Mechanism of inhibition of the GluA2 AMPA receptor channel opening: Consequences of adding an N- 3 methylcarbamoyl group to the diazepine ring of 2,3-benzodiazepine derivatives

Biochemistry

Volumn 50, Issue 33, 2011, Pages 7284-7293

  Wang, Congzhou ^a   Sheng, Zhenyu ^a,b   Niu, Li ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b RUTGERS NEW JERSEY MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMPA-RECEPTOR; CURRENT AMPLITUDE; DIAZEPINE; INHIBITOR COMPLEX; INHIBITORY EFFECT; MECHANISM OF ACTION; NEUROLOGICAL DISEASE; POTENTIAL DRUG; SOLUTION FLOWS;

PHOTOLYSIS;

RATE CONSTANTS;

1 (4 AMINOPHENYL) 3,4 DIHYDRO 4 METHYL 3 METHYLCARBAMOYL 7,8 METHYLENEDIOXY 5H 2,3 BENZODIAZEPINE; 1 (4 AMINOPHENYL) 4 METHYL 7,8 METHYLENEDIOXY 5H 2,3 BENZODIAZEPINE; AMPA RECEPTOR; AZOMETHINE YLIDE; BENZODIAZEPINE DERIVATIVE; DIAZEPINE DERIVATIVE; GLUA2 AMPA RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATION; DRUG MECHANISM; EMBRYO; HUMAN; HUMAN CELL; INHIBITION KINETICS; LASER PULSE PHOTOLYSIS; PHOTOLYSIS; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

BENZODIAZEPINES; CELLS, CULTURED; HUMANS; ION CHANNEL GATING; KIDNEY; KINETICS; LASERS; PHOTOLYSIS; PROTEIN BINDING; RECEPTORS, AMPA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80051719677     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi2007977     Document Type: Article

References (26)

1. Ritz, M., Micale, N., Grasso, S., and Niu, L. (2008) Mechanism of inhibition of the GluR2 AMPA receptor channel opening by 2,3-benzodiazepine derivatives Biochemistry 47, 1061-1069
2. Ritz, M., Wang, C. Z., Micale, N., Ettari, R., and Niu, L. Mechanism of Inhibition of the GluA2 AMPA Receptor Channel Opening: the Role of 4-Methyl versus 4-Carbonyl Group on the Diazepine Ring of 2,3-Benzodiazepine Derivatives. ACS Chem. Neurosci. 2011, in press.
3. Davies, J. and Watkins, J. C. (1981) Differentiation of kainate and quisqualate receptors in the cat spinal cord by selective antagonism with gamma-D(and L)-glutamylglycine Brain Res. 206, 172-177 (Pubitemid 11143585)
4. Dingledine, R., Borges, K., Bowie, D., and Traynelis, S. F. (1999) The glutamate receptor ion channels Pharmacol. Rev. 51, 7-61 (Pubitemid 29113865)
5. Palmer, C. L., Cotton, L., and Henley, J. M. (2005) The molecular pharmacology and cell biology of alpha-amino-3-hydroxy-5-methyl-4- isoxazolepropionic acid receptors Pharmacol. Rev. 57, 253-277 (Pubitemid 41043886)
6. Cull-Candy, S., Kelly, L., and Farrant, M. (2006) Regulation of Ca2+-permeable AMPA receptors: synaptic plasticity and beyond Curr. Opin. Neurobiol. 16, 288-297
7. Liu, S. J. and Zukin, R. S. (2007) Ca2+-permeable AMPA receptors in synaptic plasticity and neuronal death Trends Neurosci. 30, 126-134 (Pubitemid 46283597)
8. Hume, R. I., Dingledine, R., and Heinemann, S. F. (1991) Identification of a site in glutamate receptor subunits that controls calcium permeability Science 253, 1028-1031 (Pubitemid 21917250)
9. Zappala, M., Grasso, S., Micale, N., Polimeni, S., and De Micheli, C. (2001) Synthesis and structure-activity relationships of 2,3-benzodiazepines as AMPA receptor antagonists Mini-Rev. Med. Chem. 1, 243-253
10. Solyom, S. and Tarnawa, I. (2002) Non-competitive AMPA antagonists of 2,3-benzodiazepine type Curr. Pharm. Des. 8, 913-939 (Pubitemid 34516329)
11. Tarnawa, I., Farkas, S., Berzsenyi, P., Pataki, A., and Andrasi, F. (1989) Electrophysiological studies with a 2,3-benzodiazepine muscle relaxant: GYKI 52466 Eur. J. Pharmacol. 167, 193-199 (Pubitemid 19215469)
12. Li, G., Pei, W., and Niu, L. (2003) Channel-opening kinetics of GluR2Q(flip) AMPA receptor: a laser-pulse photolysis study Biochemistry 42, 12358-12366 (Pubitemid 37296512)
13. Wieboldt, R., Gee, K. R., Niu, L., Ramesh, D., Carpenter, B. K., and Hess, G. P. (1994) Photolabile precursors of glutamate: synthesis, photochemical properties, and activation of glutamate receptors on a microsecond time scale Proc. Natl. Acad. Sci. U. S. A. 91, 8752-8756
14. Li, G., Oswald, R. E., and Niu, L. (2003) Channel opening kinetics of GluR6 kainate receptor Biochemistry 42, 12367-12375 (Pubitemid 37296513)
15. Chen, C. and Okayama, H. (1987) High-efficiency transformation of mammalian cells by plasmid DNA Mol. Cell. Biol. 7, 2745-2752
16. Huang, Z., Li, G., Pei, W., Sosa, L. A., and Niu, L. (2005) Enhancing protein expression in single HEK 293 cells J. Neurosci. Methods 142, 159-166 (Pubitemid 40138041)
17. Udgaonkar, J. B. and Hess, G. P. (1987) Chemical kinetic measurements of a mammalian acetylcholine receptor by a fast-reaction technique Proc. Natl. Acad. Sci. U. S. A. 84, 8758-8762
18. Li, G. and Niu, L. (2004) How fast does the GluR1Qflip channel open? J. Biol. Chem. 279, 3990-3997. Epub 2003 Nov 3910. (Pubitemid 38198981)
19. Sommer, B., Keinanen, K., Verdoorn, T. A., Wisden, W., Burnashev, N., Herb, A., Kohler, M., Takagi, T., Sakmann, B., and Seeburg, P. H. (1990) Flip and flop: a cell-specific functional switch in glutamate-operated channels of the CNS Science 249, 1580-1585
20. Mayer, M. L. and Vyklicky, L., Jr. (1989) Concanavalin A selectively reduces desensitization of mammalian neuronal quisqualate receptors Proc. Natl. Acad. Sci. U. S. A. 86, 1411-1415 (Pubitemid 19061556)
21. Koike, M., Tsukada, S., Tsuzuki, K., Kijima, H., and Ozawa, S. (2000) Regulation of kinetic properties of GluR2 AMPA receptor channels by alternative splicing J. Neurosci. 20, 2166-2174 (Pubitemid 30230069)
22. Lee, C. J., Labrakakis, C., Joseph, D. J., and Macdermott, A. B. (2004) Functional similarities and differences of AMPA and kainate receptors expressed by cultured rat sensory neurons Neuroscience 129, 35-48 (Pubitemid 39360939)
23. Brorson, J. R., Manzolillo, P. A., Gibbons, S. J., and Miller, R. J. (1995) AMPA receptor desensitization predicts the selective vulnerability of cerebellar Purkinje cells to excitotoxicity J. Neurosci. 15, 4515-4524
24. Pei, W., Huang, Z., Wang, C., Han, Y., Park, J. S., and Niu, L. (2009) Flip and flop: a molecular determinant for AMPA receptor channel opening Biochemistry 48, 3767-3777
25. Lodge, D., Bond, A., O'Neill, M. J., Hicks, C. A., and Jones, M. G. (1996) Stereoselective effects-of 2,3-benzodiazepines in vivo: electrophysiology and neuroprotection studies Neuropharmacology 35, 1681-1688 (Pubitemid 27090787)
26. Bleakman, D., Ballyk, B. A., Schoepp, D. D., Palmer, A. J., Bath, C. P., Sharpe, E. F., Woolley, M. L., Bufton, H. R., Kamboj, R. K., Tarnawa, I., and Lodge, D. (1996) Activity of 2,3-benzodiazepines at native rat and recombinant human glutamate receptors in vitro: stereospecificity and selectivity profiles Neuropharmacology 35, 1689-1702 (Pubitemid 27090788)