Citation: Chena Yahui, Wei Tingwen, Zhang Zhijie, Zhang Wei, Lv Jing, Chen Tiantian, Chi Bo, Wang Fang, Chen Xiaoqiang. A mitochondria-targeted fluorescent probe for ratiometric detection of hypochlorite in living cells[J]. Chinese Chemical Letters, ;2017, 28(10): 1957-1960. doi: 10.1016/j.cclet.2017.05.010 shu

A mitochondria-targeted fluorescent probe for ratiometric detection of hypochlorite in living cells

Chena Yahui ^a ,
Wei Tingwen ^a ,
Zhang Zhijie ^a ,
Zhang Wei ^a ,
Lv Jing ^a ,
Chen Tiantian ^a ,
Chi Bo ^b ,
Wang Fang ^a,, ,
Chen Xiaoqiang ^a,,

a.
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemical Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials (SICAM), Nanjing Tech University, Nanjing 210009, China
b.
College of Food Science and Light Industry, Nanjing Tech University, Nanjing 211816, China

Corresponding author: Wang Fang, wf620@126.com Chen Xiaoqiang, chenxq@njtech.edu.cn
Received Date: 13 March 2017
Revised Date: 25 April 2017
Accepted Date: 10 May 2017
Available Online: 13 October 2017

Figures(5)

Hypochlorous acid (HOCl) plays a vital role in many physiological and pathological processes as one of reactive oxygen species (ROS). Developing highly sensitive and selective methods for HOCl detection is of significant interest. In this work, we developed a benzothiazole based probe 1 for ratiometric fluorescence detection of hypochlorite in living cells. The probe can detect HOCl with high selectivity, fast response (within 30 s) as well as low detection limit (0.18 mmol/L). Fluorescence co-localization studies demonstrated that probe 1 was a mitochondria-targeted fluorescent probe. Furthermore, confocal fluorescence images of HeLa cell indicated that probe 1 could be used for monitoring intracellular HOCl in living cells. Finally, test strips experiment suggests that the probe 1 can detect the hypochlorous acid in tap water accompanied by remarkable color change.
- Fluorescent probe,
- Mitochondria-targeted,
- Ratiometric detection,
- Hypochlorous acid,
- ROS
1. [1]
  S. Kenmoku, Y. Urano, H. Kojima, T. Nagano, J. Am. Chem. Soc.129(2007) 7313-7318. doi: 10.1021/ja068740g
2. [2]
  J.L. Fan, H.Y. Mu, H. Zhu, et al., Ind. Eng. Chem. Res. 54(2015) 8842-8846. doi: 10.1021/acs.iecr.5b01904
3. [3]
  X.Q. Chen, X.Z. Tian, I. Shin, J. Yoon, J. Chem. Soc. Rev. 40(2011) 4783-4804. doi: 10.1039/c1cs15037e
4. [4]
  J. Qiao, Z. Liu, Y. Tian, M. Wu, Z.W. Niu, Chem. Commun. 51(2015) 3641-3644. doi: 10.1039/C4CC09120E
5. [5]
  H.S. Wang, W.J. Bao, S.B. Ren, et al., Anal. Chem. 87(2015) 6828-6833. doi: 10.1021/acs.analchem.5b01104
6. [6]
  H. Zhu, J.L. Fan, J.Y. Wang, H.Y. Mu, X.J. Peng, J. Am. Chem. Soc. 136(2014) 12820-12823. doi: 10.1021/ja505988g
7. [7]
  G.W. Chen, F.L. Song, J.Y. Wang, et al., Chem. Commun. 48(2012) 2949-2951. doi: 10.1039/c2cc17617c
8. [8]
  Y. Zhou, J.Y. Li, K.H. Chu, et al., Chem. Commun. 48(2012) 4677-4679. doi: 10.1039/c2cc30265a
9. [9]
  B.H. Wang, D. Chen, S. Kambam, et al., Dyes Pigments 120(2015) 22-29. doi: 10.1016/j.dyepig.2015.03.022
10. [10]
  Z.C. Dai, L. Tian, Y.N. Xiao, et al., J. Mater. Chem. B 1(2013) 924-927.
11. [11]
  H.X. Tong, J.W. Du, H. Li, et al., Chem. Commun. 52(2016) 11935-11938. doi: 10.1039/C6CC06439F
12. [12]
  R.L. Zhang, J. Zhao, G.M. Han, et al., J. Am. Chem. Soc. 138(2016) 3769-3778. doi: 10.1021/jacs.5b12848
13. [13]
  X. Wang, F.L. Song, X.J. Peng, Dyes Pigments 125(2016) 89-94. doi: 10.1016/j.dyepig.2015.10.012
14. [14]
  J.L. Fan, H.Y. Mu, H. Zhu, J.Y. Wang, X.J. Peng, Analyst 140(2015) 4594-4598. doi: 10.1039/C5AN00777A
15. [15]
  G.H. Cheng, J.L. Fan, W. Sun, et al., Chem. Commun. 50(2014) 1018-1020. doi: 10.1039/C3CC47864E
16. [16]
  J.J. Du, M.M. Hu, J.L. Fan, X.J. Peng, Chem. Soc. Rev. 41(2012) 4511-4535. doi: 10.1039/c2cs00004k
17. [17]
  X.Q. Chen, F. Wang, J.Y. Hyun, et al., Chem. Soc. Rev. 45(2016) 2976-3016. doi: 10.1039/C6CS00192K
18. [18]
  D.P. Li, Z.Y. Wang, X.J. Cao, et al., Chem. Commun. 52(2016) 2760-2763. doi: 10.1039/C5CC09092J
19. [19]
  R. Noubade, K. Wong, N. Ota, et al., Nature 509(2014) 235-239. doi: 10.1038/nature13152
20. [20]
  M. Yu, X. Wu, B. Lin, et al., Anal. Chem. 87(2015) 6688-6695. doi: 10.1021/acs.analchem.5b00847
21. [21]
  M.S. Shim, Y.N. Xia, Angew. Chem. Int. Ed. 52(2013) 6926-6929. doi: 10.1002/anie.201209633
22. [22]
  J. Kim, Y. Kim, Analyst 139(2014) 2986-2989. doi: 10.1039/C4AN00466C
23. [23]
  S. Goswami, S. Paul, A. Manna, Dalton Trans. 42(2013) 10097-10101. doi: 10.1039/c3dt51238j
24. [24]
  Q.A. Best, N. Sattenapally, D.J. Dyer, C.N. Scott, M.E. McCarroll, J. Am. Chem. Soc. 135(2013) 13365-13370. doi: 10.1021/ja401426s
25. [25]
  G.P. Li, D.J. Zhu, Q. Liu, L. Xue, H. Jiang, Org. Lett. 15(2013) 2002-2005. doi: 10.1021/ol4006823
26. [26]
  L. Yuan, W. Lin, J. Song, Y. Yang, Chem. Commun. 47(2011) 12691-12693. doi: 10.1039/c1cc15762k
27. [27]
  L. Li, C.W. Zhang, G.Y.J. Chen, et al., Nat. Commun. 5(2014) 3276-4276.
28. [28]
  W. Feng, Q.L. Qiao, S. Leng, et al., Chin. Chem. Lett. 27(2016) 1554-1558. doi: 10.1016/j.cclet.2016.06.016
29. [29]
  X. Chen, K.A. Lee, E.M. Ha, et al., Chem. Commun. 47(2011) 4373-4375. doi: 10.1039/c1cc10589b
30. [30]
  X. Chen, K.A. Lee, X. Ren, J. Yoon, et al., Nat. Protoc. 11(2016) 1219-1228. doi: 10.1038/nprot.2016.062
31. [31]
  H. Zhu, J.L. Fan, B.H. Wang, X.J. Peng, Chem. Soc. Rev. 44(2015) 4337-4366. doi: 10.1039/C4CS00285G
32. [32]
  Y. Xiao, R. Zhang, Z. Ye, et al., Anal. Chem. 84(2012) 10785-10792. doi: 10.1021/ac3028189
33. [33]
  J. Lv, F. Wang, T. Wei, X. Chen, Ind. Eng. Chem. Res. 56(2017) 3757-3764. doi: 10.1021/acs.iecr.7b00381
34. [34]
  S.C. Burdette, G.K. Walkup, B. Spingler, R.Y. Tsien, S.J. Lippard, J. Am. Chem. Soc. 123(2001) 7831-7841. doi: 10.1021/ja010059l
35. [35]
  N. Jiang, J.L. Fan, F. Xu, et al., Angew. Chem. Int. Ed. 54(2015) 2510-2514. doi: 10.1002/anie.201410645
36. [36]
  X.G. Yang, Y.B. Zhou, X.F. Zhang, et al., Chem. Commun. 52(2016) 10289-10292. doi: 10.1039/C6CC05254A
37. [37]
  A.S. Abdelfattah, V. Rancic, B. Rawal, K. Ballanyi, R.E. Campbell, Chem. Commun. 52(2016) 14153-14156. doi: 10.1039/C6CC06810C
38. [38]
  S.K. Bae, C.H. Heo, D.J. Choi, et al., J. Am. Chem. Soc. 135(2013) 9915-9923. doi: 10.1021/ja404004v
39. [39]
  H.J. Kim, C.H. Heo, H.M. Kim, J. Am. Chem. Soc. 135(2013) 17969-17977. doi: 10.1021/ja409971k
40. [40]
  C. Huang, T. Jia, M.F. Tang, et al., J. Am. Chem. Soc. 136(2014) 14237-14244. doi: 10.1021/ja5079656
41. [41]
  C.C. Zhao, X.L. Zhang, K.B. Li, et al., J. Am. Chem. Soc. 137(2015) 8490-8498. doi: 10.1021/jacs.5b03248
42. [42]
  J.L. Fan, M.M. Hu, P. Zhan, X.J. Peng, Chem. Soc. Rev. 42(2013) 29-43. doi: 10.1039/C2CS35273G
43. [43]
  G.H. Cheng, J.L. Fan, W. Sun, et al., Analyst. 138(2013) 6091-6096. doi: 10.1039/c3an01152f
44. [44]
  W.S. Shin, M.G. Lee, P. Verwilst, et al., Chem. Sci. 7(2016) 6050-6059. doi: 10.1039/C6SC02236G
45. [45]
  J.T. Hou, M.Y. Wu, K. Li, et al., Chem. Commun. 50(2014) 8640-8643. doi: 10.1039/C4CC02673J
46. [46]
  Y. Liu, K. Li, M.Y. Wu, et al., Chem. Commun. 51(2015) 10236-10239. doi: 10.1039/C5CC03055B
47. [47]
  H.D. Li, Q.C. Yao, J.L. Fan, et al., Ind. Eng. Chem. Res. 55(2016) 1477-1483. doi: 10.1021/acs.iecr.5b04530
48. [48]
  Q. Wang, W. Wang, S. Li, et al., Dyes Pigments 134(2016) 297-305. doi: 10.1016/j.dyepig.2016.07.030
49. [49]
  H.D. Xiao, K. Xin, H.F. Dou, et al., Chem. Commun. 51(2015) 1442-1445. doi: 10.1039/C4CC07411D
50. [50]
  C.C. Chang, F. Wang, J. Qiang, et al., Sens. Actuators B:Chem. 243(2017) 22-28. doi: 10.1016/j.snb.2016.11.123
51. [51]
  T.T. Chen, T.W. Wei, Z.J. Zhang, et al., Dyes Pigments 140(2017) 392-398. doi: 10.1016/j.dyepig.2017.01.063
52. [52]
  Y. Yue, F. Huo, C. Yin, et al., RSC Adv. 5(2015) 77670-77672. doi: 10.1039/C5RA16097A
1. [1]
  Bin Fang , Jiaqi Yang , Limin Wang , Haoqin Li , Jiaying Guo , Jiaxin Zhang , Qingyuan Guo , Bo Peng , Kedi Liu , Miaomiao Xi , Hua Bai , Li Fu , Lin Li . A mitochondria-targeted H₂S-activatable fluorogenic probe for tracking hepatic ischemia-reperfusion injury. Chinese Chemical Letters, 2024, 35(6): 108913-. doi: 10.1016/j.cclet.2023.108913
2. [2]
  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
3. [3]
  Ke Gong , Jinghan Liao , Jiangtao Lin , Quan Wang , Zhihua Wu , Liting Wang , Jiali Zhang , Yi Dong , Yourong Duan , Jianhua Chen . Mitochondria-targeted nanoparticles overcome chemoresistance via downregulating BACH1/CD47 axis in ovarian carcinoma. Chinese Chemical Letters, 2024, 35(5): 108888-. doi: 10.1016/j.cclet.2023.108888
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  Simin Wei , Yaqing Yang , Junjie Li , Jialin Wang , Jinlu Tang , Ningning Wang , Zhaohui Li . The Mn/Yb/Er triple-doped CeO₂ nanozyme with enhanced oxidase-like activity for highly sensitive ratiometric detection of nitrite. Chinese Chemical Letters, 2024, 35(6): 109114-. doi: 10.1016/j.cclet.2023.109114
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  Maosen Xu , Pengfei Zhu , Qinghong Cai , Meichun Bu , Chenghua Zhang , Hong Wu , Youzhou He , Min Fu , Siqi Li , Xingyan Liu . In-situ fabrication of TiO₂/NH₂−MIL-125(Ti) via MOF-driven strategy to promote efficient interfacial effects for enhancing photocatalytic NO removal activity. Chinese Chemical Letters, 2024, 35(10): 109524-. doi: 10.1016/j.cclet.2024.109524
14. [14]
  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
15. [15]
  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
16. [16]
  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
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]
  Kun-Heng Li , Hong-Yang Zhao , Dan-Dan Wang , Ming-Hui Qi , Zi-Jian Xu , Jia-Mi Li , Zhi-Li Zhang , Shi-Wen Huang . Mitochondria-targeted nano-AIEgens as a powerful inducer for evoking immunogenic cell death. Chinese Chemical Letters, 2024, 35(5): 108882-. doi: 10.1016/j.cclet.2023.108882
19. [19]
  Zhiyu Yu , Xiang Luo , Cheng Zhang , Xin Lu , Xiaohui Li , Pan Liao , Zhongqiu Liu , Rong Zhang , Shengtao Wang , Zhiqiang Yu , Guochao Liao . Mitochondria-targeted carrier-free nanoparticles based on dihydroartemisinin against hepatocellular carcinoma. Chinese Chemical Letters, 2024, 35(10): 109519-. doi: 10.1016/j.cclet.2024.109519
20. [20]
  Jie ZHANG , Xin LIU , Zhixin LI , Yuting PEI , Yuqi YANG , Huimin LI , Zhiqiang LIU . Assembling a luminescence silencing system based on post-synthetic modification strategy: A highly sensitive and selective turn-on metal-organic framework probe for ascorbic acid detection. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 823-833. doi: 10.11862/CJIC.20230310

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(780)
HTML views(27)

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