Issue 3, 2011

Synthesis and utility of fluorogenic acetoxymethyl ethers

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

Supplementary files

Article information

Article type
Edge Article
Submitted
04 Sep 2010
Accepted
18 Oct 2010
First published
15 Nov 2010

Chem. Sci., 2011,2, 521-530

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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