Citation: Huimin Jiang, Guoxing Yin, Yabing Gan, Ting Yu, Youyu Zhang, Haitao Li, Peng Yin. A multisite-binding fluorescent probe for simultaneous monitoring of mitochondrial homocysteine, cysteine and glutathione in live cells and zebrafish[J]. Chinese Chemical Letters, ;2022, 33(3): 1609-1612. doi: 10.1016/j.cclet.2021.09.036 shu

A multisite-binding fluorescent probe for simultaneous monitoring of mitochondrial homocysteine, cysteine and glutathione in live cells and zebrafish

Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research (Ministry of Education), College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, China

yinpeng@hunnu.edu.cn

Received Date: 25 May 2021
Revised Date: 7 September 2021
Accepted Date: 8 September 2021
Available Online: 15 September 2021

Figures(6)

Homocysteine (Hcy), cysteine (Cys) and glutathione (GSH) play crucial roles in redox homeostasis during mitochondria functions. Simultaneous differentiation and visualization of mitochondrial biothiols dynamics are significant for understanding cell metabolism and their related diseases. Herein, a multisite-binding fluorescent probe (MCP) was developed for simultaneous sensing of mitochondrial Cys, GSH and Hcy from three fluorescence channels for the first time. This novel probe exhibited rapid fluorescence turn-on, good water-solubility, high selectivity and large spectral separation for discriminating Cys, GSH and Hcy with 131-, 96-, 748-fold fluorescence increasement at 471, 520, 567 nm through different excitation wavelengths, respectively. Importantly, this probe was successfully applied to simultaneous monitoring of mitochondrial Cys, GSH, and Hcy in live cells and zebrafish from three fluorescence channels, promoting the understanding of the functions of Hcy, Cys and GSH.
- Fluorescent probe,
- Multiple sites,
- Biothiols,
- Mitochondrial-targeted,
- Homocysteine,
- Imaging
1. [1]
  Y.F. Kang, L.Y. Niu, Q. Z. Yang, Chin. Chem. Lett. 30 (2019) 1791-1798 doi: 10.1016/j.cclet.2019.08.013
2. [2]
  Y. Yue, F. Huo, F. Cheng, et al., Chem. Soc. Rev. 48 (2019) 4155-4177 doi: 10.1039/c8cs01006d
3. [3]
  L. Yang, H. Xiong, Y. Su, et al., Chin. Chem. Lett. 30 (2019) 563-565 doi: 10.1016/j.cclet.2018.12.017
4. [4]
  A.J. Kowaltowski, N.C. de Souza-Pinto, R.F. Castilho, A.E. Vercesi, Free Radical Bio. Med. 47 (2009) 333-343 doi: 10.1161/hypertensionaha.109.130054
5. [5]
  E. Bertero, C. Maack, Circ. Res. 122 (2018) 1460-1478 doi: 10.1161/circresaha.118.310082
6. [6]
  S. Kausar, F. Wang, H. Cui, Cells 7 (2018) 274 doi: 10.3390/cells7120274
7. [7]
  L. He, Y. Jiang, J. Green, H. Blevins, S. Zhang, Bioorg. Med. Chem. Lett. 29 (2019) 1957-1961 doi: 10.1016/j.bmcl.2019.05.035
8. [8]
  P. Hernansanz-Agustín, J.A. Enríquez, Antioxidants 10 (2021) 415 doi: 10.3390/antiox10030415
9. [9]
  S.S. Liew, X. Qin, J. Zhou, et al., Angew. Chem. Int. Ed. 60 (2021) 2232-2256 doi: 10.1002/anie.201915826
10. [10]
  S. Lee, J. Li, X. Zhou, J. Yin, J. Yoon, Coordin. Chem. Rev. 366 (2018) 29-68 doi: 10.1016/j.ccr.2018.03.021
11. [11]
  Y. Yue, F. Huo, C. Yin, Chem. Sci. 12 (2021) 1220-1226 doi: 10.1039/d0sc04960c
12. [12]
  N. Zhou, F. Huo, Y. Yue, K. Ma, C. Yin, Chin. Chem. Lett. 31 (2020) 2970-2974 doi: 10.1016/j.cclet.2020.07.001
13. [13]
  H. Zhang, P. Xu, X. Zhang, et al., Chin. Chem. Lett. 31 (2020) 1083-1086 doi: 10.1016/j.cclet.2019.10.005
14. [14]
  D. Li, W. Chen, S.H. Liu, X. Chen, J. Yin, Chin. Chem. Lett. 31 (2020) 2891-2896 doi: 10.1016/j.cclet.2020.02.047
15. [15]
  L. He, X. Yang, K. Xu, X. Kong, W. Lin, Chem. Sci. 8 (2017) 6257-6265 doi: 10.1039/C7SC00423K
16. [16]
  M. Sibrian-Vazquez, J.O. Escobedo, S. Lim, G.K. Samoei, R.M. Strongin, Proc. Natl. Acad. Sci. U. S. A. 107 (2010) 551-554 doi: 10.1073/pnas.0909737107
17. [17]
  Y. Huang, Y. Zhang, F. Huo, et al., J. Am. Chem. Soc. 142 (2020) 18706-18714 doi: 10.1021/jacs.0c10210
18. [18]
  J. Liu, Y.Q. Sun, Y. Huo, et al., J. Am. Chem. Soc. 136 (2014) 574-577 doi: 10.1021/ja409578w
19. [19]
  Y. Li, W. Liu, P. Zhang, et al., Biosens. Bioelectron. 90 (2017) 117-124 doi: 10.1016/j.bios.2016.11.021
20. [20]
  Y. Li, W. Liu, H. Zhang, et al., Chem. Asian J. 12 (2017) 2098-2103 doi: 10.1002/asia.201700583
21. [21]
  S.V. Mulay, Y. Kim, M. Choi, et al., Anal. Chem. 90 (2018) 2648-2654 doi: 10.1021/acs.analchem.7b04375
22. [22]
  C. Cao, Y. Feng, H. Li, et al., Talanta 219 (2020) 121353 doi: 10.1016/j.talanta.2020.121353
23. [23]
  Z. Xu, T. Qin, X. Zhou, L. Wang, B. Liu, Trends Anal. Chem. 121 (2019) 115672
24. [24]
  S. Yang, C. Guo, Y. Li, et al., ACS Sens. 3 (2018) 2415-2422 doi: 10.1021/acssensors.8b00919
25. [25]
  K. Xiong, F. Huo, J. Chao, Y. Zhang, C. Yin, Anal. Chem. 91 (2019) 1472-1478 doi: 10.1021/acs.analchem.8b04485
26. [26]
  G. Yin, Y. Gan, H. Jiang, et al., Anal. Chem. 93 (2021) 9878-9886 doi: 10.1021/acs.analchem.1c01945
27. [27]
  J. Zhang, X. Bao, J. Zhou, et al., Biosens. Bioelectron. 85 (2016) 164-170 doi: 10.4103/2045-9912.191362
28. [28]
  T.B. Ren, Q.L. Zhang, D. Su, et al., Chem. Sci. 9 (2018) 5461-5466
29. [29]
  J. Chen, X. Jiang, C. Zhang, et al., ACS Sens. 2 (2017) 1257-1261 doi: 10.1021/acssensors.7b00425
30. [30]
  X. Zhang, Y. Huang, X. Han, et al., Anal. Chem. 91 (2019) 14728-14736 doi: 10.1021/acs.analchem.9b04082
31. [31]
  R. Zhang, J. Yong, J. Yuan, Z. Ping Xu, Coordin. Chem. Rev. 408 (2020) 213182
32. [32]
  P. Gao, W. Pan, N. Li, B. Tang, Chem. Sci. 10 (2019) 6035-6071 doi: 10.1039/c9sc01652j
33. [33]
  Z. Xu, X. Huang, X. Han, et al., Chem 4 (2018) 1609-1628
34. [34]
  Z. Xu, X. Huang, M.X. Zhang, et al., Anal. Chem. 91 (2019) 11343-11348 doi: 10.1021/acs.analchem.9b02458
35. [35]
  G. x. Yin, T. t. Niu, Y. b. Gan, et al., Angew. Chem. Int. Ed. 57 (2018) 4991-4994 doi: 10.1002/anie.201800485
36. [36]
  G. Yin, T. Niu, T. Yu, et al., Angew. Chem. Int. Ed. 58 (2019) 4557-4561 doi: 10.1002/anie.201813935
37. [37]
  D.I. Danylchuk, P.H. Jouard, A.S. Klymchenko, J. Am. Chem. Soc. 143 (2021) 912-924 doi: 10.1021/jacs.0c10972
38. [38]
  S. Gong, Z. Zheng, X. Guan, S. Feng, G. Feng, Anal. Chem. 93 (2021) 5700-5708 doi: 10.1021/acs.analchem.0c04639
1. [1]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
2. [2]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
3. [3]
  Han-Min Wang , Yan-Chen Li , Lu-Lu Sun , Ming-Ye Tang , Jia Liu , Jiahao Cai , Lei Dong , Jia Li , Yi Zang , Hai-Hao Han , Xiao-Peng He . Protein-encapsulated long-wavelength fluorescent probe hybrid for imaging lipid droplets in living cells and mice with non-alcoholic fatty liver. Chinese Chemical Letters, 2024, 35(11): 109603-. doi: 10.1016/j.cclet.2024.109603
4. [4]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
5. [5]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
6. [6]
  Chuan-Zhi Ni , Ruo-Ming Li , Fang-Qi Zhang , Qu-Ao-Wei Li , Yuan-Yuan Zhu , Jie Zeng , Shuang-Xi Gu . A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells. Chinese Chemical Letters, 2024, 35(10): 109862-. doi: 10.1016/j.cclet.2024.109862
7. [7]
  Yunkang Tong , Haiqiao Huang , Haolan Li , Mingle Li , Wen Sun , Jianjun Du , Jiangli Fan , Lei Wang , Bin Liu , Xiaoqiang Chen , Xiaojun Peng . Cooperative bond scission by HRP/H₂O₂ for targeted prodrug activation. Chinese Chemical Letters, 2024, 35(12): 109663-. doi: 10.1016/j.cclet.2024.109663
8. [8]
  Lei Shen , Hongmei Liu , Ming Jin , Jinchao Zhang , Caixia Yin , Shuxiang Wang , Yutao Yang . “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone. Chinese Chemical Letters, 2024, 35(10): 109572-. doi: 10.1016/j.cclet.2024.109572
9. [9]
  Jiajia Lv , Jie Gao , Hongyu Li , Zeli Yuan , Nan Dong . Rational design of hydroxytricyanopyrrole-based probes with high affinity and rapid visualization for amyloid-β aggregates in vitro and in vivo. Chinese Chemical Letters, 2024, 35(5): 108940-. doi: 10.1016/j.cclet.2023.108940
10. [10]
  Chao Liu , Chao Jia , Shi-Xian Gan , Qiao-Yan Qi , Guo-Fang Jiang , Xin Zhao . A luminescent one-dimensional covalent organic framework for organic arsenic sensing in water. Chinese Chemical Letters, 2024, 35(11): 109750-. doi: 10.1016/j.cclet.2024.109750
11. [11]
  Quan Zhang , Shunjie Xing , Jingqian Han , Li Feng , Jianchun Li , Zhaosheng Qian , Jin Zhou . Organic pollutant sensing for human health based on carbon dots. Chinese Chemical Letters, 2025, 36(1): 110117-. doi: 10.1016/j.cclet.2024.110117
12. [12]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
13. [13]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
14. [14]
  Zhihui Zhang , Ru Sun , Chong Bian , Hongbo Wang , Zhen Zhao , Panpan Lv , Jianzhong Lu , Haixin Zhang , Hulie Zeng , Yuanyuan Chen , Zhijuan Cao . A dual-protease-triggered chemiluminescent probe for precise tumor imaging. Chinese Chemical Letters, 2025, 36(2): 109784-. doi: 10.1016/j.cclet.2024.109784
15. [15]
  Botao QU , Qian WANG , Xiaogang NING , Yuxin ZHOU , Ruiping ZHANG . Deeply penetrating photoacoustic imaging in tumor tissues based on dual-targeted melanin nanoparticle. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 1025-1032. doi: 10.11862/CJIC.20230416
16. [16]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
17. [17]
  Linfang Wang , Jing Liu , Minghao Ren , Wei Guo . A highly sensitive fluorescent HClO probe for discrimination between cancerous and normal cells/tissues. Chinese Chemical Letters, 2024, 35(6): 108945-. doi: 10.1016/j.cclet.2023.108945
18. [18]
  Yang Liu , Leilei Zhang , Kaixuan Liu , Ling-Ling Wu , Hai-Yu Hu . Penicillin G acylase-responsive near-infrared fluorescent probe: Unravelling biofilm regulation and combating bacterial infections. Chinese Chemical Letters, 2024, 35(11): 109759-. doi: 10.1016/j.cclet.2024.109759
19. [19]
  Pei Huang , Weijie Zhang , Junping Wang , Fangjun Huo , Caixia Yin . Rapid and specific fluorescent probe visualizes dynamic correlation of Cys and HClO in OGD/R. Chinese Chemical Letters, 2025, 36(1): 109778-. doi: 10.1016/j.cclet.2024.109778
20. [20]
  Lanyun Zhang , Weisi Wang , Yu-Qiang Zhao , Rui Huang , Yuxun Lu , Ying Chen , Liping Duan , Ying Zhou . Mechanism study of the molluscicide candidate PBQ on Pomacea canaliculata using a viscosity-sensitive fluorescent probe. Chinese Chemical Letters, 2025, 36(1): 109798-. doi: 10.1016/j.cclet.2024.109798

Get Citation

PDF

XML

Metrics

PDF Downloads(7)
Abstract views(563)
HTML views(52)

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