Stereochemistry of glutamate receptor agonist efficacy: Engineering a dual-specificity AMPA/kainate receptor

Biochemistry

Volumn 43, Issue 50, 2004, Pages 15838-15844

  Madden, Dean R ^b,c   Cheng, Qing ^a   Thiran, Shalita ^d   Rajan, Shanti ^a   Rigo, Frank ^d   Keinänen, Kari ^e   Reinelt, Stefan ^c   Zimmermann, Herbert ^c   Jayaraman, Vasanthi ^a  

^a UNIVERSITY OF TEXAS MEDICAL SCHOOL   (United States)

^b DARTMOUTH MEDICAL SCHOOL   (United States)

^c MAX PLANCK INSTITUTE FOR MEDICAL RESEARCH   (Germany)

^d MARQUETTE UNIVERSITY   (United States)

^e UNIVERSITY OF HELSINKI   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; AMINO ACIDS; BINDING ENERGY; CONFORMATIONS; FLUORESCENCE; MUTAGENESIS;

CHANNEL ACTIVATION; IONOTROPIC GLUTAMATE RECEPTORS (IGLUR); LIGAND-BINDING; PARTIAL AGONISM;

STEREOCHEMISTRY;

ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; AMPA RECEPTOR; GLUTAMATE RECEPTOR 2; GLUTAMATE RECEPTOR 4; GLUTAMIC ACID; KAINIC ACID; KAINIC ACID RECEPTOR;

ARTICLE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SPECIFICITY; FLUORESCENCE SPECTROSCOPY; HUMAN; HUMAN CELL; LIGAND BINDING; PRIORITY JOURNAL; RECEPTOR UPREGULATION; STEREOCHEMISTRY; WILD TYPE;

ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID; CELL LINE; ELECTRIC CONDUCTIVITY; EXCITATORY AMINO ACID AGONISTS; HUMANS; KAINIC ACID; MUTATION; PROTEIN ENGINEERING; RECEPTORS, AMPA; RECEPTORS, KAINIC ACID;

EID: 10844261750     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi048447y     Document Type: Article

References (31)

1. Mayer, M. L., and Armstrong, N. (2004) Structure and function of glutamate receptor ion channels, Annu. Rev. Physiol. 66, 161-81.
2. McFeeters, R. L., and Oswald, R. E. (2004) Emerging structural explanations of ionotropic glutamate receptor function, Faseb J. 18, 428-38.
3. Gouaux, E. (2004) Structure and function of AMPA receptors, J. Physiol. 554, 249-53.
4. Madden, D. R. (2002) The inner workings of the AMPA receptors, Curr. Opin Drug Discovery Dev. 5, 741-8.
5. Madden, D. R. (2002) The structure and function of glutamate receptor ion channels, Nat. Rev. Neurosci. 3, 91-101.
6. Dingledine, R., Borges, K., Bowie, D., and Traynelis, S. F. (1999) The glutamate receptor ion channels, Pharm. Rev. 51, 7-61.
7. Nakanishi, S., and Masu, M. (1994) Molecular diversity and functions of glutamate receptors, Annu. Rev. Biophys. Biomol. Struct. 23, 329-348.
8. Hollmann, M., and Heinemann, S. (1994) Cloned glutamate receptors, Annu. Rev. Neurosci. 17, 31-108.
9. Armstrong, N. A., 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.
10. Hogner, A., Kastrup, J. S., Jin, R., Liljefors, T., Mayer, M. L., Egebjerg, J., Larsen, I. K., and Gouaux, E. (2002) Structural basis for AMPA receptor activation and ligand selectivity: Crystal structures of five agonist complexes with the GluR2 ligand-binding core, J. Mol. Biol. 322, 93-109.
11. Jin, R., Banke, T. G., Mayer, M. L., Traynelis, S. F., and Gouaux, E. (2003) Structural basis for partial agonist action at ionotropic glutamate receptors, Nat. Neurosci. 6, 803-10.
12. McFeeters, R. L., and Oswald, R. E. (2002) Structural mobility of the extracellular ligand-binding core of an ionotropic glutamate receptor. Analysis of NMR relaxation dynamics, Biochemistry 41, 10472-81.
13. Mano, I., Lamed, Y., and Teichberg, V. I. (1996) A venus flytrap mechanism for activation and desensitization of alpha-amino-3-hydroxy-5-methyl- 4-isoxazole propionic acid receptors, J. Biol. Chem. 271, 15299-302.
14. Armstrong, N., Mayer, M., and Gouaux, E. (2003) Tuning activation of the AMPA-sensitive GluR2 ion channel by genetic adjustment of agonist-induced conformational changes, Proc. Natl. Acad. Sci. U.S.A. 100, 5736-41.
15. Arinaminpathy, Y., Sansom, M. S., and Biggin, P. C. (2002) Molecular dynamics simulations of the ligand-binding domain of the ionotropic glutamate receptor GluR2, Biophys. J. 82, 676-83.
16. Jayaraman, V., Keesey, R., and Madden, D. R. (2000) Ligand-protein interactions in the glutamate receptor, Biochemistry 39, 8693-8697.
17. Madden, D. R., Thiran, S., Zimmermann, H., Romm, J., and Jayaraman, V. (2001) Stereochemistry of quinoxaline antagonist binding to a glutamate receptor investigated by Fourier transform infrared spectroscopy, J. Biol. Chem. 276, 37821-37826.
18. Abele, R., Keinänen, K., and Madden, D. R. (2000) Agonist-induced isomerization in a glutamate receptor ligand-binding domain: A kinetic and mutagenetic analysis, J. Biol. Chem. 275, 21355-21363.
19. Lampinen, M., Pentikäinen, O., Johnson, M. S., and Keinänen, K. (1998) AMPA receptors and bacterial periplasmic amino acid-binding proteins share the ionic mechanism of ligand recognition, EMBO J. 17, 4704-4711.
20. Jacobsen, N., Kolind-Andersen, H., and Christensen, J. (1984) Synthesis of 3-isoxazolols revisited: Diketene and beta ketoesters as starting materials, Can. J. Chem. 62, 1940-1944.
21. Sørensen, U. S., Falch, E., and Krogsgaard-Larsen, P. (2000) A novel route to 5-substituted 3-isoxazolols. Cyclization of N,O-DiBoc β-keto hydroxamic acids synthesized via acyl Meldrum's acids, J. Org. Chem. 65, 1003-1007.
22. Honore, T., and Lauridsen, J. (1980) Structural analogues of ibotenic acid. Syntheses of 4-methyl-homoibotenic acid and AMPA, including the crystal structure of AMPA, monohydrate, Acta. Chem. Scand. 34 (4B), 235-240.
23. Begtrup, M., and Sløk, F. A. (1993) Equilibrium control in bromomethylation: An expedient route to 2-amino-3-(3-hydroxy-5-methylisoxazol-4- yl)propionic acid (AMPA), Synthesis 1993, 861-863.
24. Cheng, Q., Thiran, S., Yernool, D., Gouaux, E., and Jayaraman, V. (2002) A vibrational spectroscopic investigation of interactions of agonists with GluR0, a prokaryotic glutamate receptor, Biochemistry 41, 1602-8.
25. Cheng, Q., and Jayaraman, V. (2004) Chemistry and conformation of the ligand-binding domain of GluR2 subtype of glutamate receptors, J. Biol. Chem. 279, 26346-50.
26. Li, H. M., and Thomas, G. J. (1991) Cysteine Conformation and Sulfhydryl Interactions in Proteins and Viruses. 1. Correlation of the Raman S-H Band with Hydrogen-Bonding and Intramolecular Geometry in Model Compounds, J. Am. Chem. Soc. 113, 456-462.
27. Ippolito, J. A., Alexander, R. S., and Christianson, D. W. (1990) Hydrogen bond stereochemistry in protein structure and function, J. Mol. Biol. 215, 457-471.
28. Armstrong, N., Sun, Y., Chen, G. Q., and Gouaux, E. (1998) Structure of a glutamate receptor ligand-binding core in complex with kainate, Nature 395, 913-7.
29. Spiro, T. G. (1987) Biological applications of Raman spectroscopy, Wiley, New York.
30. Byler, D. M., and Susi, H. (1986) Examination of the secondary structure of proteins by deconvolved FTIR spectra, Biopolymers 25, 469-487.
31. Chapman, D., Jackson, M., and Haris, P. I. (1989) Investigation of Membrane-Protein Structure Using Fourier Transform Infrared-Spectroscopy, Biochem. Soc. Trans. 17, 617-619.