Tuning photochromic ion channel blockers

ACS Chemical Neuroscience

Volumn 2, Issue 9, 2011, Pages 536-543

  Mourot, Alexandre ^a,c   Kienzler, Michael A ^a,b,c   Banghart, Matthew R ^a   Fehrentz, Timm ^b   Huber, Florian M E ^b   Stein, Marco ^b   Kramer, Richard H ^a   Trauner, Dirk ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF MUNICH   (Germany)

^c Munich Center for Integrated Protein Science   (Germany)

Author keywords

Azobenzenes; Ion channel blockers; Photochromic molecules; Photopharmacology; Voltage gated potassium channels

Indexed keywords

AZOBENZENE; ION CHANNEL; POTASSIUM CHANNEL; DELAYED RECTIFIER POTASSIUM CHANNEL; POTASSIUM CHANNEL BLOCKING AGENT; SOLVENT;

ARTICLE; BLUE LIGHT; CONTROLLED STUDY; DARKNESS; NERVE CONDUCTION; ULTRAVIOLET A RADIATION; ANIMAL; CELL STRAIN HEK293; CEREBELLUM; DRUG EFFECT; ELECTRON; ELECTROPHYSIOLOGY; HUMAN; METABOLISM; MICROELECTRODE; PATCH CLAMP; PHOTOCHEMISTRY; RAT; SPRAGUE DAWLEY RAT; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS; ULTRAVIOLET SPECTROPHOTOMETRY;

ANIMALS; CEREBELLUM; DELAYED RECTIFIER POTASSIUM CHANNELS; ELECTRONS; ELECTROPHYSIOLOGICAL PHENOMENA; HEK293 CELLS; HUMANS; MICROELECTRODES; PATCH-CLAMP TECHNIQUES; PHOTOCHEMISTRY; POTASSIUM CHANNEL BLOCKERS; RATS; RATS, SPRAGUE-DAWLEY; SOLVENTS; SPECTROPHOTOMETRY, ULTRAVIOLET; STEREOISOMERISM; THERMODYNAMICS;

EID: 83055164886     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn200037p     Document Type: Article

References (25)

1. Banghart, M. R., Volgraf, M., and Trauner, D. (2006) Engineering light-gated ion channels. Biochemistry 45 (51), 15129-15141.
2. Gorostiza, P., and Isacoff, E. Y. (2008) Optical switches for remote and noninvasive control of cell signaling. Science 322 (5900), 395-399.
3. Kramer, R. H., Fortin, D. L., and Trauner, D. (2009) New photochemical tools for controlling neuronal activity. Curr. Opin. Neurobiol. 19 (5), 544-552.
4. Mayer, G., and Heckel, A. (2006) Biologically active molecules with a "light switch. Angew. Chem., Int. Ed. 45 (30), 4900-4921.
5. Deisseroth, K. (2011) Optogenetics. Nat. Methods 8 (1), 26-29.
6. Hegemann, P., and Moglich, A. (2011) Channelrhodopsin engineering and exploration of new optogenetic tools. Nat. Methods 8 (1), 39-42.
7. Banghart, M. R., Mourot, A., Fortin, D. L., Yao, J. Z., Kramer, R. H., and Trauner, D. (2009) Photochromic blockers of voltage-gated potassium channels. Angew. Chem., Int. Ed. 48 (48), 9097-9101.
8. Bartels, E., Wassermann, N. H., and Erlanger, B. F. (1971) Photochromic activators of the acetylcholine receptor. Proc. Natl. Acad. Sci. U.S.A. 68 (8), 1820-1823.
9. Fortin, D. L., Banghart, M. R., Dunn, T. W., Borges, K., Wagenaar, D. A., Gaudry, Q., Karakossian, M. H., Otis, T. S., Kristan, W. B., Trauner, D., and Kramer, R. H. (2008) Photochemical control of endogenous ion channels and cellular excitability. Nat. Methods 5 (4), 331-338.
10. Lester, H. A., and Chang, H. W. (1977) Response of acetylcholine receptors to rapid photochemically produced increases in agonist concentration. Nature 266 (5600), 373-374.
11. nded., pp 89.1-89.16.
12. Gorostiza, P., Volgraf, M., Numano, R., Szobota, S., Trauner, D., and Isacoff, E. Y. (2007) Mechanisms of photoswitch conjugation and light activation of an ionotropic glutamate receptor. Proc. Natl. Acad. Sci. U.S.A. 104 (26), 10865-10870.
13. Sadovski, O., Beharry, A. A., Zhang, F., and Woolley, G. A. (2009) Spectral tuning of azobenzene photoswitches for biological applications. Angew. Chem., Int. Ed. 48 (8), 1484-1486.
14. Schanze, K. S., Mattox, T. F., and Whitten, D. G. (1983) Solvent Effects upon the Thermal Cis-Trans Isomerization and Charge-Transfer Absorption of 4-(Diethylamino)-40-nitrobenzene. J. Org. Chem. 48 (17), 2808-2813.
15. Whitten, D. G., Wildes, P. D., Pacifici, J. G., and Irick, G., Jr. (1971) Solvent and substituent on the thermal isomerization of substituted azobenzenes. Flash spectroscopic study. J. Am. Chem. Soc. 93 (8), 2004-2008.
16. Kamei, T., Kudo, M., Akiyama, H., Wada, M., Nagasawa, J., Funahashi, M., Tamaoki, N., and Uyeda, T. Q. P. (2007) Visible-Light Photoresponsivity of a 4-(Dimethylamino)azobenzene Unit Incorporated into Single-Stranded DNA: Demonstration of a Large Spectral Change Accompanying Isomerization in DMSO and Detection of Rapid (Z)-to-(E) Isomerization in Aqueous Solution. Eur. J. Org. Chem. 2007 (11), 1846-1853.
17. Kamei, T., Akiyama, H., Morii, H., Tamaoki, N., and Uyeda, T. Q. (2009) Visible-light photocontrol of (E)/(Z) isomerization of the 4-(dimethylamino)azobenzene pseudo-nucleotide unit incorporated into an oligonucleotide and DNA hybridization in aqueous media. Nucleosides, Nucleotides Nucleic Acids 28 (1), 12-28.
18. Kessler, M., Kiliman, B., Humes, C., and Arai, A. C. (2008) Spontaneous activity in Purkinje cells: multi-electrode recording from organotypic cerebellar slice cultures. Brain Res. 1218, 54-69.
19. Volgraf, M., Gorostiza, P., Szobota, S., Helix, M. R., Isacoff, E. Y., and Trauner, D. (2007) Reversibly caged glutamate: a photochromic agonist of ionotropic glutamate receptors. J. Am. Chem. Soc. 129 (2), 260-261.
20. Abrams, Z. R., Warrier, A., Trauner, D., and Zhang, X. (2010) A Signal Processing Analysis of Purkinje Cells in vitro. Front. Neural Circuits 4, 13.
21. Banghart, M., Borges, K., Isacoff, E., Trauner, D., and Kramer, R. H. (2004) Light-activated ion channels for remote control of neuronal firing. Nat. Neurosci. 7 (12), 1381-1386.
22. Chambers, J. J., Banghart, M. R., Trauner, D., and Kramer, R. H. (2006) Light-induced depolarization of neurons using a modified Shaker K(+) channel and a molecular photoswitch. J. Neurophysiol. 96 (5), 2792-2796.
23. Szobota, S., Gorostiza, P., Del Bene, F., Wyart, C., Fortin, D. L., Kolstad, K. D., Tulyathan, O., Volgraf, M., Numano, R., Aaron, H. L., Scott, E. K., Kramer, R. H., Flannery, J., Baier, H., Trauner, D., and Isacoff, E. Y. (2007) Remote control of neuronal activity with a lightgated glutamate receptor. Neuron 54 (4), 535-545.
24. Volgraf, M., Gorostiza, P., Numano, R., Kramer, R. H., Isacoff, E. Y., and Trauner, D. (2006) Allosteric control of an ionotropic glutamate receptor with an optical switch. Nat. Chem. Biol. 2 (1), 47-52.
25. Hoshi, T., Zagotta, W. N., and Aldrich, R. W. (1990) Biophysical and molecular mechanisms of Shaker potassium channel inactivation. Science 250 (4980), 533-538.