Two-stage ratiometric fluorescent responsive probe for rapid glutathione detection based on BODIPY thiol-halogen nucleophilic mono- or disubstitution

文献类型: 外文期刊

第一作者: Gong, Deyan

作者: Gong, Deyan;Cao, Ting;Qian, Jing;Liu, Wei;Iqbal, Anam;Liu, Weisheng;Qin, Wenwu;Gong, Deyan;Cao, Ting;Qian, Jing;Liu, Wei;Iqbal, Anam;Liu, Weisheng;Qin, Wenwu;Ru, Jiaxi;Guo, Huichen;Ru, Jiaxi;Guo, Huichen

作者机构:

关键词: BODIPY;Two-stage ratiometric fluorescent probes;Nucleophilic mono- or disubstitution;Glutathione;Bioimaging

期刊名称:SENSORS AND ACTUATORS B-CHEMICAL ( 影响因子:7.46; 五年影响因子:6.743 )

ISSN: 0925-4005

年卷期: 2018 年 258 卷

页码:

收录情况: SCI

摘要: 3,5-dichloro-8-phenyl-4,4-difluoro-4-bora-3a, 4a-diaza-s-indacene (BOD-2Cl) (1) as a classical fluorescent dye was synthesized for the purpose of functionalization of BODIPY dye. Herein, it was applied for the purpose of achieving two-stage ratiometric fluorescent detection of glutathione based on the two-step thiolhalogen substitution reaction with the sulfhydryl group of glutathione at the 3 (mono-substitution) and 3,5-position (disubstitution) of 1 in CTAB micelles. The first stage induced fluorescent color change from green (lambda(em) = 530 nm) to yellow (lambda(em) = 562 nm) (I-562nm/I-530nm, mono-substitution), excess addition of glutathione caused the second stage fluorescent color change from yellow to red (lambda(em) = 597 nm) (I-597nm/I-562nm, disubstitution). It exhibits excellent properties with specific colorimetric and ratiometric fluorescent change to glutathione over cysteine and homocysteine. Further application to cellular ratiometric fluorescence imaging indicated that the probe was highly responsive to the glutathione in cells. (c) 2017 Elsevier B.V. All rights reserved.

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