Structure-activity relationships for allosteric NMDA receptor inhibitors based on 2-naphthoic acid

Neuropharmacology

Volumn 62, Issue 4, 2012, Pages 1730-1736

  Costa, Blaise Mathias ^a   Irvine, Mark W ^b   Fang, Guangyu ^b   Eaves, Richard J ^b   Mayo Martin, Maria Belen ^b   Laube, Bodo ^c   Jane, David E ^b   Monaghan, Daniel T ^a  

^a NEBRASKA MEDICAL CENTER   (United States)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

^c DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Allosteric modulator; Antagonist; Glutamate; NMDA receptors; Oocyte

Indexed keywords

2 NAPHTHOIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR 1; N METHYL DEXTRO ASPARTIC ACID RECEPTOR 2A; N METHYL DEXTRO ASPARTIC ACID RECEPTOR 2C; N METHYL DEXTRO ASPARTIC ACID RECEPTOR 2D; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT;

ALLOSTERISM; ANIMAL CELL; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MECHANISM; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; IC 50; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

ALLOSTERIC REGULATION; ANIMALS; DOSE-RESPONSE RELATIONSHIP, DRUG; NAPHTHALENES; RECEPTORS, N-METHYL-D-ASPARTATE; STRUCTURE-ACTIVITY RELATIONSHIP; XENOPUS;

EID: 84856448885     PISSN: 00283908     EISSN: 18737064     Source Type: Journal    
DOI: 10.1016/j.neuropharm.2011.11.019     Document Type: Article

References (28)

1. V. Balannik, F.S. Menniti, A.V. Paternain, J. Lerma, and Y. Stern-Bach Molecular mechanism of AMPA receptor noncompetitive antagonism Neuron 48 2 2005 279 288 (Pubitemid 41476361)
2. E. Bettini, A. Sava, C. Griffante, C. Carignani, A. Buson, and A.M. Capelli Identification and characterisation of novel NMDA receptor antagonists selective for NR2A- over NR2B-containing receptors J. Pharmacol. Exp. Ther. 335 3 2010 636 644
3. A.L. Buller, H.C. Larson, R.A. Morrisett, and D.T. Monaghan Glycine modulates ethanol inhibition of heteromeric N-methyl-d-aspartate receptors expressed in Xenopus oocytes Mol. Pharmacol. 48 4 1995 717 723
4. 50) of an enzymatic reaction Biochem. Pharmacol. 22 23 1973 3099 3108 (Availability)
5. G. Collingridge Synaptic plasticity. The role of NMDA receptors in learning and memory Nature 330 6149 1987 604 605
6. B.M. Costa, B. Feng, T.S. Tsintsadze, R.M. Morley, M.W. Irvine, and V. Tsintsadze N-methyl-d-aspartate (NMDA) receptor NR2 subunit selectivity of a series of novel piperazine-2,3-dicarboxylate derivatives: preferential blockade of extrasynaptic NMDA receptors in the rat hippocampal CA3-CA1 synapse J. Pharmacol. Exp. Ther. 331 2 2009 618 626
7. B.M. Costa, M.W. Irvine, G. Fang, R.J. Eaves, M.B. Mayo-Martin, and D.A. Skifter A novel family of negative and positive allosteric modulators of NMDA receptors J. Pharmacol. Exp. Ther. 335 3 2010 614 621
8. C.W. Cotman, D.T. Monaghan, and A.H. Ganong Excitatory amino acid neurotransmission: NMDA receptors and Hebb-type synaptic plasticity Annu. Rev. Neurosci. 11 1988 61 80 (Pubitemid 18081033)
9. H. Furukawa, S.K. Singh, R. Mancusso, and E. Gouaux Subunit arrangement and function in NMDA receptors Nature 438 7065 2005 185 192 (Pubitemid 41599865)
10. K.B. Hansen, and S.F. Traynelis Structural and mechanistic determinants of a novel site for noncompetitive inhibition of GluN2D-containing NMDA receptors J. Neurosci. 31 10 2011 3650 3661
11. L.V. Kalia, S.K. Kalia, and M.W. Salter NMDA receptors in clinical neurology: excitatory times ahead Lancet Neurol. 7 8 2008 742 755 (Pubitemid 351957932)
12. T. Kenakin Allosteric modulators: the new generation of receptor antagonist Mol. Interv. 4 4 2004 222 229 (Pubitemid 39199604)
13. T. Kutsuwada, N. Kashiwabuchi, H. Mori, K. Sakimura, E. Kushiya, and K. Araki Molecular diversity of the NMDA receptor channel Nature 358 6381 1992 36 41
14. A.H. Lee, and E.T. Kool Exploring the limits of DNA size: naphtho-homologated DNA bases and pairs J. Am. Chem. Soc. 128 28 2006 9219 9230 (Pubitemid 44079004)
15. D.R. Lynch, J.J. Lawrence, S. Lenz, N.J. Anegawa, M. Dichter, and D.B. Pritchett Pharmacological characterization of heterodimeric NMDA receptors composed of NR 1a and 2B subunits: differences with receptors formed from NR 1a and 2A J. Neurochem. 64 4 1995 1462 1468
16. 2+ inhibition and glycine affinity of N-methyl-d-aspartate receptors Mol. Pharmacol. 72 6 2007 1535 1544 (Pubitemid 350146090)
17. H. Monyer, R. Sprengel, R. Schoepfer, A. Herb, M. Higuchi, and H. Lomeli Heteromeric NMDA receptors: molecular and functional distinction of subtypes Science 256 5060 1992 1217 1221
18. K. Moriyoshi, M. Masu, T. Ishii, R. Shigemoto, N. Mizuno, and S. Nakanishi Molecular cloning and characterization of the rat NMDA receptor Nature 354 6348 1991 31 37 (Pubitemid 21896774)
19. C.A. Mosley, T.M. Acker, K.B. Hansen, P. Mullasseril, K.T. Andersen, and P. Le Quinazolin-4-one derivatives: a novel class of noncompetitive NR2C/D subunit-selective N-methyl-d-aspartate receptor antagonists J. Med. Chem. 53 15 2010 5476 5490
20. R.A. Murphy, H.F. Kung, M.P. Kung, and J. Billings Synthesis and characterization of iodobenzamide analogues: potential D-2 dopamine receptor imaging agents J. Med. Chem. 33 1 1990 171 178 (Pubitemid 20038189)
21. V.E. O'Collins, M.R. Macleod, G.A. Donnan, L.L. Horky, B.H. van der Worp, and D.W. Howells 1,026 experimental treatments in acute stroke Ann. Neurol. 59 3 2006 467 477 (Pubitemid 43358067)
22. C.P. Ptak, A.H. Ahmed, and R.E. Oswald Probing the allosteric modulator binding site of GluR2 with thiazide derivatives Biochemistry 48 36 2009 8594 8602
23. J. Rachline, F. Perin-Dureau, A. Le Goff, J. Neyton, and P. Paoletti The micromolar zinc-binding domain on the NMDA receptor subunit NR2B J. Neurosci. 25 2 2005 308 317 (Pubitemid 40105601)
24. G. Sanacora, C.A. Zarate, J.H. Krystal, and H.K. Manji Targeting the glutamatergic system to develop novel, improved therapeutics for mood disorders Nat. Rev. Drug Discov. 7 5 2008 426 437 (Pubitemid 351619114)
25. S.F. Traynelis, L.P. Wollmuth, C.J. McBain, F.S. Menniti, K.M. Vance, and K.K. Ogden Glutamate receptor ion channels: structure, regulation, and function Pharmacol. Rev. 62 3 2010 405 496
26. C. Villmann, and C.M. Becker On the hypes and falls in neuroprotection: targeting the NMDA receptor Neuroscientist 13 6 2007 594 615 (Pubitemid 350077310)
27. J.C. Watkins Pharmacology of excitatory amino acid transmitters Adv. Biochem. Psychopharmacol. 29 1981 205 212
28. +) accumulation and cell death J. Pharmacol. Exp. Ther. 293 3 2000 747 754 (Pubitemid 30417838)