Discovery of a new class of ionotropic glutamate receptor antagonists by the rational design of (2 S,3 R)-3-(3-carboxyphenyl)-pyrrolidine-2-carboxylic acid

ACS Chemical Neuroscience

Volumn 2, Issue 2, 2011, Pages 107-114

  Larsen, Ann M ^a   Venskutonytè, Raminta ^a   Valadés, Elena Antón ^a   Nielsen, Birgitte ^a   Pickering, Darryl S ^a   Bunch, Lennart ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

antagonist; Glutamate receptors; kainic acid receptors; rational design

Indexed keywords

3 (3 CARBOXYPHENYL)PYRROLIDINE 2 CARBOXYLIC ACID; AMPA RECEPTOR; GLUTAMATE RECEPTOR; GLUTAMATE RECEPTOR ANTAGONIST; KAINIC ACID RECEPTOR; LY 466195; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; PYRROLIDINE DERIVATIVE; UBP 310; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; DRUG TARGETING; HUMAN; HUMAN CELL; NONHUMAN; PRIORITY JOURNAL; RAT; STEREOCHEMISTRY; VOLTAGE CLAMP;

ANTAGONIST; GLUTAMATE RECEPTORS; KAINIC ACID RECEPTORS; RATIONAL DESIGN;

ANIMALS; CELL LINE; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; DRUG DISCOVERY; EXCITATORY AMINO ACID ANTAGONISTS; FEMALE; INSECTS; PROTEIN BINDING; PROTEIN STRUCTURE, SECONDARY; PYRROLIDINES; RATS; RECEPTORS, IONOTROPIC GLUTAMATE; XENOPUS LAEVIS;

EID: 79951847471     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn100093f     Document Type: Article

References (36)

1. Kaczor, A. A. and Matosiuk, D. (2010) Molecular structure of ionotropic glutamate receptors Curr. Med. Chem. 17, 2608-2635
2. Chen, P. E. and Wyllie, D. J. A. (2006) Pharmacological insights obtained from structure-function studies of ionotropic glutamate receptors Br. J. Pharmacol. 147, 839-853
3. Ferraguti, F. and Shigemoto, R. (2006) Metabotropic glutamate receptors Cell Tissue Res. 326, 483-504
4. Bartolotto and Clarke, Z. A. (1999) Kainate receptors are involved in synaptic plasticity Nature 402, 297
5. Mellor, J. R. (2006) Synaptic plasticity of kainate receptors Biochem. Soc. Trans. 34, 949-951 (Pubitemid 44796457)
6. Bloss, E. B. and Hunter, R. G. (2010) Hippocampal kainate receptors Vitam. Horm. 82, 167-184
7. Nistico, R., Dargan, S., Fitzjohn, S. M., Lodge, D., Jane, D. E., Collingridge, G. L., and Bortolotto, Z. A. (2009) GLUK1 receptor antagonists and hippocampal mossy fiber function Int. Rev. Neurobiol. 85, 13-27
8. Lau, A. and Tymianski, M. (2010) Glutamate receptors, neurotoxicity and neurodegeneration Pflugers Arch. 460, 525-542
9. Jane, D. E., Lodge, D., and Collingridge, G. L. (2009) Kainate receptors: pharmacology, function and therapeutic potential Neuropharmacology 56, 90-113
10. Bunch, L. and Krogsgaard-Larsen, P. (2009) Subtype selective kainic acid receptor agonists: discovery and approaches to rational design Med. Res. Rev. 29, 3-28
11. Gill, A., Birdsey-Benson, A., Jones, B. L., Henderson, L. P., and Madden, D. R. (2008) Correlating AMPA receptor activation and cleft closure across subunits: crystal structures of the GluR4 ligand-binding domain in complex with full and partial agonists Biochemistry 47, 13831-13841
12. Armstrong, N. and Gouaux, E. (2000) Mechanisms for activation and antagonism of an AMPA-sensitive glutamate receptor: Crystal structures of the GluR2 ligand binding core Neuron 28, 165-181
13. Mayer, M. L., Ghosal, A., Dolman, N. P., and Jane, D. E. (2006) Crystal structures of the kainate receptor GluR5 ligand binding core dimer with novel GluR5-selective antagonists J. Neurosci. 26, 2852-2861
14. Acevedo, C. M., Kogut, E. F., and Lipton, M. A. (2001) Synthesis and analysis of the sterically constrained l -glutamine analogues (3S,4R)-3,4-dimethyl- l -glutamine and (3S,4R)-3,4-dimethyl- l -pyroglutamic acid Tetrahedron 57, 6353-6359
15. Bunch, L., Krogsgaard-Larsen, P., and Madsen, U. (2002) Mixed cyano-gilman cuprates: advances in conjugate addition to alpha,beta-unsaturated pyroglutaminol Synthesis 31-33
16. Bunch, L., Nielsen, B., Jensen, A. A., and Brauner-Osborne, H. (2006) Rational design and enantioselective synthesis of (1R,4S,5R,6S)-3-azabicyclo[3. 3.0]octane-4,6-dicarboxylic acid-A novel inhibitor at human glutamate transporter subtypes 1, 2, and 3 J. Med. Chem. 49, 172-178
17. Bunch, L., Norrby, P. O., Frydenvang, K., Krogsgaard-Larsen, P., and Madsen, U. (2001) Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol Org. Lett. 3, 433-435
18. Carlsen, P. H. J., Katsuki, T., Martin, V. S., and Sharpless, K. B. (1981) A greatly improved procedure for ruthenium tetraoxide catalyzed oxidations of organic-compounds J. Org. Chem. 46, 3936-3938
19. Perrais, D., Pinheiro, P. S., Jane, D. E., and Mulle, C. (2009) Antagonism of recombinant and native GluK3-containing kainate receptors Neuropharmacology 56, 131-140
20. Moller, E. H., Egebjerg, J., Brehm, L., Stensbol, T. B., Johansen, T. N., Madsen, U., and Krogsgaard-Larsen, P. (1999) Resolution, absolute stereochemistry, and enantiopharmacology of the GluR1-4 and GluR5 antagonist 2-amino-3-[5-tert-butyl-3-(phosphonomethoxy)-4-isoxazolyl]propionic acid Chirality 11, 752-759
21. Weiss, B., Alt, A., Ogden, A. M., Gates, M., Dieckman, D. K., Clemens-Smith, A., Ho, K. H., Jarvie, K., Rizkalla, G., Wright, R. A., Calligaro, D. O., Schoepp, D., Mattiuz, E. L., Stratford, R. E., Johnson, B., Salhoff, C., Katofiasc, M., Phebus, L. A., Schenck, K., Cohen, M., Filla, S. A., Ornstein, P. L., Johnson, K. W., and Bleakman, D. (2006) Pharmacological characterization of the competitive GLU(K5) receptor antagonist decahydroisoquinoline LY466195 in vitro and in vivo J. Pharmacol. Exp. Ther. 318, 772-781
22. Weston, M. C., Schuck, P., Ghosal, A., Rosenmund, C., and Mayer, M. L. (2006) Conformational restriction blocks glutamate receptor desensitization Nat. Struct. Mol. Biol 13, 1120-1127
23. Perrais, D., Coussen, F., and Mulle, C. (2009) Atypical functional properties of GluK3-containing kainate receptors J. Neurosci. 29, 15499-15510
24. Wahl, P., Anker, C., Traynelis, S. F., Egebjerg, J., Rasmussen, J. S., Krogsgaard-Larsen, P., and Madsen, U. (1998) Antagonist properties of a phosphono isoxazole amino acid at glutamate R1-4 (R,S)-2-amino-3-(3-hydroxy-5- methyl-4-isoxazolyl)propionic acid receptor subtypes Mol. Pharmacol. 53, 590-596
25. Micheli, F., Di Fabio, R., and Marchioro, C. (1999) Asymmetric synthesis of some substituted-3-phenyl prolines Farmaco 54, 461-464
26. Doucet-Personeni, C., Bentley, P. D., Fletcher, R. J., Kinkaid, A., Kryger, G., Pirard, B., Taylor, A., Taylor, R., Taylor, J., Viner, R., Silman, I., Sussman, J. L., Greenblatt, H. M., and Lewis, T. (2001) A structure-based design approach to the development of novel, reversible AChE inhibitors J. Med. Chem. 44, 3203-3215
27. Honore, T. and Nielsen, M. (1985) Complex structure of quisqualate-sensitive glutamate receptors in rat cortex Neurosci, Lett. 54, 27-32
28. Braitman, D. J. and Coyle, J. T. (1987) Inhibition of [H-3] kainic acid receptor-binding by divalent-cations correlates with ion affinity for the calcium-channel Neuropharmacology 26, 1247-1251
29. Sills, M. A., Fagg, G., Pozza, M., Angst, C., Brundish, D. E., Hurt, S. D., Wilusz, E. J., and Williams, M. (1991) [H-3] Cgp-39653-A new N-methyl- d -aspartate antagonist radioligand with low nanomolar affinity in rat-brain Eur. J. Pharmacol. 192, 19-24
30. Hermit, M. B., Greenwood, J. R., Nielsen, B., Bunch, L., Jorgensen, C. G., Vestergaard, H. T., Stensbol, T. B., Sanchez, C., Krogsgaard-Larsen, P., Madsen, U., and Bräuner-Osborne, H. (2004) Ibotenic acid and thioibotenic acid: a remarkable difference in activity at group III metabotropic glutamate receptors Eur. J. Pharmacol. 486, 241-250
31. Clausen, R. P., Hansen, K. B., Cali, P., Nielsen, B., Greenwood, J. R., Begtrup, M., Egebjerg, J., and Brauner-Osborne, H. (2004) The respective N-hydroxypyrazole analogues of the classical glutamate receptor ligands ibotenic acid and (RS)-2-amino-2-(3-hydroxy-5-methyl-4-isoxazolyl)acetic acid Eur. J. Pharmacol. 499, 35-44
32. Vogensen, S. B., Clausen, R. P., Greenwood, J. R., Johansen, T. N., Pickering, D. S., Nielsen, B., Ebert, B., and Krogsgaard-Larsen, P. (2005) Convergent synthesis and pharmacology of substituted tetrazolyl-2-amino-3-(3- hydroxy-5-methyl-4-isoxazolyl)propionic acid analogues J. Med. Chem. 48, 3438-3442
33. Sagot, E., Pickering, D. S., Pu, X., Umberti, M., Stensbøl, T. B., Nielsen, B., Chapelet, M., Bolte, J., Gefflaut, T., and Bunch, L. (2008) Chemo-enzymatic synthesis of a series of 2,4-syn-functionalized (S)-glutamate analogues: new insight into the structure-activity-relation of ionotropic glutamate receptor subtypes 5, 6 and 7 J. Med. Chem. 51, 4093-4103
34. Nielsen, B. S., Banke, T. G., Schousboe, A., and Pickering, D. S. (1998) Pharmacological properties of homomeric and heteromeric GluR1(o) and GluR3(o) receptors Eur. J. Pharmacol. 360, 227-238
35. Greenwood, J. R., Mewett, K. N., Allan, R. D., Martin, B. O., and Pickering, D. S. (2006) 3-hydroxypyridazine 1-oxides as carboxylate bioisosteres: a new series of subtype-selective AMPA receptor agonists Neuropharmacology 51, 52-59
36. Leff, P. and Dougall, I. G. (1993) Further concerns over Cheng-Prusoff analysis Trends Pharmacol. Sci. 14, 110-112