Citation: 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[J]. Chinese Chemical Letters, ;2024, 35(5): 109156. doi: 10.1016/j.cclet.2023.109156 shu

A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system

Yudi Cheng ^{a, b, 1} ,
Xiao Wang ^{a, 1} ,
Jiao Chen ^{a, b} ,
Zihan Zhang ^a ,
Jiadong Ou ^a ,
Mengyao She ^{a, b} ,
Fulin Chen ^{b, *,} ,
Jianli Li ^{a, *,}

a.
Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, Xi'an Key Laboratory of Functional Supramolecular Structure and Materials, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, China
b.
Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, Biomedicine Key Laboratory of Shaanxi Province, Lab of Tissue Engineering, the College of Life Sciences, Faculty of Life Science & Medicine, Northwest University, Xi'an 710069, China

chenfl@nwu.edu.cn

lijianli@nwu.edu.cn

Received Date: 2 August 2023
Revised Date: 23 September 2023
Accepted Date: 25 September 2023
Available Online: 27 September 2023

Figures(4)

Sulfydryl-contained (-SH) substances including hydrogen sulfide (H₂S), cysteine (Cys), homocysteine (Hcy) and glutathione (GSH) play crucial roles in living systems, and their variations are closely associated with various diseases. Herein, we developed a near-infrared intramolecular charge transfer (ICT) based fluorescent probe Y-NBD, achieving detection of Cys/Hcy and H₂S with different fluorescent signals (green-red for Cys/Hcy, red for H₂S), large Stokes shifts (~100/105 nm or 191 nm) and high signal-background-ratio, but not responding to GSH. Y-NBD was successfully applied to image exogenous/endogenous Cys/Hcy and H₂S in various living cancer cells (HeLa, A549, and HepG2) and in zebrafish. It not only visualized the transformation pathway of several thiols in HepG2 cells but also verified that the intestine is the main site for the activation and metabolism of Y-NBD in zebrafish, as well as realized to evaluate the degree of drug-induced liver injury. This work provides a promising tool for imaging Cys/Hcy and H₂S in living systems and shows great potency in evaluating drug-induced liver injury and its treatment.
- Fluorescent probe,
- Near-infrared,
- Hydrogen sulfide,
- Cysteine/homocysteine,
- Large Stokes shift,
- Dicyanoisophorone,
- Drug-induced liver injury
1. [1]
  Y. Yue, F. Huo, F. Cheng, et al., Chem. Soc. Rev. 48 (2019) 4155–4177. doi: 10.1039/c8cs01006d
2. [2]
  B.J. Bezner, L.S. Ryan, A.R. Lippert, Anal. Chem. 92 (2020) 309–326. doi: 10.1021/acs.analchem.9b04990
3. [3]
  Y. Yue, F. Huo, C. Yin, Chem. Sci. 12 (2020) 1220–1226.
4. [4]
  K. Ma, H. Yang, T. Shen, et al., Chem. Sci. 13 (2022) 3706–3712. doi: 10.1039/d2sc00328g
5. [5]
  W. Zhang, F. Huo, F. Cheng, et al., J. Am. Chem. Soc. 142 (2020) 6324–6331. doi: 10.1021/jacs.0c00992
6. [6]
  S. Singh, D. Padovani, R.A. Leslie, et al., J. Biol. Chem. 284 (2009) 22457–22466. doi: 10.1074/jbc.M109.010868
7. [7]
  B. Fowler, Semin. Vasc. Med. 5 (2005) 77–86. doi: 10.1055/s-2005-872394
8. [8]
  G. Caliendo, G. Cirino, V. Santagada, et al., J. Med. Chem. 53 (2010) 6275–6286. doi: 10.1021/jm901638j
9. [9]
  V.D.B. Bonifacio, S.A. Pereira, J. Serpa, et al., Br. J. Cancer 124 (2021) 862–879. doi: 10.1038/s41416-020-01156-1
10. [10]
  B. Ke, W. Wu, W. Liu, et al., Anal. Chem. 88 (2016) 592–595. doi: 10.1021/acs.analchem.5b03636
11. [11]
  K. Wang, R. Guo, X.Y. Chen, et al., Chem. Eng. J. 468 (2023) 143611. doi: 10.1016/j.cej.2023.143611
12. [12]
  W. Su, L. Huang, L. Zhu, et al., Sens. Actuat. B: Chem. 369 (2022) 132297. doi: 10.1016/j.snb.2022.132297
13. [13]
  Y. Shen, Q. Zhou, W. Li, et al., Chem. Asian. J. 17 (2022) e202200320. doi: 10.1002/asia.202200320
14. [14]
  W. Li, Y. Shen, X. Gong, et al., Anal. Chem. 93 (2021) 16673–16682. doi: 10.1021/acs.analchem.1c04246
15. [15]
  P. Sun, H.C. Chen, S. Lu, et al., Anal. Chem. 94 (2022) 11573–11581. doi: 10.1021/acs.analchem.2c01850
16. [16]
  S.K. Bae, C.H. Heo, D.J. Choi, et al., J. Am. Chem. Soc. 135 (2013) 9915–9923. doi: 10.1021/ja404004v
17. [17]
  S. Gong, Z. Zheng, X. Guan, et al., Anal. Chem. 93 (2021) 5700–5708. doi: 10.1021/acs.analchem.0c04639
18. [18]
  X. Dong, L. Sun, Z. Zhang, et al., Sci. China Chem. 66 (2023) 1869–1876. doi: 10.1007/s11426-023-1579-y
19. [19]
  Y. Zhang, J. Fang, S. Ye, et al., Nat. Commun. 13 (2022) 1685. doi: 10.1007/s42765-022-00213-z
20. [20]
  R. Kaushik, N. Nehra, V. Novakova, et al., ACS Omega 8 (2023) 98–126. doi: 10.1021/acsomega.2c06218
21. [21]
  J. Chen, Z. Wang, M. She, et al., ACS Appl. Mater. Inter. 11 (2019) 32605–32612. doi: 10.1021/acsami.9b08522
22. [22]
  J. Chen, D. Huang, M. She, et al., ACS Sens. 6 (2021) 628–640. doi: 10.1021/acssensors.0c02343
23. [23]
  P. Zhou, M. She, P. Liu, et al., Sens. Actuat. B Chem. 318 (2020) 128258. doi: 10.1016/j.snb.2020.128258
24. [24]
  G. Yin, Y. Gan, H. Jiang, et al., Anal. Chem. 95 (2023) 8932–8938. doi: 10.1021/acs.analchem.3c00799
25. [25]
  F. Wei, Y. Ding, J. Ou, et al., Anal. Chem. 95 (2023) 9173–9181. doi: 10.1021/acs.analchem.2c05441
26. [26]
  Y. Huang, Y. Zhang, F. Huo, et al., J. Am. Chem. Soc. 142 (2020) 18706–18714. doi: 10.1021/jacs.0c10210
27. [27]
  H. Yan, F. Huo, Y. Yue, et al., J. Am. Chem. Soc. 143 (2020) 318–325. doi: 10.1177/2050157919884718
28. [28]
  S. Li, P. Wang, M. Ye, et al., Anal. Chem. 95 (2023) 5133–5141. doi: 10.1021/acs.analchem.3c00226
29. [29]
  W. Dou, H. Han, A. Sedgwick, et al., Sci. Bull. 67 (2022) 853–878. doi: 10.1016/j.scib.2022.01.014
30. [30]
  L. Chen, Y. Lyu, X. Zhang, et al., Sci. China Chem. 66 (2023) 1336–1383. doi: 10.1007/s11426-022-1461-3
31. [31]
  H. Fang, Y. Chen, Z. Jiang, et al., Acc. Chem. Res. 56 (2023) 258–269. doi: 10.1021/acs.accounts.2c00643
32. [32]
  J. Yin, J. Zhan, Q. Hu, et al., Chem. Soc. Rev. 52 (2023) 2011–2030. doi: 10.1039/d2cs00454b
33. [33]
  Z. Wang, J. Li, J. Chen, et al., Chin. Chem. Lett. 34 (2023) 108507. doi: 10.1016/j.cclet.2023.108507
34. [34]
  X. Ma, Y. Huang, W. Chen, et al., Angew. Chem. Int. Ed. 62 (2023) e202216109. doi: 10.1002/anie.202216109
35. [35]
  H. Zhang, C. He, L. Shen, et al., Chin. Chem. Lett. 34 (2023) 108160. doi: 10.1016/j.cclet.2023.108160
36. [36]
  D. Li, T. Shen, X. Xue, et al., Sci. China Chem. 66 (2023) 2329–2338. doi: 10.1007/s11426-023-1661-6
37. [37]
  L. Kong, W. Lu, X. Cao, et al., J. Mater. Chem. B 10 (2022) 7924–7954. doi: 10.1039/d2tb01210c
38. [38]
  Z. Xu, T. Qin, X. Zhou, et al., Trend. Anal. Chem. 121 (2019) 115672. doi: 10.1016/j.trac.2019.115672
39. [39]
  X. Jiao, Y. Li, J. Niu, et al., Anal. Chem. 90 (2018) 533–555. doi: 10.1021/acs.analchem.7b04234
40. [40]
  L. Yang, Y. Su, Y. Geng, et al., ACS Sens. 3 (2018) 1863–1869. doi: 10.1021/acssensors.8b00685
41. [41]
  C. Yin, K. Xiong, F. Huo, et al., Angew. Chem. Int. Ed. 56 (2017) 13188–13198. doi: 10.1002/anie.201704084
42. [42]
  S. Li, F. Huo, Y. Yue, et al., Chin. Chem. Lett. 32 (2021) 3870–3875. doi: 10.1016/j.cclet.2021.05.026
43. [43]
  L. Dai, Q. Zhang, Q. Ma, et al., Coord. Chem. Rev. 489 (2023) 215193. doi: 10.1016/j.ccr.2023.215193
44. [44]
  Y. Zheng, Z. Chai, W. Tang, et al., Sens. Actuat. B: Chem. 330 (2021) 129343. doi: 10.1016/j.snb.2020.129343
45. [45]
  S. Ding, W. Feng, G. Feng, Sens. Actuat. B: Chem. 238 (2017) 619–625. doi: 10.1016/j.snb.2016.07.117
46. [46]
  Y. Kang, L. Niu, Q. Yang, Chin. Chem. Lett. 30 (2019) 1791–1798. doi: 10.1016/j.cclet.2019.08.013
47. [47]
  Y. Kim, J. Kim, J.M. An, et al., ACS Sens. 8 (2023) 1723–1732. doi: 10.1021/acssensors.3c00004
48. [48]
  J. Chen, Y. Li, X. Feng, et al., Spectrochim. Acta A Mol. Biomol. Spectrosc. 246 (2021) 119041. doi: 10.1016/j.saa.2020.119041
49. [49]
  S.E. Wilkie, G. Borland, R.N. Carter, et al., Biochem. J. 478 (2021) 3485–3504. doi: 10.1042/bcj20210517
50. [50]
  R. Montanaro, V. Vellecco, R. Torregrossa, et al., Redox Bio. 62 (2023) 102657. doi: 10.1016/j.redox.2023.102657
51. [51]
  H.M.S. Al Ubeed, R.B.H. Wills, M.C. Bowyer, et al., Postharvest Biol. Technol. 147 (2019) 54–58. doi: 10.1016/j.postharvbio.2018.09.011
52. [52]
  P. Zhang, X. Nie, M. Gao, et al., Mater. Chem. Front. 1 (2017) 838–845. doi: 10.1039/C6QM00223D
53. [53]
  X. Wang, J. Zhang, K. He, et al., Front. Pharmacol. 12 (2021) 713963. doi: 10.3389/fphar.2021.713963
54. [54]
  S.M. Alavi Naini, N. Soussi-Yanicostas, Front. Cell Dev. Biol. 6 (2018) 163. doi: 10.3389/fcell.2018.00163
55. [55]
  Y. Yang, K. Zhou, M. Ma, et al., Chem. Eng. J. 452 (2023) 139020. doi: 10.1016/j.cej.2022.139020
56. [56]
  C. Srinivasan, W.M. Williams, H.T. Nagasawa, et al., Biochem. Pharmacol. 61 (2001) 925–931. doi: 10.1016/S0006-2952(01)00539-1
57. [57]
  R. Chen, W. Li, R. Li, et al., Chin. Chem. Lett. 34 (2023) 107845. doi: 10.1016/j.cclet.2022.107845
58. [58]
  W.M. Lee, J. Hepatol. 67 (2017) 1324–1331. doi: 10.1016/j.jhep.2017.07.005
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沈阳化工大学材料科学与工程学院沈阳 110142

A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H2S and its applications in living system

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通讯作者: 陈斌, bchen63@163.com

A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system