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2019 , Vol. 39 >Issue 11: 3250 - 3257

DOI: https://doi.org/10.6023/cjoc201904078

研究论文

基于激发态分子内质子转移(ESIPT)和聚集诱导发光(AIE)活性的菲并咪唑Fe3+荧光探针及细胞成像研究

  • 何玉倩 ,
  • 赵冰 ,
  • 阚伟 ,
  • 王丽艳 ,
  • 宋波 ,
  • 殷广明 ,
  • 毕野 ,
  • 陈书文
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  • a齐齐哈尔大学化学与化学工程学院 黑龙江齐齐哈尔 161006
    b 辽宁科技大学材料与冶金学院 辽宁鞍山 114051

收稿日期: 2019-04-30

  网络出版日期: 2019-06-19

基金资助

国家自然科学基金(21506106);黑龙江省科学基金(LC2017004);黑龙江省高校基本业务费(135209209);黑龙江省高校基本业务费(YSTSXK201853);黑龙江省高校基本业务费(YSTSXK201859);齐齐哈尔大学研究生创新科研(YJSCX2018-ZD18)

收起

An Excited-State Intramolecular Proton Transfer (ESIPT) Plus Ag-gregation Induced Emission (AIE) Phenanthro[9, 10-d]imidazole-Based Fluorescence Probe for Detection of Fe3+ in Living Cells

  • Yuqian He ,
  • Bing Zhao ,
  • Wei Kan ,
  • Liyan Wang ,
  • Bo Song ,
  • Guangming Yin ,
  • Ye Bi ,
  • Shuwen Chen
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  • a Chemistry and Chemical Engineering Institute, Qiqihar University, Qiqihar, Heilongjiang 161006
    b School of Materials and Metallurgy, University of Science and Technology Liaoning, Anshan, Liaoning 114051

Received date: 2019-04-30

  Online published: 2019-06-19

Supported by

the National Natural Science Foundation of China(21506106);the Natural Science Foundation of Heilongjiang Province(LC2017004);the Fundamental Research Funds in Heilongjiang Provincial Universities(135209209);the Fundamental Research Funds in Heilongjiang Provincial Universities(YSTSXK201853);the Fundamental Research Funds in Heilongjiang Provincial Universities(YSTSXK201859);the Qiqihar University Graduate Innovation Fund Grants(YJSCX2018-ZD18)

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摘要

设计合成具有激发态分子内质子转移（ESIPT）和聚集诱导发光（AIE）特征的酚羟基菲并咪唑Fe3+荧光探针PIP-o-OH，对其结构进行了表征和确认，并通过单晶结构确认了探针PIP-o-OH中的O-H与咪唑N的分子内氢键.紫外和荧光光谱分析表明，探针PIP-o-OH与Fe3+形成络合物后实现Fe3+的选择性识别，并通过质谱和离散傅立叶变换（DFT）计算确定了探针PIP-o-OH与Fe3+的配位方式.探针PIP-o-OH与Fe3+络合前后的荧光变化成功应用于HeLa细胞和实际水样中Fe3+的检测.

关键词： 菲并咪唑; Fe3+; 荧光探针; 细胞成像; 水样

本文引用格式

何玉倩 , 赵冰 , 阚伟 , 王丽艳 , 宋波 , 殷广明 , 毕野 , 陈书文 . 基于激发态分子内质子转移(ESIPT)和聚集诱导发光(AIE)活性的菲并咪唑Fe3+荧光探针及细胞成像研究[J]. 有机化学, 2019 , 39(11) : 3250 -3257 . DOI: 10.6023/cjoc201904078

Abstract

Selective detection of Fe3+ has considerable importance due to its active involvement in various biological processes. Based on the mechanism of excited-state intramolecular proton transfer (ESIPT) plus aggregation induced emission (AIE), a fluorescence probe of phenanthro[9, 10-d]imidazole modified by the phenolic hydroxyl (PIP-o-OH) had been designed, synthesized and applied in the detection of Fe3+. The structure of PIP-o-OH was characterized by 1H NMR, 13C NMR, IR, HRMS and X-ray single diffraction. Furthermore, a clear intramolecular hydrogen bond was observed between hydroxyl O-H and imidazole N atom in X-ray single structure, which improved the impossibility of ESIPT activity. ESIPT and AIE activities of PIP-o-OH were adequately determined by absorption, emission spectra and scanning electron microscope (SEM). The aggregated PIP-o-OH in MeOH/H2O (V:V=1:9, Hepes 10 μmol/L, pH=7.4) exhibited a good sensitivity towards Fe3+ with "turn-off" fluorescence response just after 20 s. The limit of detection (LOD) was calculated as low as 0.49 μmol/L. So it could be utilized to detect Fe3+ in biology and environmental samples. In addition, the calculation of the density functional theory (DFT) confirmed the formation of PIP-o-OH-Fe3+ complex. Also, PIP-o-OH was successfully applied to monitor Fe3+ in HeLa cells by the fluorescence change and quantificationally detect Fe3+ in water samples.

Key words： phenanthro[9, 10-d]imidazole; Fe3+; fluorescence probe; cell imaging; water samples

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