Document Type: Article

References (44)

1. T.J. Raedler, F.P. Bymaster, R. Tandon, D. Copolov, and B. Dean Mol. Psychiatry 12 2007 232
2. T.E. Goldberg, J.M. Gold, R. Greenberg, S. Griffin, S.C. Schulz, and D. Pickar Am. J. Psychiatry 150 1993 1355
3. T.W. Weickert, T.E. Goldberg, J.M. Gold, L.B. Bigelow, M.F. Egan, and D.R. Weinberg Arch. Gen. Psychiatry 57 2000 907
4. S.G. Siris Schizophrenia 1995 Blackwell Science Ltd Oxford pp. 128-146
5. M.F. Green Am. J. Psychiatry 153 1996 321
6. A. Carlsson Neuropsychopharmacology 1 1988 179
7. A. Shekhar, W.Z. Potter, J. Lightfoot, J. Lienemann, S. Dube, C. Mallinckrodt, F.P. Bymaster, D.L. McKinzie, and C.C. Felder Am. J. Psychiatry 165 2008 1033
8. N.R. Mirza, D. Peters, and R.G. Sparks CNS Drug Rev. 9 2003 159
9. C. Sur, P.J. Mallorga, M. Wittmann, M.A. Jacobson, D. Pascarella, J.B. Williams, P.E. Brandish, D.J. Pettibone, E.M. Scolnick, and P.J. Conn PNAS 100 2003 13674
10. S. Pakrasi, S.J. Colloby, M.J. Firbank, E.K. Perry, D.J. Wyper, J. Owens, I.G. McKeith, E.D. Williams, and J.T. O'Brien J. Neurol. 254 2003 907
11. N.C. Bodick, W.W. Offen, A.I. Levey, N.R. Cutler, S.G. Gauthier, A. Satlin, H.E. Shannon, G.D. Tollefson, K. Rasmussen, F.P. Bymaster, D.J. Hurley, W.Z. Potter, and S.M. Paul Arch. Neurol. 54 1997 465
12. A. Caccamo, S. Oddo, L.M. Billings, K.N. Green, H. Martinez-Coria, A. Fisher, and F.M. LaFerla Neuron 49 2006 671
13. T.J. Raedler, F.P. Bymaster, R. Tandon, D. Copolov, and B. Dean Mol. Psychiatry 12 2007 232
14. A. Fisher Neurodegen. Dis. 5 2008 237
15. P.J. Conn, C. Jones, and C.W. Lindsley Trends Pharm. Sci. 30 2009 148
16. P.J. Conn, C. Tamminga, D.D. Schoepp, and C. Lindsley Mol. Interv. 8 2008 99
17. P.J. Conn, A. Christopolous, and C.W. Lindsley Nat. Rev. Drug Disc. 8 2009 41
18. B.J. Melancon, C.R. Hopkins, M.R. Wood, K.A. Emmitte, C.M. Niswender, A. Christopoulos, P.J. Conn, and C.W. Lindsley J. Med. Chem. 55 2012 1445
19. C.K. Jones, A.E. Brady, A.A. Davis, Z. Xiang, M. Bubser, M.N. Tantawy, A. Kane, T.M. Bridges, J.P. Kennedy, S.R. Bradley, T. Peterson, R.M. Baldwin, R. Kessler, A. Deutch, J.L. Lah, A.I. Levey, C.W. Lindsley, and P.J. Conn J. Neurosci. 28 2008 10422
20. J.E. Marlo, C.M. Niswender, Q. Luo, A.E. Brady, J.K. Shirey, A.L. Rodriguez, T.M. Bridges, R. Williams, E. Days, N.T. Nalywajko, C. Austin, M. Williams, Y. Xiang, D. Orton, H.A. Brown, K. Kim, C.W. Lindsley, C.D. Weaver, and P.J. Conn Mol. Pharm. 75 2009 577
21. N.R. Miller, N.R. Daniels, T.M. Bridges, A.E. Brady, P.J. Conn, and C.W. Lindsley Bioorg. Med. Chem. Lett. 18 2008 5443
22. T.M. Bridges, A.E. Brady, J.P. Kennedy, N.R. Daniels, N.R. Miller, K. Kim, M.L. Breininger, P.R. Gentry, J.T. Brogan, J.K. Jones, P.J. Conn, and C.W. Lindsley Bioorg. Med. Chem. Lett. 18 2008 5439
23. L. Ma, M. Seager, M. Wittman, N. Bickel, M. Burno, K. Jones, V.K. Graufelds, G. Xu, M. Pearson, A. McCampbell, R. Gaspar, P. Shughrue, A. Danzinger, C. Regan, S. Garson, S. Doran, C. Kreatsoulas, L. Veng, C.W. Lindsley, W. Shipe, S. Kuduk, M. Jacobson, C. Sur, G. Kinney, G.R. Seabrook, and W.J. Ray Proc. Natl. Acad. Sci. U.S.A. 106 2009 15950
24. J.K. Shirey, A.E. Brady, P.J. Jones, A.A. Davis, T.M. Bridges, S.B. Jadhav, U. Menon, E.P. Christain, J.J. Doherty, M.C. Quirk, D.H. Snyder, A.I. Levey, M.L. Watson, M.M. Nicolle, C.W. Lindsley, and P.J. Conn J. Neurosci. 29 2009 14271
25. F.V. Yang, W.D. Shipe, J.L. Bunda, M.B. Nolt, D.D. Wisnoski, Z. Zhao, J.C. Barrow, W.J. Ray, L. Ma, M. Wittman, M. Seager, K. Koeplinger, G.D. Hartman, and C.W. Lindsley Bioorg. Med. Chem. Lett. 20 2010 531
26. E.P. Lebois, T.M. Bridges, E.S. Dawson, J.P. Kennedy, Z. Xiang, S.B. Jadhav, H. Yin, J. Meiler, C.K. Jones, P.J. Conn, C.D. Weaver, and C.W. Lindsley ACS Chem. Neurosci. 1 2010 104
27. T.M. Bridges, J.P. Kennedy, H.P. Cho, P.J. Conn, and C.W. Lindsley Bioorg. Med. Chem. Lett. 20 2010 1972
28. E.P. LeBois, D.J. Sheffler, G.J. Digby, B.J. Melancon, J.C. Tarr, H.P. Cho, R. Morrison, T.M. Bridges, Z. Xiang, J.S. Daniels, M.R. Wood, P.J. Conn, and C.W. Lindsley Bioorg. Med. Chem. Lett. 21 2011 6451
29. P.R. Reid, T.M. Bridges, D.A. Sheffler, H.P. Cho, L.M. Lewis, E. Days, J.S. Daniels, C.K. Jones, C.M. Niswender, C.D. Weaver, P.J. Conn, C.W. Lindsley, and M.R. Wood Bioorg. Med. Chem. Lett. 21 2011 2697
30. G.J. Digby, M.J. Noetzel, M. Bubser, T.J. Utley, A.G. Walker, N.B. Byun, E.P. LeBois, Z. Xiang, D.J. Sheffler, C.M. Niswender, H.C. Plumley, A.A. Davis, N.E. Nemirovsky, S. Mennenga, B.W. Camp, H.A. Bimonte-Nelson, R. Morrison, S. Daniels, C.W. Lindsley, M.F. Olive, and P.J. Conn J. Neurosci. 32 2012 8532
31. S.D. Kuduk, R.K. Chang, C.N. DiMarco, W.J. Ray, L. Ma, M. Wittman, M.A. Seager, K.A. Koeplinger, C.D. Thompson, G.D. Hartman, and M.T. Bilodeau ACS Med. Chem. Lett. 1 2010 263
32. T.A. Spalding, C. Trotter, N. Skaaerbaek, T.L. Meissner, E.A. Curreier, E.S. Burstein, D. Li, U. Hacksell, and M.R. Brann Mol. Pharmacol. 61 2002 1297
33. T.A. Spalding, J.N. Ma, T.R. Ott, M. Friberg, A. Bajpai, S.R. Bradley, R.E. Davis, M.R. Brann, and E.S. Burstein Mol. Pharmacol. 70 2006 1974
34. C. Sur, P.J. Mallorga, M. Wittman, M.A. Jacobson, D. Pascarella, J.B. Williams, P.E. Brandish, D.J. Pettibone, E.M. Scolnick, and P.J. Conn Proc. Natl. Acad. Sci. U.S.A. 100 2003 13674
35. S.D. Kuduk, R.K. Chang, C.N. DiMarco, D.R. Pitts, T.J. Greshok, L. Ma, M. Wittman, M.A. Seager, K.A. Koeplinger, C.D. Thompson, G.D. Hartman, M.T. Bilodeau, and W. Ray J. Med. Chem. 54 2011 4773
36. C.J. Langmead, N.E. Austin, C.L. Branch, K.A. Buchanan, C.H. Davies, I.T. Fores, V.A.H. Fry, and J.J. Hagan Br. J. Pharmacol. 154 2008 1104
37. S.D. Kuduk, R.K. Chang, C.N. DiMArco, W.J. Ray, L. Ma, M. Wittman, M.A. Seager, K.A. Koeplinger, C.D. Thompson, G.D. Hartman, and M.D. Bilodeau Bioorg. Med. Chem. Lett. 21 2011 1710
38. S.D. Kuduk, C.N. DiMarco, V. Cofre, D.R. Pitts, W.J. Ray, L. Ma, M. Wittman, M.A. Seager, K.A. Koeplinger, C.D. Thompson, G.D. Hartman, and M.D. Bilodeau Bioorg. Med. Chem. Lett. 20 2010 657
39. B. Budzik, V. Garzya, D. Shi, G. Walker, Y. Lauchart, A.J. Lucas, R.A. Rivero, C.J. Langmead, J. Watson, Z. Wu, I.T. Forbes, and J. Jin Bioorg. Med. Chem. Lett. 20 2010 3545
40. M.A. Jacobson, C. Kreatsoulas, D.M. Pascarella, J.A. O'Brien, and C. Sur Mol. Pharmacol. 78 2010 648
41. M.R. Wood, C.R. Hopkins, J.T. Brogan, P.J. Conn, and C.W. Lindsley Biochemistry 50 2011 2403
42. Digby, G.J.; Utley, T.J.; Lamsal, A.; Sevel, C.; Sheffler, D.J.; Lebois, E.P.; Bridges, T.M.; Wood, M.R.; Niswender, C.M.; Lindsley, C.W.; Conn, P.J. ACS Chem. Neurosci., in press, http://dx.doi.org/10.1021/cn300103e.
43. V.A. Alvani, C.J. Langmead, E. Guida, M.D. Wood, B.G. Tehan, H.J. Hedron, J.M. Watson, P.M. Sexton, and A. Christopoulos Mol. Pharmacol. 78 2010 94 104
44. O. Fadeyi, and C.W. Lindsley Org. Lett. 11 2009 943