Citation: Tongxia Jin, Mengyu Cui, Dan Wu, Weiping Zhu, Yufang Xu, Xuhong Qian. NCL-based mitochondrial-targeting fluorescent probe for the detection of Glutathione in living cells[J]. Chinese Chemical Letters, ;2021, 32(12): 3899-3902. doi: 10.1016/j.cclet.2021.06.033 shu

NCL-based mitochondrial-targeting fluorescent probe for the detection of Glutathione in living cells

State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China

wpzhu@ecust.edu.cn

xhqian@ecust.edu.cn

Received Date: 16 April 2021
Revised Date: 11 June 2021
Accepted Date: 14 June 2021
Available Online: 21 June 2021

Figures(4)

Glutathione (GSH) plays a critical role in maintaining cellular redox homeostasis in biological system. Mitochondrion is a pivotal organelle for cellular aerobic respiration and its disorder is associated with impaired redox balance, leading to cell death. In this work, we designed and synthesized a non-invasive "off-on" mitochondrial-targeting fluorescent probe QZ for the detection of GSH in living cells. Based on the mechanism of native chemical ligation (NCL) and fluorescence resonance energy transfer (FRET), a rhodamine B derivative, QZ was prepared, by choosing aromatic thioester bond as the selective reaction site. QZ exhibited excellent detection capability for GSH over Cys and Hcy. Upon addition of GSH to QZ solution, a remarkably enhanced fluorescence was observed with a limit of detection of 2.98 μmol/L. Furthermore, QZ was found to possess the specific mitochondrial localization ability in cell imaging experiments. Moreover, with exogenous and endogenous stimulations, QZ could image GSH in living cells.
- Fluorescent probe,
- Glutathione,
- NCL,
- In vivo imaging
1. [1]
  K. Van Laer, C.J. Hamilton, J. Messens, Antioxid. Redox Signaling 18(2013) 1642-1653. doi: 10.1089/ars.2012.4964
2. [2]
  C.X. Yin, K.M. Xiong, F.J. Huo, J.C. Salamanca, R.M. Strongin, Angew. Chem. Int. Ed. 56(2017) 13188-13198. doi: 10.1002/anie.201704084
3. [3]
  L.E. Hernandez, J. Sobrino Plata, M.B. Montero Palmero, et al., J. Exp. Bot. 66(2015) 2901-2911. doi: 10.1093/jxb/erv063
4. [4]
  F.Q. Schafer, G.R. Buettner, Free Radicals Chem., Biol. Med. 30(2001) 1191-1212. doi: 10.1016/S0891-5849(01)00480-4
5. [5]
  R.S. Balaban, S. Nemoto, T. Finkel, Cell 120(2005) 483-495. doi: 10.1016/j.cell.2005.02.001
6. [6]
  H. Kamata, H. Hirata, Cell. Signalling 11(1999) 1-14. doi: 10.1016/S0898-6568(98)00037-0
7. [7]
  M.P. Murphy, Biochem. J. 417(2009) 1-13. doi: 10.1042/BJ20081386
8. [8]
  J.F. Turrens, J. Physiol. 552(2003) 335-344. doi: 10.1113/jphysiol.2003.049478
9. [9]
  P. Li, Y. Jia, N. Zhao, et al., Anal. Chem. 92(2020) 12987-12995. doi: 10.1021/acs.analchem.0c01703
10. [10]
  K.R. Atkuri, T.M. Cowan, T. Kwan, et al., Proc. Natl. Acad. Sci. U. S. A. 106(2009) 3941-3945. doi: 10.1073/pnas.0813409106
11. [11]
  M.T. Lin, M.F. Beal, Nature 443(2006) 787-795. doi: 10.1038/nature05292
12. [12]
  G. Calabrese, B. Morgan, J. Riemer, Antioxid. Redox Signaling 27(2017) 1162-1177. doi: 10.1089/ars.2017.7121
13. [13]
  Y. Wang, H. Duan, H. Shi, et al., Chin. Chem. Lett. 31(2020) 2933-2936. doi: 10.1016/j.cclet.2020.05.028
14. [14]
  H. Duan, Y. Ding, C. Huang, et al., Chin. Chem. Lett. 30(2019) 55-57. doi: 10.1016/j.cclet.2018.03.016
15. [15]
  L.M. Hyman, K.J. Franz, Coord. Chem. Rev. 256(2012) 2333-2356. doi: 10.1016/j.ccr.2012.03.009
16. [16]
  W. Xu, Z. Zeng, J.H. Jiang, Y.T. Chang, L. Yuan, Angew. Chem. Int. Ed. 55(2016) 13658-13699. doi: 10.1002/anie.201510721
17. [17]
  S. Lee, J. Li, X. Zhou, J. Yin, J. Yoon, Coord. Chem. Rev. 366(2018) 29-68. doi: 10.1016/j.ccr.2018.03.021
18. [18]
  Y.F. Kang, L.Y. Niu, Q.Z. Yang, Chin. Chem. Lett. 30(2019) 1791-1798. doi: 10.1016/j.cclet.2019.08.013
19. [19]
  Y. Yang, Y. Feng, H. Li, et al., Sens. Actuators B 333(2021) 129189. doi: 10.1016/j.snb.2020.129189
20. [20]
  Y.L. Zheng, H.C. Zhang, D.H. Tian, et al., Spectrochim. Acta A 238(2020) 118429. doi: 10.1016/j.saa.2020.118429
21. [21]
  S.Y. Lim, K.H. Hong, D.I. Kim, H. Kwon, H.J. Kim, J. Am. Chem. Soc. 136(2014) 7018-7025. doi: 10.1021/ja500962u
22. [22]
  Y. Li, K.N. Wang, B. Liu, et al., Sens. Actuators B 255(2018) 193-202. doi: 10.1016/j.snb.2017.08.041
23. [23]
  Z. Xu, X. Huang, X. Han, et al., Chem 4(2018) 1609-1628. doi: 10.1016/j.chempr.2018.04.003
24. [24]
  L.Y. Niu, Y.Z. Chen, H.R. Zheng, et al., Chem. Soc. Rev. 44(2015) 6143-6160. doi: 10.1039/C5CS00152H
25. [25]
  G.J. Kim, D.H. Yoon, M.Y. Yun, et al., Sens. Actuators B 211(2015) 245-249. doi: 10.1016/j.snb.2015.01.102
26. [26]
  J.X. Lu, Y.C. Song, W. Shi, X.H. Li, H.M. Ma, Sens. Actuators B 161(2012) 615-620. doi: 10.1016/j.snb.2011.11.009
27. [27]
  J. Yin, Y. Kwon, D. Kim, et al., J. Am. Chem. Soc. 136(2014) 5351-5358. doi: 10.1021/ja412628z
28. [28]
  Z. Yang, J.H. Lee, H.M. Jeon, et al., J. Am. Chem. Soc. 135(2013) 11657-11662. doi: 10.1021/ja405372k
29. [29]
  X. Li, H. Wang, Y. Zhang, Q. Cao, Y. Chen, Chin. Chem. Lett. 32(2020) 1541-1544. doi: 10.1016/j.cclet.2019.11.014
30. [30]
  B. Tang, Y.L. Xing, P. Li, et al., J. Am. Chem. Soc. 129(2007) 11666-11667. doi: 10.1021/ja072572q
31. [31]
  L. Chen, J.S. Park, D. Wu, C.H. Kim, J. Yoon, Sens. Actuators B 262(2018) 306-312. doi: 10.1016/j.snb.2018.02.023
32. [32]
  L.W. He, Q.Y. Xu, Y. Liu, et al., ACS Appl. Mater. Interfaces 7(2015) 12809-12813. doi: 10.1021/acsami.5b01934
33. [33]
  Z. Xue, L. Xiao, H. Chen, et al., Bioorg. Med. Chem. 26(2018) 1823-1831. doi: 10.1016/j.bmc.2018.02.030
34. [34]
  X. Ren, L. Liao, Z. Yang, et al., Chin. Chem. Lett. 32(2020) 1061-1065. doi: 10.1016/j.cclet.2020.09.024
35. [35]
  P.E. Dawson, S.B.H. Kent, Annu. Rev. Biochem. 69(2000) 923-960. doi: 10.1146/annurev.biochem.69.1.923
36. [36]
  J. Liu, Y.Q. Sun, H.X. Zhang, et al., RSC Adv. 4(2014) 64542-64550. doi: 10.1039/C4RA10865E
37. [37]
  M.F. Tang, L.L. Wu, D. Wu, et al., RSC Adv. 6(2016) 34996-35000. doi: 10.1039/C6RA00832A
38. [38]
  Q. Cai, T. Yu, W.P. Zhu, Y.F. Xu, X.H. Qian, Chem. Commun. 51(2015) 14739-14741. doi: 10.1039/C5CC05518K
39. [39]
  J. Kalia, R.T. Raines, ChemBioChem 7(2006) 1375-1383. doi: 10.1002/cbic.200600150
40. [40]
  R. Miyajima, Y. Tsuda, T. Inokuma, et al., Pept. Sci. 106(2016) 531-546. doi: 10.1002/bip.22757
41. [41]
  K.G. Casey, E.L. Quitevis, J. Phys. Chem. 92(1988) 6590-6594. doi: 10.1021/j100334a023
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
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]
  Yong-Dan Zhao , Yidan Wang , Rongrong Wang , Lina Chen , Hengtong Zuo , Xi Wang , Jihong Qiang , Geng Wang , Qingxia Li , Canqi Ping , Shuqiu Zhang , Hao Wang . Reversing artemisinin resistance by leveraging thermo-responsive nanoplatform to downregulating GSH. Chinese Chemical Letters, 2024, 35(6): 108929-. doi: 10.1016/j.cclet.2023.108929
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]
  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
12. [12]
  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
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]
  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
15. [15]
  Shihong Wu , Ronghui Zhou , Hang Zhao , Peng Wu . Sonoafterglow luminescence for in vivo deep-tissue imaging. Chinese Chemical Letters, 2024, 35(10): 110026-. doi: 10.1016/j.cclet.2024.110026
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  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
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(527)
HTML views(36)

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