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A novel ratiometric fluorescent probe for differential detection of HSO3− and ClO− and application in cell imaging and tumor recognition

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Abstract

By connecting 1,8-naphthalimide and indole sulfonate, a ratio fluorescent probe capable of differential detection of hydrogen sulfite and hypochlorite was synthesized for the first time. It was able to achieve the qualitative detection of HSO3− and ClO− with high sensitivity and selectivity, respectively. It provides a multi-purpose probe and is based on different emission channels without mutual interference. The probe has the advantages of larger Stokes shift (ClO−: 115 nm, HSO3−: 88 nm), longer λem (ClO−: 515 nm, HSO3−: 548 nm) and better water solubility (DMF/PBS = 1:99, v/v). In addition, the probe is a ratio fluorescence probe, which can detect fluorescence intensity with two different emission waves. It provides internal self-calibration, reduces interference from the background and increases detection accuracy. In vitro cytotoxicity and imaging experiments show that the probe can effectively perform the detection of exogenous HSO3− and ClO− in cells. It can also achieve the detection of HSO3− and ClO− in the plasma environment. Because the probe can detect endogenous ClO−, it also has a good prospect for biological application in identifying tumor cells.

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References

  1. Zgliczynski JM, Stelmaszynska T, Ostrowiski W, Naskalski J, Sznajd J. Myeloperoxidase of human leukaemic leucocytes. Oxidation of amino acids in the presence of hydrogen peroxide. Eur J Biochem. 1968;4(4):540–7.

    Article  CAS  Google Scholar 

  2. Guerard S, Holmdahl R, Wing K. Reactive oxygen species regulate innate but not adaptive inflammation in ZAP70-mutated SKG arthritic mice. Am J Pathol. 2016;186(9):2353–63.

    Article  CAS  Google Scholar 

  3. Chang EY-C, Tsai S-H, Shun C-T, Hee S-W, Chang Y-C, Tsai Y-C, et al. Prostaglandin reductase 2 modulates ROS-mediated cell death and tumor transformation of gastric Cancer cells and is associated with higher mortality in gastric Cancer patients. Am J Pathol. 2012;181(4):1316–26.

    Article  CAS  Google Scholar 

  4. Zhu B, Wu L, Zhang M, Zhao Z, Wang Z, Duan Q, et al. A highly specific and ultrasensitive fluorescent probe for monitoring hypochlorous acid and its applications in live cells. Sens Actuator B-Chem. 2018;267:589–96.

    Article  CAS  Google Scholar 

  5. Yap YW, Whiteman M, Cheung NS. Chlorinative stress: an under appreciated mediator of neurodegeneration? Cell Signal. 2007;19(2):219–28.

    Article  CAS  Google Scholar 

  6. Pak YL, Park SJ, Song G, Yim Y, Kang H, Kim HM, et al. Endoplasmic reticulum-targeted Ratiometric N-heterocyclic Carbene borane probe for two-photon microscopic imaging of Hypochlorous acid. Anal Chem. 2018;90(21):12937–43.

    Article  CAS  Google Scholar 

  7. Kotchey GP, Gaugler JA, Kapralov AA, Kagan VE, Star A. Effect of antioxidants on enzyme-catalysed biodegradation of carbon nanotubes. J Mat Chem B. 2013;1(3):302–9.

    Article  CAS  Google Scholar 

  8. Gorrini C, Harris IS, Mak TW. Modulation of oxidative stress as an anticancer strategy. Nat Rev Drug Discov. 2013;12(12):931–47.

    Article  CAS  Google Scholar 

  9. Yang J, Zhang X, Yuan P, Yang J, Xu Y, Grutzendler J, et al. Oxalate-curcumin-based probe for micro- and macroimaging of reactive oxygen species in Alzheimer’s disease. Proc Natl Acad Sci U S A. 2017;114(47):12384–9.

    Article  CAS  Google Scholar 

  10. Y-j W, Y-r Y. Protective effects of Astragalus membranaceus on free fatty acid-induced vascular endothelial cell dysfunction. Sichuan da xue xue bao Yi xue ban = J Sichuan Univ Med Sci Edit. 2011;42(1):48–51.

    Google Scholar 

  11. Hileman EO, Liu J, Albitar M, Keating MJ, Huang P. Intrinsic oxidative stress in cancer cells: a biochemical basis for therapeutic selectivity. Cancer Chemother Pharmacol. 2004;53(3):209–19.

    Article  CAS  Google Scholar 

  12. Yue Y, Huo F, Yin C, Escobedo JO, Strongin RM. Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid. Analyst. 2016;141(6):1859–73.

    Article  CAS  Google Scholar 

  13. Zhu H, Fan J, Wang J, Mu H, Peng X. An "enhanced PET"-based fluorescent probe with ultrasensitivity for imaging basal and elesclomol-induced HClO in cancer cells. J Am Chem Soc. 2014;136(37):12820–3.

    Article  CAS  Google Scholar 

  14. National food safety standard. Standards for uses of food additives. National Standards of the People’s Republic of China. GB2760–2011. 2011.

  15. Zhu B, Wu L, Zhang M, Zhao Z, Wang Z, Duan Q, et al. A highly specific and ultrasensitive fluorescent probe for monitoring hypochlorous acid and its applications in live cells. Sens. Actuator B-Chem. 2018;267:589–96.

    Article  CAS  Google Scholar 

  16. Wu L, Yang Q, Liu L, Sedgwick AC, Cresswell AJ, Bull SD, et al. ESIPT-based fluorescence probe for the rapid detection of hypochlorite (HOCl/ClO−). Chem Commun. 2018;54(61):8522–5.

    Article  CAS  Google Scholar 

  17. Wang J, Guo J, Dou L, Wang R, Song Y, Yang Q, et al. A novel fluorescence sensor towards hydrazine in living cells. Chem Res Chin Univ. 2019;35(4):570–6.

    Article  CAS  Google Scholar 

  18. Wang JJ, Qi SL, Du JS, Yang QB, Song Y, Li YX. Synthesis of Benzothiazole fluorescent probe for detection of N2H4 .H2O and HSO3−. Chem J Chin Univ-Chin. 2019;40(7):1397–404.

    CAS  Google Scholar 

  19. Li J, Li P, Huo F, Yin C, Liu T, Chao J, et al. Ratiometric fluorescent probes for ClO− and in vivo applications. Dyes Pigment. 2016;130:209–15.

    Article  CAS  Google Scholar 

  20. Zhang WQ, Li QY, Cheng JY, Cheng K, Yang X, Li Y, et al. Ratiometric luminescent detection of organic amines due to the induced lactam-Lactim Tautomerization of organic linker in a metal-organic framework. ACS Appl Mater Interfaces. 2017;9(37):31352–6.

    Article  CAS  Google Scholar 

  21. Li Z, Zhang W, Liu C, Yu M, Zhang H, Guo L, et al. A colorimetric and ratiometric fluorescent probe for hydrazine and its application in living cells with low dark toxicity. Sens Actuator B-Chem. 2017;241:665–71.

    Article  CAS  Google Scholar 

  22. Duan C, Won M, Verwilst P, Xu J, Kim HS, Zeng L, et al. In vivo imaging of endogenously produced HClO in zebrafish and mice using a bright, Photostable Ratiometric fluorescent probe. Anal Chem. 2019;91(6):4172–8.

    Article  CAS  Google Scholar 

  23. Hou JT, Kim HS, Duan C, Ji MS, Wang S, Zeng L, et al. A ratiometric fluorescent probe for detecting hypochlorite in the endoplasmic reticulum. Chem Commun. 2019;55(17):2533–6.

    Article  CAS  Google Scholar 

  24. Geng Y, Tian H, Yang L, Liu X, Song X. An aqueous methylated chromenoquinoline-based fluorescent probe for instantaneous sensing of thiophenol with a red emission and a large stokes shift. Sens Actuator B-Chem. 2018;273:1670–5.

    Article  CAS  Google Scholar 

  25. Zhou S, Rong Y, Wang H, Liu X, Wei L, Song X. A naphthalimide-indole fused chromophore-based fluorescent probe for instantaneous detection of thiophenol with a red emission and a large stokes shift. Sens Actuator B-Chem. 2018;276:136–41.

    Article  CAS  Google Scholar 

  26. Xiong H, He L, Zhang Y, Wang J, Song X, Yang Z. A ratiometric fluorescent probe for the detection of hypochlorous acid in living cells and zebra fish with a long wavelength emission. Chin Chem Lett. 2019;30(5):1075–7.

    Article  CAS  Google Scholar 

  27. Ma Q, Wang C, Bai Y, Xu J, Zhang J, Li Z, et al. A lysosome-targetable and ratiometric fluorescent probe for hypochlorous acid in living cells based on a 1,8-naphthalimide derivative. Spectroc Acta Pt A-Molec Biomolec Spectr. 2019;223:117334.

    Article  CAS  Google Scholar 

  28. Wang W, Han X-J, Liu J-T, Miao J-Y, Zhao B-X. A novel lipid droplets-targeted ratiometric fluorescence probe for HSO3−/SO32− in living cells. Dyes Pigments. 2020;173:107892.

  29. Yang D, He XY, Wu XT, Shi HN, Miao JY, Zhao BX, et al. A novel mitochondria-targeted ratiometric fluorescent probe for endogenous sulfur dioxide derivatives as a cancer-detecting tool. J Mat Chem B. 2020;8(26):5722–8.

    Article  CAS  Google Scholar 

  30. Dutta T, Chandra F, Koner AL. A rapid, naked-eye detection of hypochlorite and bisulfite using a robust and highly-photostable indicator dye Quinaldine red in aqueous medium. Spectroc Acta Pt A-Molec Biomolec Spectr. 2018;191:217–20.

    Article  CAS  Google Scholar 

  31. Zhu L, Nie J, Li Q, Du J, Fan X, Bai F, et al. Reaction-based fluorescent probe for differential detection of cyanide and bisulfite in the aqueous media. J Lumines. 2019;215:116620.

    Article  CAS  Google Scholar 

  32. Guo B, Nie H, Yang W, Tian Y, Jing J, Zhang X. A highly sensitive and rapidly responding fluorescent probe with a large stokes shift for imaging intracellular hypochlorite. Sens Actuator B-Chem. 2016;236:459–65.

    Article  CAS  Google Scholar 

  33. Shu W, Jia P, Chen X, Li X, Huo Y, Liu F, et al. A highly selective ratiometric fluorescent probe for the sensitive detection of hypochlorous acid and its bioimaging applications. RSC Adv. 2016;6(69):64315–22.

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We thank the Department of Science and Technology of Jilin Province (No. 20180201085GX), the National Natural Science Foundation of China (No. 21174052) and the Natural Science Foundation of Jilin Province of China (No. 20170101105JC) for their generous financial support.

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Author notes

  1. Liangqiang Wu and Shaolong Qi contributed equally to this work.

Authors and Affiliations

  1. College of Chemistry, Jilin University, Changchun, 130021, Jilin, China

    Liangqiang Wu, Shaolong Qi, Yan Liu, Lubao Zhu, Qingbiao Yang, Hai Xu & Yaoxian Li

  2. Key Laboratory of Lymphatic Surgery Jilin Province, Engineering Laboratory of Lymphatic Surgery Jilin Province, China-Japan Union Hospital of Jilin University, Changchun, 130031, Jilin, China

    Shaolong Qi, Xinyu Wang, Qingbiao Yang & Jianshi Du

Authors
  1. Liangqiang Wu
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  2. Shaolong Qi
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  3. Yan Liu
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  4. Xinyu Wang
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  5. Lubao Zhu
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  6. Qingbiao Yang
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  8. Hai Xu
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Correspondence to Qingbiao Yang, Jianshi Du or Hai Xu.

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Wu, L., Qi, S., Liu, Y. et al. A novel ratiometric fluorescent probe for differential detection of HSO3− and ClO− and application in cell imaging and tumor recognition. Anal Bioanal Chem 413, 1137–1148 (2021). https://doi.org/10.1007/s00216-020-03077-7

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  • DOI: https://doi.org/10.1007/s00216-020-03077-7

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