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2021 , Vol. 41 >Issue 3: 1168 - 1176

DOI: https://doi.org/10.6023/cjoc202008049

研究论文

诺蒎酮基喹唑啉-2-胺型铜离子荧光探针的合成及其应用研究

  • 张明光 ,
  • 李明新 ,
  • 杨益琴 ,
  • 徐徐 ,
  • 宋杰 ,
  • 王忠龙 ,
  • 王石发
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  • a 南京林业大学轻工与食品学院 南京林业大学林业资源高效加工利用协同创新中心 南京 210037
    b 密西根大学菲林特分校化学与生物化学系 菲林特 密西根 48502

收稿日期: 2020-08-26

  修回日期: 2020-10-22

  网络出版日期: 2020-11-04

基金资助

国家自然科学基金(32071707); 江苏省高校重点学科建设资助项目

收起

Synthesis of Nopinone-Based Quinazolin-2-amine Fluorescent Probe for Detection of Cu2+ and Its Application Research

  • Mingguang Zhang ,
  • Mingxin Li ,
  • Yiqin Yang ,
  • Xu Xu ,
  • Jie Song ,
  • Zhonglong Wang ,
  • Shifa Wang
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  • a Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Light Industry and Food,Nanjing Forestry University, Nanjing 210037, China
    b Department of Chemistry and Biochemistry, University of Michigan-Flint, Flint, MI 48502, USA
* Corresponding authors. E-mail: ;

Received date: 2020-08-26

  Revised date: 2020-10-22

  Online published: 2020-11-04

Supported by

National Natural Science Foundation of China(32071707); Jiangsu Provincial Key Lab for the Chemistry and Utilization of Agro-Forest Biomass, and the Priority Academic Program Development of Jiangsu Higher Education Institutions

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摘要

以可再生的β-蒎烯衍生物诺蒎酮为原料, 设计合成了一种新型的诺蒎酮基喹唑啉-2-胺铜离子荧光探针N-苄基- 4-(4-(二乙氨基)苯基)-7,7-二甲基-5,6,7,8-四氢-6,8-桥亚甲基喹唑啉-2-胺(BNQ). 探针BNQ在PBS/THF (V/V=8/2, 10 mmol?L–1, pH=7.4)溶液中对Cu2+表现出高度选择性的荧光猝灭效应, 并能在较宽pH范围(4~10)内有效识别Cu2+. 同时, 荧光滴定实验结果表明, 探针BNQ对Cu2+具有良好的灵敏度, 其检测限为0.09 μmol?L –1, 远低于世界卫生组织(WHO)规定在饮用水中Cu2+的最高含量(<30 μmol?L–1). 而且, 采用高分辨质谱以及密度泛函理论计算确定了探针BNQ与Cu2+的络合作用机理. 探针BNQ还可以对不同水环境中的微摩尔级Cu2+进行快速检测. 生物成像实验发现, 探针BNQ还可检测斑马鱼体内的Cu2+, 并呈现出良好的荧光成像效果.

关键词： 诺蒎酮; 喹唑啉-2-胺; 荧光探针; 铜离子; 生物成像

本文引用格式

张明光 , 李明新 , 杨益琴 , 徐徐 , 宋杰 , 王忠龙 , 王石发 . 诺蒎酮基喹唑啉-2-胺型铜离子荧光探针的合成及其应用研究[J]. 有机化学, 2021 , 41(3) : 1168 -1176 . DOI: 10.6023/cjoc202008049

Abstract

In this study, a novel nopinone-based quinazolin-2-amine fluorescent probe N-benzyl-4-(4-(diethylamino)phenyl)- 7,7-dimethyl-5,6,7,8-tetrahydro-6,8-methanoquinazolin-2-amine (BNQ) was synthesized from renewable β-pinene derivative nopinone. The probe BNQ exhibited a high selective fluorescence quenching response toward Cu2+in PBS/THF (V/V=8/2, 10 mmol?L–1, pH=7.4) solution, and could effectively recognize Cu2+ within a wide pH range (4~10). Meanwhile, the fluorescent titration experiment showed that the probe BNQ was high sensitive for detecting Cu2+, and its detection limit was found to be 0.09 μmol?L –1, which was much lower than that of stated by World Health Organization (WHO) in drinking water (<30 μmol?L–1). Furthermore, the coordination mechanism of probe BNQ with Cu2+ was confirmed by high resolution mass spectrum (HRMS) and density functional theory (DFT) calculations. The probe BNQ could detect micromolar Cu2+ in different environmental water samples. The results of bio-imaging experiment demonstrated that the probe BNQwas also successfully used for monitoring Cu2+ in living zebrafish, and showed an excellent fluorescence imaging performance.

Key words： nopinone; quinazolin-2-amine; fluorescent probe; Cu2+ ion; bioimaging

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