肼二腙类多功能长波发射荧光探针的合成及其铜配合物对H2S的识别

doi:10.6023/cjoc201802014

有机化学 ›› 2018, Vol. 38 ›› Issue (7): 1786-1791.DOI: 10.6023/cjoc201802014 上一篇下一篇

所属专题：荧光探针-生物传感合辑

研究论文

肼二腙类多功能长波发射荧光探针的合成及其铜配合物对H₂S的识别

钟克利^a,b, 赵杰^a, 李秋莹^b, 侯淑华^a, 汤轶伟^b, 边延江^a, 汤立军^a

a 渤海大学化学化工学院锦州 121013;
b 渤海大学食品科学与工程学院生鲜农产品贮藏加工及安全控制技术国家地方联合工程研究中心锦州 121013

收稿日期:2018-02-08 修回日期:2018-03-16 发布日期:2018-04-04
通讯作者: 汤轶伟, 汤立军 E-mail:tangyiwei81@163.com;ljtang@bhu.edu.cn
基金资助:
辽宁省自然科学基金（No.20170540019）、国家自然科学基金（Nos.21304009，21476029，U1608222）和辽宁省博士科研启动基金（No.20170520416）资助项目.

Synthesis of Multifunctional Long-Wavelength-Emitting Fluorescent Probe Based on Hydrazine Dihydrazone and Its Copper Complex for Detection of H₂S

Zhong Keli^a,b, Zhao Jie^a, Li Qiuying^b, Hou Shuhua^a, Tang Yiwei^b, Bian Yanjiang^a, Tang Lijun^a

a College of Chemistry and Chemical Engineering, Bohai University, Jinzhou 121013;
b National & Local Joint Engineering Research Center of Storage, Processing and Safety Control Technology for Fresh Agricultural and Aquatic Products, College of Food Science and Technology, Bohai University, Jinzhou 121013

Received:2018-02-08 Revised:2018-03-16 Published:2018-04-04
Contact: 10.6023/cjoc201802014 E-mail:tangyiwei81@163.com;ljtang@bhu.edu.cn
Supported by:
Project supported by the Natural Science Foundation of Liaoning Province (No. 20170540019), the National Natural Science Foundation of China (Nos. 21304009, 21476029, U1608222) and the Doctoral Scientific Research Foundation of Liaoning Province (No. 20170520416).

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摘要/Abstract

以1，4-二乙基-7-羟基四氢喹喔啉-6-甲醛为基础，设计合成了一种具有长波长发射、较大斯托克斯位移的新型肼二腙类荧光探针L.在探针L的二甲基亚砜（DMSO）溶液中加入Cu²⁺和Co²⁺后，溶液颜色由黄色分别变为粉色和无色，可裸眼识别Cu²⁺和Co²⁺.利用L与Cu²⁺形成的配合物，在DMSO/H₂O（V∶V=7∶3，HEPES，1×10^-2 mol/L，pH=7.4）缓冲溶液中可荧光“OFF-ON”识别H₂S.试纸条实验表明，L-Cu²⁺对不同浓度H₂S显色明显，可以通过裸眼和荧光双通道快速检测H₂S.此外，利用Discovery Studio分子模拟软件，通过分子L结构反向找靶，并用CDOCKER程序进行分子对接，发现分子L对2x0v蛋白（来自人类的P53蛋白）有很好的结合作用，有望在医药领域得到应用.

关键词: 长波长发射, 荧光探针, H₂S, 识别, 分子对接

A novel fluorescent probe L with long wavelength emission and large Stokes shift was designed and synthesized based on 1,4-diethyl-7-hydroxytetrahydroquinoxaline-6-carboxaldehyde. The color of L was changed from yellow to pink and colorless upon addition of Cu²⁺ and Co²⁺ respectively in dimethylsulfoxide (DMSO), which illustrated that probe L could recognize Cu²⁺ and Co²⁺ by naked eyes. The complex L-Cu²⁺ could recognize H₂S with fluorescence "OFF-ON" in DMSO/H₂O (V:V=7:3, HEPES, 1×10^-2 mol/L, pH=7.4). The test strip assay showed that the L-Cu²⁺ pretreated test strip showed obvious color changes toward different concentrations of H₂S, which indicated that H₂S could be rapidly detected by naked eyes and fluorescent double channel. In addition, the molecular target of compound L can be searched by utilizing the reverse docking method in Discovery Studio (DS) software. Then, docking analysis was performed using CDOCKER module of DS, and it was found that molecule L has a good combination to 2x0v protein (P53_human). Therefore, it is expected to be applied in the medicine field.

Key words: long wavelength emission, fluorescent probe, H₂S, recognization, molecular docking

引用此文

钟克利, 赵杰, 李秋莹, 侯淑华, 汤轶伟, 边延江, 汤立军. 肼二腙类多功能长波发射荧光探针的合成及其铜配合物对H₂S的识别[J]. 有机化学, 2018, 38(7): 1786-1791.

Zhong Keli, Zhao Jie, Li Qiuying, Hou Shuhua, Tang Yiwei, Bian Yanjiang, Tang Lijun. Synthesis of Multifunctional Long-Wavelength-Emitting Fluorescent Probe Based on Hydrazine Dihydrazone and Its Copper Complex for Detection of H₂S[J]. Chin. J. Org. Chem., 2018, 38(7): 1786-1791.

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肼二腙类多功能长波发射荧光探针的合成及其铜配合物对H₂S的识别

Synthesis of Multifunctional Long-Wavelength-Emitting Fluorescent Probe Based on Hydrazine Dihydrazone and Its Copper Complex for Detection of H₂S

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