Structure - Activity analysis of a novel NR2C/NR2D-preferring NMDA receptor antagonist: 1-(phenanthrene-2-carbonyl) piperazine-2,3-dicarboxylic acid

British Journal of Pharmacology

Volumn 141, Issue 3, 2004, Pages 508-516

  Feng, Bihua ^a   Tse, Heong W ^b,c   Skifter, Donald A ^a,d   Morley, Richard ^b   Jane, David E ^b   Monaghan, Daniel T ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

^c Langford House   (United Kingdom)

^d INVITROGEN CORPORATION   (United States)

Author keywords

Antagonist; Autoradiography; NMDA receptor; NR2; NR2C; NR2D; Recombinant; Xenopus oocyte

Indexed keywords

1 (1 PHENYLCYCLOPROPANECARBONYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (2 BIPHENYL 4 YLACETYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (2' BROMOBIPHENYL 4 CARBONYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (3 PHENYLACRYLOYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (4 FLUOROBENZOYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (4 IODOBENZOYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (4 NITROBENZOYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (4' FLUOROBIPHENYL 4 CARBONYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (9 OXO 9H FLUORENE 2 CARBONYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (BIPHENYL 4 CARBONYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (NAPHTHALENE 2 CARBONYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 (PHENANTHRENE 2 CARBONYL)PIPERAZINE 2,3 DICARBOXYLIC ACID; 1 BENZOYLPIPERAZINE 2,3 DICARBOXYLIC ACID; 1 DIPHENYLACETYLPIPERAZINE 2,3 DICARBOXYLIC ACID; ALPHA AMINO 5 (PHOSPHONOMETHYL)[1,1' BIPHENYL] 3 PROPANOIC ACID; DECAHYDRO 6 (2H TETRAZOL 5 YLMETHYL) 3 ISOQUINOLINECARBOXYLIC ACID; FLUORENONE DERIVATIVE; FUNCTIONAL GROUP; GLUTAMIC ACID; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; PHENANTHRENE DERIVATIVE; RECEPTOR SUBTYPE; UBP 101; UBP 102; UBP 104; UBP 106; UBP 107; UBP 108; UBP 109; UBP 112; UBP 120; UBP 121; UBP 122; UBP 130; UBP 131; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; MALE; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; XENOPUS LAEVIS;

ANIMALS; BIPHENYL COMPOUNDS; BRAIN; DIAZONIUM COMPOUNDS; DICARBOXYLIC ACIDS; EXCITATORY AMINO ACID ANTAGONISTS; FEMALE; MALE; PHENANTHRENES; PIPERAZINES; PYRIDINES; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, N-METHYL-D-ASPARTATE; STRUCTURE-ACTIVITY RELATIONSHIP; XENOPUS LAEVIS;

EID: 1542269774     PISSN: 00071188     EISSN: None     Source Type: Journal    
DOI: 10.1038/sj.bjp.0705644     Document Type: Article

References (33)

1. ANDALORO, V.J., JANE, D.J., TSE, H.W., WATKINS, J.C. & MONAGHAN, D.T. (1996). Pharmacology of NMDA receptor subtypes. Soc. Neurosci. Abstr., 22, 604.
2. ARMSTRONG, N., SUN, Y., CHEN, G.Q. & GOUAUX, E. (1998). Structure of a glutamate-receptor ligand-binding core in complex with kainate. Nature, 395, 913-917.
3. AUBERSON, Y.P., ALLGEIER, H., BISCHOFF, S., LINGENHOEHL, K., MORETTI, R. & SCHMUTZ, M. (2002). 5-Phosphonomethylquinoxalinediones as competitive NMDA receptor antagonists with a preference for the human 1A/2A, rather than 1A/2B receptor composition. Bioorg. Med. Chem. Lett., 12, 1099-1102.
4. BEATON, J.A., STEMSRUD, K. & MONAGHAN, D.T. (1992). Identification of a novel N-methyl-D-aspartate receptor population in the rat medial thalamus. J. Neurochem., 59, 754-757.
5. BIGGE, C.F. (1993). Structural requirements for the development of potent N-methyl-D-aspartic acid (NMDA) receptor antagonists. Biochem. Pharmacol., 45, 1547-1561.
6. BINNS, K.E., TURNER, J.P. & SALT, T.E. (1999). Visual experience alters the molecular profile of NMDA-receptor-mediated sensory transmission. Eur. J. Neurosci., 11, 1101-1104.
7. BULLER, A.L., LARSON, H.C., SCHNEIDER, B.E., BEATON, J.A., MORRISETT, R.A. & MONAGHAN, D.T. (1994). The molecular basis of NMDA receptor subtypes: native receptor diversity is predicted by subunit composition. J. Neurosci., 14, 5471-5484.
8. BULLER, A.L. & MONAGHAN, D.T. (1997). Pharmacological heterogeneity of NMDA receptors: characterization of NR1a/NR2D heteromers expressed in Xenopus oocytes. Eur. J. Pharmacol., 320, 87-94.
9. CHENG, Y. & PRUSOFF, W.H. (1973). Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol., 22, 3099-3108.
10. CHEUNG, N.S., O'ALLAGHAN, D., RYAN, M.C., DUTTON, R., WONG, M.G. & BEART, P.M. (1996). Structure - activity relationships of competitive NMDA receptor antagonists. Eur. J. Pharmacol., 313, 159-162.
11. CHOI, D. (1998). Antagonizing excitotoxicity: a therapeutic strategy for stroke? Mt. Sinai J. Med., 65, 133-138.
12. CHRISTIE, J.M., JANE, D.E. & MONAGHAN, D.T. (2000). Native N-methyl-D-aspartate receptors containing NR2A and NR2B subunits have pharmacologically distinct competitive antagonist binding sites. J. Pharmacol. Exp. Ther., 292, 1169-1174.
13. DINGLEDINE, R., BORGES, K., BOWIE, D. & TRAYNELIS, S.F. (1999). The glutamate receptor ion channels. Pharmacol. Rev., 51, 7-61.
14. DURAND, G.M., GREGOR, P., ZHENG, X., BENNETT, M.V., UHL, G.R. & ZUKIN, R.S. (1992). Cloning of an apparent splice variant of the rat N-methyl-D-aspartate receptor NMDAR1 with altered sensitivity to polyamines and activators of protein kinase C. Proc. Natl. Acad. Sci. U.S.A., 89, 9359-9363.
15. FELDER, E, MAFFEI, S., PIETRA, S. & PITRÈ, D. (1960). Catalytic hydrogenation of piperazine carboxylic acids. Helv. Chim. Acta, 117, 888-896.
16. HARRIS, N.C. & DAVIES, J. (1992). Cortically evoked excitatory synaptic transmission in the cat red nucleus is antagonised by D-AP5 but not by D-AP7. Brain Res, 594, 176-180.
17. HOLLMANN, M., BOULTER, J., MARON, C., BEASLEY, L., SULLIVAN, J., PECHT, G. & HEINEMANN, S. (1993). Zinc potentiates agonist-induced currents at certain splice variants of the NMDA receptor. Neuron, 10, 943-954.
18. HRABETOVA, S., SERRANO, P., BLACE, N., TSE, H.W., SKIFTER, D.A., JANE, D.E., MONAGHAN, D.T. & SACKTOR, T.C. (2000). Distinct NMDA receptor subpopulations contribute to long-term potentiation and long-term depression induction. J. Neurosci. (Online), 20, RC81.
19. IKEDA, K., NAGASAWA, M., MORI, H., ARAKI, K., SAKIMURA, K., WATANABE, M., INOUE, Y. & MISHINA, M. (1992). Cloning and expression of the epsilon 4 subunit of the NMDA receptor channel. FEBS Lett., 313, 34-38.
20. ISHII, T., MORIYOSHI, K., SUGIHARA, H., SAKURADA, K., KADOTANI, H., YOKOI, M., AKAZAWA, C., SHIGEMOTO, R., MIZUNO, N., MASU, M. & NAKANISHI, S. (1993). Molecular characterization of the family of the N-methyl-D-aspartate receptor subunits. J. Biol. Chem., 268, 2836-2843.
21. JANE, D.E., OLVERMAN, H.J. & WATKINS, J.C. (1994). Agonists and Competitive Antagonists: Structure - Activity and Molecular Modelling Studies. Oxford: Oxford University Press.
22. KENDRICK, S.J., LYNCH, D.R. & PRITCHETT, D.B. (1996). Characterization of glutamate binding sites in receptors assembled from transfected NMDA receptor subunits. J. Neurochem., 67, 608-616.
23. LAUBE, B., HIRAI, H., STURGESS, M., BETZ, H. & KUHSE, J. (1997). Molecular determinants of agonist discrimination by NMDA receptor subunits: analysis of the glutamate binding site on the NR2B subunit. Neuron, 18, 493-503.
24. LAURIE, D.J. & SEEBURG, P.H. (1994). Ligand affinities at recombinant N-methyl-D-aspartate receptors depend on subunit composition. Eur. J. Pharmacol., 268, 335-345.
25. MINAMI, T., MATSUMURA, S., OKUDA-ASHITAKA, E., SHIMAMOTO, K., SAKIMURA, K., MISHINA, M., MORI, H. & ITO, S. (2001). Characterization of the glutamatergic system for induction and maintenance of allodynia. Brain Res., 895, 178-185.
26. MONAGHAN, D.T., ANDALORO, V.J. & SKIFTER, D.A. (1998). Molecular determinants of NMDA receptor pharmacological diversity. Prog. Brain Res., 116, 158-177.
27. MONAGHAN, D.T. & COTMAN, C.W. (1986). Identification and properties of N-methyl-D-aspartate receptors in rat brain synaptic plasma membranes. Proc. Natl. Acad. Sci. U.S.A., 83, 7532-7536.
28. MONAGHAN, D.T., OLVERMAN, H.J., NGUYEN, L., WATKINS, J.C. & COTMAN, C.W. (1988). Two classes of N-methyl-D-aspartate recognition sites: differential distribution and differential regulation by glycine. Proc. Natl. Acad. Sci. U.S.A., 85, 9836-9840.
29. MONYER, H., BURNASHEV, N., LAURIE, D.J., SAKMANN, B. & SEEBURG, P.H. (1994). Developmental and regional expression in the rat brain and functional properties of four NMDA receptors. Neuron, 12, 529-540.
30. NAKANISHI, S., NAKAJIMA, Y., MASU, M., UEDA, Y., NAKAHARA, K., WATANABE, D., YAMAGUCHI, S., KAWABATA, S. & OKADA, M. (1998). Glutamate receptors: brain function and signal transduction. Brain Res. Brain Res. Rev., 26, 230-235.
31. VICINI, S., WANG, J.F., LI, J.H., ZHU, W.J., WANG, Y.H., LUO, J.H., WOLFE, B.B. & GRAYSON, D.R. (1998). Functional and pharmacological differences between recombinant N-methyl-D-aspartate receptors. J. Neurophysiol., 19, 555-566.
32. WATANABE, M., INOUE, Y., SAKIMURA, K. & MISHINA, M. (1992). Developmental changes in distribution of NMDA receptor channel subunit mRNAs. Neuroreport, 3, 1138-1140.
33. WATANABE, M., INOUE, Y., SAKIMURA, K. & MISHINA, M. (1993). Distinct spatio-temporal distributions of the NMDA receptor channel subunit mRNAs in the brain. Ann. N.Y. Acad. Sci., 707, 463-466.