title: o-Fluorination of aromatic azides yields improved azido-based fluorescent probes for hydrogen sulfide: synthesis, spectra, and bioimaging.
abstract: Hydrogen sulfide (H2S) is an endogenously produced gaseous signaling molecule with multiple biological functions. To visualize the endogenous in situ production of H2S in real time, new coumarin- and boron-dipyrromethene-based fluorescent turn-on probes were developed for fast sensing of H2S in aqueous buffer and in living cells. Introduction of a fluoro group in the ortho position of the aromatic azide can lead to a greater than twofold increase in the rate of reaction with H2S. On the basis of o-fluorinated aromatic azides, fluorescent probes with high sensitivity and selectivity toward H2S over other biologically relevant species were designed and synthesized. The probes can be used to in situ to visualize exogenous H2S and D-cysteine-dependent endogenously produced H2S in living cells, which makes them promising tools for potential applications in H2S biology.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry and Department of Chemical Biology, National Pesticide Engineering Research Center (Tianjin), Nankai University, 94 Weijin Road, Tianjin 300071 (P. R. China); Collaborative Innovation Center of Chemical Science and Engineering (Tianjin).
authors.forename: Chao
authors.initials: C
authors.lastname: Wei
authors.forename: Runyu
authors.initials: R
authors.lastname: Wang
authors.forename: Lv
authors.initials: L
authors.lastname: Wei
authors.forename: Longhuai
authors.initials: L
authors.lastname: Cheng
authors.forename: Zhifei
authors.initials: Z
authors.lastname: Li
authors.forename: Zhen
authors.initials: Z
authors.lastname: Xi
authors.forename: Long
authors.initials: L
authors.lastname: Yi
mesh_terms: D001386:Azides / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D057809:HEK293 Cells; D006801:Humans; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry*; D006862:Hydrogen Sulfide / Q000032:analysis*; D057054:Molecular Imaging; D015394:Molecular Structure; D013050:Spectrometry, Fluorescence; D021241:Spectrometry, Mass, Electrospray Ionization; D013997:Time Factors
chemical_list: D001386:Azides; D005456:Fluorescent Dyes; D006841:Hydrocarbons, Aromatic; D006845:Hydrocarbons, Fluorinated; D006862:Hydrogen Sulfide
keywords: FRET; bioimaging; dyes/pigments; fluorescent probes; hydrogen sulfide