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一种基于苯并噻唑的新型过氧亚硝酸盐荧光探针的合成及应用
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作者单位
张春香,王慧平,刘梦琴,申有名,谷标 1.湖南文理学院化学与材料工程学院
2.衡阳师范学院化学与材料科学学院功能金属有机化合物湖南省高校重点实验室 
基金项目:国家自然科学基金项目(21907026);湖南省自然科学基金资助项目(2019JJ50009);湖南省教育厅资助项目(18B369,19K011);衡阳师范学院环境监测与评价中心项目(KYJG1803);常德市指导性科技计划项目( 2019ZD09)
中文摘要:作为一种典型的活性氮物质,过氧亚硝酸盐(ONOO-)在生理和病理过程中发挥着重要作用。但目前已有的用于检测ONOO-的荧光探针大多存在对ONOO-响应时间长、选择性不足、灵敏性差等缺点,极大地限制了生物体内ONOO-的实时、原位检测。此外,一些探针合成复杂和纯化困难,不利于探针推广使用。该文以2-(2′-羟基-3′-醛基-5′-甲基苯基)苯并噻唑和1,1-二甲基肼为原料,通过一步缩合,简单过滤处理得到一种基于苯并噻唑的新型ONOO-荧光探针BD。但由于N—N单键旋转产生非辐射能量损失,探针BD荧光较弱。在引入ONOO-后,探针BD上的腙水解成醛基,N—N单键脱落,荧光增强,同时可观察到明显的颜色变化。在PBS缓冲溶液(DMSO∶H2O=2∶8,体积比,pH 7.4)中,探针BD对ONOO-具有快速响应(25 s)、高灵敏度(7 nmol/L)和高选择性的特点,可在较宽pH值范围内工作。此外,探针BD还成功地用于肝癌细胞中ONOO-的荧光成像,因此,可作为揭示ONOO-在细胞中作用的一个很有潜力的分析工具。
中文关键词:过氧亚硝酸盐  荧光探针  苯并噻唑  细胞成像
 
A Novel Fluorescent Probe Based on Benzothiazole Dye for Peroxynitrite Detection and Its Application in Cell Imaging
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.
Key Words:peroxynitrite  fluorescent probe  benzothiazole  cell imaging
引用本文:张春香,王慧平,刘梦琴,申有名,谷标.一种基于苯并噻唑的新型过氧亚硝酸盐荧光探针的合成及应用[J].分析测试学报,2020,39(12):1494-1500.
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