Literature DB >> 21372812

A practical guide to the synthesis of dinitroindolinyl-caged neurotransmitters.

Graham C R Ellis-Davies1.   

Abstract

This protocol describes a method for efficient chemical synthesis of dinitroindolinyl derivatives of glutamate and γ-aminobutyric acid. These caged neurotransmitters are currently the most chemically and photochemically efficient probes for two-photon photolysis in living brain slices. The protocol only requires basic organic synthesis equipment, and no silica gel column chromatography or NMR spectroscopy is needed at any stage. HPLC is used to purify the caged transmitters at the end of the syntheses. Thus, the synthesis of dinitroindolinyl-caged neurotransmitters is within the scope of a modestly equipped chemistry laboratory.

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Year:  2011        PMID: 21372812      PMCID: PMC4207260          DOI: 10.1038/nprot.2010.193

Source DB:  PubMed          Journal:  Nat Protoc        ISSN: 1750-2799            Impact factor:   13.491


  38 in total

1.  An astrocytic basis of epilepsy.

Authors:  Guo-Feng Tian; Hooman Azmi; Takahiro Takano; Qiwu Xu; Weiguo Peng; Jane Lin; NancyAnn Oberheim; Nanhong Lou; Xiaohai Wang; H Ronald Zielke; Jian Kang; Maiken Nedergaard
Journal:  Nat Med       Date:  2005-08-14       Impact factor: 53.440

2.  NMDA receptor subunit-dependent [Ca2+] signaling in individual hippocampal dendritic spines.

Authors:  Aleksander Sobczyk; Volker Scheuss; Karel Svoboda
Journal:  J Neurosci       Date:  2005-06-29       Impact factor: 6.167

Review 3.  Principles of two-photon excitation microscopy and its applications to neuroscience.

Authors:  Karel Svoboda; Ryohei Yasuda
Journal:  Neuron       Date:  2006-06-15       Impact factor: 17.173

4.  Two-photon laser scanning fluorescence microscopy.

Authors:  W Denk; J H Strickler; W W Webb
Journal:  Science       Date:  1990-04-06       Impact factor: 47.728

5.  An antenna-sensitized nitroindoline precursor to enable photorelease of L-glutamate in high concentrations.

Authors:  George Papageorgiou; David Ogden; John E T Corrie
Journal:  J Org Chem       Date:  2004-10-15       Impact factor: 4.354

6.  An antenna triplet sensitiser for 1-acyl-7-nitroindolines improves the efficiency of carboxylic acid photorelease.

Authors:  George Papageorgiou; Matthew Lukeman; Peter Wan; John E T Corrie
Journal:  Photochem Photobiol Sci       Date:  2004-02-09       Impact factor: 3.982

7.  Synaptic strength of individual spines correlates with bound Ca2+-calmodulin-dependent kinase II.

Authors:  Brent Asrican; John Lisman; Nikolai Otmakhov
Journal:  J Neurosci       Date:  2007-12-19       Impact factor: 6.167

8.  Single-spike detection in vitro and in vivo with a genetic Ca2+ sensor.

Authors:  Damian J Wallace; Stephan Meyer zum Alten Borgloh; Simone Astori; Ying Yang; Melanie Bausen; Sebastian Kügler; Amy E Palmer; Roger Y Tsien; Rolf Sprengel; Jason N D Kerr; Winfried Denk; Mazahir T Hasan
Journal:  Nat Methods       Date:  2008-09       Impact factor: 28.547

9.  A genetically encoded calcium indicator for chronic in vivo two-photon imaging.

Authors:  Marco Mank; Alexandre Ferrão Santos; Stephan Direnberger; Thomas D Mrsic-Flogel; Sonja B Hofer; Valentin Stein; Thomas Hendel; Dierk F Reiff; Christiaan Levelt; Alexander Borst; Tobias Bonhoeffer; Mark Hübener; Oliver Griesbeck
Journal:  Nat Methods       Date:  2008-09       Impact factor: 28.547

10.  Surface mobility of postsynaptic AMPARs tunes synaptic transmission.

Authors:  Martin Heine; Laurent Groc; Renato Frischknecht; Jean-Claude Béïque; Brahim Lounis; Gavin Rumbaugh; Richard L Huganir; Laurent Cognet; Daniel Choquet
Journal:  Science       Date:  2008-04-11       Impact factor: 47.728

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  13 in total

1.  A practical guide to the synthesis and use of membrane-permeant acetoxymethyl esters of caged inositol polyphosphates.

Authors:  Srinivas Kantevari; Grant R J Gordon; Brian A MacVicar; Graham C R Ellis-Davies
Journal:  Nat Protoc       Date:  2011-02-17       Impact factor: 13.491

2.  Development of Anionically Decorated Caged Neurotransmitters: In Vitro Comparison of 7-Nitroindolinyl- and 2-(p-Phenyl-o-nitrophenyl)propyl-Based Photochemical Probes.

Authors:  Srinivas Kantevari; Stefan Passlick; Hyung-Bae Kwon; Matthew T Richers; Bernardo L Sabatini; Graham C R Ellis-Davies
Journal:  Chembiochem       Date:  2016-04-09       Impact factor: 3.164

3.  Caged Proline in Photoinitiated Organocatalysis.

Authors:  Charitha Guruge; Saad Y Rfaish; Chanel Byrd; Shukun Yang; Anthony K Starrett; Eric Guisbert; Nasri Nesnas
Journal:  J Org Chem       Date:  2019-04-03       Impact factor: 4.354

4.  Dendrimer Conjugation Enables Multiphoton Chemical Neurophysiology Studies with an Extended π-Electron Caging Chromophore.

Authors:  Matthew T Richers; Stefan Passlick; Hitesh Agarwal; Graham C R Ellis-Davies
Journal:  Angew Chem Int Ed Engl       Date:  2019-07-19       Impact factor: 15.336

5.  Caged compounds for multichromic optical interrogation of neural systems.

Authors:  Joseph M Amatrudo; Jeremy P Olson; Hitesh K Agarwal; Graham C R Ellis-Davies
Journal:  Eur J Neurosci       Date:  2014-12-04       Impact factor: 3.386

6.  Improved Synthesis of Caged Glutamate and Caging Each Functional Group.

Authors:  Charitha Guruge; Yannick P Ouedraogo; Richard L Comitz; Jingxuan Ma; Attila Losonczy; Nasri Nesnas
Journal:  ACS Chem Neurosci       Date:  2018-05-25       Impact factor: 4.418

7.  Optofluidic control of rodent learning using cloaked caged glutamate.

Authors:  Romain Durand-de Cuttoli; Pradeep S Chauhan; Adriana Pétriz Reyes; Philippe Faure; Alexandre Mourot; Graham C R Ellis-Davies
Journal:  Proc Natl Acad Sci U S A       Date:  2020-03-09       Impact factor: 11.205

8.  GABA promotes the competitive selection of dendritic spines by controlling local Ca2+ signaling.

Authors:  Tatsuya Hayama; Jun Noguchi; Satoshi Watanabe; Noriko Takahashi; Akiko Hayashi-Takagi; Graham C R Ellis-Davies; Masanori Matsuzaki; Haruo Kasai
Journal:  Nat Neurosci       Date:  2013-08-25       Impact factor: 24.884

9.  Exclusive photorelease of signalling lipids at the plasma membrane.

Authors:  André Nadler; Dmytro A Yushchenko; Rainer Müller; Frank Stein; Suihan Feng; Christophe Mulle; Mario Carta; Carsten Schultz
Journal:  Nat Commun       Date:  2015-12-21       Impact factor: 14.919

Review 10.  Correlative Light Electron Microscopy: Connecting Synaptic Structure and Function.

Authors:  Isabell Begemann; Milos Galic
Journal:  Front Synaptic Neurosci       Date:  2016-08-23
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