基于<i>β</i>-二酮类铕(Ⅲ)配合物的一氧化氮荧光探针的设计、合成及应用研究

引用本文: 闵盼, 郑德泽, 车婉萌, 邢月, 吴晶. 基于β-二酮类铕(Ⅲ)配合物的一氧化氮荧光探针的设计、合成及应用研究[J]. 分析化学, 2021, 49(10): 1704-1712. doi: 10.19756/j.issn.0253-3820.211233 shu

Citation: MIN Pan, ZHENG De-Ze, CHE Wan-Meng, XING Yue, WU Jing. Design and Synthesis of A β-Diketonate-Europium(Ⅲ) Complex-based Fluorescent Probe for Nitric Oxide Detection and Its Application in Bioimaging[J]. Chinese Journal of Analytical Chemistry, 2021, 49(10): 1704-1712. doi: 10.19756/j.issn.0253-3820.211233 shu

基于β-二酮类铕(Ⅲ)配合物的一氧化氮荧光探针的设计、合成及应用研究

辽宁师范大学化学化工学院, 大连 116029

通讯作者: 吴晶,E-mail:wujing@lnnu.edu.cn

基金项目:
2019年国家大学生创新训练计划项目（No.201910165118）资助。

摘要: 以含一氧化氮（NO）识别基团邻二氨基苯基的联三吡啶衍生物4-（4-[2，2'：6'，2″]三联吡啶-4'-基-苯氧基）-苯-1，2-二胺（TPBD）为配位体，β-二酮类化合物5-（1'，1″-二苯基-4'-基）-1，1，1，2，2，3，3-七氟-4，6-己二酮（DHH）为共配体，设计并合成了一种用于检测NO的β-二酮类铕(Ⅲ)配合物荧光探针[Eu （DHH）₃（TPBD）]，采用质谱和元素分析确证其结构。光谱研究结果表明，探针[Eu （DHH）₃（TPBD）]本身仅发出微弱的光，与NO反应后荧光强度增强近10倍，定量检测NO的线性浓度范围为0.017~0.83 μmol/L，检出限为7.4 nmol/L。探针[Eu （DHH）₃（TPBD）]对几种常见的活性氧/氮物种基本上不响应，对NO显示出良好的选择性。荧光成像实验表明，探针[Eu （DHH）₃（TPBD）]具有低细胞毒性和线粒体靶向定位性能，并成功实现对RAW 264.7活细胞和斑马鱼体内的NO的时间分辨荧光成像检测。

关键词:

English

Design and Synthesis of A β-Diketonate-Europium(Ⅲ) Complex-based Fluorescent Probe for Nitric Oxide Detection and Its Application in Bioimaging

School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, China

Corresponding author: WU Jing, wujing@lnnu.edu.cn

Received Date: 19 March 2021
Revised Date: 03 August 2021
Fund Project:
Supported by the Undergraduate Training Programs for Innovation and Entrepreneurship of Liaoning Province (No.201910165118).

Abstract: By using NO-recognizable o-diaminophenyl-substituted terpyridine derivative ligand 4-(4-[(2,2':6',2″-terpyridin)-4'-yl]phenoxy)benzene-1,2-diamine (TPBD) as the ligand, and β-diketone 6-(1',1″-diphenyl-4'-yl)-1,1,1,2,2,3,3-heptafluoro-4,6-hexanedione (DHH) as the coligand, a new β-diketonate-Eu³⁺ complex-based fluorescent probe,[Eu(DHH)₃(TPBD)], was designed and synthesized for detection of NO, and its structure was characterized by mass spectrum and elemental analysis methods. The spectral results indicated that the probe[Eu(DHH)₃(TPBD)] had only weak fluorescence, and its fluorescence intensity was increased by nearly 10 times after reacting with NO. The probe could be used to quantitatively detect NO at concentrations ranging from 0.017-0.83 μmol/L with a detection limit of 7.4 nmol/L. Meanwhile,[Eu(DHH)₃(TPBD)] showed approximately no response to other common reactive oxygen/nitrogen species, which demonstrated the good NO sensitivity of the probe. The fluorescence imaging experiments proved that the probe[Eu(DHH)₃(TPBD)] had low cytotoxicity and mitochondria targetability, and was successfully applied to the time-gated fluorescence imaging of NO in living cells and zebrafish.

Key words:

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沈阳化工大学材料科学与工程学院沈阳 110142

基于β-二酮类铕(Ⅲ)配合物的一氧化氮荧光探针的设计、合成及应用研究

通讯作者: 吴晶,E-mail:wujing@lnnu.edu.cn

English

Design and Synthesis of A β-Diketonate-Europium(Ⅲ) Complex-based Fluorescent Probe for Nitric Oxide Detection and Its Application in Bioimaging

Corresponding author: WU Jing, wujing@lnnu.edu.cn

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

基于β-二酮类铕(Ⅲ)配合物的一氧化氮荧光探针的设计、合成及应用研究

通讯作者: 吴晶,E-mail:wujing@lnnu.edu.cn

English

Design and Synthesis of A β-Diketonate-Europium(Ⅲ) Complex-based Fluorescent Probe for Nitric Oxide Detection and Its Application in Bioimaging

Corresponding author: WU Jing, wujing@lnnu.edu.cn

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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