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Two-stage ratiometric fluorescent responsive probe for rapid glutathione detection based on BODIPY thiol-halogen nucleophilic mono- or disubstitution
Sensors and Actuators B: Chemical ( IF 8.0 ) Pub Date : 2017-11-21 , DOI: 10.1016/j.snb.2017.11.092
Deyan Gong , Jiaxi Ru , Ting Cao , Jing Qian , Wei Liu , Anam Iqbal , Weisheng Liu , Wenwu Qin , Huichen Guo

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 thiol-halogen 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 (λem = 530 nm) to yellow (λem = 562 nm) (I562nm/I530nm, mono-substitution), excess addition of glutathione caused the second stage fluorescent color change from yellow to red (λem = 597 nm) (I597nm/I562nm, 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.



中文翻译:

基于BODIPY硫醇-卤素亲核性单双峰或双峰化的快速检测谷胱甘肽的两阶段比例式荧光响应探针

合成3,5-dichloro-8-phenyl-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene(BOD-2Cl)(1)作为经典的荧光染料,用于功能化的BODIPY染料。在本文中,其用于基于谷胱甘肽的3位(单取代)和3,5-位的巯基与巯基的两步硫醇-卤素取代反应,实现谷胱甘肽的两步比例荧光检测(的二取代)1在CTAB胶束。第一阶段诱导的荧光颜色从绿色(λem  = 530 nm)变为黄色(λem  = 562 nm)(I 562nm / I 530nm),单取代),过量添加谷胱甘肽导致第二阶段荧光颜色从黄色变为红色(λem  = 597 nm)(I 597nm / I 562nm分散)。与半胱氨酸和高半胱氨酸相比,它具有出色的特性,并具有特定的比色和比例荧光改变为谷胱甘肽。进一步应用于细胞比例荧光成像表明该探针对细胞中的谷胱甘肽具有高度的响应性。

更新日期:2017-11-21
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