A protecting group for carboxylic acids that can be photolyzed by visible light

Biochemistry

Volumn 44, Issue 19, 2005, Pages 7107-7114

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

^a Department of Obstetrics Gynecology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; AMINES; COMPLEXATION; KINETIC THEORY; LIGHT SOURCES; PH EFFECTS; PHOTOLYSIS;

7-N,N-DIETHYL AMINCOUMARIN (DECM); CAGING GROUPS; VISIBLE LIGHT; VISIBLE WAVELENGTH;

CARBOXYLIC ACIDS;

4 CARBOXYGLUTAMIC ACID; CARBOXYLIC ACID; COUMARIN DERIVATIVE; GLUTAMATE RECEPTOR; GLUTAMIC ACID; NEUROTRANSMITTER RECEPTOR;

ARTICLE; CONTROLLED STUDY; HUMAN; HUMAN CELL; LIGHT; PHOTOLYSIS; PRIORITY JOURNAL; PROTEIN EXPRESSION; QUANTUM YIELD; SIGNAL TRANSDUCTION; ULTRAVIOLET RADIATION;

CELL LINE; COUMARINS; GLUTAMATES; GLUTAMIC ACID; HUMANS; LASERS; LIGHT; PHOTOLYSIS; RECEPTORS, KAINIC ACID;

MUS;

EID: 18544369446     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi047665o     Document Type: Article

References (53)

1. De Mayo, P. (1960) Ultraviolet photochemistry of simple unsaturated systems, Adv. Org. Chem. 2, 367-425.
2. Barltrop, J. A., Plant, P. J., and Schofield, P. (1966) Photosensitive protective groups, J. Chem. Soc., Chem. Commun., 822-823.
3. Knowles, J. R. (1972) Photogenerated reagents for biological receptor-site labeling, Acc. Chem. Res. 5, 155-160.
4. Patchornik, A., Amit, B., and Woodward, R. B. (1970) Photosensitive protecting groups, J. Am. Chem. Soc. 92, 6333-6335.
5. 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.
6. 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.
7. Jayaraman, V., Thiran, S., and Hess, G. P. (1999) How fast does the gamma-aminobutyric acid receptor channel open? Kinetic investigations in the microsecond time region using a laser-pulse photolysis technique, Biochemistry 38, 11372-11378.
8. Grewer, C., and Hess, G. P. (1999) On the mechanism of inhibition of the nicotinic acetylcholine receptor by the anticonvulsant MK-801 investigated by laser-pulse photolysis in the microsecond-to-millisecond time region, Biochemistry 38, 7837-7846.
9. Ramakrishnan, L., and Hess, G. P. (2004) On the mechanism of a mutated and abnormally functioning γ-aminobutyric acid (A) receptor linked to epilepsy, Biochemistry 43, 7534-7540.
10. Hess, G. P. (2003) Rapid chemical reaction techniques developed for use in investigations of membrane-bound proteins (neurotransmitter receptors), Biophys. Chem. 100, 493-506.
11. 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.
12. Gee, K. R., Niu, L., Schaper, K., and Hess, G. P. (1995) Caged bioactive carboxylates. Synthesis, photolysis studies, and biological characterization of a new caged N-methyl-D-aspartic acid, J. Org. Chem. 60, 4260-4263.
13. Niu, L., Gee, K. R., Schaper, K., and Hess, G. P. (1996) Synthesis and photochemical properties of a kainate precursor and activation of kainate and AMPA receptor channels on a microsecond time scale, Biochemistry 35, 2030-2036.
14. Wieboldt, R., Ramesh, D., Carpenter, B. K., and Hess, G. P. (1994) Synthesis and photochemistry of photolabile derivatives of gamma-aminobutyric acid for chemical kinetic investigations of the gamma-aminobutyric acid receptor in the millisecond time region, Biochemistry 33, 1526-1533.
15. Gee, K. R., Wieboldt, R., and Hess, G. P. (1994) Synthesis and photochemistry of a new photolabile derivative of GABA - neurotransmitter release and receptor activation in the microsecond time region, J. Am. Chem. Soc. 116, 8366-8367.
16. 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.
17. Grewer, C., Jäger, J., Carpenter, B. K., and Hess, G. P. (2000) A new photolabile precursor of glycine with improved properties: A tool for chemical kinetic investigations of the glycine receptor, Biochemistry 39, 2063-2070.
18. (3) receptor, Biochemistry 39, 5500-5508.
19. 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.: Caged Compd 291, 443-473.
20. 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.: Caged Compd 291, 30-50.
21. Gee, K. R., Kueper, L. W., III, Barnes, J., Dudley, G., and Givens, R. S. (1996) Desyl esters of amino acid neurotransmitters. Phototriggers for biologically active neurotransmitters, J. Org. Chem. 61, 1228-1233.
22. Sheehan, J. C., and Wilson, R. M. (1964) Photolysis of desyl compounds. A new photolytic cyclization, J. Am. Chem. Soc. 86, 5277-5281.
23. Kuzmic, P., Pavlickova, L., and Soucek, M. (1986) Photochemical hydrolysis of some nitrophenyl acetates, Collect. Czech. Chem. Commun. 51, 1293-1300.
24. Ramesh, D., Wieboldt, R., Niu, L., Carpenter, B. K., and Hess, G. P. (1993) Photolysis of a protecting group for the carboxyl function of neurotransmitters within 3 microseconds and with product quantum yield of 0.2, Proc. Natl. Acad. Sci. U.S.A. 90, 11074-11078.
25. Denk, W., Stickler, J. H., and Webb, W. W. (1990) Two-photon laser scanning fluorescence microscopy, Science 248, 73-76.
26. Fedoryak, O. D., and Dore, T. M. (2000) Brominated ydroxyquinoline as a photolabile protecting group with sensitivity to multiphoton excitation, Org. Lett. 4, 3419-3422.
27. Pillai, V. N. R. (1987) Photolytic deprotection and activation of functional group, Org. Photochem. 9, 225-317.
28. Bochet, C. G. (2002) Photolabile protecting groups and linkers, J. Chem. Soc., Perkin Trans. 1, 125-142.
29. Singh, A. K., and Khade, P. K. (2002) Synthesis and photochemical properties of nitro-naphthyl chromophore and the corresponding immunoglobulin bioconjugate, Bioconjugate Chem. 13, 1286-1291.
30. Mizuta, H., Watanabe, S., Sakurai, Y., Nishiyama, K., Furuta, T., Kobayashi, Y., and Iwamura, M. (2002) Design, synthesis, photochemical properties and cytotoxic activities of water-soluble caged L-leucyl-L-leucine methyl esters that control apoptosis of immune cells, Bioorg. Med. Chem. 10, 675-683.
31. Furuta, T., Wang, S. H., Dantzker, J. L., Dore, T. M., Bybee, W. J., Callaway, E. M., Denk, W., and Tsien, R. Y. (1999) Brominated 7-hydroxycoumarin-4-ylmethyls: photolabile protecting groups with biologically useful cross-sections for two photon photolysis, Proc. Natl. Acad. Sci., U.S.A. 96, 1193-1200.
32. Xu, C., Zipfel, W., Shear, J. B., Williams, R. M., and Webb, W. W. (1996) Multiphoton fluorescence excitation: new spectral windows for biological nonlinear microscopy, Proc. Natl. Acad. Sci. U.S.A. 93, 10763-10768.
33. Bochet, C. G. (2001) Orthogonal photolysis of protecting groups, Angew. Chem., Int. Ed. 40, 2071-2073.
34. Canepari, M., Nelson, L., Papageorgiou, G., Corie, J. E. T., and Ogden, D. (2001) Photochemical and pharmacological evaluation of 7-nitroindolinyl-and 4-methoxy-7-nitroindolinyl-amino acids as novel, fast caged neurotransmitters, J. Neurosci. Methods 112, 29-42.
35. Banerjee, A., Lee, K., Yu, Q., Fang, A. G., and Falvey, D. E. (1998) Protecting group release through photoinduced electron transfer: wavelength control through sensitized irradiation, Tetrahedron Lett. 39, 4635-4638.
36. 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.
37. 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.
38. Takaoka, K., Tatsu, Y., Yumoto, N., Nakajima, T., and Shimamoto, K. (2003) Synthesis and photoreactivity of caged blockers for glutamate transporters, Bioorg. Med. Chem. Lett. 13, 965-970.
39. Takaoka, K., Tatsu, Y., Yumoto, N., Nakajima, T., and Shimamoto, K. (2004) Synthesis of carbamate-type caged derivatives of a novel glutamate transporter blocker, Bioorg. Med. Chem. 12, 3687-3694.
40. Bochet, C. G. (2000) Wavelength-selective cleavage of photolabile protecting groups, Tetrahedron Lett. 41, 6341-6346.
41. 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.
42. Murov, S. L., Carmichael, I., and Hug, G. L. (1993) Handbook of Photochemistry, M. Dekker, New York, 298-305.
43. 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.
44. Krishtal, O. A., and Pidoplichko, V. I. (1980) A receptor for protons in the nerve cell membrane, Neuroscience 5, 2325-2327.
45. 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, 139-149.
46. Hess, G. P., Udgaonkar, J. B., and Olbricht, W. L. (1987) Chemical kinetic measurements of transmembrane processes using rapid reaction techniques: acetylcholine receptor, Annu. Rev. Biophys. Chem. 16, 507-534.
47. Li, G., Oswald, E., and Niu, L. (2003) Channel-opening kinetics of GluR6 kainate receptor, Biochemistry 42, 12367-12375.
48. Kandel, E. R., Schwartz, J. H., and Jessell, T. M. (2000) Principles of Neuronal Sciences, 4th ed., McGraw-Hill Inc., New York.
49. Hardman, J. G., Limbird, L. E., Molinoff, P. B., Ruddou, R. W., and Gilman, A. G. (1996) Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th Ed., McGraw-Hill Inc., New York.
50. Hess, G. P., Ulrich, H., Breitinger, H., Niu, L., Gameiro, A. M., Grewer, C., Srivastava, S., Ippolito, J. E., Lee, S. M., Jayaraman, V., and Coombs, S. E. (2000) Mechanism-based discovery of ligands that counteract inhibition of the nicotinic acetylcholine receptor by cocaine and MK-801, Proc. Natl. Acad. Sci. U.S.A. 97, 13895-13900.
51. Hess, G. P., Gameiro, A. M., Schoenfeld, R. C., Chen, Y., Ulrich, H., Nye, J. A., Sit, B., Carroll, F. I. and Ganem, B. (2003) Reversing the action of noncompetitive inhibitors (MK-801 and cocaine) on a protein (nicotinic acetylcholine receptor)-mediated reaction, Biochemistry 42, 6106-6114.
52. Baulac, S., Huberfeld, G., Gourfinkel-An, I., Mitropoulou, G., Beranger, A., Prud'homme, J., Baulac, M., Brice, A., Bruzzone, R., and LeGuern, E. (2001) First genetic evidence of GABAA receptor dysfunction in epilepsy: a mutation in the γ2-subunit gene, Nat. Genet. 28, 46-48.
53. Cui, Y., Rajasethupathy, P., and Hess, G. P. (2004) Selection of stable RNA molecules that can regulate the channel-opening equilibrium of the membrane-bound γ-aminobutyric acid receptor, Biochemistry 43, 16442-16449.