title: A BODIPY-based turn-on fluorescent probe for the selective detection of hydrogen sulfide in solution and in cells.
abstract: A new turn-on fluorescent probe, incorporating 7-nitrobenzoxadiazole (NBD) ether group into a BODIPY molecule, was synthesized and studied for the detection of H2S and biothiols in aqueous solution and in living cells. The design was based on thiol-induced thiolysis of the NBD ether bond and followed by the cleavage and the release of free meso-(4-hydroxybenzyl)-substituted BODIPY fluorophore. The BODIPY-based probe displayed highly sensitive and selective fluorescence enhancement respond to H2S over competing biothiols such as cysteine (Cys) and glutathione (GSH), mainly due to the weak reactivity of biothiols toward the probe. There was a good linearity between the fluorescence intensity and the concentrations of H2S in the range of 1-200 µM with a detection limit of 2.6 µM. The proposed reaction mechanism was confirmed by mass spectrometry and optical spectroscopy, and the mechanism of turn-on fluorescent response was further determinated by the density functional theory (DFT) calculations using Gaussian 03 program. Moreover, the probe was successfully applied for the fluorescence imaging of H2S in HeLa cells under physiological conditions (pH 7.4).
authors.affiliation: Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China.
authors.forename: Jiamin
authors.initials: J
authors.lastname: Wang
authors.affiliation: Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China; University of Chinese Academy of Sciences, Beijing 100049, PR China.
authors.forename: Hui
authors.initials: H
authors.lastname: Yu
authors.affiliation: Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China.
authors.forename: Qian
authors.initials: Q
authors.lastname: Li
authors.affiliation: Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, PR China. Electronic address: sjshao@licp.cas.cn.
authors.forename: Shijun
authors.initials: S
authors.lastname: Shao
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D006862:Hydrogen Sulfide / Q000032:analysis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D061848:Optical Imaging; D011789:Quantum Theory; D012996:Solutions
chemical_list: C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D001896:Boron Compounds; D005456:Fluorescent Dyes; D012996:Solutions; D006862:Hydrogen Sulfide
keywords: 7-Nitrobenzoxadiazole (NBD); BODIPY; Bioimaging; Fluorescent probe; H(2)S