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| A Novel Fluorescent Probe Based on Benzothiazole Dye for Peroxynitrite Detection and Its Application in Cell Imaging |
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| DOI： |
| KeyWord:peroxynitrite fluorescent probe benzothiazole cell imaging |
| Author | Institution |
| ZHANG Chun-xiang,WANG Hui-ping,LIU Meng-qin,SHEN You-ming,GU Biao |
1.College of Chemistry and Materials Engineering,Hunan University of Arts and Science;2.College of Chemistry and Materials Science,Hengyang Normal University;Key Laboratory of Functional Metal-Organic Compounds of Hunan Province |
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| Abstract: |
| As a typical reactive nitrogen species(RNS),peroxynitrite(ONOO-) plays an important role in physiological and pathological processes.In the past few years,a number of fluorescent probes have been reported in ONOO- detection.However,most of probes suffer from delayed response time,low selectivity and sensitivity,which greatly limits the real time,in situ detection of ONOO- in living organisms.Besides,some probes need complicated synthetic and purification procedures,which restricts their promotion and application.In this work,a novel benzothiazole-based fluorescent probe(E)-2-(benzo［d］thiazol-2-yl)-6-((2,2-dimethylhydrazono)-methyl)-4-methylphenol(BD) for ONOO- detection was prepared through the condensation reaction of 2-(2′-hydroxy-3′-aldehyde-5′-methylphenyl)benzothiazole and 1,1 dimethylhydrazine.The free probe showed weak fluorescence due to the nonradiative deactivation induced by the rotation of N—N single bond.Upon treatment with ONOO-,the hydrazone in the probe BD was hydrolyzed into aldehyde group,and thus the N—N single bond was removed,which resulted in a dramatic fluorescence enhancement with naked eye colorimetric and fluorescence color changes.The sensing mechanism of probe BD for ONOO- was verified by high resolution mass spectrometry.In PBS buffer solution(DMSO∶H2O=2∶8,by volume,pH 7.4),the probe exhibited many advantages,including rapid response(25 s),low detection limit(7 nmol/L),high selectivity to ONOO- over other biological related species and tolerance of a wide range of pH values including physiological pH.More importantly,this probe was successfully applied to the fluorescence imaging of ONOO- in HepG2 cells with excellent cell-membrane permeability.Therefore,it could be used as a potential analytical tool to reveal the role of ONOO- in living cells. |
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