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Enhanced response speed and selectivity of fluorescein-based H2S probe via the cleavage of nitrobenzene sulfonyl ester assisted by ortho aldehyde groups

Lv, Jing, Wang, Fang, Qiang, Jian, Ren, Xintong, Chen, Yahui, Zhang, Zhijie, Wang, Yong, Zhang, Wei, Chen, Xiaoqiang
Biosensors & bioelectronics 2017 v.87 pp. 96-100
aldehydes, biosensors, cysteine, detection limit, diastereomers, fluorescein, fluorescence, homocysteine, hydrogen sulfide, thiolysis
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.