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A Rapid Near-Infrared Fluorescent Probe for Cysteine Based on Isophorone and its Application in B16 Cell Imaging

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Abstract

A novel near-infrared fluorescent probe SWJT-5 based on dicyanoisophorone was synthesized. It achieved the rapid (within 40 s) and discriminative detection of Cys over Hcy and GSH with a large Stokes shift (205 nm). It showed high selectivity and sensitivity for Cys, and had an obvious enhancement of fluorescence emission. The detection limit was 0.43 μM. This probe also had low background interference and little damage to biological samples. Therefore, SWJT-5 had been applied to bioimaging in living cells successfully.

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References

  1. He L, Yang X, Xu K, Kong X, Lin W (2017) Chem Sci 8:6257–6265

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Wang P, Wang Y, Li N, Huang J, Wang Q, Gu Y (2017) Sens Actuators B 245:297–304

    Article  CAS  Google Scholar 

  3. Niu L-Y, Chen Y-Z, Zheng H-R, Wu L-Z, Tung C-H, Yang Q-Z (2015) Chem Soc Rev 44:6143–6160

    Article  CAS  PubMed  Google Scholar 

  4. Zhang H, Feng W, Feng G (2017) Dyes Pigm 139:73–78

    Article  CAS  Google Scholar 

  5. Niu L-Y, Guan Y-S, Chen Y-Z, Wu L-Z, Tung C-H, Yang Q-Z (2012) J Am Chem Soc 134:18928–18931

    Article  CAS  PubMed  Google Scholar 

  6. Zhang J, Wang J, Liu J, Ning L, Zhu X, Yu B, Liu X, Yao X, Zhang H (2015) Anal Chem 87:4856–4863

    Article  CAS  PubMed  Google Scholar 

  7. Liu Y, Yu D, Ding S, Xiao Q, Guo J, Feng G (2014) ACS Appl Mater Interfaces 6:17543–17550

    Article  CAS  PubMed  Google Scholar 

  8. Lee S, Li J, Zhou X, Yin J, Yoon J (2018) Coord Chem Rev 366:29–68

    Article  CAS  Google Scholar 

  9. Jung HS, Chen X, Kim JS, Yoon J (2013) Chem Soc Rev 42:6019–6031

    Article  CAS  PubMed  Google Scholar 

  10. Hernandez LE, Sobrino-Plata J, Montero-Palmero MB, Carrasco-Gil S, Flores-Caceres ML, Ortega-Villasante C, Escobar C (2015) J Exp Bot 66:2901–2911

    Article  CAS  PubMed  Google Scholar 

  11. Mao G-J, Liang Z-Z, Bi J, Zhang H, Meng H-M, Su L, Gong Y-J, Feng S, Zhang G (2019) Anal Chim Acta 1048:143–153

    Article  CAS  PubMed  Google Scholar 

  12. Mao G-J, Gao G-Q, Liang Z-Z, Wang Y-Y, Su L, Wang Z-X, Zhang H, Ma Q-J, Zhang G (2019) Anal Chim Acta 1081:184–192

    Article  CAS  PubMed  Google Scholar 

  13. Mao G-J, Liang Z-Z, Gao G-Q, Wang Y-Y, Guo X-Y, Su L, Zhang H, Ma Q-J, Zhang G (2019) Anal Chim Acta 1092:117–125

    Article  CAS  PubMed  Google Scholar 

  14. Mao G-J, Gao G-Q, Dong W-P, Wang Q-Q, Wang Y-Y, Li Y, Su L, Zhang G (2021) Talanta 221:121607–121613

    Article  CAS  PubMed  Google Scholar 

  15. Mao G-J, Wang Y-Y, Dong W-P, Meng H-M, Wang Q-Q, Luo X-F, Li Y, Zhang G (2021) Spectrochim Acta A 249:119326–119333

    Article  CAS  Google Scholar 

  16. Maeda H, Matsuno H, Ushida M, Katayama K, Saeki K, Itoh N (2005) Angew Chem Int Ed 44:2922–2925

    Article  CAS  Google Scholar 

  17. Shao J, Guo H, Ji S, Zhao J (2011) Biosens Bioelectron 26:3012–3017

    Article  CAS  PubMed  Google Scholar 

  18. Fan L, Zhang W, Wang X, Dong W, Tong Y, Dong C, Shuang S (2019) Analyst 144:439–447

    Article  CAS  PubMed  Google Scholar 

  19. Li M, Wu X, Wang Y, Li Y, Zhu W, James TD (2014) Chem Commun 50:1751–1753

    Article  CAS  Google Scholar 

  20. Kim T-K, Lee D-N, Kim H-J (2008) Tetrahedron Lett 49:4879–4881

    Article  CAS  Google Scholar 

  21. Kong F, Liu R, Chu R, Wang X, Xu K, Tang B (2013) Chem Commun 49:9176–9178

    Article  CAS  Google Scholar 

  22. Li Y (2017) Luminescence 32:1385–1390

    Article  CAS  PubMed  Google Scholar 

  23. Feng S, Fang Y, Feng W, Xia Q, Feng G (2017) Dyes Pigm 146:103–111

    Article  CAS  Google Scholar 

  24. Manna S, Karmakar P, Ali SS, Guria UN, Samanta SK, Sarkar R, Datta P, Mahapatra AK (2019) Anal Methods 11:1199–1207

    Article  CAS  Google Scholar 

  25. Qi Y, Huang Y, Li B, Zeng F, Wu S (2018) Anal Chem 90:1014–1020

    Article  CAS  PubMed  Google Scholar 

  26. Zhou J, Yu C, Li Z, Peng P, Zhang D, Han X, Tang H, Wu Q, Li L, Huang W (2019) Anal Methods 11:1312–1316

    Article  CAS  Google Scholar 

  27. Xu H, Wu S-L, Lin N-J, Lu Y, Xiao J, Wang Y-W, Peng Y (2021) Sens Actuators B 346:130484–130489

    Article  CAS  Google Scholar 

  28. Liu H-B, Xu H, Guo X, Xiao J, Cai Z-H, Wang Y-W, Peng Y (2021) Org Biomol Chem 19:873–877

    Article  CAS  PubMed  Google Scholar 

  29. Fu Z-H, Han X, Shao Y, Fang J, Zhang Z-H, Wang Y-W, Peng Y (2017) Anal Chem 89:1937–1944

    Article  CAS  PubMed  Google Scholar 

  30. Wang B-J, Liu R-J, Fang J, Wang Y-W, Peng Y (2019) Chem Commun 55:11762–11765

    Article  CAS  Google Scholar 

  31. Yang Y-L, Zhang F-M, Wang Y-W, Zhang B-X, Fang R, Fang JG, Peng Y (2015) Chem-Asian J 10:422–426

    Article  CAS  PubMed  Google Scholar 

  32. Du W, Liu R-J, Fang J, Gao H, Wang Y-W, Peng Y (2019) Tetrahedron 75:130477–130481

    Article  CAS  Google Scholar 

  33. Zhu M, Fan F, Zhao Z, Wu X, Wang L, Na R, Wang Y (2019) J Mol Liq 296:111832–111841

    Article  CAS  Google Scholar 

  34. Zacuto MJ (2019) J Org Chem 84:6465–6474

    Article  CAS  PubMed  Google Scholar 

  35. Lee S-C, Lee C-L, Heo J, Jeong C-U, Lee G-H, Kim S, Yoon W, Yun H, Park SO, Kwak SK, Park S-H, Kwon O-P (2018) Chem-Eur J 24:2888–2897

    Article  CAS  PubMed  Google Scholar 

  36. Wang J, Li B, Zhao W, Zhang X, Luo X, Corkins ME, Cole SL, Wang C, Xiao Y, Bi X, Pang Y, McElroy CA, Bird AJ, Dong Y (2016) ACS Sens 1:882–887

    Article  CAS  Google Scholar 

  37. Tamima U, Song CW, Santra M, Reo YJ, Banna H, Islam MR, Ahn KH (2020) Sens Actuators B 322:128588–128597

    Article  CAS  Google Scholar 

  38. Guo Z, Nam S, Park S, Yoon J (2012) Chem Sci 3:2760–2765

    Article  CAS  Google Scholar 

  39. Zhang X, Zhang L, Ma WW, Zhou Y, Lu ZN, Xu S (2019) Front Chem 7:00032–00039

    Article  CAS  Google Scholar 

  40. Zhang H, Yan C, Li H, Shi L, Wang R, Guo Z, Zhu W-H (2020) ACS Appl Bio Mater 4:2001–2008

    Article  PubMed  CAS  Google Scholar 

  41. Niu W, Guo L, Li Y, Shuang S, Dong C, Wong MS (2016) Anal Chem 88:1908–1914

    Article  CAS  PubMed  Google Scholar 

  42. Lee C, Yang W, Parr RG (1988) Phys Rev B Condens Matter 37:785–789

    Article  CAS  PubMed  Google Scholar 

  43. Yellaturu CR, Bhanoori M, Neeli I, Rao GN (2002) J Biol Chem 277:40148–40155

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

We would like to thank Analytical and Testing Center of Southwest Jiaotong University for the laser confocal microscope test.

Funding

This work was supported by the National Natural Science Foundation of China (No. 22071200), and the Fundamental Research Funds for the Central Universities (Nos. 2682020CX55, 2682021ZTPY011 and XJ2021KJZK004) by MoE of China. We also thank Science and Technology Department of Sichuan Province (2020JDRC0021), and Key Research Project of Sichuan Province Science and Technology Plan (2020YFS0489).

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Contributions

Yan-Ya Wang: conceived the work and performed most of the experiments. Xue-Shuang Yu, Xin-Jie Li, and Hong-Bo Liu carried out the bioimaging. Yan-Ya Wang, Xue-Shuang Yu, Xin-Jie Li, Hong-Bo Liu, Xi Zhu,Ya-Wen Wang, and Yu Peng analyzed the data and wrote the manuscript. Yu Peng supervised the project and conceived the style of the manuscript.

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Correspondence to Yu Peng.

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Wang, YY., Yu, XS., Li, XJ. et al. A Rapid Near-Infrared Fluorescent Probe for Cysteine Based on Isophorone and its Application in B16 Cell Imaging. J Fluoresc 32, 1661–1667 (2022). https://doi.org/10.1007/s10895-022-02964-9

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