| 一种基于菲并咪唑的新型次氯酸荧光探针及细胞成像研究 |
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| 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)；衡阳师范学院省级平台开放基金项目(MO18K03)；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) |
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| 中文摘要:该文设计并合成了一种基于菲并咪唑的新型次氯酸荧光探针，该探针由商用试剂9,10-菲醌和4-(甲基巯基)苯甲醛通过一步反应生成，只需简单后处理(过滤和水洗)即可得到大量纯品(产率达85%)。由于硫的重原子效应，探针荧光较弱。但在次氯酸存在下，探针分子内的硫原子被氧化成亚砜，重原子效应减弱，同时分子内电荷转移效应(ICT)加强，导致荧光增强。借助高分辨质谱，证明了探针与次氯酸盐的反应机理。在PBS缓冲溶液中(DMF∶H2O=2∶8，体积比，pH 7.4)，探针MPI可定量检测0~100 μmol/L范围内的HClO，检出限为0.26 μmol/L。该探针对次氯酸具有较高的灵敏性和选择性。更重要的是，MPI具有良好生物相容性和细胞渗透性，可用于活细胞内次氯酸的可视化成像。探针MPI有望为机体内次氯酸的检测与追踪提供一种可靠、有效的方法。 |
| 中文关键词:荧光探针 次氯酸 菲并咪唑 荧光成像 |
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| A Novel Fluorescent Probe Based on Phenanthroimidazole for Hypochlorite and Its Cell Imaging Application |
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| Abstract:In this paper,a novel fluorescence probe was designed and synthesized for the detection of HClO based on phenanthroimidazole.The probe 2-(4-(methylthio)phenyl) 1H-phenanthro［9,10-d］imidazole(MPI) was prepared through one step reaction with commercial reagents 9,10-phenanthroquinone and 4 (methylthio)benzaldehyde,and obtained in good yield(85%) by simple filtration and washing.The free MPI displayed relatively weak fluorescence due to the heavy atom effect of sulfur atom.However,addition of HClO into the MPI solution triggered a strong fluorescence at 445 nm as the HClO promoted oxidation of sulfide into sulfoxide reduced the heavy atom effect and strengthened the intramolecular charge transfer(ICT) process.The reaction mechanism of MPI and HClO was confirmed using high resolution mass spectrometry.In PBS buffer(DMF∶H2O=2 ∶8,by volume,pH 7.4),the probe MPI could be used for quantitative detection of HClO in the range of 0-100 μmol/L with a detection limit of 0.26 μmol/L as it has high sensitivity and selectivity to HClO other than other analytes.More importantly,with good biocompatibility and cell membrane permeability,the probe MPI could be applied in the visual imaging of HClO in living cells.Therefore,The probe MPI provides a reliable and effective tool for detection and tracing of HClO in biological systems. |
| Key Words:fluorescent probe hypochlorite phenanthroimidazole cell imaging |
| 引用本文：申有名，杨玉芬，谷标.一种基于菲并咪唑的新型次氯酸荧光探针及细胞成像研究[J].分析测试学报,2020,39(8):961-966. |
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