title: Nile-red and Nile-blue-based near-infrared fluorescent probes for in-cellulo imaging of hydrogen sulfide.
abstract: 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.
authors.affiliation: College of Chemistry, Chemical Engineering and Material Science, Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, 199 Ren'Ai Road, Suzhou, 215123, China.
authors.forename: Xiao-Dong
authors.initials: XD
authors.lastname: Liu
authors.forename: Chen
authors.initials: C
authors.lastname: Fan
authors.forename: Ru
authors.initials: R
authors.lastname: Sun
authors.forename: Yu-Jie
authors.initials: YJ
authors.lastname: Xu
authors.forename: Jian-Feng
authors.initials: JF
authors.lastname: Ge
mesh_terms: D003952:Diagnostic Imaging; D005456:Fluorescent Dyes / Q000737:chemistry; D006367:HeLa Cells; D006801:Humans; D006862:Hydrogen Sulfide / Q000032:analysis*; D015394:Molecular Structure; D010078:Oxazines / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D005456:Fluorescent Dyes; D010078:Oxazines; C008619:Nile Blue; C044808:nile red; D006862:Hydrogen Sulfide