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Issue 6, 2013
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A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells

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Abstract

We describe the design and synthesis of a cyanine-based near-infrared ratiometric fluorescent probe, HS–Cy, for H2S detection, which features rapid response, high sensitivity, and mitochondria targeting. After a rapid quenching at 780 nm by initial nucleophilic addition on the aldehyde group, HS–Cy experienced a polymethine π-electron conjugation modulation triggered by a second nucleophilic addition on the ester, releasing the cyanine fluorophore which underwent tautomerism from enol form to ketone form. Therefore, gradual emergence of a new peak at 625 nm was observed, constructing a ratiometric signal for H2S with a detection limit of 5.0–10 nM, which is the most sensitive among the reported H2S-sensing fluorescent probes. HS–Cy was proven to selectively locate into mitochondria with faster trapping kinetics towards H2S. Based on this, the endogenously generated H2S in human A549 cells was ratiometrically detected and imaged by HS–Cy.

Graphical abstract: A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells

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Supplementary files

Article information


Submitted
07 Feb 2013
Accepted
03 Apr 2013
First published
05 Apr 2013

Chem. Sci., 2013,4, 2551-2556
Article type
Edge Article

A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells

X. Wang, J. Sun, W. Zhang, X. Ma, J. Lv and B. Tang, Chem. Sci., 2013, 4, 2551
DOI: 10.1039/C3SC50369K

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