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Issue 3, 2011
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Synthesis and utility of fluorogenic acetoxymethyl ethers

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Abstract

Phenolic fluorophores such as fluorescein, Tokyo Green, resorufin, and their derivatives are workhorses of biological science. Acylating the phenolic hydroxyl group(s) in these fluorophores masks their fluorescence. The ensuing ester is a substrate for cellular esterases, which can restore fluorescence. These esters are, however, notoriously unstable to hydrolysis, severely compromising their utility. The acetoxymethyl (AM) group is an esterase-sensitive motif that can mask polar functionalities in small molecules. Here, we report on the use of AM ether groups to mask phenolic fluorophores. The resulting profluorophores have a desirable combination of low background fluorescence, high chemical stability, and high enzymatic reactivity, both in vitro and in cellulo. These simple phenyl ether-based profluorophores could supplement or supplant the use of phenyl esters for imaging biochemical and biological systems.

Graphical abstract: Synthesis and utility of fluorogenic acetoxymethyl ethers

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Publication details

The article was received on 04 Sep 2010, accepted on 18 Oct 2010 and first published on 15 Nov 2010


Article type: Edge Article
DOI: 10.1039/C0SC00466A
Chem. Sci., 2011,2, 521-530

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    Synthesis and utility of fluorogenic acetoxymethyl ethers

    L. D. Lavis, T. Chao and R. T. Raines, Chem. Sci., 2011, 2, 521
    DOI: 10.1039/C0SC00466A

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