SIOC English
化学学报
高级检索

化学学报 >

2013 , Vol. 71 >Issue 11: 1496 - 1499

DOI: https://doi.org/10.6023/A13070796

研究通讯

一种基于苯并噁唑类的可视化检测汞离子的荧光探针

  • 张勇 ,
  • 李伟 ,
  • 王强 ,
  • 张若璇 ,
  • 熊启杰 ,
  • 沈祥 ,
  • 郭靖 ,
  • 陈雪梅
展开
  • a 湖北理工学院化学与材料工程学院 黄石 435003;
    b 矿区环境污染控制与修复湖北省重点实验室 黄石 435003

收稿日期: 2013-07-29

  网络出版日期: 2013-09-10

基金资助

项目受湖北省教育厅青年人才项目(No. Q20134402)、湖北理工学院校级创新人才项目(No. 12xjz21C)和矿区环境污染控制与修复湖北省重点实验室开放基金(No. 2012103)资助.

收起

A Benzoxazole-Based Fluorescent Probe for Visual Detection of Hg2+

  • Zhang Yong ,
  • Li Wei ,
  • Wang Qiang ,
  • Zhang Ruoxuan ,
  • Xiong Qijie ,
  • Shen Xiang ,
  • Guo Jing ,
  • Chen Xuemei
Expand
  • a School of Chemical and Materials Engineering, Hubei Polytechnic University, Huangshi 435003;
    b Hubei Key Laboratory of Mine Environmental Pollution Control & Remediation, Huangshi 435003

Received date: 2013-07-29

  Online published: 2013-09-10

Supported by

Project supported by the Youth Program of Educational Commission of Hubei Province (No. Q20134402), the Hubei Polytechnic University Innovation Program (No. 12xjz21C) and the Open Foundation of Hubei Key Laboratory of Mine Environmental Pollution Control & Remediation (No. 2012103).

Fold

摘要

设计合成了一种用于检测Hg2+的苯并噁唑类荧光探针4-(苯并[d]噁唑-2-基)-2-((二(2-(乙巯基)乙基)氨基)甲基)苯酚(ZY1), 用质谱、核磁氢谱和X射线单晶衍射等方法对其进行了结构表征, 并考察了其光谱性能. 研究结果表明, ZY1对Hg2+有较高的选择性和灵敏度, 它们之间的结合比为1:1, 共存离子及pH值(3.0～9.0)对其测定影响小. ZY1能够可视化检测Hg2+, 并在HeLa活细胞中实现了汞离子的成像, 这对检测生物体内的Hg2+将具有潜在的应用价值.

关键词： 苯并噁唑; 汞离子; 荧光探针; 可视化检测; 荧光成像

本文引用格式

张勇 , 李伟 , 王强 , 张若璇 , 熊启杰 , 沈祥 , 郭靖 , 陈雪梅 . 一种基于苯并噁唑类的可视化检测汞离子的荧光探针[J]. 化学学报, 2013 , 71(11) : 1496 -1499 . DOI: 10.6023/A13070796

Abstract

A benzoxazole-based fluorescent probe 4-(benzo[d]oxazol-2-yl)-2-((bis(2-(ethylthio)ethyl)amino)methyl)phenol (ZY1) was designed and synthesized, and characterized by mass spectrometry (MS), nuclear magnetic resonance (NMR) and X-ray single crystal diffraction, etc. ZY1 was prepared by Mannich reaction, and its pale yellow crystals suitable for X-ray diffraction studies were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of a few days. The results showed that ZY1 exhibited good sensitivity and selectivity to Hg2+. The fluorescence of ZY1 was quenched dramatically in the presence of Hg2+, and it remained nearly constant in the range of pH 3.0～9.0. Other metal ions, such as K+, Ca2+, Na+, Mg2+, Mn2+, Fe2+, Fe3+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Pb2+, induced negligible fluorescence quenching for ZY1 under the same conditions. When the concentration of Hg2+ was increased from 0 to 30 μmol/L, the fluorescence of ZY1 (10 μmol/L) quenched gradually. Binding analysis using the method of continuous variations (Job's plot) established that the stoichiometry of ZY1-Hg2+ complex was estimated to be 1:1. The fluorescence intensity varied almost linearly vs. the concentration of Hg2+ (0.5～4.8 μmol/L), and the detection limit of Hg2+ was estimated to be 0.08 μmol/L. Moreover, ZY1 was used for the visual detection of Hg2+ and applied to image intracelluar Hg2+ in living HeLa cells, indicating that it could be a useful tool in bioanalytical applications.

Key words： benzoxazole; mercuric ion; fluorescent probe; visual detection; fluorescent imaging

参考文献

[1] Clarkson, T. W.; Magos, L.; Myers, G. J. N. Engl. J. Med. 2003, 349, 1731.

[2] Nolan, E. M.; Lippard, S. J. Chem. Rev. 2008, 108, 3443.

[3] Du, M.-H.; Han, Z.-X.; Wu, X.-Y.; Liang, G.-X.; Zhao, T.; Zhang, H.-Q. Chin. J. Spectrosc. Lab. 2012, 29, 3170. (杜明辉, 韩志湘, 吴向阳, 梁国熙, 赵婷, 张浩琪, 光谱实验室, 2012, 29, 3170.)

[4] Wu, X.-L.; Lai, J.-P.; Zhao, Y.-B. Chem. J. Chin. Univ. 2012, 33, 695. (吴小丽, 赖金平, 赵一兵, 高等学校化学学报, 2012, 33, 695.)

[5] Huang, W.-J.; Wu, W.-H.; Liang, J.-X. Acta Chim. Sinica 2012, 70, 873. (黄文君, 吴文辉, 梁嘉香, 化学学报, 2012, 70, 873.)

[6] Chi, X.-B.; Liu, Y. Chin. J. Org. Chem. 2013, 33, 1545. (迟兴宝, 刘洋, 有机化学, 2013, 33, 1545.)

[7] Lü, S.-Y.; Ye, T.; Jiang, X.; Wang, J.-J.; Wei, G.-F.; Lü, J.-Q. Acta Chim. Sinica 2011, 69, 831. (吕诗言, 叶泰, 姜欣, 王晶晶, 魏国芬, 吕鉴泉, 化学学报, 2011, 69, 831.)

[8] Nolan, E. M.; Lippard, S. J. J. Am. Chem. Soc. 2007, 129, 5910.

[9] Yang, Y.-M.; Zhao, Q.; Feng, W.; Li, F.-Y. Chem. Rev. 2013, 113, 192.

[10] Meng, Q.-H.; Cheng, S.; Lan, M.-B.; Wei, G. Chin. J. Chem. 2012, 30, 249

[11] Liu, J.; Sun, Y.-Q.; Wang, P.; Zhang, J.-Y.; Guo, W. Analyst 2013, 138, 2654.

[12] Priyanka, S.; Rashid, A.; Syed, S. R.; Mohammad, S.; Satyakam, P.; Arvind, M. Tetrahedron Lett. 2013, 54, 3688.

[13] Lin, Q.; Chen, P.; Liu, J.; Fu, Y.-P.; Zhang, Y.-M.; Wei, T.-B. Prog. Chem. 2013, 25, 1177. (林奇, 陈佩, 刘娟, 符永鹏, 张有明, 魏太保, 化学进展, 2013, 25, 1177.)

[14] Wang, X.-M.; Wang, J.-G.; Xu, W.-C. Dyestuffs Coloration, 2005, 42, 8. (王雪梅, 王景国, 胥维昌, 染料与染色, 2005, 42, 8.)

[15] Pan, J.-X.; Wang, C.-J.; Gao, Z.-H.; Yao, X.-K.; Wang, R.-J. Chem. J. Chin. Univ. 1990, 11, 31. (潘家杏, 王超杰, 高振衡, 姚心侃, 王如骥, 高等学校化学学报, 1990, 11, 31.)

[16] Fan, J.-L.; Guo, K.-X.; Peng, X.-J.; Du, J.-J.; Wang, J.-Y.; Sun, S.-G.; Li, H.-L. Sens. Actuators, B: Chem. 2009, 142, 191.

[17] Taki, M.; Akaoka, K.; Iyoshi, S.; Yamamoto, Y. Inorg. Chem. 2012, 51, 13075.

[18] Du, J.-J.; Fan, J.-L.; Peng, X.-J.; Sun, P.-P.; Wang, J.-Y.; Li, H.-L.; Sun, S.-G. Org. Lett. 2010, 12, 476.

[19] Chen, X.-Q.; Nam, S.-W.; Jou, M. J.; Kim, Y.; Kim, S.-J.; Park, S.; Yoon, J. Org. Lett. 2008, 10, 5235.

[20] Chen, M.-L.; Lv, X.; Liu, Y.-L.; Zhao, Y.; Liu, J.; Wang, P.; Guo, W. Org. Biomol. Chem. 2011, 9, 2345.

[21] Chen, W.-H.; Xing, Y.; Pang, Y. Org. Lett. 2011, 13, 1362.

[22] Kwon, J. E.; Lee, S.; You, Y.; Baek, K. H.; Ohkubo, K.; Cho, J.; Fukuzumi, S.; Shin, I.; Park, S. Y.; Nam, W. Inorg. Chem. 2012, 51, 8760.

[23] Shortreed, M.; Kopelman, R.; Kuhn, M.; Hoyland, B. Anal. Chem. 1996, 68, 1414.

Options
文章导航

/

〈 〉