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A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells
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.
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Cited by
Zielonka, J., Joseph, J., Sikora, A., Hardy, M., Ouari, O., Vasquez-Vivar, J., Cheng, G., Lopez, M., & Kalyanaraman, B. (2017) · Chemical Reviews · doi:10.1021/acs.chemrev.7b00042 · Cited by 1,683
Ultrasensitive Near-Infrared Fluorescence-Enhanced Probe for in Vivo Nitroreductase Imaging
Li, Y., Sun, Y., Li, J., Su, Q., Yuan, W., Dai, Y., Han, C., Wang, Q., Feng, W., & Li, F. (2015) · Journal of the American Chemical Society · doi:10.1021/jacs.5b04097 · Cited by 516
Taking Up the Cyanine Challenge with Quantum Tools
Le Guennic, B., & Jacquemin, D. (2015) · Accounts of Chemical Research · doi:10.1021/ar500447q · Cited by 305
Huang, L., Lv, F., Bin, Y., Zhao, J., Li, C., Zhao, S., Hu, S., & Zhang, L. (2025) · Small · doi:10.1002/smll.202501269 · Cited by 8
Metadata
- Authors
- Wang, X., Sun, J., Zhang, W., Ma, X., Lv, J., & Tang, B.
- Venue
- Chemical Science
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2013
- Volume
- 4
- Issue
- 6
- Pages
- 2551
- ISSN
- 2041-6520 (ISSN-L)
- 2041-6539
- OpenAlex
- W2144056199
- Cited by
- 330
- References
- 0
- FWCI
- 18.76
- Type
- journal article
- Language
- en
- Open access
- closed
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- Wang, X., Sun, J., Zhang, W., Ma, X., Lv, J., & Tang, B. (2013). A near-infrared ratiometric fluorescent probe for rapid and highly sensitive imaging of endogenous hydrogen sulfide in living cells. Chemical Science. https://doi.org/10.1039/c3sc50369k
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