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Issue 2, 2010
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Toward the development of prochelators as fluorescent probes of copper-mediated oxidative stress

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Abstract

A fluorescent sensor prochelator, FlamB (fluorescein hydrizido 2-imidophenylboronic ester), has been developed that selectively probes for copper under conditions of oxidative stress. High levels of hydrogen peroxide trigger the release of a boronic ester masking group from the prochelator to unveil a metal chelator, FlamS (fluorescein hydrizido 2-imidophenol), that provides a modest fluorescence increase in response to Cu2+ but not other metal ions. X-Ray crystal structures of FlamB, FlamS, and Cu-bound FlamS are all reported. The fluorescence turn-on results from opening of a fluorescein spirolactam ring upon Cu2+ binding to FlamS in aqueous solution. Oxidation of the aryl boronic ester of FlamB to the metal-binding phenol of FlamS proceeds in organic solvents. However, in aqueous solution a competing mechanism occurs due to hydrolytic instability of the masked prochelator. Hydrolysis of FlamB leads to formation of fluorescein hydrazide, which interacts with copper or H2O2 to produce fluorescein and a significant fluorescence increase.

Graphical abstract: Toward the development of prochelators as fluorescent probes of copper-mediated oxidative stress

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Supplementary files

Article information


Submitted
21 Jul 2009
Accepted
23 Sep 2009
First published
16 Oct 2009

Dalton Trans., 2010,39, 568-576
Article type
Paper

Toward the development of prochelators as fluorescent probes of copper-mediated oxidative stress

L. M. Hyman, C. J. Stephenson, M. G. Dickens, K. D. Shimizu and K. J. Franz, Dalton Trans., 2010, 39, 568
DOI: 10.1039/B914568K

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