Literature DB >> 24856540

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

Matthias Schoenberger1, Arunas Damijonaitis, Zinan Zhang, Daniel Nagel, Dirk Trauner.   

Abstract

Photochromic blockers of voltage gated ion channels are powerful tools for the control of neuronal systems with high spatial and temporal precision. We now introduce fotocaine, a new type of photochromic channel blocker based on the long-lasting anesthetic fomocaine. Fotocaine is readily taken up by neurons in brain slices and enables the optical control of action potential firing by switching between 350 and 450 nm light. It also provides an instructive example for "azologization", that is, the systematic conversion of an established drug into a photoswitchable one.

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Year:  2014        PMID: 24856540      PMCID: PMC4102962          DOI: 10.1021/cn500070w

Source DB:  PubMed          Journal:  ACS Chem Neurosci        ISSN: 1948-7193            Impact factor:   4.418


  19 in total

Review 1.  [Fomocaine from the chemical, pharmacokinetic and pharmacologic viewpoint: current status and overview].

Authors:  H Oelschläger
Journal:  Pharm Unserer Zeit       Date:  2000-11

Review 2.  Optochemical genetics.

Authors:  Timm Fehrentz; Matthias Schönberger; Dirk Trauner
Journal:  Angew Chem Int Ed Engl       Date:  2011-11-23       Impact factor: 15.336

3.  Photochromic blockers of voltage-gated potassium channels.

Authors:  Matthew R Banghart; Alexandre Mourot; Doris L Fortin; Jennifer Z Yao; Richard H Kramer; Dirk Trauner
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Development and characterization of novel derivatives of the antiepileptic drug lacosamide that exhibit far greater enhancement in slow inactivation of voltage-gated sodium channels.

Authors:  Yuying Wang; Ki Duk Park; Christophe Salome; Sarah M Wilson; James P Stables; Rihe Liu; Rajesh Khanna; Harold Kohn
Journal:  ACS Chem Neurosci       Date:  2011-02-16       Impact factor: 4.418

5.  Selective photostimulation of genetically chARGed neurons.

Authors:  Boris V Zemelman; Georgia A Lee; Minna Ng; Gero Miesenböck
Journal:  Neuron       Date:  2002-01-03       Impact factor: 17.173

6.  Restoring visual function to blind mice with a photoswitch that exploits electrophysiological remodeling of retinal ganglion cells.

Authors:  Ivan Tochitsky; Aleksandra Polosukhina; Vadim E Degtyar; Nicholas Gallerani; Caleb M Smith; Aaron Friedman; Russell N Van Gelder; Dirk Trauner; Daniela Kaufer; Richard H Kramer
Journal:  Neuron       Date:  2014-02-19       Impact factor: 17.173

Review 7.  Voltage-gated potassium channels as therapeutic targets.

Authors:  Heike Wulff; Neil A Castle; Luis A Pardo
Journal:  Nat Rev Drug Discov       Date:  2009-12       Impact factor: 84.694

8.  [On a novel Fomocaine synthesis/10th communication: on syntheses of new compounds with local anaesthetic activity (author's transl)].

Authors:  H Oelschläger; J Iglesias-Meier; G Götze; W Schatton
Journal:  Arzneimittelforschung       Date:  1977

9.  Optogenetics.

Authors:  Karl Deisseroth
Journal:  Nat Methods       Date:  2010-12-20       Impact factor: 28.547

10.  Rapid optical control of nociception with an ion-channel photoswitch.

Authors:  Alexandre Mourot; Timm Fehrentz; Yves Le Feuvre; Caleb M Smith; Christian Herold; Deniz Dalkara; Frédéric Nagy; Dirk Trauner; Richard H Kramer
Journal:  Nat Methods       Date:  2012-02-19       Impact factor: 28.547

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  14 in total

Review 1.  Artificial Molecular Machines.

Authors:  Sundus Erbas-Cakmak; David A Leigh; Charlie T McTernan; Alina L Nussbaumer
Journal:  Chem Rev       Date:  2015-09-08       Impact factor: 60.622

Review 2.  Optochemical Control of Biological Processes in Cells and Animals.

Authors:  Nicholas Ankenbruck; Taylor Courtney; Yuta Naro; Alexander Deiters
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-01       Impact factor: 15.336

Review 3.  Molecular photoswitches in aqueous environments.

Authors:  Jana Volarić; Wiktor Szymanski; Nadja A Simeth; Ben L Feringa
Journal:  Chem Soc Rev       Date:  2021-11-15       Impact factor: 54.564

4.  New Chemical Biology Tools for the Histamine Receptor Family.

Authors:  Yang Zheng; Gábor Wágner; Niels Hauwert; Xiaoyuan Ma; Henry F Vischer; Rob Leurs
Journal:  Curr Top Behav Neurosci       Date:  2022

Review 5.  Optical control of neuronal ion channels and receptors.

Authors:  Pierre Paoletti; Graham C R Ellis-Davies; Alexandre Mourot
Journal:  Nat Rev Neurosci       Date:  2019-09       Impact factor: 34.870

6.  "Photo-Rimonabant": Synthesis and Biological Evaluation of Novel Photoswitchable Molecules Derived from Rimonabant Lead to a Highly Selective and Nanomolar "Cis-On" CB1R Antagonist.

Authors:  Diego A Rodríguez-Soacha; Julia Fender; Yesid A Ramírez; Juan Antonio Collado; Eduardo Muñoz; Rangan Maitra; Christoph Sotriffer; Kristina Lorenz; Michael Decker
Journal:  ACS Chem Neurosci       Date:  2021-04-15       Impact factor: 5.780

7.  Illuminating Phenylazopyridines To Photoswitch Metabotropic Glutamate Receptors: From the Flask to the Animals.

Authors:  Xavier Gómez-Santacana; Silvia Pittolo; Xavier Rovira; Marc Lopez; Charleine Zussy; James A R Dalton; Adèle Faucherre; Chris Jopling; Jean-Philippe Pin; Francisco Ciruela; Cyril Goudet; Jesús Giraldo; Pau Gorostiza; Amadeu Llebaria
Journal:  ACS Cent Sci       Date:  2016-12-19       Impact factor: 14.553

8.  Reversible optical control of F1 Fo -ATP synthase using photoswitchable inhibitors.

Authors:  Bianca Eisel; Felix W W Hartrampf; Thomas Meier; Dirk Trauner
Journal:  FEBS Lett       Date:  2018-02-01       Impact factor: 4.124

9.  Azologization of serotonin 5-HT3 receptor antagonists.

Authors:  Karin Rustler; Galyna Maleeva; Piotr Bregestovski; Burkhard König
Journal:  Beilstein J Org Chem       Date:  2019-03-25       Impact factor: 2.883

10.  Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors.

Authors:  Christoph W Grathwol; Nathalie Wössner; Sören Swyter; Adam C Smith; Enrico Tapavicza; Robert K Hofstetter; Anja Bodtke; Manfred Jung; Andreas Link
Journal:  Beilstein J Org Chem       Date:  2019-09-16       Impact factor: 2.883

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