期刊
ANALYTICAL CHEMISTRY
卷 89, 期 24, 页码 13112-13119出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.analchem.7b02311
关键词
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资金
- State Key Laboratory of Veterinary Etiological Biology, Lanzhou Veterinary Research Institute, Chinese Academy of Agricultural Sciences
- funds of the Ministry of Science and Technology of China [2014DFA31890]
- Natural Science Foundation of China [21771092]
Two fluorescent, m-nitrophenol-substituted difluoroboron dipyrromethene dyes have been designed by nucleophilic substitution reaction of 3,5-dichloro-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY). Nonsymmetric and symmetric probes, that is. BODIPY 1 (with one nitrophenol group at the position 3) and BODIPY 2 (with two nitrophenol groups at the positions 3 and 5) were applied to ratiometric fluorescent glutathione detection. The detection is based on the two-step nucleophilic aromatic substitution of the nitrophenol groups of the probes by glutathione in buffer solution containing CTAB. In the first stage, probe 1 showed ratiometric fluorescent color change from green (lambda(em) = 530 nm) to yellow (lambda(em) = 561 nm) because of monosubstitution with glutathione (I-561nm/I-530nm). Addition of excess glutathione caused the second stage of ratiometric fluorescent color change from yellow to reddish orange (lambda(em) = 596 mu, I-596nm/I-561nm) due to disubstitution with glutathione. Therefore, different concentration ranges of glutathione (from less to excess) could be rapidly detected by the two-stage ratiometric fluorescent probe 1 in 5 min. While, probe 2 shows single-stage ratiometric fluorescent detection to GSH (from green to reddish orange, I-596nm/I-535nm). Probes 1 and 2 exhibit excellent properties with sensitive, specific colorimetric response and ratiometric fluorescent response to glutathione over other sulfur nucleophiles. Application to cellular ratiometric fluorescence imaging indicated that the probes were highly responsive to intracellular glutathione.
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