研究论文

四苯乙烯酰胺类化合物的合成及其高灵敏度、高选择性识别Cu2+

  • 苏小龙 ,
  • 李健鹏 ,
  • 刘孟鑫 ,
  • 邹莉 ,
  • 杨得锁 ,
  • 冯海涛
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  • 宝鸡文理学院化学化工学院 聚集诱导发光研究中心 陕西宝鸡 721000

收稿日期: 2024-03-27

  修回日期: 2024-05-23

  网络出版日期: 2024-07-15

基金资助

国家自然科学基金(52173152); 国家自然科学基金(21805002); 陕西省科技创新团队(2022TD-36); 陕西省自然科学基金(2024JC-YBMS-123); 陕西省教育厅服务地方(23JC001)

Synthesis of Tetraphenylethylene Based Amides for Detection of Copper(II) Ion with High Sensitivity and Selectivity

  • Xiaolong Su ,
  • Jianpeng Li ,
  • Mengxin Liu ,
  • Li Zou ,
  • Desuo Yang ,
  • Haitao Feng
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  • Aggregation-Induced Emission Research Center, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721000

Received date: 2024-03-27

  Revised date: 2024-05-23

  Online published: 2024-07-15

Supported by

National Natural Science Foundation of China(52173152); National Natural Science Foundation of China(21805002); Scientific and Technological Innovation Team of Shaanxi Province(2022TD-36); Natural Science Foundation of Shaanxi Province(2024JC-YBMS-123); Service Local Projects in Shaanxi Provincial Education Department(23JC001)

摘要

设计合成了一种四苯乙烯基酰胺类荧光探针TPE-Py, 并对其结构进行了表征. 通过荧光发射光谱和HeLa细胞成像实验研究了其金属离子识别性能. 结果表明: 探针TPE-Py对Cu2+具有较好的选择性和灵敏性, 在H2O/THF (VV=9∶1)溶液中对Cu2+显示出荧光淬灭效应, 且不受其他金属离子干扰. 细胞成像实验表明, 探针TPE-Py可以检测细胞脂滴中的Cu2+.

本文引用格式

苏小龙 , 李健鹏 , 刘孟鑫 , 邹莉 , 杨得锁 , 冯海涛 . 四苯乙烯酰胺类化合物的合成及其高灵敏度、高选择性识别Cu2+[J]. 有机化学, 2024 , 44(8) : 2581 -2587 . DOI: 10.6023/cjoc202403043

Abstract

The fluorescent probe TPE-Py was designed and synthesized, and its structure was confirmed by NMR and HRMS. The recognition properties of probe TPE-Py for metal ions have been studied through fluorescence spectrophotometry and cell imaging experiments in HeLa cells. The results showed that TPE-Py had good selectivity and sensitivity for Cu2+. Among various metal ions, TPE-Py only showed exclusive fluorescence turn-off sensing on Cu2+ in H2O/THF (VV=9∶1). The results of cell imaging experiments showed that the probe TPE-Py could detect Cu2+ in lipid droplets of cells.

参考文献

[1]
Sona, B. W.; Prashant, S. K. J. Lumin. 2018, 199, 407.
[2]
Gaggelli, E.; Kozlowski, H.; Valensin, D.; Valensin, G. Chem. Rev. 2006, 106, 1995.
[3]
Zhang, Y.; You, C.; Yang, Y.; Liu, X.; Guo, H.; Dong, Y. J. Org. Chem. 2016, 36, 1401 (in Chinese).
[3]
(张应鹏, 尤彩霞, 杨云裳, 刘小育, 郭慧琛, 董玉莹, 有机化学, 2016, 36, 1401.)
[4]
Waggoner, D. J.; Bartnikas, T. B.; Gitlin, J. D. Neurobiol. Dis. 1999, 6, 221.
[5]
Camakaris, J.; Voskoboinik, I.; Mercer, J. F. Biochem. Biophys. Res. Commun. 1999, 261, 225.
[6]
Bruijn, L. I.; Miller, T. M.; Cleveland, D. W. Annu. Rev. Neurosci. 2004, 27, 723.
[7]
Hung, Y. H.; Bush, A. I.; Cherny, R. A. J. Biol. Inorg. Chem. 2010, 15, 61.
[8]
Brown, D. R.; Kozlowski, H. Dalton Tran.. 2004, 13, 1907.
[9]
Fan, J. L.; Xu, Q. L.; Zhu, H.; Peng, X. J. Chin. J. Org. Chem. 2014, 34, 1623 (in Chinese).
[9]
(樊江莉, 徐群利, 朱浩, 彭孝军, 有机化学, 2014, 34, 1623.)
[10]
Du, J. J. Ph.D. Dissertatio., Dalian University of Technology, Dalian, 2009 (in Chinese).
[10]
(杜建军, 博士论文, 大连理工大学, 大连, 2009.)
[11]
Ma, W. H.; Xia, W.; Xu, Q.; Han, H. Y.; Song, B.; Sun, L. W.; Liang, C. H. Acta Chim. Sinic. 2012, 70, 917 (in Chinese).
[11]
(马文辉, 夏威, 徐群, 韩宏彦, 宋波, 孙丽微, 梁春花, 化学学报, 2012, 70, 917.)
[12]
Chen, K.; Guo, Y.; Lu, Z.; Yang, B.; Shi, Z. Chin. J. Chem. 2010, 28, 55.
[13]
Pan, M.; Lin, X. M.; Li, G. B.; Su, C. Y. Coord. Chem. Rev. 2011, 255, 1921.
[14]
Guerchais, V.; Fillaut, J. L. Coord. Chem. Rev. 2011, 255, 2448.
[15]
Ding, D.; Li, K.; Liu, B.; Tang, B. Z. Acc. Chem. Re.. 2013, 46, 2441.
[16]
Luo, J.; Xie, Z.; Lam, J. W.; Cheng, L.; Chen, H.; Qiu, C.; Kwok, H. S.; Zhan, X.; Liu, Y.; Zhu, D.; Tang, B. Z. Chem. Commun. 2001, 18, 1740.
[17]
Zeng, C. Y.; Hu, P.; Wang, B. Q.; Fang, W. Y.; Zhao, K. Q. Acta Chim. Sinic. 2023, 81, 469 (in Chinese).
[17]
(曾崇洋, 胡平, 汪必琴, 方文彦, 赵可清, 化学学报, 2023, 81, 469.)
[18]
Liu, B.; Chen, P. K. Acta Chim. Sinic. 2022, 80, 929 (in Chinese).
[18]
(刘斌, 陈磅宽, 化学学报, 2022, 80, 929.)
[19]
Feng, X. C.; Zhu, L. L.; Yue, B. B. Acta Chim. Sinic. 2022, 80, 647 (in Chinese).
[19]
(冯锡成, 朱亮亮, 岳兵兵, 化学学报, 2022, 80, 647.)
[20]
Zhang, L. L.; Wang, Y. Y.; Zhu, G. N.; Dai, W. B.; Zhao, Z. X.; Zhao, Y.; Zhi, J. G.; Dong, Y. P. Acta Chim. Sinic. 2022, 80, 282 (in Chinese).
[20]
(张璐璐, 王媛媛, 朱贵楠, 戴文博, 赵紫璇, 赵盈, 支俊格, 董宇平, 化学学报, 2022, 80, 282.)
[21]
Zhao, Y. Q.; Zhang, X.; Yang, Y. R.; Zhu, L. P.; Zhou, Y. Acta Chim. Sinic. 2024, 82, 265 (in Chinese).
[21]
(赵玉强, 张霞, 杨芸如, 朱立平, 周莹, 化学学报, 2024, 82, 265.)
[22]
Zhao, Y.; Chen, P. P.; Han, L.; Wang, E. Chin. J. Org. Chem. 2023, 43, 2454. (in Chinese).
[22]
(赵洋, 陈盼盼, 韩立志, 王恩举, 有机化学, 2023, 43, 2454.)
[23]
Zhao, Y.; Chen, P. P.; Li, G. N.; Niu, Z. G.; Wang, E. J. Chin. J. Org. Chem. 2023, 43, 2156 (in Chinese).
[23]
(赵洋, 陈盼盼, 李高楠, 钮智刚, 王恩举, 有机化学, 2023, 43, 2156.)
[24]
Feng, H.-T.; Yuan, Y.-X.; Xiong, J.-B.; Zheng, Y.-S.; Tang, B. Z. Chem. Soc. Rev. 2018, 47, 7452.
[25]
Yang, J.; Fang, M. M.; Li, Z. Aggregat. 2020, 1, 6.
[26]
Zhou, Y.; Tang, R.; Wang, D.; Wang, J.; Huang, Y.; Ding, Y.; Shi, J.; Yan, C.; Wang, Y.; Yao, Y. Inorg. Che.. 2023, 62, 15015
[27]
Liu, R. J.; Zeng, J. Chin. J. Org. Chem. 2017, 37, 3274 (in Chinese).
[27]
(刘瑞姣, 曾竟, 有机化学, 2017, 37, 3274.)
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