Citation: Li Wei, Jia Xu, Guo Zhenbo, Jiang Wenting, Zhang Pingzhu, Wei Chao, Li Xiaoliu. Imaging of Hydrogen Peroxide During the Ischemia Reperfusion Process in Living Cells with An Aggregation Induced-Emission Probe[J]. Chinese Journal of Organic Chemistry, ;2020, 40(7): 1934-1940. doi: 10.6023/cjoc202003042 shu

Imaging of Hydrogen Peroxide During the Ischemia Reperfusion Process in Living Cells with An Aggregation Induced-Emission Probe

Key Laboratory of Chemical Biology of Hebei Province, Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of Ministry of Education, College of Chemistry and Environmental Science, Hebei University, Baoding, Hebei 071002

Corresponding author: Wei Chao, lweichao@hbu.edu.cn Li Xiaoliu, lixl@hbu.cn
Received Date: 16 March 2020
Revised Date: 30 April 2020
Available Online: 15 May 2020
Fund Project: the Natural Science Foundation of Hebei Province B2018201234the Colleges and Universities Science Technology Research Project of Hebei Province QN2017015Project supported by the Natural Science Foundation of Hebei Province (No. B2018201234) and the Colleges and Universities Science Technology Research Project of Hebei Province (No. QN2017015)

Figures(8)

As an important endogenous signaling molecule, hydrogen peroxide (H₂O₂) is involved in regulating many physiological and pathological processes. Ischemia-reperfusion can induce the production of large amount of endogenous hydrogen peroxide, which can cause seriously damage to cells and tissues. The fluorescent probe with aggregation induced emission can avoid the shortage of the aggregation caused quenching of conventional fluorophores. A H₂O₂ fluorescent probe with aggregation induced emission properties was designed and synthesized by using 4-vinylpyridinyl modified tetraphenylethylene as the fluorophore and phenylboronic acid as the H₂O₂ sensing group. The structure of the probe was characterized by NMR and HRMS. The recognition behaviors of the probe to H₂O₂ were investigated by the UV-Vis absorption and fluorescence spectra, and the results exhibit its good selectivity and high sensitivity to H₂O₂. The fluorescence off-on enhancement was ca. 100-fold and the detection limit was 6.9×10^-8 mol/L. The reaction of the probe and H₂O₂ resulted in the H₂O₂-mediated oxidation of phenylboronic acid, followed by hydrolysis and 1, 6-elimination of p-quinone-methide to generate (E)-4-(4-(2, 2-bis(4-methoxyphenyl)-1-phenylvinyl)styryl)pyridine (TPE-Py), which was confirmed by ¹H NMR. The results of confocal imaging indicated that the probe was cell-permeable and capable of visualization of endogenous H₂O₂ in oxygen glucose deprivation/reoxygenation (OGD/R) model HeLa cells and lipopolysaccharide-treated zebrafish.
- hydrogen peroxide,
- oxygen glucose deprivation/reoxygenation (OGD/R),
- aggregation induced-emission,
- fluorescent probe,
- bioimaging
1. [1]
  Rhee, S. G. Science 2006, 312, 1882. doi: 10.1126/science.1130481
2. [2]
  Mishina, N. M.; Tyurin-Kuzmin, P. A.; Markvicheva, K. N.; Vorotnikov, A. V.; Tkachuk, V. A.; Laketa, V.; Schultz, C.; Lukyanov, S.; Belousov, V. V. Antioxid. Redox Signaling 2011, 15, 1. doi: 10.1089/ars.2010.3560
3. [3]
  Hurd, T. R.; DeGennaro, M.; Lehmann, R. Trends Cell Biol. 2012, 22, 107. doi: 10.1016/j.tcb.2011.11.002
4. [4]
  Ohshima, H.; Tatemichi, M.; Sawa, T. Arch. Biochem. Biophys. 2003, 417, 3. doi: 10.1016/S0003-9861(03)00283-2
5. [5]
  Silva, G. F.; Ming, L. J. Angew. Chem., Int. Ed. 2007, 46, 3337. doi: 10.1002/anie.200604421
6. [6]
  Barnham, K. J.; Masters, C. L.; Bush, A. I. Nat. Rev. Drug Discovery 2004, 3, 205. doi: 10.1038/nrd1330
7. [7]
  Gottlieb, R. A.; Burleson, K. O.; Kloner, R. A.; Babior, B. M.; Engler, R. L. J. Clin. Invest. 1994, 94, 1621. doi: 10.1172/JCI117504
8. [8]
  Li, L.; Zhang, Y.; Zhang, L. N.; Ge, S. G.; Liu, H. Y.; Ren, N.; Yan, M.; Yu, J. H. Anal. Chem. 2016, 88, 5369. doi: 10.1021/acs.analchem.6b00693
9. [9]
  Matsubara, C.; Kawamoto, N.; Takamura, K. Analyst 1992, 117, 1781.
10. [10]
  Yang, S. M.; Huang, A.-H.; Cha, W. L.; Wei, Z. P.; Zheng, L, Z. Acta Chim. Sinica 2011, 69, 2143(in Chinese).
11. [11]
  Li, Z. Z.; Xin, Y. M.; Wu, W. L.; Fu, B. L.; Zhang, Z. H. Anal. Chem. 2016, 88, 7724. doi: 10.1021/acs.analchem.6b01637
12. [12]
  Lippert, A. R.; Bittner, G. C.; Chang, C. J. Acc. Chem. Res. 2011, 44, 793.
13. [13]
  Andina, D.; Leroux, J.-C.; Luciani, P. Chem.-Eur. J. 2017, 23, 13549. doi: 10.1002/chem.201702458
14. [14]
  Rezende, F.; Brandes, R. P.; Schroeder, K. Antioxid. Redox Signaling 2018, 29, 585. doi: 10.1089/ars.2017.7401
15. [15]
  Liu, Y.; Jiao, C.; Lu, W.; Zhang, P.; Wang, Y. RSC Adv. 2019, 9, 18027. doi: 10.1039/C9RA02467K
16. [16]
  Chang, M. C.; Pralle, A.; Isacoff, E. Y.; Chang, C. J. J. Am. Chem. Soc. 2004, 126, 15392. doi: 10.1021/ja0441716
17. [17]
  Chung, C.; Srikun, D.; Lim, C. S.; Chang, C. J.; Cho, B. R. Chem. Commun. 2011, 47, 9618. doi: 10.1039/c1cc13583j
18. [18]
  Ang, C. Y.; Tan, S. Y.; Wu, S. J.; Qu, Q. Y.; Wong, M. F. E.; Luo, Z.; Li, P. Z.; Selvan, S. T.; Zhao, Y. L. J. Mater. Chem. C 2016, 4, 2761. doi: 10.1039/C5TC01465D
19. [19]
  Liu, J.; Ren, J.; Bao, X. J.; Gao, W.; Wu, C. L.; Zhao, Y. B. Anal. Chem. 2016, 88, 5865. doi: 10.1021/acs.analchem.6b00654
20. [20]
  Ren, M. G.; Deng, B. B.; Wang, J. Y.; Kong, X. Q.; Liu, Z. R.; Zhou, K.; He, L. W.; Lin, W. Y. Biosens. Bioelectron. 2016, 79, 237. doi: 10.1016/j.bios.2015.12.046
21. [21]
  Xiao, H.; Li, P.; Hu, X.; Shi, X.; Zhang, W.; Tang, B. Chem. Sci. 2016, 7, 6153. doi: 10.1039/C6SC01793B
22. [22]
  Liu, X.; He, L.; Yang, L.; Geng, Y.; Yang, L.; Song, X. Sens. Actuators, B 2018, 259, 803.
23. [23]
  Shen, Y.; Zhang, X.; Zhang, Y.; Wu, Y.; Zhang, C.; Chen, Y.; Jin, J.; Li, H. Sens. Actuators, B 2018, 255, 42. doi: 10.1016/j.snb.2017.08.020
24. [24]
  Zhu, B.; Wu, L.; Wang, Y.; Zhang, M.; Zhao, Z.; Liu, C.; Wang, Z.; Duan, Q.; Jia, P. Sens. Actuators, B 2018, 259, 797. doi: 10.1016/j.snb.2017.12.135
25. [25]
  Zhang, J.; Shi, L.; Li, Z.; Li, D.; Tian, X.; Zhang, C. Analyst 2019, 144, 3643. doi: 10.1039/C9AN00385A
26. [26]
  Abo, M.; Urano, Y.; Hanaoka, K.; Terai, T.; Komatsu, T.; Nagano, T. J. Am. Chem. Soc. 2011, 133, 10629. doi: 10.1021/ja203521e
27. [27]
  Zhang, K. M.; Dou, W.; Li, P. X.; Shen, R.; Ru, J. X.; Liu, W.; Cui, Y. M.; Chen, C. Y.; Liu, W. S.; Bai, D. C. Biosens. Bioelectron. 2015, 64, 542. doi: 10.1016/j.bios.2014.09.073
28. [28]
  Xie, X.; Yang, X. E.; Wu, T.; Li, Y.; Li, M.; Tan, Q.; Wang, X.; Tang, B. Anal. Chem. 2016, 88, 8019. doi: 10.1021/acs.analchem.6b01256
29. [29]
  Peng, J.; Hou, X.; Zeng, F.; Wu, S. Biosens. Bioelectron. 2017, 94, 278. doi: 10.1016/j.bios.2017.03.003
30. [30]
  Luo, J. D.; Xie, Z. L.; Zhu, D. B.; Tang, B. Z. Chem. Commun. 2011, 18, 1740.
31. [31]
  Zhang, J.; Wang, Q.; Guo, Z.; Zhang, S.; Yan, C.; Tian, H.; Zhu, W. Adv. Funct. Mater. 2019, 29, 1808153. doi: 10.1002/adfm.201808153
32. [32]
  Zhang, W.; Liu, W.; Li, P.; Huang, F.; Wang, H.; Tang, B. Anal. Chem. 2015, 87, 9825. doi: 10.1021/acs.analchem.5b02194
33. [33]
  Hu, F.; Huang, Y.; Zhang, G.; Zhao, R.; Zhang, D. Tetrahedron Lett. 2014, 55, 1471. doi: 10.1016/j.tetlet.2014.01.056
34. [34]
  Xu, J.; Zhang, Y.; Yu, H.; Gao, X.; Shao, S. Anal. Chem. 2016, 88, 1455.
35. [35]
  Li, Y.; Wang, X.; Yang, J.; Xie, X. L.; Li, M. M.; Niu, J. Y.; Tong, L. L.; Tang, B. Anal. Chem. 2016, 88, 11154. doi: 10.1021/acs.analchem.6b03376
36. [36]
  Kumar, R.; Han, J.; Lim, H.-J.; Ren, W. X.; Lim, J.-Y.; Kim, J.-H.; Kim, J. S. J. Am. Chem. Soc. 2014, 136, 17836. doi: 10.1021/ja510421q
1. [1]
  Jinlong YAN , Weina WU , Yuan WANG . A simple Schiff base probe for the fluorescent turn-on detection of hypochlorite and its biological imaging application. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1653-1660. doi: 10.11862/CJIC.20240154
2. [2]
  Yanxi LIU , Mengjia XU , Haonan CHEN , Quan LIU , Yuming ZHANG . A fluorescent-colorimetric probe for peroxynitrite-anion-imaging in living cells. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1112-1122. doi: 10.11862/CJIC.20240423
3. [3]
  Jiaxi Xu , Yuan Ma . Influence of Hyperconjugation on the Stability and Stable Conformation of Ethane, Hydrazine, and Hydrogen Peroxide. University Chemistry, 2024, 39(11): 374-377. doi: 10.3866/PKU.DXHX202402049
4. [4]
  Hongxia Yan , Rui Wu , Weixu Feng , Yan Zhao , Yi Yan . Innovation Inspired by Classical Chemistry: Luminescent Hyperbranched Polysiloxanes. University Chemistry, 2025, 40(4): 154-159. doi: 10.12461/PKU.DXHX202409010
5. [5]
  Yanyang Li , Zongpei Zhang , Kai Li , Shuangquan Zang . Ideological and Political Design for the Comprehensive Experiment of the Synthesis and Aggregation-Induced Emission (AIE) Performance Study of Salicylaldehyde Schiff-Base. University Chemistry, 2024, 39(2): 105-109. doi: 10.3866/PKU.DXHX202307020
6. [6]
  Jun LUO , Baoshu LIU , Yunchang ZHANG , Bingkai WANG , Beibei GUO , Lan SHE , Tianheng CHEN . Europium(Ⅲ) metal-organic framework as a fluorescent probe for selectively and sensitively sensing Pb²⁺ in aqueous solution. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2438-2444. doi: 10.11862/CJIC.20240240
7. [7]
  Lina Feng , Guoyu Jiang , Xiaoxia Jian , Jianguo Wang . Application of Organic Radical Materials in Biomedicine. University Chemistry, 2025, 40(4): 253-260. doi: 10.12461/PKU.DXHX202405171
8. [8]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
9. [9]
  Hongxia Yan , Weixu Feng , Junyan Yao , Wei Tian , Rui Wang . Illuminating the Teaching of Science and Engineering Graduate Courses with “Curriculum Ideology and Politics”. University Chemistry, 2024, 39(6): 122-127. doi: 10.3866/PKU.DXHX202310059
10. [10]
  Jian Li , Yu Zhang , Rongrong Yan , Kaiyuan Sun , Xiaoqing Liu , Zishang Liang , Yinan Jiao , Hui Bu , Xin Chen , Jinjin Zhao , Jianlin Shi . 高效靶向示踪钙钛矿纳米系统光电增效抗肿瘤. Acta Physico-Chimica Sinica, 2025, 41(5): 100042-. doi: 10.1016/j.actphy.2024.100042
11. [11]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
12. [12]
  Yu SU , Xinlian FAN , Yao YIN , Lin WANG . From synthesis to application: Development and prospects of InP quantum dots. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2105-2123. doi: 10.11862/CJIC.20240126
13. [13]
  Zhuoya WANG , Le HE , Zhiquan LIN , Yingxi WANG , Ling LI . Multifunctional nanozyme Prussian blue modified copper peroxide: Synthesis and photothermal enhanced catalytic therapy of self-provided hydrogen peroxide. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2445-2454. doi: 10.11862/CJIC.20240194
14. [14]
  Yu Dai , Xueting Sun , Haoyu Wu , Naizhu Li , Guoe Cheng , Xiaojin Zhang , Fan Xia . Determination of the Michaelis Constant for Gold Nanozyme-Catalyzed Decomposition of Hydrogen Peroxide. University Chemistry, 2025, 40(5): 351-356. doi: 10.12461/PKU.DXHX202407052
15. [15]
  Ke Li , Chuang Liu , Jingping Li , Guohong Wang , Kai Wang . 钛酸铋/氮化碳无机有机复合S型异质结纯水光催化产过氧化氢. Acta Physico-Chimica Sinica, 2024, 40(11): 2403009-. doi: 10.3866/PKU.WHXB202403009
16. [16]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
17. [17]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
18. [18]
  Shuwen SUN , Gaofeng WANG . Design and synthesis of a Zn(Ⅱ)-based coordination polymer as a fluorescent probe for trace monitoring 2, 4, 6-trinitrophenol. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 753-760. doi: 10.11862/CJIC.20240399
19. [19]
  Zhifeng CAI , Ying WU , Yanan LI , Guiyu MENG , Tianyu MIAO , Yihao ZHANG . Effective detection of malachite green by folic acid stabilized silver nanoclusters. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 983-993. doi: 10.11862/CJIC.20240394
20. [20]
  Wei GAO , Meiqi SONG , Xuan REN , Jianliang BAI , Jing SU , Jianlong MA , Zhijun WANG . A self-calibrating fluorescent probe for the selective detection and bioimaging of HClO. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1173-1182. doi: 10.11862/CJIC.20250112

Get Citation

PDF

XML

Metrics

PDF Downloads(15)
Abstract views(1422)
HTML views(298)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142