title: Enhanced response speed and selectivity of fluorescein-based H2S probe via the cleavage of nitrobenzene sulfonyl ester assisted by ortho aldehyde groups.
abstract: In this work, we developed three fluorescent probes (F-1, F-2, and F-3) based on fluorescein, mono-formylated fluorescein, and bis-formylated fluorescein for hydrogen sulfide (H2S) detection. The probe F-3, which bears two aldehyde groups, exhibited the fastest response. This fast response is attributed to the ortho effect of the aldehyde group, which enables fast nucleophilic addition of H2S to an aldehyde group and subsequent intramolecular thiolysis of dinitrophenyl ether. In addition, the aldehyde groups on F-3 react with biothiols (e.g., cysteine, homocysteine) to form thiazolidine diastereomers, which suppress the fluorescence of fluorescein. The introduction of two aldehyde groups also resulted in high selectivity of F-3 towards H2S. Furthermore, good linearity was observed between F-3 fluorescence intensity at 510nm and H2S concentration in the range of 0-10µM. F-3 exhibited a detection limit as low as 0.024μM. Confocal laser scanning micrographs of HeLa cells incubated with F-3 confirmed that F-3 is cell-permeable and can successfully detect H2S in living cells.
authors: State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 210009 China.
authors: Jing
authors: J
authors: Lv
authors: State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 210009 China.
authors: Fang
authors: F
authors: Wang
authors: State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 210009 China.
authors: Jian
authors: J
authors: Qiang
authors: State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 210009 China.
authors: Xintong
authors: X
authors: Ren
authors: State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 210009 China.
authors: Yahui
authors: Y
authors: Chen
authors: State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 210009 China.
authors: Zhijie
authors: Z
authors: Zhang
authors: State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 210009 China.
authors: Yong
authors: Y
authors: Wang
authors: State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 210009 China.
authors: Wei
authors: W
authors: Zhang
authors: State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing, 210009 China. Electronic address: chenxq@njtech.edu.cn.
authors: Xiaoqiang
authors: X
authors: Chen
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D015374:Biosensing Techniques / Q000379:methods; D004951:Esterification; D019793:Fluorescein / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D006367:HeLa Cells; D006801:Humans; D006862:Hydrogen Sulfide / Q000032:analysis*; D057230:Limit of Detection; D009578:Nitrobenzenes / Q000737:chemistry*; D061848:Optical Imaging / Q000379:methods; D013050:Spectrometry, Fluorescence / Q000379:methods*
chemical_list: D000447:Aldehydes; D005456:Fluorescent Dyes; D009578:Nitrobenzenes; C036077:nitrobenzene; D019793:Fluorescein; D006862:Hydrogen Sulfide
keywords: Fluorescent probe; Formylated fluorescein; H(2)S; Ortho effect; Thiolysis