Skip to main content
Log in

A Water-soluble Near-infrared Fluorescent Probe for Cysteine/ Homocysteine and Its Application in Live Cells and Mice

  • Published:
Analytical Sciences Aims and scope Submit manuscript

Abstract

A near-infrared (NIR) and water-soluble probe was synthesized and studied for the detection of Cys/Hcy in aqueous solution, living cells and mice. The probe was composed of cyanine derivative as the NIR fluorescent reporting unit and pyrimidiny-thioether moiety as the Cys/Hcy responsive unit. Treatment with Cys/Hcy induced the formation of sulfur-substituted products, then intramolecular rearrangement reaction would occur to produce amino-substituted products and resulting in enhanced red fluorescence emissions. It could be applied to sense Cys/Hcy both in solution with the detection limit of 0.17 μM (or 0.32 μM) and in living cells. Cell imaging experiments proved that such a probe exhibited good cell penetration. In addition, the probe could detect Cys/Hcy in live mice with strong turn-on fluorescent response.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. H. Tapiero, D. M. Townsend, and K. D. Tew, Biomed. Pharmacother., 2003, 57, 134.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. S. Seshadri, A. Beiser, J. Selhub, P. F. Jacques, I. H. Rosenberg, R. B. D’Agostino, P. W. F. Wilson, and P. A. Wolf, N. Engl. J. Med., 2002, 346, 476.

    Article  CAS  PubMed  Google Scholar 

  3. H. Refsum, P. M. Ueland, O. Nygard, and S. E. Vollset, Annu. Rev. Med., 1998, 49, 31.

    Article  CAS  PubMed  Google Scholar 

  4. S. Shahrokhian, Anal. Chem., 2001, 73, 5972.

    Article  CAS  PubMed  Google Scholar 

  5. Z. A. Wood, E. Schröder, H. J. Robin, and L. B. Poole, Trends Biochem Sci., 2003, 28, 32.

    Article  CAS  PubMed  Google Scholar 

  6. R. O. Ball, G. Courtney-Martin, and P. B. Pencharz, J. Nutr., 2006, 136, 16825.

    Article  Google Scholar 

  7. D. P. Jones, Y. M. Go, C. L. Anderson, T. R. Ziegler, J. J. Kinkade, and W. G. Kirlin, FASEB J., 2004, 18, 1246.

    Article  CAS  PubMed  Google Scholar 

  8. X. Q. Jiang, J. W. Chen, A. Bajic, C. W. Zhang, X. Z. Song, S. L. Carroll, Z. L. Cai, M. L. Tang, M. S. Xue, N. H. Cheng, C. P. Schaaf, F. Li, K. R. MacKenzie, A. C. M. Ferreon, F. Xia, M. C. Wang, M. M. Maletic-Savatic, and J. Wang, Nat. Commun., 2017, 8, 16163.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Y. W. Sun, S. G. Guo, C. Hu, J. L. Fan, and X. J. Peng, Chem. Rev., 2016, 116, 7768.

    Article  CAS  PubMed  Google Scholar 

  10. H. S. Jung, X. Q. Chen, J. S. Kim, and J. Yoon, Chem. Soc. Rev., 2013, 42, 6019.

    Article  CAS  PubMed  Google Scholar 

  11. L. Y. Niu, Y. Z. Chen, H. R. Zhang, L. Z. Wu, C. H. Tung, and Q. Z. Yang, Chem. Soc. Rev., 2015, 44, 6143.

    Article  CAS  PubMed  Google Scholar 

  12. X. H. Li, X. H. Gao, W. Shi, and H. M. Ma, Chem. Rev., 2014, 114, 590.

    Article  CAS  PubMed  Google Scholar 

  13. Z. Q. Guo, S. Park, J. Yoon, and I. Shin, Chem. Soc. Rev., 2014, 43, 16.

    Article  PubMed  Google Scholar 

  14. W. Xu, X. Li, J. Yin, W. Liu, Y. Yang, and W. Li, Anal. Sci., 2019, 35, 1341.

    Article  CAS  PubMed  Google Scholar 

  15. H. Wu, X. Yang, J. Men, H. Zhang, and J. Zhou, Anal. Sci., 2019, 35, 1305.

    Article  CAS  PubMed  Google Scholar 

  16. Y. Wang, L. W. Zhang, S. Z. Zhang, Z. Liu, and L. X. Chen, Anal. Chem., 2019, 91, 7812.

    Article  CAS  PubMed  Google Scholar 

  17. H. Y. Li, X. H. Li, W. Shi, Y. H. Xu, and H. M. Ma, Angew. Chem., Int. Ed., 2018, 57, 12830.

    Article  CAS  Google Scholar 

  18. D. D. Li, S. F. Wang, Z. H. Lei, C. X. Sun, A. M. El-Toni, M. S. Alhoshan, Y. Fan, and F. Zhang, Anal. Chem., 2019, 91, 4771.

    Article  CAS  PubMed  Google Scholar 

  19. X. Wang, P. Li, Q. Ding, C. C. Wu, W. Zhang, and B. Tang, Angew. Chem., Int. Ed., 2019, 58, 4674.

    Article  CAS  Google Scholar 

  20. Y.-B. Hao, D. Yuan, Y.-X. Chang, W.-J. Song, and H.-S. Wang, Anal. Sci., 2018, 34, 1379.

    Article  CAS  PubMed  Google Scholar 

  21. S. C. Lee and C. Kim, Anal. Sci., 2019, 35, 1189.

    Article  CAS  PubMed  Google Scholar 

  22. F. P. Qi, Y. Zhang, B. H. Wang, W. Q. Chen, L. Yang, Z. G. Yang, and X. Z. Song, Sens. Actuators, B, 2019, 296, 126533.

    Article  CAS  Google Scholar 

  23. J. Zhang, X. Ji, J. L. Zhou, Z. J. Chen, X. C. Dong, and W. L. Zhao, Sens. Actuators, B, 2018, 257, 1076.

    Article  CAS  Google Scholar 

  24. N. N. Wang, M. Chen, J. H. Gao, X. Ji, J. L. He, J. Zhang, and W. L. Zhao, Talanta, 2019, 195, 281.

    Article  CAS  PubMed  Google Scholar 

  25. X. F. Hou, Z. S. Li, B. L. Li, C. H. Liu, and Z. H. Xu, Sens. Actuators, B, 2018, 260, 295.

    Article  CAS  Google Scholar 

  26. J. Zhang, X. Ji, H. Ren, J. L. Zhou, Z. J. Chen, X. C. Dong, and W. L. Zhao, Sens. Actuators, B, 2018, 260, 861.

    Article  CAS  Google Scholar 

  27. X. L. Xie, M. M. Li, F. Y. Tang, Y. Li, L. L. Zhang, X. Y. Jiao, X. Wang, and B. Tang, Anal. Chem., 2017, 89, 3015.

    Article  CAS  PubMed  Google Scholar 

  28. J. Xu, H. Yu, Y. Hu, M. Z. Chen, and S. J. Shao, Biosens. Bioelectron., 2016, 75, 1.

    Article  PubMed  Google Scholar 

  29. L. W. He, X. L. Yang, K. X. Xu, X. Q. Kong, and W. Y. Lin, Chem. Sci., 2017, 8, 6257.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. A. C. Sedgwick, J. E. Gardiner, G. Kim, M. Yevglevskis, M. D. Lloyd, T. A. Jenkins, S. D. Bull, J. Yoon, and T. D. James, Chem. Commun., 2018, 54, 4786.

    Article  CAS  Google Scholar 

  31. H. S. Jung, J. H. Han, T. Pradhan, S. Kim, S. W. Lee, J. L. Sessler, T. W. Kim, C. Kang, and J. S. Kim, Biomaterials, 2017, 33, 945.

    Article  Google Scholar 

  32. M. Zhang, M. X. Fu, F. Y. Li, M. W. Zhu, M. Y. Li, Y. H. Gao, L. Li, Z. Q. Liu, J. P. Zhang, D. Q. Zhang, T. Yi, and C. H. Huang, J. Am. Chem. Soc., 2007, 129, 10322.

    Article  CAS  PubMed  Google Scholar 

  33. F. Y. Wang, L. Zhou, C. C. Zhao, R. Wang, Q. Fei, S. H. Luo, Z. Q. Guo, H. Tian, and W. H. Zhu, Chem. Sci., 2015, 6, 2584.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. X. Yang and Y. Qian, New J. Chem., 2019, 43, 3725.

    Article  CAS  Google Scholar 

  35. H. Zhu, C. Liu, H. Zhang, P. Jia, Z. Li, X. Zhang, Y. Yu, W. Sheng, and B. Zhu, Anal. Sci., 2020, 36, 255.

    Article  CAS  PubMed  Google Scholar 

  36. W. Zhou, J. W. Shultz, N. Murphy, E. M. Hawkins, L. Bernad, T. Good, L. Moothart, S. Frackman, D. H. Klaubert, R. F. Bulleitb, and K. V. Wood, Chem. Commun., 2006, 4620.

    Google Scholar 

  37. M. Hemmi, Y. Ikeda, Y. Shindo, T. Nakajima, S. Nishiyama, K. Oka, M. Sato, Y. Hiruta, D. Citterio, and K. Suzuki, Chem. Asian J., 2018, 13, 648.

    Article  CAS  PubMed  Google Scholar 

  38. N. Nomura, R. Nishihara, T. Nakajima, S. B. Kim, N. Iwasawa, Y. Hiruta, S. Nishiyama, M. Sato, D. Citterio, and K. Suzuki, Anal. Chem., 2019, 91, 9546.

    Article  CAS  PubMed  Google Scholar 

  39. X. Li, Y. F. Tang, J. Li, X. M. Hu, C. Yin, Z. Yang, Q. Wang, Z. Z. Wu, X. M. Lu, W. J. Wang, W. Huang, and Q. L. Fan, Chem. Commun., 2019, 55, 5934.

    Article  CAS  Google Scholar 

  40. J. P. Wang, Y. Wen, F. J. Huo, and C. X. Yin, Sens. Actuators, B, 2019, 297, 126773.

    Article  CAS  Google Scholar 

  41. Y. Huang, N. He, Y. D. Wang, L. W. Zhang, Q. Kang, Y. Q. Wang, D. Z. Shen, J. Choo, and L.X. Chen, J. Mater. Chem. B, 2019, 7, 2557.

    Article  CAS  PubMed  Google Scholar 

  42. D. Lee, K. Jeong, X. Luo, G. Kim, Y. J. Yang, X. Q. Chen, S. Kim, and J. Yoon, J. Mater. Chem. B, 2018, 6, 2541.

    Article  CAS  PubMed  Google Scholar 

  43. X. Q. Chen, D. Lee, S. Yu, G. Kim, S. Lee, Y. Cho, H. Jeong, K. T. Nam, and J. Yoon, Biomaterials, 2017, 122, 130.

    Article  CAS  PubMed  Google Scholar 

  44. R. Wang, F. B. Yu, L. X. Chen, H. Chen, L. J. Wang, and W. W. Zhang, Chem. Commun., 2012, 48, 11757.

    Article  CAS  Google Scholar 

  45. X. Y. Han, F. B. Yu, X. Y. Song, and L. X. Chen, Chem. Sci., 2016, 7, 5098.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  46. X. Q. Chen, Y. Zhou, X. J. Peng, and J. Y. Yoon, Chem. Soc. Rev., 2010, 39, 2120.

    Article  CAS  PubMed  Google Scholar 

  47. Y. Zhou and J. Y. Yoon, Chem. Soc. Rev., 2012, 41, 52.

    Article  CAS  PubMed  Google Scholar 

  48. Y. M. Yang, Q. Zhao, W. Feng, and F. Y. Li, Chem. Rev., 2013, 113, 192.

    Article  CAS  PubMed  Google Scholar 

  49. J. H. Gao, Y. F. Tao, J. Zhang, N. N. Wang, X. Ji, J. L. He, Y. B. Si, and W. L. Zhao, Chem.—Eur. J., 2019, 25, 11246.

    CAS  PubMed  Google Scholar 

  50. J. Zhang, N. N. Wang, X. Ji, Y. F. Tao, J. M. Wang, and W. L. Zhao, Chem.—Eur. J., 2020, 26, 4172.

    Article  CAS  PubMed  Google Scholar 

  51. J. M. Wang, L. Q. Niu, J. Huang, Z. J. Yan, and J. H. Wang, Spectrochim. Acta, Part A, 2018, 192, 52.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the Key Scientific Research Program of the Higher Education Institution of Henan Province (18A150003).

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Jiamin Wang or Jianhong Wang.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Men, Y., Zhou, X., Yan, Z. et al. A Water-soluble Near-infrared Fluorescent Probe for Cysteine/ Homocysteine and Its Application in Live Cells and Mice. ANAL. SCI. 36, 1053–1057 (2020). https://doi.org/10.2116/analsci.20P016

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2116/analsci.20P016

Keywords

Navigation