Issue 6, 2013
From the journal:

Chemical Science

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

Xu Wang,a   Juan Sun,a   Weihong Zhang,a   Xiaoxu Ma,a   Jianzheng Lva  and  Bo Tang*a  

* Corresponding authors

a College of Chemistry, Chemical Engineering and Materials Science, Engineering Research Center of Pesticide and Medicine Intermediate Clean Production, Ministry of Education, Key Laboratory of Molecular and Nano Probes, Ministry of Education, Shandong Provincial Key Laboratory of Clean Production of Fine Chemicals, Shandong Normal University, Jinan 250014, P. R. China
E-mail: tangb@sdnu.edu.cn
Fax: +86 531-8618-0017

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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Article information

DOI
https://doi.org/10.1039/C3SC50369K
Article type
Edge Article
Submitted
07 Feb 2013
Accepted
03 Apr 2013
First published
05 Apr 2013

Chem. Sci., 2013,4, 2551-2556

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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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