Coumarin-caged glycine that can be photolyzed within 3 μs by visible light

Biochemistry

Volumn 46, Issue 18, 2007, Pages 5479-5484

  Shembekar, Vishakha R ^a   Chen, Yongli ^a   Carpenter, Barry K ^a   Hess, George P ^a  

^a Department of Molecular Biology and Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; NEUROLOGY; PHOTOLYSIS; REACTION KINETICS; SYNTHESIS (CHEMICAL); ULTRAVIOLET RADIATION;

GLYCINE RECEPTORS; NEUROTRANSMITTER RECEPTOR; VISIBLE LIGHT;

AMINO ACIDS;

CARBOXYL GROUP; COUMARIN DERIVATIVE; GLYCINE; GLYCINE RECEPTOR; NEUROTRANSMITTER RECEPTOR;

ARTICLE; CELL SURFACE; CHEMICAL ANALYSIS; CONTROLLED STUDY; COVALENT BOND; HUMAN; HUMAN CELL; LIGHT; PHOTOLYSIS; PRIORITY JOURNAL; PROTEIN ANALYSIS; QUANTUM YIELD;

CELL LINE; COUMARINS; GLYCINE; HUMANS; LASERS; PHOTOLYSIS; RECEPTORS, NEUROTRANSMITTER;

EID: 34248196084     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi700280e     Document Type: Article

References (41)

1. Kaplan, J. H., Forbush, B., III, and Hoffman, J. F. (1978) Rapid photolytic release of adenosine 5′-triphosphate from a protected analogue: Utilization by the Na:K pump of human red blood cell ghosts, Biochemistry 17, 1929-1935.
2. Mariott, G., Ed. (1998) Methods in Enzymology: Caged Compounds, Vol. 291, Academic Press, New York.
3. Milburn, T., Matsubara, N., Billington, A. P., Udgaonkar, J. B., Walker, J. W., Carpenter, B. K., Webb, W. W., Marque, J., Denk, W., McCray, J. A., and Hess, G. P. (1989) Synthesis, photochemistry, and biological activity of a caged photolabile acetylcholine receptor ligand, Biochemistry 28, 49-55.
4. Corrie, J. E. T., and Trentham, D. R. (1993) Caged nucleotides and neurotransmitters, Bioorg. Photochem. 2, 243-305.
5. Adams, S. R., and Tsien, R. Y. (1993) Controlling cell chemistry with caged compounds, Annu. Rev. Physiol. 55, 755-784.
6. Pelliccioli, A. P., and Wirz, J. (2002) Photoremovable protecting groups: Reaction mechanisms and applications, Photochem. Photobiol. Sci. 1, 441-458.
7. Hess, G. P., and Grewer, C. (1998) Development and application of caged ligands for neurotransmitter receptors in transient kinetic and neuronal circuit mapping studies, Methods Enzymol. 291, 443-473.
8. Goeldner, M., and Givens, R. S., Eds. (2005) Dynamic Studies in Biology: Phototriggers, Photoswitches, and Caged Biomolecules, Wiley-VCH, Weinheim, Germany.
9. Gutfreund, H. (1995) Kinetics for the Life Sciences. Receptor, Transmitters and Catalysts, Cambridge University Press, Cambridge, U.K.
10. Fersht, A. (1999) Enzyme Structure and Mechanism, W. H. Freeman, New York.
11. Hammes, G. G. (2000) Thermodynamics and Kinetics for the Biological Sciences, John Wiley & Sons, New York.
12. Johnson, K. A. (2003) Kinetic Analysis of Macromolecules, Oxford University Press, Oxford, U.K.
13. Landau, V. G., and Lifshitz, E. M. (1959) Fluid Mechanics, Pergamon Press, Oxford, U.K.
14. 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.
15. Furuta, T., Torigai, H., Sugimoto, M., and Iwamura, M. (1995) Photochemical properties of new photolabile cAMP derivatives in a physiological saline solution, J. Org. Chem. 60, 3953-3956.
16. Givens, R. S., and Matuszewski, B. J. (1984) Photochemistry of phosphate esters: An efficient method for the generation of electrophiles, J. Am. Chem. Soc. 106, 6860-6861.
17. Hagen, V., Bendig, J., Frings, S., Wiesner, B., Schade, B., Helm, S., Lorenz, D., and Kaupp, U. B. (1999) Synthesis, photochemistry and application of (7-methoxycoumarin-4-yl)methyl-caged 8-bromoadenosine cyclic 3′,5′-monophosphate and 8-bromoguanosine cyclic 3′,5′- monophosphate photolyzed in the nanosecond time region, J. Photochem. Photobiol., B 53, 91-102.
18. Hagen, V., Bendig, J., Frings, S., Eckardt, T., Helm, S., Reuter, D., and Kaupp, U. B. (2001) Highly efficient and ultrafast phototriggers for cAMP and cGMP by using long-wavelength UV/Vis-activation, Angew. Chem., Int. Ed. 40, 1045-1048.
19. Geissler, D., Kresse, W., Wiesner, B., Bendig, J., Kettenmann, H., and Hagen, V. (2003) DMACM-caged adenosine nucleotides: Ultrafast phototriggers for ATP, ADP, and AMP activated by long-wavelength irradiation, ChemBioChem 4, 162-170.
20. Geissler, D., Antonenko, Y. A., Schmidt, R., Keller, S., Krylova, O. O., Wiesner, B., Bendig, J., Pohl, P., and Hagen, V. (2005) (Coumarin-4-yl)methyl esters as highly efficient, ultrafast phototriggers for protons and their application to acidifying membrane surfaces, Angew. Chem., Int. Ed. 44, 1195-1198.
21. Shembekar, V. R., Chen, Y., Carpenter, B. K., and Hess, G. P. (2005) A protecting group for carboxylic acids that can be photolyzed by visible light, Biochemistry 44, 7107-7114.
22. Lin, W., and Lawrence, D. S. (2002) A strategy for the construction of caged diols using a photolabile protecting group, J. Org. Chem. 67, 2723-2726.
23. Suzuki, A. Z., Watanabe, T., Kawamoto, M., Nishiyama, K., Yamashita, H., Ishii, M., Iwamura, M., and Furuta, T. (2003) Coumarin-4-ylmethoxycarbonyls as phototriggers for alcohols and phenols, Org. Lett. 5, 4867-4870.
24. Lu, M., Fedoryak, O. D., Moister, D. R., and Dore, T. M. (2003) Bhc-diol as a photolabile protecting group for aldehydes and ketones, Org. Lett. 5, 2119-2122.
25. Legendre, P. (2001) The glycinergic inhibitory synapse, Cell. Mol. Life Sci. 58, 760-793.
26. Jones, M. V., and Harrison, N. L. (1993) Effects of volatile anesthetics on the kinetics of inhibitory postsynaptic currents in cultured rat hippocampal neurons, J. Neurophysiol. 70, 1339-1349.
27. Mascia, M. P., Machu, T. K., and Harris, R. A. (1996) Enhancement of homomeric glycine receptor function by long-chain alcohols and anesthetics, Br. J. Pharmacol. 119, 1331-1336.
28. Daniels, S., and Roberts, R. J. (1998) Post-synaptic inhibitory mechanisms of anaesthesia: Glycine receptors, Toxicol. Lett. 100-101, 71-76.
29. Becker, C. M., Schmieden, V., Tarroni, P., Strasser, U., and Betz, H. (1992) Isoform-selective deficit of glycine receptors in the mouse mutant spastic, Neuron 8, 283-289.
30. Shiang, R., Ryan, S. G., Zhu, Y. Z., Hahn, A. F., O'Connell, P., and Wasmuth, J. J. (1993) Mutations in the α1 subunit of the inhibitory glycine receptor cause the dominant neurologic disorder, hyperekplexia, Nat. Genet. 5, 351-358.
31. Hagen, V., Frings, S., Wiesner, B., Helm, S., Kaupp, U. B., and Bendig, J. (2003) [7-(Dialkylamino)coumarin-4-yl]methyl-caged compounds as ultrafast and effective long-wavelength phototriggers of 8-bromo-substituted cyclic nucleotides, ChemBioChem 4, 434-442.
32. Murov, S. L., Carmichael, I., and Hug, G. L. (1993) Handbook of Photochemistry, pp 298-305, Marcel Dekker, New York.
33. Betz, H., and Laube, B. (2006) Glycine receptors: Recent insights into their structural organization and functional diversity, J. Neurochem. 97, 1600-1610.
34. Chalfie, M., Tu, Y., Euskirchen, G., Ward, W. W., and Prasher, D. C. (1994) Green fluorescent protein as a marker for gene expression, Science 263, 802-805.
35. Hamill, O. P., Marty, A., Neher, E., Sakmann, B., and Sigworth, F. J. (1981) Improved patch-clamp techniques for high-resolution current recording from cells and cell-free membrane patches, Pfluegers Arch. 391, 85-100.
36. Krishtal, O. A., and Pidoplichko, V. I. (1980) A receptor for protons in the nerve cell membrane, Neuroscience 5, 2325-2327.
37. Niu, L., Grewer, C., and Hess, G. P. (1996) Chemical kinetic investigations of neurotransmitter receptors on a cell surface in the μs time region, Tech. Protein Chem. VII, [Symp. Protein Soc.], 139-149.
38. Grewer, C. (1999) Investigation of the α1-glycine receptor channel-opening kinetics in the submillisecond time domain, Biophys. J. 77, 727-738.
39. Gee, K. R., Carpenter, B. K., and Hess, G. P. (1998) Synthesis, photochemistry, and biological characterization of photolabile protecting groups for carboxylic acids and neurotransmitters, Methods Enzymol. 291, 30-50.
40. Hess, G. P. (2003) Rapid chemical reaction techniques developed for use in investigations of membrane-bound proteins (neurotransmitter receptors), Biophys. Chem. 100, 493-506.
41. Banerjee, A., Grewer, C., Ramakrishnan, L., Jäger, J., Gameiro, A., Breitinger, H. A., Gee, K. R., Carpenter, B. K., and Hess, G. P. (2003) Toward the development of new photolabile protecting groups that can rapidly release bioactive compounds upon photolysis with visible light, J. Org. Chem. 68, 8361-8367.