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Fluorescent Probe for Simultaneous Discrimination of GSH, Cys, and SO2 Derivatives.
Analytical Chemistry ( IF 6.7 ) Pub Date : 2020-07-01 , DOI: 10.1021/acs.analchem.0c02255 Lu Jia 1 , Li-Ya Niu 1 , Qing-Zheng Yang 1
Analytical Chemistry ( IF 6.7 ) Pub Date : 2020-07-01 , DOI: 10.1021/acs.analchem.0c02255 Lu Jia 1 , Li-Ya Niu 1 , Qing-Zheng Yang 1
Affiliation
Biothiols and SO2 derivatives, as essential reactive sulfur species (RSS), play vital roles in various physiological processes and have a close network of generation and metabolic pathways among them. To clarify their complex correlations, fluorescent probes to simultaneously detect GSH, Cys, and SO2 derivatives are highly desirable. Herein, we develop the first fluorescent probe (BO-HEM) to simultaneously discriminate GSH, Cys, and SO2 derivatives. The fluorescent probe is designed by integration of hemicyanine and BODIPY fluorophores through an ether bond. The ether bond of the probe is rapidly replaced by thiolates through nucleophilic aromatic substitution (SNAr) to generate hemicyanine with NIR fluorescence and sulfur-BODIPY. The amino groups of Cys but not GSH then further replace the thiolate to form amino-BODIPY. As for SO32–, nucleophilic addition to the double bond of BO-HEM generates adduct O-BODIPY with green fluorescence. To further improve the sensing performance, the nanoprobe with increased reactivity and biocompatibility is constructed by encapsulation of BO-HEM into the polymeric micelle. More importantly, by taking advantage of the hydrophilicity of the reaction products, the spectral discrimination was further enhanced to avoid signal interference. The nanoprobe is applied to discriminate biothiols and SO2 derivatives in living cells through three-color fluorescence imaging.
中文翻译:
同时鉴别GSH,Cys和SO2衍生物的荧光探针。
生物硫醇和SO 2衍生物作为必需的反应性硫物种(RSS),在各种生理过程中起着至关重要的作用,并且在它们之间具有紧密的生成和代谢途径网络。为了阐明它们的复杂相关性,非常需要同时检测GSH,Cys和SO 2衍生物的荧光探针。本文中,我们开发了第一个荧光探针(BO-HEM)以同时区分GSH,Cys和SO 2衍生物。荧光探针是通过将半菁和BODIPY荧光团通过醚键整合而设计的。探针的醚键通过亲核芳香取代(S NAr)生成具有NIR荧光和硫-BODIPY的半花菁。然后,Cys的氨基而不是GSH的氨基进一步取代硫醇盐以形成氨基-BODIPY。对于SO 3 2-,BO-HEM双键的亲核加成生成带有绿色荧光的加合物O-BODIPY。为了进一步改善传感性能,通过将BO-HEM封装到聚合物胶束中,构建了具有更高反应性和生物相容性的纳米探针。更重要的是,通过利用反应产物的亲水性,光谱分辨力进一步增强以避免信号干扰。纳米探针用于区分生物硫醇和SO通过三色荧光成像,活细胞中的2种衍生物。
更新日期:2020-08-04
中文翻译:
同时鉴别GSH,Cys和SO2衍生物的荧光探针。
生物硫醇和SO 2衍生物作为必需的反应性硫物种(RSS),在各种生理过程中起着至关重要的作用,并且在它们之间具有紧密的生成和代谢途径网络。为了阐明它们的复杂相关性,非常需要同时检测GSH,Cys和SO 2衍生物的荧光探针。本文中,我们开发了第一个荧光探针(BO-HEM)以同时区分GSH,Cys和SO 2衍生物。荧光探针是通过将半菁和BODIPY荧光团通过醚键整合而设计的。探针的醚键通过亲核芳香取代(S NAr)生成具有NIR荧光和硫-BODIPY的半花菁。然后,Cys的氨基而不是GSH的氨基进一步取代硫醇盐以形成氨基-BODIPY。对于SO 3 2-,BO-HEM双键的亲核加成生成带有绿色荧光的加合物O-BODIPY。为了进一步改善传感性能,通过将BO-HEM封装到聚合物胶束中,构建了具有更高反应性和生物相容性的纳米探针。更重要的是,通过利用反应产物的亲水性,光谱分辨力进一步增强以避免信号干扰。纳米探针用于区分生物硫醇和SO通过三色荧光成像,活细胞中的2种衍生物。