Citation: Jin Li, Qinglong Qiao, Yiyan Ruan, Ning Xu, Wei Zhou, Guixin Zhang, Jingli Yuan, Zhaochao Xu. A fluorogenic probe for SNAP-tag protein based on ESPT ratiometric signals[J]. Chinese Chemical Letters, ;2023, 34(5): 108266. doi: 10.1016/j.cclet.2023.108266 shu

A fluorogenic probe for SNAP-tag protein based on ESPT ratiometric signals

Jin Li ^{a, b, c} ,
Qinglong Qiao ^b ,
Yiyan Ruan ^{b, c} ,
Ning Xu ^b ,
Wei Zhou ^b ,
Guixin Zhang ^{d, *,} ,
Jingli Yuan ^a ,
Zhaochao Xu ^{b, *,}

a.
State Key Laboratory of Fine Chemicals, School of Chemistry, Dalian University of Technology, Dalian 116024, China
b.
CAS Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China
d.
General Surgery Department, The First Affiliated Hospital of Dalian Medical University, Dalian 116011, China

zgx0109@yeah.net

zcxu@dicp.ac.cn

Received Date: 6 January 2023
Revised Date: 22 February 2023
Accepted Date: 24 February 2023
Available Online: 2 March 2023

Figures(4)

Protein self-labeling tags achieve selective fusion and labeling of target proteins through genetic coding technology, but require exogenous fluorescent probes with fluorogenicity for protein tag binding to have the performance of wash-free fluorescence imaging in live cells. In this paper, we reported a fluorogenic probe 1 capable of ratiometric fluorescence recognition of SNAP-tag proteins. In this probe, the O⁶-benzylguanine derivative of 3–hydroxy-1,8-naphthalimide underwent a selective covalent linkage reaction with SNAP-tag protein. The hydroxyl group on the naphthalimide fluorophore formed a hydrogen bond with the functional group near the protein cavity. The excited state proton transfer occurred after illumination, to obtain the ratio fluorescence signal from blue emission to red emission, realizing the wash-free fluorescence imaging of the target proteins.
- Fluorogenic probe,
- Ratiometric,
- ESPT,
- SNAP-tag,
- Wash-free imaging
1. [1]
  J. Chen, W. Liu, X. Fang, et al., Chin. Chem. Lett. 33 (2022) 5042–5046. doi: 10.1016/j.cclet.2022.03.120
2. [2]
  J. Chen, C. Wang, W. Liu, et al., Angew. Chem. Int. Ed. 60 (2021) 25104–25113. doi: 10.1002/anie.202111052
3. [3]
  W. Liu, J. Chen, Q. Qiao, et al., Chin. Chem. Lett. 33 (2022) 4943–4947. doi: 10.1016/j.cclet.2022.03.121
4. [4]
  Q. Qiao, W. Liu, J. Chen, et al., Angew. Chem. Int. Ed. 61 (2022) e202202961.
5. [5]
  Q. Qiao, W. Liu, Y. Zhang, et al., Angew. Chem. Int. Ed. 61 (2022) e202208678.
6. [6]
  C. Li, Y. Xu, L. Tu, et al., Chem. Sci. 13 (2022) 6541–6549. doi: 10.1039/d2sc01518h
7. [7]
  Y. Xu, C. Li, J. An, et al., Sci. China Chem. 66 (2022) 155–163.
8. [8]
  Y. Xu, C. Li, X. Ma, et al., Proc. Natl. Acad. Sci. U. S. A. 119 (2022) e2209904119. doi: 10.1073/pnas.2209904119
9. [9]
  P. Wang, H. Yang, C. Liu, et al., Chin. Chem. Lett. 32 (2021) 168–178. doi: 10.1016/j.cclet.2020.11.056
10. [10]
  X. Zhang, L. Wang, N. Li, et al., Chin. Chem. Lett., 32 (2021) 2395–2399. doi: 10.1016/j.cclet.2021.02.031
11. [11]
  K. Lang, J.W. Chin, Chem. Rev. 114 (2014) 4764–4806. doi: 10.1021/cr400355w
12. [12]
  W. Chi, Q. Qiao, C. Wang, et al., Angew. Chem. Int. Ed. 59 (2020) 20215–20223. doi: 10.1002/anie.202010169
13. [13]
  L. Miao, W. Zhou, C. Yan, et al., Acta. Pharm. Sin. B 12 (2022) 3739–3742. doi: 10.1016/j.apsb.2022.05.033
14. [14]
  W. Chi, Q. Qi, R. Lee, et al., J. Phys. Chem. C 124 (2020) 3793–3801. doi: 10.1021/acs.jpcc.9b11673
15. [15]
  M.E. Norako, M.J. Greaney, R.L. Brutchey, J. Am. Chem. Soc. 134 (2012) 23–26. doi: 10.1021/ja206929s
16. [16]
  S. Leng, Q.L. Qiao, Y. Gao, et al., Chin. Chem. Lett. 28 (2017) 1911–1915. doi: 10.1016/j.cclet.2017.03.034
17. [17]
  A. Gautier, A. Juillerat, C. Heinis, et al., Chem. Biol. 15 (2008) 128–136. doi: 10.1016/j.chembiol.2008.01.007
18. [18]
  W. Liu, Q. Qiao, J. Zheng, et al., Biosens. Bioelectron. 176 (2021) 112886. doi: 10.1016/j.bios.2020.112886
19. [19]
  Q. Qiao, W. Liu, W. Chi, et al., Aggregate (2022), doi: org/10.1002/agt2.258. doi: 10.1002/agt2.258
20. [20]
  C. Wang, W. Chi, Q. Qiao, et al., Chem. Soc. Rev. 50 (2021) 12656–12678. doi: 10.1039/d1cs00239b
21. [21]
  D. Bu, Y. Wang, N. Wu, et al., Chin. Chem. Lett. 32 (2021) 1799–1802. doi: 10.1016/j.cclet.2020.12.044
22. [22]
  S. Wang, B. Zhu, B. Wang, et al., Chin. Chem. Lett. 32 (2021) 1795–1798. doi: 10.1016/j.cclet.2020.12.039
23. [23]
  S. Leng, Q. Qiao, L. Miao, et al., Chem. Commun. 53 (2017) 6448–6451. doi: 10.1039/C7CC01483J
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