NDLI: Two-photon sensitive protecting groups operating <i>via</i> intramolecular electron transfer: uncaging of GABA and tryptophan

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Two-photon sensitive protecting groups operating via intramolecular electron transfer: uncaging of GABA and tryptophan

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Back cover

Chemical Science Vol - 6 Issue - 3

Chemical Science Vol - 6 Issue - 2

Chemical Science Vol -5

Chemical Science Vol -4

Chemical Science Vol -3

Chemical Science Vol -2

Chemical Science Vol -1

Two-photon sensitive protecting groups operating via intramolecular electron transfer: uncaging of GABA and tryptophan

Content Provider	Royal Society of Chemistry (RSC)
Author	Blanchard-Desce, Mireille Drobizhev, Mikhail Cueto-Diaz, Eduardo Jose Anderson, Harry L. Bennett, Philip M. Wicks, Geoffrey Rebane, Aleksander Korzycka, Karolina A.
Copyright Year	2015
Abstract	Improved photo-labile protecting groups, with high sensitivity to two-photon excitation, are needed for the controlled release of drugs, as tools in neuroscience and physiology. Here we present a new modular approach to the design of caging groups based on photoinduced electron transfer from an electron-rich two-photon dye to an electron acceptor, followed by scission of an ester to release a carboxylic acid. Three different electron acceptors were tested: nitrobenzyl, phenacyl and pyridinium. The nitrobenzyl system was ineffective, giving only photochemical decomposition and no release of the carboxylic acid. The phenacyl system also performed poorly, liberating the carboxylic acid in 20% chemical yield and 0.2% photochemical yield. The pyridinium system was most successful, and was tested for the release of two carboxylic acids: γ-amino butyric acid (GABA) and tryptophan. The caged GABA undergoes photochemical cleavage with a chemical yield of >95% and a photochemical yield of 1%; it exhibits a two-photon absorption cross section of 1100 GM at 700 nm, corresponding to a two-photon uncaging cross section of 10 ± 3 GM.
Starting Page	2419
Ending Page	2426
Page Count	8
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	6
Issue Number	4
Journal	Chemical Science
DOI	10.1039/c4sc03775h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	GM Photoinduced electron transfer Pyridinium Tryptophan Dye Ester Neuroscience Carboxylic acid Yield (chemistry) Two-photon absorption Physiology Gamma-Aminobutyric acid Electron acceptor Photochemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry

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