Development of a new photochromic ion channel blocker via azologization of fomocaine

ACS Chemical Neuroscience

Volumn 5, Issue 7, 2014, Pages 514-518

  Schoenberger, Matthias ^a   Damijonaitis, Arunas ^a   Zhang, Zinan ^b   Nagel, Daniel ^c   Trauner, Dirk ^a  

^a UNIVERSITY OF MUNICH   (Germany)

^b PRINCETON UNIVERSITY   (United States)

^c MAX PLANCK INSTITUTE OF NEUROBIOLOGY   (Germany)

Author keywords

action potential firing control; azobenzene photoswitch; azologization; fomocaine; local anesthetics; Photopharmacology

Indexed keywords

AZOBENZENE DERIVATIVE; FOMOCAINE; FOTOCAINE; ION TRANSPORT AFFECTING AGENT; UNCLASSIFIED DRUG; AGENTS AFFECTING WATER, MOLECULE OR ION TRANSPORT; AZO COMPOUND; DIPHENYL ETHER DERIVATIVE; MORPHOLINE DERIVATIVE;

ACTION POTENTIAL; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; AZOLOGIZATION; BRAIN SLICE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG SYNTHESIS; HIPPOCAMPAL NEURONAL CULTURE; ILLUMINATION; MOUSE; NONHUMAN; OPTICS; PRIORITY JOURNAL; ULTRAVIOLET RADIATION; ULTRAVIOLET SPECTROSCOPY; ANIMAL; CELL CULTURE; CHEMISTRY; DRUG EFFECTS; HIPPOCAMPUS; NERVE CELL; PATCH CLAMP TECHNIQUE; PHOTOCHEMISTRY; PHOTOSTIMULATION; PHYSIOLOGY; SPECTROSCOPY; SYNTHESIS;

ACTION POTENTIALS; ANIMALS; AZO COMPOUNDS; CELLS, CULTURED; HIPPOCAMPUS; MEMBRANE TRANSPORT MODULATORS; MICE; MORPHOLINES; NEURONS; PATCH-CLAMP TECHNIQUES; PHENYL ETHERS; PHOTIC STIMULATION; PHOTOCHEMICAL PROCESSES; SPECTRUM ANALYSIS;

EID: 84904424162     PISSN: None     EISSN: 19487193     Source Type: Journal    
DOI: 10.1021/cn500070w     Document Type: Article

References (19)

1. Deisseroth, K. (2011) Optogenetics Nat. Methods 8, 26-29
2. Zemelman, B. V., Lee, G. A., Ng, M., and Miesenbock, G. (2002) Selective photostimulation of genetically chARGed neurons Neuron 33, 15-22 (Pubitemid 34088175)
3. Fehrentz, T., Schonberger, M., and Trauner, D. (2011) Optochemical genetics Angew. Chem., Int. Ed. Engl. 50, 12156-12182
4. 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. Engl. 48, 9097-10001
5. 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, 1381-1386 (Pubitemid 41057762)
6. Mourot, A., Fehrentz, T., Le Feuvre, Y., Smith, C. M., Herold, C., Dalkara, D., Nagy, F., Trauner, D., and Kramer, R. H. (2012) Rapid optical control of nociception with an ion-channel photoswitch Nat. Methods 9, 396-402
7. Polosukhina, A., Litt, J., Tochitsky, I., Nemargut, J., Sychev, Y., De Kouchkovsky, I., Huang, T., Borges, K., Trauner, D., Van Gelder, R. N., and Kramer, R. H. (2012) Photochemical restoration of visual responses in blind mice Neuron 75, 271-282
8. Tochitsky, I., Polosukhina, A., Degtyar, V. E., Gallerani, N., Smith, C. M., Friedman, A., Van Gelder, R. N., Trauner, D., Kaufer, D., and Kramer, R. H. (2014) Restoring Visual Function to Blind Mice with a Photoswitch that Exploits Electrophysiological Remodeling of Retinal Ganglion Cells Neuron 81, 800-813
9. Mourot, A., Kienzler, M. A., Banghart, M. R., Fehrentz, T., Huber, F. M., Stein, M., Kramer, R. H., and Trauner, D. (2011) Tuning photochromic ion channel blockers ACS Chem. Neurosci. 2, 536-543
10. Moldovan, M., Alvarez, S., Romer Rosberg, M., and Krarup, C. (2013) Axonal voltage-gated ion channels as pharmacological targets for pain Eur. J. Pharmacol. 708, 105-112
11. Wulff, H., Castle, N. A., and Pardo, L. A. (2009) Voltage-gated potassium channels as therapeutic targets Nat. Rev. Drug Discovery 8, 982-1001
12. Wang, Y., Park, K. D., SalomeÌ, C., Wilson, S. M., Stables, J. P., Liu, R., Khanna, R., and Kohn, H. (2011) Development and Characterization of Novel Derivatives of the Antiepileptic Drug Lacosamide That Exhibit Far Greater Enhancement in Slow Inactivation of Voltage-Gated Sodium Channels ACS Chem. Neurosci. 2, 90-106
13. Wang, Y., Wilson, S. M., Brittain, J. M., Ripsch, M. S., SalomeÌ, C., Park, K. D., White, F. A., Khanna, R., and Kohn, H. (2011) Merging Structural Motifs of Functionalized Amino Acids and α-Aminoamides Results in Novel Anticonvulsant Compounds with Significant Effects on Slow and Fast Inactivation of Voltage-Gated Sodium Channels and in the Treatment of Neuropathic Pain ACS Chem. Neurosci. 2, 317-332
14. Oelschlager, H. (2000) Fomocaine from the chemical, pharmacokinetic and pharmacologic viewpoint: current status and overview Pharm. Unserer Zeit 29, 358-364
15. Oelschlager, H., Iglesias-Meier, J., Gotze, G., and Schatton, W. (1977) On a novel Fomocaine synthesis/10th communication: on syntheses of new compounds with local anaesthetic activity Arzneimittelforschung 27, 1625-8 (Pubitemid 8146946)
16. Sadovski, O., Beharry, A. A., Zhang, F., and Woolley, G. A. (2009) Spectral tuning of azobenzene photoswitches for biological applications Angew. Chem., Int. Ed. Engl. 48, 1484-6
17. Schonberger, M. and Trauner, D. A Photochromic Agonist for mu-Opioid Receptors. Angew. Chem., Int. Ed. Engl. 2014, in press
18. Nau, C. and Wang, G. K. (2004) Interactions of local anesthetics with voltage-gated Na+ channels J. Membr. Biol. 201, 1-8 (Pubitemid 40064276)
19. Kaech, S. and Banker, G. (2006) Culturing hippocampal neurons Nat. Protoc. 1, 2406-2415