Issue 47, 2013

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

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

Supplementary files

Article information

Article type
Paper
Submitted
26 Aug 2013
Accepted
12 Oct 2013
First published
15 Oct 2013

Org. Biomol. Chem., 2013,11, 8214-8220

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements