高等学校化学学报

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2-(2-羟基-3-甲氧基苯基)-C60吡咯烷衍生物的合成及电化学传感应用

吴杨仪1,陈建平2,艾益静1,高飞3,高凤1   

  1. 1. 闽南师范大学
    2. 闽南师范大学化学化工与环境学院
    3. 闽南师范大学化学与环境学院
  • 收稿日期:2020-10-13 修回日期:2020-11-16 出版日期:2020-11-25 发布日期:2020-11-25
  • 通讯作者: 高凤

2-(2-羟基-3-甲氧基苯基)-C60吡咯烷衍生物的合成及电化学传感应用

  • Received:2020-10-13 Revised:2020-11-16 Online:2020-11-25 Published:2020-11-25
  • Contact: Feng Gao

摘要: 采用1, 3-偶极[3+2]环加成反应,合成了2-(2-羟基-3-甲氧基苯基)-C60吡咯烷衍生物(HMP-C60),并采用红外光谱、紫外吸收光谱、元素分析和液质联用技术对产物的化学结构进行了表征。通过滴涂法将HMP-C60固定在玻碳电极表面上,并以Zr4+为桥联试剂将探针DNA组装到HMP-C60修饰电极表面,构建了基于HMP-C60修饰电极的电化学DNA传感器。以[Fe(CN)6]3-/4-为电活性探针,对不同修饰电极进行了电化学表征,并采用电化学交流阻抗法考察了传感器对花椰菜花叶病毒(CaMV35S)启动子特征片段的分析性能。实验结果表明,在1.0×10-13 ~ 1.0×10-9 mol/L的浓度范围内,该电化学传感器电子转移阻抗变化值(ΔRet)与目标序列浓度对数(lgCS2)呈现良好的线性关系,检出限达到4.0×10-14 mol/L(S/N=3)。该传感器能有效识别完全互补序列、碱基错配序列和非互补序列,表现出良好的选择性。

Abstract: A new pyrrolidine derivative of 2-(2-hydroxy-3-methoxyphenyl)-C60 pyrrolidine derivative (HMP-C60) was synthesized by a 1, 3-dipolar [3+2] cycloaddition reaction, and the chemical structure of the product was characterized by infrared spectroscopy, ultraviolet absorption spectroscopy, elemental analysis and liquid-mass spectrometry. The HMP-C60 was then immobilized on the surface of the glassy carbon electrode by coating. Then, on the basis of the strong coordination between Zr4+ and the oxygen-containing groups, the Zr4+ was used as a bridging reagent to tether probe DNA with the 5'-end modified phosphate group on the surface of the HMP-C60 modified electrode. Thus, an electrochemical DNA sensor based on HMP-C60 modified electrode was constructed. Using [Fe(CN)6]3-/4- as the electroactive probe, the electrochemical characterization of different modified electrodes was carried out, and the performance of the sensors for analyzing the characteristic DNA fragments of cauliflower Mosaic virus (CaMV35S) promoter was investigated by impedance method. The experimental results showed that in the concentration range of 1.0×10-13 ~ 1.0×10-9 mol/L, the electron transfer impedance changes (ΔRet) of the biosensor had a good linear relationship with the logthrim values of the target DNA concentrations (lgCS2), and the detection limit was estimated to be 4.0×10-14 mol/L (S/N=3). The biosensor can effectively identify complementary sequences, base-mismatched sequences and non-complementary sequences, showing a good selectivity.