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Issue 47, 2013
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A coumarin-based fluorescent probe for biological thiols and its application for living cell imaging

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Abstract

In this work, compound 1 has been rationally designed and synthesized as a new fluorescent probe for biological thiols. Notably, probe 1 has almost no background fluorescence (Φf < 0.0001) in aqueous solutions; however, it exhibited fluorescence turn-on response to thiols with high sensitivity (a 246-fold fluorescence enhancement and a low detection limit of 0.22 μM for Cys). Moreover, probe 1 showed excellent thiol specificity over other biologically relevant species. The kinetic studies indicated that the probe responded to thiols rapidly, and the pseudo-first-order rate constants of probe 1 reaction with Cys, Hcy, and GSH were determined to be 1.85842, 0.67656, and 0.51519 min−1, respectively. A possible detection mechanism was proposed to involve the Michael addition of the thiol to the α,β-unsaturated ketone, followed by a cleavage of the hemiketal group, thereby leading to the formation of a fluorescent 7-hydroxyl coumarin derivative. Furthermore, the optical responses of probe 1 to thiols were studied by TD-DFT calculations. Finally, probe 1 has been successfully applied to the detection of biological thiols in human blood serum. And the intracellular imaging applications established that probe 1 can be used to detect different concentrations of intracellular thiols in living cells.

Graphical abstract: A coumarin-based fluorescent probe for biological thiols and its application for living cell imaging

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Publication details

The article was received on 26 Aug 2013, accepted on 12 Oct 2013 and first published on 15 Oct 2013


Article type: Paper
DOI: 10.1039/C3OB41741G
Citation: Org. Biomol. Chem., 2013,11, 8214-8220
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    A coumarin-based fluorescent probe for biological thiols and its application for living cell imaging

    L. Long, L. Zhou, L. Wang, S. Meng, A. Gong, F. Du and C. Zhang, Org. Biomol. Chem., 2013, 11, 8214
    DOI: 10.1039/C3OB41741G

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