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A red-emission fluorescence probe based on 1,4-addition reaction mechanism for the detection of biothiols in vitro and in vivo

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Abstract

In this work, a new fluorescence probe (DC) with a donor–π–acceptor (D–π–A) structure was designed and synthesized for the detection of three kinds of biothiols (Cys, Hcy and GSH) in live cells and organisms. DC displayed an intense red-emission centered at 625 nm. In the presence of biothiols, the nucleophilic addition reaction between the C=C double bond of DC and the sulfhydryl group (–SH) of biothiols occurred, resulting in obvious fluorescence quenching responses. DC exhibited high selectivity towards biothiols over other common bioactive species with low detection limits (0.26, 0.43, and 0.44 µM for Cys, Hcy and GSH, respectively). In addition, DC displayed a rapid response to biothiols within 4 min. The applications of DC in biothiols detection and imaging were then successfully demonstrated for the real-time monitoring of endogenous and exogenous biothiols in live cells and live animals.

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References

  1. B. Gao, L. Cui, Y. Pan, G. Zhang, Y. Zhou, C. Zhang, S. Shuang, C. Dong, RSC Adv. 6, 43028 (2016)

    Article  CAS  Google Scholar 

  2. J.S. Lan, R.F. Zeng, Y. Liu, Y.W. Xiang, X.Y. Jiang, L. Liu, S.S. Xie, Y. Ding, T. Zhang, Analyst 144, 3676 (2019)

    Article  CAS  Google Scholar 

  3. X. Chen, Y. Zhou, X. Peng, J. Yoon, Chem Soc Rev. 39, 2120 (2010)

    Article  CAS  Google Scholar 

  4. X. Xia, Y. Qian, B. Shen, J. Mater. Chem. B 6, 3023 (2018)

    Article  CAS  Google Scholar 

  5. Y. Cao, J. Liu, L. Zou, B. Ye, G. Li, Anal. Chim. Acta 1145, 46 (2021)

    Article  CAS  Google Scholar 

  6. Y. Hu, C.H. Heo, G. Kim, E.J. Jun, J. Yin, H.M. Kim, J. Yoon, Anal. Chem. 87, 3308 (2015)

    Article  CAS  Google Scholar 

  7. Z.H. Fu, X. Han, Y. Shao, J. Fang, Z.H. Zhang, Y.W. Wang, Y. Peng, Anal. Chem. 2017, 89 (1937)

    Google Scholar 

  8. L.Y. Niu, Y.Z. Chen, H.R. Zheng, L.Z. Wu, C.H. Tung, Q.Z. Yang, Chem. Soc. Rev. 44, 6143 (2015)

    Article  CAS  Google Scholar 

  9. Y. Yue, F. Huo, P. Ning, Y. Zhang, J. Chao, X. Meng, C. Yin, J. Am. Chem. Soc. 139, 3181 (2017)

    Article  CAS  Google Scholar 

  10. S. Feng, Y. Fang, W. Feng, Q. Xia, G. Feng, Dyes Pigm. 146, 103 (2017)

    Article  CAS  Google Scholar 

  11. J. Zheng, J. Li, H. Luo, L. Sun, M. Sang, X. Yu, RSC Adv. 11, 4356 (2021)

    Article  CAS  Google Scholar 

  12. W. Zhang, H. Zhang, M. Wang, P. Li, P.C. Ding, W. Zhang, H. Wang, B. Tang, Anal. Chem. 92, 16221 (2020)

    Article  CAS  Google Scholar 

  13. Y. Yue, F. Huo, Y. Wang, K. Ma, X. Li, C. Yin, Chem. Commun. 56, 9146 (2020)

    Article  CAS  Google Scholar 

  14. P. Hu, Y. Zhang, D. Wang, G. Qi, Y. Jin, Anal. Chem. 93, 4240 (2021)

    Article  CAS  Google Scholar 

  15. J. Vacek, B. Klejdus, J. Petrlova, L. Lojkova, V. Kuban, Analyst 131, 1167 (2006)

    Article  CAS  Google Scholar 

  16. T. Inoue, J.R. Kirchhoff, Anal. Chem. 74, 1349 (2002)

    Article  CAS  Google Scholar 

  17. N. Burford, M.D. Eelman, D.E. Mahony, M. Morash, Chem. Commun. (2003). https://doi.org/10.1039/b210570e

    Article  Google Scholar 

  18. R.F. Zeng, J.S. Lan, T. Wu, L. Liu, Y. Liu, R.J.Y. Ho, Y. Ding, T. Zhang, Food Chem. 318, 126358 (2020)

    Article  CAS  Google Scholar 

  19. A.S.K. Kumar, W.B. Tseng, M.J. Wu, Y.Y. Huang, W.L. Tseng, Anal. Chim. Acta 1113, 43 (2020)

    Article  Google Scholar 

  20. Y. Zou, M. Li, Y. Xing, T. Duan, X. Zhou, F. Yu, ACS Sens. 5, 242 (2020)

    Article  CAS  Google Scholar 

  21. S. Lee, J. Li, X. Zhou, J. Yin, J. Yoon, Coord. Chem. Rev. 366, 29 (2018)

    Article  CAS  Google Scholar 

  22. Q. Hu, C. Yu, X. Xia, F. Zeng, S. Wu, Biosens. Bioelectron. 81, 341 (2016)

    Article  CAS  Google Scholar 

  23. H. Feng, Z. Zhang, Q. Meng, H. Jia, Y. Wang, R. Zhang, Adv. Sci. 5, 1800397 (2018)

    Article  Google Scholar 

  24. W. Wan, Y. Huang, Q. Xia, Y. Bai, Y. Chen, W. Jin, M. Wang, D. Shen, H. Lyu, Y. Tang, X. Dong, Z. Gao, Q. Zhao, L. Zhang, Y. Liu, Angew. Chem. Int. Ed. 60, 11335 (2021)

    Article  CAS  Google Scholar 

  25. W. Wan, W. Jin, Y. Huang, Q. Xia, Y. Bai, H. Lyu, D. Liu, X. Dong, W. Li, Y. Liu, Anal. Chem. 93, 1717 (2021)

    Article  CAS  Google Scholar 

  26. Z. Xu, T. Qin, X. Zhou, L. Wang, B. Liu, Trends Anal. Chem. 121, 115672 (2019)

    Article  CAS  Google Scholar 

  27. W. Liu, J. Chen, Z. Xu, Coord. Chem. Rev. 429, 213638 (2021)

    Article  CAS  Google Scholar 

  28. Y.F. Kang, L.Y. Niu, Q.Z. Yang, Chin. Chem. Lett. 30, 1791 (2019)

    Article  CAS  Google Scholar 

  29. N. Kaur, S. Chopra, G. Singh, P. Raj, A. Bhasin, S.K. Sahoo, A. Kuwar, N. Sing, J. Mater. Chem. B 6, 4872 (2018)

    Article  CAS  Google Scholar 

  30. M.-Y. Wu, K. Li, C.-Y. Li, J.-T. Hou, X.-Q. Yu, Chem. Commun. 50, 183 (2014)

    Article  CAS  Google Scholar 

  31. H. Feng, Y. Wang, J. Liu, Z. Zhang, X. Yang, R. Chen, Q. Meng, R. Zhang, J. Mater. Chem. B 7, 3909 (2019)

    Article  CAS  Google Scholar 

  32. K. Xiong, F. Huo, J. Chao, Y. Zhang, C. Yin, Anal. Chem. 91, 1472 (2019)

    Article  CAS  Google Scholar 

  33. C. Liu, R. Zhang, W. Zhang, J. Liu, Y.L. Wang, Z. Du, B. Song, Z.P. Xu, J.L. Yuan, J. Am. Chem. Soc. 141, 8462 (2019)

    Article  CAS  Google Scholar 

  34. F. Liu, S. Zang, J. Jing, X. Zhang, Anal. Methods 12, 3797 (2020)

    Article  CAS  Google Scholar 

  35. Y.L. Fu, X.G. Chen, H. Li, W. Feng, Q.H. Song, New J. Chem. 44, 13781 (2020)

    Article  CAS  Google Scholar 

  36. S. Chakraborty, M.M. Joseph, S. Varughese, S. Ghosh, K.K. Maiti, A. Samanta, A. Ajayaghosh, Chem. Sci. 11, 12695 (2020)

    Article  CAS  Google Scholar 

  37. H. Zhang, L. Xu, W. Chen, J. Huang, C. Huang, J. Sheng, X. Song, ACS Sens. 3, 2513 (2018)

    Article  CAS  Google Scholar 

  38. L. Zhang, D. Duan, Y. Liu, C. Ge, X. Cui, J. Sun, J. Fang, J. Am. Chem. Soc. 136, 226 (2014)

    Article  CAS  Google Scholar 

  39. Q. Miao, Q. Li, Q. Yuan, L. Li, Z. Hai, S. Liu, G. Liang, Anal. Chem. 87, 3460 (2015)

    Article  CAS  Google Scholar 

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Acknowledgements

This work was supported by the Talent Program-Outstanding Youth Science Project, Liaoning (no. XLYC1807199), the Distinguished Professor Program of Liaoning (XLYC1802074), the “Seeding Raising” Project of Young Scientific and Technological Talents of Liaoning Provincial Department of Education (2019LNQN03; 2019LNJC18), and the Youth Fund of University of Science and Technology Liaoning (2018QN02).

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  1. Yaoyun Hu and Zhuye Shang have contributed equally to this work.

Authors and Affiliations

  1. School of Chemical Engineering, University of Science and Technology Liaoning, Anshan, 114051, Liaoning, People’s Republic of China

    Yaoyun Hu, Zhuye Shang, Qingtao Meng & Zhiqiang Zhang

  2. School of Forensic Medicine, Xinxiang Medical University, Jinsui Road No. 601, Xinxiang, 453003, Henan, People’s Republic of China

    Pengli Gu & Guangjie He

  3. Australian Institute for Bioengineering and Nanotechnology, The University of Queensland, Brisbane, 4072, Australia

    Run Zhang

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  1. Yaoyun Hu
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  2. Zhuye Shang
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  4. Guangjie He
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Correspondence to Guangjie He, Qingtao Meng or Zhiqiang Zhang.

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Advanced Publication Released Online by J-STAGE July 30, 2021.

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Hu, Y., Shang, Z., Gu, P. et al. A red-emission fluorescence probe based on 1,4-addition reaction mechanism for the detection of biothiols in vitro and in vivo. ANAL. SCI. 38, 505–514 (2022). https://doi.org/10.2116/analsci.21P177

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