Journal
ANALYTICAL AND BIOANALYTICAL CHEMISTRY
Volume 406, Issue 28, Pages 7059-7070Publisher
SPRINGER HEIDELBERG
DOI: 10.1007/s00216-014-8131-y
Keywords
Chemo sensor; Optical probes; Near-infrared; Nile red and Nile blue; Hydrogen sulfide
Funding
- National Natural Science Foundation of China [51273136]
- Priority Academic Program Development of Jiangsu Higher Education Institutions
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Hydrogen sulfide has recently been identified as a biologically responsive species. The design and synthesis of fluorescence probes, which are constructed with Nile-red or Nile-blue fluorophores and a fluorescence-controllable dinitrophenyl group, for hydrogen sulfide are reported in this paper. The Nile-red-dinitrophenyl-ether-group-based probe (1a) is essentially non-fluorescent because of the inhibition of the photo-induced electron-transfer process; when the dinitrobenzene moiety is removed by nucleophilic substitution with the hydrosulfide anion, probe 1a is converted into hydroxy Nile red, eliciting a H2S-induced fluorescence turn-on signal. Furthermore, probe 1a has high selectivity and sensitivity for the hydrosulfide anion, and its potential for biological applications was confirmed by using it for real-time fluorescence imaging of hydrogen sulfide in live HeLa cells. The Nile-blue-dinitrobenzene-based probe (1b) has gradually diminishing brightness in the red-emission channel with increased hydrogen-sulfide concentration. Thus, this paper reports a comparative study of Nile-red and Nile-blue-based hydrogen-sulfide probes.
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