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Colorimetric and Ratiometric Fluorescence Detection of HSO3− With a NIR Fluorescent Dye

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Abstract

Bisulfite (HSO3−) has been widely used in food and industry, which has brought convenience to human life, but also seriously endangered human health. In this work, the probe PBI was designed and synthesized to detect bisulfite (HSO3−) through nucleophilic addition reaction. The probe PBI showed a selective reaction to HSO3− and can quantitatively detect HSO3−. At the same time, the color of the probe PBI changed significantly, which provided a simple method for the naked eye to identify HSO3−. Finally, it was successfully applied to the fluorescence imaging of HSO3− in living cells.

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Data Availability

All data generated or analysed during this study are included in this published article and its supplementary information files.

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All data were obtained using word, origin and chemBioDraw.

References

  1. Lin VS, Chen W, Xian M, Chang CJ (2015) Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems. Chem Soc Rev 44:4596–4618

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Singha S, Jun YW, Sarkar S, Ahn KH (2019) An endeavor in the reaction-based approach to fluorescent probes for biorelevant analytes: challenges and achievements. Acc Chem Res 52:2571–2581

    Article  CAS  PubMed  Google Scholar 

  3. Ci Q, Qin X, Liu J, Wang R, Li Z, Qin W, Lim K-L, Zhang C-W, Li L (2020) Mitochondria-targeted polydopamine nanoprobes for visualizing endogenous sulfur dioxide derivatives in a rat epilepsy model. Chem Commun 56:11823–11826

    Article  CAS  Google Scholar 

  4. Tamima U, Santra M, Song CW, Reo YJ, Ahn KH (2019) A benzopyronin-based two-photon fluorescent probe for ratiometric imaging of lysosomal bisulfite with complete spectral separation. Anal Chem 91:10779–10785

    Article  CAS  PubMed  Google Scholar 

  5. Zeng R-F, Lan J-S, Wu T, Liu L, Liu Y, Ho RJY, Ding Y, Zhang T (2020) A novel mitochondria-targetted near-infrared fluorescent probe for selective and colorimetric detection of sulfite and its application in vitro and vivo. Food Chem 318:1914–1921

    Article  CAS  Google Scholar 

  6. Zhang W, Liu T, Huo F, Ning P, Meng X, Yin C (2017) Reversible ratiometric fluorescent probe for sensing bisulfate/H2O2 and its application in zebrafish. Anal Chem 89:8079–8083

    Article  CAS  PubMed  Google Scholar 

  7. Everitt KR, Schmitz HC, Macke A, Shan J, Jang E, Luedtke BE, Carlson KA, Cao H (2020) Investigation of a sensing strategy based on a nucleophilic addition reaction for quantitative detection of bisulfite (HSO3-). J Fluoresc 30:977–983

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Gao C, Tian Y, Zhang R, Jing J, Zhang X (2019) Mitochondrial directed ratiometric fluorescent probe for quantitive detection of sulfur dioxide derivatives. New J Chem 43:5255–5259

    Article  CAS  Google Scholar 

  9. Han X, Zhai Z, Yang X, Zhang D, Tang J, Zhu J, Zhu X, Ye Y (2020) A FRET-based ratiometric fluorescent probe to detect cysteine metabolism in mitochondria. Org Biomol Chem 18:1487–1492

    Article  CAS  PubMed  Google Scholar 

  10. He X, Xu W, Ding F, Xu C, Li Y, Chen H, Shen J (2020) Reaction-based ratiometric and colorimetric chemosensor for bioimaging of biosulfite in live cells, zebrafish, and food samples. J Agric Food Chem 68:11774–11781

    Article  CAS  PubMed  Google Scholar 

  11. Dutta T, Chandra F, Koner AL (2018) A rapid, naked-eye detection of hypochlorite and bisulfite using a robust and highly-photostable indicator dye Quinaldine Red in aqueous medium. Spectrochim Acta Part A 191:217–220

    Article  CAS  Google Scholar 

  12. Bi K, Tan R, Hao R, Miao L, He Y, Wu X, Zhang J, Xu R (2019) A carbazole-hemicyanine dye based ratiometric fluorescent probe for selective detection of bisulfite (HSO3-) in cells and C. elegans. Chin Chem Lett 30:545–548

    Article  CAS  Google Scholar 

  13. Gao H, Qi H, Peng Y, Qi H, Zhang C (2018) Rapid “turn-on” photoluminescence detection of bisulfite in wines and living cells with a formyl bearing bis-cyclometalated Ir( III) complex. Analyst 143:3670–3676

    Article  CAS  PubMed  Google Scholar 

  14. Nie J, Sun H, Zhao Y, Dai X, Ni Z (2021) An efficient hemicyanine dyes-based ratiometric fluorescence probe for sulfur dioxide derivatives in live-cells and seawater. Spectrochim Acta Part A 247:119–128

    Article  CAS  Google Scholar 

  15. Pan X, Cheng S, Zhang C, Qi X (2020) Two highly sensitive fluorescent probes based on cinnamaldehyde with large Stokes shift for sensing of HSO3- in pure water and living cells. Anal Bioanal Chem 412:6959–6968

    Article  CAS  PubMed  Google Scholar 

  16. Guo S, Liu G, Fan C, Pu S (2018) A highly selective fluorescent probe for detection of Cd2+ and HSO3- based on photochromic diarylethene with a triazole-bridged coumarin-quinoline group. RSC Adv 8:22786–22798

    Article  CAS  Google Scholar 

  17. Shi J, Shu W, Tian Y, Wu Y, Jing J, Zhang R, Zhang X (2019) A real-time ratiometric fluorescent probe for imaging of SO2 derivatives in mitochondria of living cells. RSC Adv 9:22348–22354

    Article  CAS  Google Scholar 

  18. Li X, Jin D, Du Y, Liu Y, Wang B, Chen L (2018) Several fluorescent probes based on hemicyanine for the detection of SO2 derivatives. Anal Methods 10:4695–4701

    Article  CAS  Google Scholar 

  19. Li Y, Ban Y, Wang R, Wang Z, Li Z, Fang C, Yu M (2020) FRET-based ratiometric fluorescent detection of arginine in mitochondrion with a hybrid nanoprobe. Chin Chem Lett 31:443–446

    Article  CAS  Google Scholar 

  20. Lu J, Wu P, Geng Y, Wang J (2018) A simple and highly selective 1,2,4,5-tetrazine-based colorimetric probe for HSO3- ion recognition in food. RSC Adv 8:33459–33463

    Article  CAS  Google Scholar 

  21. Wu L, Chen L, Kou M, Dong Y, Deng W, Ge L, Bao H, Chen Q, Li D (2020) The ratiometric fluorescent probes for monitoring the reactive inorganic sulfur species (RISS) signal in the living cell. Spectrochim Acta Part A 231:118–141

    Article  CAS  Google Scholar 

  22. Wu L, Qi S, Liu Y, Wang X, Zhu L, Yang Q, Du J, Xu H, Li Y (2021) 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

    Article  CAS  PubMed  Google Scholar 

  23. Yan Y-H, Wu Q-R, Che Q-L, Ding M-M, Xu M, Miao J-Y, Zhao B-X, Lin Z-M (2020) A mitochondria-targeted fluorescent probe for the detection of endogenous SO2 derivatives in living cells. Analyst 145:2937–2944

    Article  CAS  PubMed  Google Scholar 

  24. Paul S, Ghoshal K, Bhattacharyya M, Maiti DK (2017) Detection of HSO3-: A rapid colorimetric and fluorimetric selective sensor for detecting biological SO2 in food and living cells. ACS Omega 2:8633–8639

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  25. Yang D, He X-Y, Wu X-T, Shi H-N, Miao J-Y, Zhao B-X, Lin Z-M (2020) A novel mitochondria-targeted ratiometric fluorescent probe for endogenous sulfur dioxide derivatives as a cancer-detecting tool. J Mater Chem B 8:5722–5728

    Article  CAS  PubMed  Google Scholar 

  26. Yang X, Yang Y, Zhou T, Jin M, Jing X, Miao CH, Li W (2019) A mitochondria-targeted ratiometric fluorescent probe for detection of SO2 derivatives in living cells and in vivo. J Photoch Photobio A 372:212–217

    Article  CAS  Google Scholar 

  27. Pan X, Zhong Y, Jiang Y, Zuo G, Li J, Dong W (2018) Reaction-based fluorescent sensor for detection of bisulfite through 1,4-addition reaction in water. Mater Chem Phys 213:83–88

    Article  CAS  Google Scholar 

  28. Zeng L, Chen T, Chen B-Q, Yuan H-Q, Sheng R, Bao G-M (2020) A distinctive mitochondrion-targeting, in situ-activatable near-infrared fluorescent probe for visualizing sulfur dioxide derivatives and their fluctuations in vivo. J Mater Chem B 8:1914–1921

    Article  CAS  PubMed  Google Scholar 

  29. Song G-J, Luo J, Xing X-j, Ma H-L, Yang D, Cao X-Q, Ge Y-Q, Zhao B-X (2018) A ratiometric fluorescence probe for rapid detection of mitochondrial SO2 derivatives. New J Chem 42:3063–3068

    Article  CAS  Google Scholar 

  30. Wang R, Wang R, Ju D, Lu W, Jiang C, Shan X, Chen Q, Sun G (2018) “ON-OFF-ON” fluorescent probes based on nitrogen-doped carbon dots for hypochlorite and bisulfite detection in living cells. Analyst 143:5834–5840

    Article  CAS  PubMed  Google Scholar 

  31. Zheng X-L, Li H, Feng W, Xia H-C, Song Q-H (2018) Two-Step Sensing, Colorimetric and Ratiometric Fluorescent Probe for Rapid Detection of Bisulfite in Aqueous Solutions and in Living Cells. ACS Omega 3:11831–11837

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. Wang S-J, Li J, Gao Y, Guo Y (2018) Highly selective and sensitive 2-(2 ’-hydroxyphenyl)benzothiazole-based turn-on fluorescent probes for detecting and imaging bisulfite in living cells. Asian J Org Chem 7:563–569

    Article  CAS  Google Scholar 

  33. Zhou F, Feng H, Li H, Wang Y, Zhang Z, Kang W, Jia H, Yang X, Meng Q, Zhang R (2020) Red-emission probe for ratiometric fluorescent detection of bisulfite and its application in live animals and food samples. ACS Omega 5:5452–5459

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Zhou F, Sultanbawa Y, Feng H, Wang Y-L, Meng Q, Wang Y, Zhang Z, Zhang R (2019) A new red-emitting fluorescence probe for rapid and effective visualization of bisulfite in food samples and live animals. J Agric Food Chem 67:4375–4383

    Article  CAS  PubMed  Google Scholar 

  35. Zhu J-L, Xu Z, Yang Y, Xu L (2019) Small-molecule fluorescent probes for specific detection and imaging of chemical species inside lysosomes. Chem Commun 55:6629–6671

    Article  CAS  Google Scholar 

  36. Yang S, Wen X, Yang X, Li Y, Guo C, Zhou Y, Li H, Yang R (2018) Visualizing endogenous sulfur dioxide derivatives in febrile-seizure-induced hippocampal damage by a two-photon energy transfer cassette. Anal Chem 90:14514–14520

    Article  CAS  PubMed  Google Scholar 

  37. Yang Y, Zhou T, Bai B, Yin C, Xu W, Li W (2018) Design of mitochondria-targeted colorimetric and ratiometric fluorescent probes for rapid detection of SO2 derivatives in living cells. Spectrochim Acta Part A 196:215–221

    Article  CAS  Google Scholar 

  38. Zou L, Zhang G, Zhou M, Xin X, Chen S, Duan X, Xu J (2019) Two reaction-based fluorescent sensors with cationic group enable high-selective detection of HSO3- in the environment. Ind Eng Chem Res 58:9231–9238

    Article  CAS  Google Scholar 

  39. Zhang Y, Teng H, Gao Y, Afzal MW, Tian J, Chen X, Tang H, James TD, Guo Y (2020) A general strategy for selective detection of hypochlorous acid based on triazolopyridine formation. Chin Chem Lett 31:2917–2920

    Article  CAS  Google Scholar 

  40. Wang W, Li N, Liu J-T, Miao J-Y, Zhao B-X, Lin Z-M (2020) A new FRET-based ratiometric fluorescent probe for the detection of SO2 derivatives in mitochondria of living cells. Dyes Pigments 181:108639

  41. Yang Y, Bai B, Xu W, Xu Z, Zhang J, Li W (2017) A highly sensitive fluorescent probe for the detection of bisulfite ion and its application in living cells. Dyes Pigments 136:830–835

    Article  CAS  Google Scholar 

  42. Zhao M, Liu D, Zhou L, Wu B, Tian X, Zhang Q, Zhou H, Yang J, Wu J, Tian Y (2018) Two water-soluble two-photon fluorescence probes for ratiometric imaging endogenous SO2 derivatives in mitochondria. Sensor Actuat B 255:1228–1237

    Article  CAS  Google Scholar 

  43. Zhang L, Wang L, Zhang X, Zhu Z-J (2020) A colorimetric and fluorescent probe for sulfite/bisulfite based on conjugated benzothiazole derivative and imaging application in living cells. J Photoch Photobio A 395:112498

  44. Chao J, Wang X, Liu Y, Zhang Y, Huo F, Yin C, Zhao M, Sun J, Xu M (2018) A pyrene-thiophene based fluorescent probe for ratiometric sensing of bisulfite and its application in vivo imaging. Sensor Actuat B 272:195–202

    Article  CAS  Google Scholar 

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Acknowledgements

We are grateful for the financial support from the National Natural Science Foundation of China (U1704161, U1504203 and 21601158) and Zhengzhou University (32210431).

Funding

This work was supported by the National Natural Science Foundation of China (U1704161, U1504203 and 21601158) and Zhengzhou University (32210431).

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Authors and Affiliations

  1. Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou, 450001, China

    Wenjie Liu, Chenchen Yang, Zhanxian Li & Mingming Yu

  2. Beijing Key Laboratory of Clothing Materials R & D and Assessment, Beijing Engineering Research Center of Textile, Beijing Institute of Fashion Technology, NanofiberBeijing, 100029, China

    Hongyan Zhang

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  1. Wenjie Liu
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Contributions

All authors contributed to the study conception and design. Material preparation, data collection and analysis were performed by Wenjie Liu, Chenchen Yang and Hongyan Zhang. Fundings were acquired by Zhanxian Li and Mingming Yu. The first draft of the manuscript was written by Wenjie Liu, all authors commented on previous versions of the manuscript and the manuscript was revised by Zhanxian Li and Mingming Yu. All authors read and approved the final manuscript.

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Correspondence to Hongyan Zhang, Zhanxian Li or Mingming Yu.

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Liu, W., Yang, C., Zhang, H. et al. Colorimetric and Ratiometric Fluorescence Detection of HSO3− With a NIR Fluorescent Dye. J Fluoresc 31, 1567–1574 (2021). https://doi.org/10.1007/s10895-021-02794-1

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  • DOI: https://doi.org/10.1007/s10895-021-02794-1

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