Citation: Dandan Bu, Yuying Wang, Na Wu, Wei Feng, Donghui Wei, Zhanxian Li, Mingming Yu. A mitochondrial-targeted ratiometric probe for detecting intracellular H₂S with high photostability[J]. Chinese Chemical Letters, ;2021, 32(5): 1799-1802. doi: 10.1016/j.cclet.2020.12.044 shu

A mitochondrial-targeted ratiometric probe for detecting intracellular H₂S with high photostability

Dandan Bu ^{a, 1} ,
Yuying Wang ^{a, 1} ,
Na Wu ^b ,
Wei Feng ^b ,
Donghui Wei ^a ,
Zhanxian Li ^{a, *,} ,
Mingming Yu ^{a, *,}

a.
Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou 450001, China
b.
Department of Chemistry, State Key Laboratory of Molecular Engineering of Polymers, Institutes of Biomedical Sciences & Collaborative Innovation Center of Chemistry for Energy Materials, Fudan University, Shanghai 200433, China

Received Date: 27 August 2020
Revised Date: 22 December 2020
Accepted Date: 23 December 2020
Available Online: 29 December 2020

Figures(6)

Based on 4-bromo-1, 8-naphthalic anhydride, one novel ratiometric fluorescence H₂S-probe (IDNA) was designed and synthesized. Further studies indicate that IDNA can sensitively recognize H₂S (detection limit of 7 μmol/L) with good selectivity and anti-interference ability. In addition, IDNA has satisfactory photostability in HeLa cells, ability of mitochondrial co-localization, and can be utilized in fluorescence imaging of H₂S.
- Ratiometric,
- H₂S,
- Mitochondrial localization,
- Fluorescent probe,
- Biological imaging
1. [1]
  O. Kabil, R. Banerjee, J. Biol. Chem. 285(2010) 21903-21907. doi: 10.1074/jbc.R110.128363
2. [2]
  A. Katsouda, S.I. Bibli, A. Pyriochou, et al., Pharmacol. Res. 113(2016) 175-185. doi: 10.1016/j.phrs.2016.08.026
3. [3]
  G. Yang, L. Wu, B. Jiang, et al., Science 322(2008) 587-590. doi: 10.1126/science.1162667
4. [4]
  L. Xie, H. Feng, S. Li, et al., Antioxid. Redox Sign. 24(2016) 329-343. doi: 10.1089/ars.2015.6331
5. [5]
  D. Wu, N. Luo, L. Wang, et al., Sci. Rep. 7(2017) 455. doi: 10.1038/s41598-017-00557-2
6. [6]
  F. Comas, J. Latorre, O. Cusso, et al., Food Chem. Toxicol. 131(2019) 110543. doi: 10.1016/j.fct.2019.05.051
7. [7]
  X.J. Cheng, J.X. Gu, Y.P. Pang, et al., ACS Chem. Neurosci. 10(2019) 3500-3509. doi: 10.1021/acschemneuro.9b00120
8. [8]
  M. Babaei-Karamshahlou, B. Hooshmand, S. Hajizadeh, et al., Eur. J. Pharmacol. 696(2012) 130-135. doi: 10.1016/j.ejphar.2012.09.039
9. [9]
  T. Panagaki, E.B. Randi, F. Augsburger, et al., PNAS 116(2019) 18769-18771. doi: 10.1073/pnas.1911895116
10. [10]
  M.D. Brown, J.R. Hall, M.H. Schoenfisch, Anal. Chim. Acta 1045(2019) 67-76. doi: 10.1016/j.aca.2018.08.054
11. [11]
  T. Ubuka, T. Abe, R. Kajikawa, et al., J. Chromatogr. B 757(2001) 31-37. doi: 10.1016/S0378-4347(01)00046-9
12. [12]
  M.L.D. Jayaranjan, A.P. Annachhatre, Water Sci. Technol. 67(2013) 311-318. doi: 10.2166/wst.2012.546
13. [13]
  C. Wei, Q. Zhu, W. Liu, et al., Org. Biomol. Chem. 12(2014) 479-485. doi: 10.1039/C3OB41870G
14. [14]
  L. Zhou, L. Xie, C. Liu, et al., Chin. Chem. Lett. 30(2019) 1799-1808. doi: 10.1016/j.cclet.2019.07.051
15. [15]
  Z. Shao, C. Zhang, X. Zhu, et al., Chin. Chem. Lett. 30(2019) 2169-2172. doi: 10.1016/j.cclet.2019.06.023
16. [16]
  L. Tu, Y. Xu, Q. Ouyang, et al., Chin. Chem. Lett. 30(2019) 1731-1737. doi: 10.1016/j.cclet.2019.05.022
17. [17]
  H.A. Henthorn, M.D. Pluth, J. Am. Chem. Soc. 137(2015) 15330-15336. doi: 10.1021/jacs.5b10675
18. [18]
  M.D. Hammers, M.J. Taormina, M.M. Cerda, et al., J. Am. Chem. Soc. 137(2015) 10216-10223. doi: 10.1021/jacs.5b04196
19. [19]
  G.J. Mao, T.T. Wei, X.X. Wang, et al., Anal. Chem. 85(2013) 7875-7881. doi: 10.1021/ac401518e
20. [20]
  K. Xiang, Y. Liu, C. Li, et al., Dyes Pigm. 123(2015) 78-84. doi: 10.1016/j.dyepig.2015.06.037
21. [21]
  H. Zhang, L. Xu, W. Chen, et al., Anal. Chem. 91(2019) 1904-1911. doi: 10.1021/acs.analchem.8b03869
22. [22]
  J. Lv, F. Wang, J. Qiang, et al., Biosen. Bioelectron. 87(2017) 96-100. doi: 10.1016/j.bios.2016.08.018
23. [23]
  Y. Chen, C. Zhu, Z. Yang, et al., Angew. Chem. Int. Ed. 52(2013) 1688-1691. doi: 10.1002/anie.201207701
24. [24]
  Y. Yang, C. Yin, F. Huo, et al., Sens. Actuators B: Chem. 203(2014) 596-601. doi: 10.1016/j.snb.2014.07.025
25. [25]
  Y. Feng, Y. Yang, Y. Wang, et al., Sens. Actuators B: Chem. 288(2019) 27-37.
26. [26]
  K. Sasakura, K. Hanaoka, N. Shibuya, et al., J. Am. Chem. Soc. 133(2011) 18003-18005. doi: 10.1021/ja207851s
27. [27]
  D.H. Joo, J.S. Mok, G.H. Bae, et al., Ind. Eng. Chem. Res. 56(2017) 8399-8407. doi: 10.1021/acs.iecr.7b01115
28. [28]
  C. Zhao, X. Zhang, K. Li, et al., J. Am. Chem. Soc. 137(2015) 8490-8498. doi: 10.1021/jacs.5b03248
29. [29]
  Y. He, Z. Li, Q. Jia, et al., Chin. Chem. Lett. 28(2017) 1969-1974. doi: 10.1016/j.cclet.2017.07.027
30. [30]
  H. Song, W. Du, C. Liu, et al., Sens. Actuators B: Chem. 273(2018) 927-934. doi: 10.1016/j.snb.2018.07.009
31. [31]
  R.M. Duke, E.B. Veale, F.M. Pfeffer, et al., Chem. Soc. Rev. 39(2010) 3936-3953. doi: 10.1039/b910560n
32. [32]
  C. Liu, J. Xu, F. Yang, et al., Sens. Actuators B: Chem. 212(2015) 364-370. doi: 10.1016/j.snb.2015.02.010
33. [33]
  L. Feng, P. Li, J. Hou, et al., Anal. Chem. 90(2018) 13341-13347. doi: 10.1021/acs.analchem.8b02857
34. [34]
  W. Zhang, F. Huo, T. Liu, et al., J. Mater. Chem. B 6(2018) 8085-8089. doi: 10.1039/C8TB02536C
35. [35]
  Y. Li, Y. Ban, R. Wang, et al., Chin. Chem. Lett. 31(2020) 443-446. doi: 10.1016/j.cclet.2019.07.047
36. [36]
  M. Yu, W. Du, H. Li, et al., Biosen. Bioelectron. 92(2017) 385-389. doi: 10.1016/j.bios.2016.10.090
37. [37]
  Y. Hou, H. Liu, Z. Li, et al., Anal. Methods 12(2020) 2835-2840. doi: 10.1039/D0AY00622J
38. [38]
  Z. Li, W. Zhao, X. Li, et al., Inorg. Chem. 51(2012) 12444-12449. doi: 10.1021/ic3018453
39. [39]
  P. Wang, S. Xue, X. Yang, Biosen. Bioelectron. 163(2020) 112283. doi: 10.1016/j.bios.2020.112283
40. [40]
  X. Yue, J. Wang, J. Han, et al., Chem. Commun. 56(2020) 2849-2852. doi: 10.1039/C9CC10028H
41. [41]
  L.L. Zhang, H.K. Zhu, C.C. Zhao, et al., Chin. Chem. Lett. 28(2017) 218-221. doi: 10.1016/j.cclet.2016.07.008
42. [42]
  J. Li, C. Yin, Y. Zhang, et al., Dyes Pigm. 172(2020) 107826. doi: 10.1016/j.dyepig.2019.107826
43. [43]
  T. Zhou, Y. Yang, K. Zhou, et al., Sens. Actuators B: Chem. 301(2019) 127116. doi: 10.1016/j.snb.2019.127116
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通讯作者: 陈斌, bchen63@163.com

A mitochondrial-targeted ratiometric probe for detecting intracellular H₂S with high photostability