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Synthesis and Properties of a Water‐soluble Fluorescent Probe Based on ICT System for Detection of Ultra‐trace SO2 Derivatives

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Abstract

SO2 and its derivatives are widely present in the environment and living organisms, endangering the environment and human health. Therefore, it is of great significance for the effective detection of sulfur dioxide (SO2) and its hydrated derivatives (HSO3− /SO32−). In this study, based on the mechanism of intramolecular charge transfer (ICT), a water-soluble colorimetric fluorescent probe (E)-2-(4-acetamidostyryl)-3-(5-carboxypentyl)-1, 1-dimethyl-1H-benzo[e]indol-3-ium (ABI) for the detection of SO2 derivatives was successfully synthesized from p-acetaminobenzaldehyde by connecting the benzo[e]indoles cationic fluorophore containing highly activated methyl via C = C double bond, and the ABI structure was characterized by HRMS and 1H NMR, 13 C NMR. Studies have shown that the ABI probe has some advantages such as good selectivity for SO2 derivatives, high sensitivity (detection limit LOD = 14.9 nM), and fast reaction rate. After adding HSO3−, the color of the probe solution changed from light yellow to colorless within 10 s, which provides a simple way to identify bisulfite with the naked eye. Studies on the effect of pH on the fluorescence performance of ABI showed that fluorescence performance of ABI was stable in the range of pH (7.0-10.26). Therefore, ABI is expected to become an effective tool for detecting SO2 derivatives in cells and organisms in the future.

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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].

References

  1. Fazio T, Warner CR (1990) A review of sulphites in foods: Analytical methodology and reported findings. Food Addit Contam 7:433–454. https://doi.org/10.1080/02652039009373907

    Article  CAS  PubMed  Google Scholar 

  2. Lisanti MT, Blaiotta G, Nioi C, Moio L (2019) Alternative methods to SO2 for microbiological stabilization of wine. Compr Rev Food Sci Food Saf 18:455–479. https://doi.org/10.1111/1541-4337.12422

    Article  CAS  PubMed  Google Scholar 

  3. Ba-Shammakh MS (2011) A multiperiod mathematical model for integrating planning and SO2 mitigation in the power generation sector. Energy Fuels 25:1504–1509. https://doi.org/10.1021/ef101569q

    Article  CAS  Google Scholar 

  4. Mapoma HWT, Tenthani C, Tsakama M, Kosamu IBM (2014) Air quality assessment of carbon monoxide, nitrogen dioxide and sulfur dioxide levels in Blantyre, Malawi: A statistical approach to a stationary environmental monitoring station. Afr J Environ Sci Technol 8:330–343. https://doi.org/10.5897/AJEST2014.1696

    Article  CAS  Google Scholar 

  5. Menz FC, Seip HM (2004) Acid rain in Europe and the United States: an update. Environ Sci Policy 7:253–265. https://doi.org/10.1016/j.envsci.2004.05.005

    Article  CAS  Google Scholar 

  6. Yue S, Li Y, Ma X, Duan L (2016) An A-π-A’structural ratiometric flfluorescent probe based on benzo[e]indolium for bisulfifite and its application in sugar samples and living cells. RSC Adv 6:79830–79835. https://doi.org/10.1039/C6RA15605C

    Article  CAS  Google Scholar 

  7. Xu J, Pan J, Jiang X, Qin C, Zeng L, Zhang H, Zhang J (2016) A mitochondria-targeted ratiometric fluorescent probe for rapid, sensitive and specific detection of biological SO2 derivatives in living cells. Biosens Bioelectron 77:725–732. https://doi.org/10.1016/j.bios.2015.10.049

    Article  CAS  PubMed  Google Scholar 

  8. Sun Y, Liu J, Zhang J, Yang T, Guo W (2013) Fluorescent probe for biological gas SO2 derivatives bisulfite and sulfite. Chem Commun 49:2637–2639. https://doi.org/10.1039/C3CC39161B

    Article  CAS  Google Scholar 

  9. Zhao C, Shang JY, Yang C, Li Z, Ning J, Li HP (2020) A water-soluble fluorescent probe for rapid detection of sulfur dioxide derivatives. Anal Sci 36:329–333. https://doi.org/10.2116/analsci.19P314

    Article  CAS  PubMed  Google Scholar 

  10. Xiao H, Xin K, Dou H, Yin G, Quan Y, Wang R (2015) A fast-responsive mitochondria-targeted fluorescent probe detecting endogenous hypochlorite in living RAW 264.7 cells and nude mouse. Chem Commun 51:1442–1445. https://doi.org/10.1039/C4CC07411D

    Article  CAS  Google Scholar 

  11. Hou P, Chen S, Voitchovsky K, Song X (2015) A colorimetric and ratiometric fluorescent probe for sulfite based on an intramolecular cleavage mechanism. Luminescence 29:749–753. https://doi.org/10.1002/bio.2616

    Article  CAS  Google Scholar 

  12. He L, Yang X, Liu Y, Kong X, Lin W (2016) A ratiometric fluorescent formaldehyde probe for bioimaging applications. Chem Commun 52:4029–4032. https://doi.org/10.1039/C5CC09796G

    Article  CAS  Google Scholar 

  13. Ding S, Feng G (2016) Smart probe for rapid and simultaneous detection and discrimination of hydrogen sulfide, cysteine/homocysteine, and glutathione. Sens Actuators B Chem 235:691–697. https://doi.org/10.1016/j.snb.2016.05.146

    Article  CAS  Google Scholar 

  14. Sun Q, Zhang W, Qian J (2017) A ratiometric fluorescence probe for selective detection of sulfite and its application in realistic samples. Talanta 162:107–113. https://doi.org/10.1016/j.talanta.2016.10.002

    Article  CAS  PubMed  Google Scholar 

  15. Cappiello M, Corso AD, Camici M, Mura U (1993) Thiol and disulfide determination by free zone capillar electrophoresis. J Biochem Biophys Methods 26:335–341. https://doi.org/10.1016/0165-022X(93)90034-L

    Article  CAS  PubMed  Google Scholar 

  16. Koch M, Köppen R, Siegel D, Witt A, Nehls I (2010) Determination of total sulfite in wine by ion chromatography after in-sample oxidation. J Agric Food Chem 58:9463–9467. https://doi.org/10.1021/jf102086x

    Article  CAS  PubMed  Google Scholar 

  17. Zhong Z, Li G, Zhu B, Luo Z, Huang L, Wu X (2012) A rapid distillation method coupled with ion chromatography for the determination of total sulphur dioxide in foods. Food Chem 131:1044–1050. https://doi.org/10.1016/j.foodchem.2011.09.086

    Article  CAS  Google Scholar 

  18. Zheng J, Tan F, Hartman R (2015) Simple spectrophotometry method for the determination of sulfur dioxide in an alcohol-thionyl chloride reaction. Anal Chim Acta 891:255–260. https://doi.org/10.1016/j.aca.2015.05.043

    Article  CAS  PubMed  Google Scholar 

  19. Claudia R, Francisco J (2009) Application of flow injection analysis for determining sulphites in food and beverages: A review. Food Chem 112:487–493. https://doi.org/10.1016/j.foodchem.2008.05.085

    Article  CAS  Google Scholar 

  20. Casella IG, Guascito MR, Desimoni E (2000) Sulfide measurements by flow injection analysis and ion chromatography with electrochemical detection. Anal Chim Acta 409:27–34. https://doi.org/10.1016/S0003-2670(99)00769-2

    Article  CAS  Google Scholar 

  21. Ekkad N, Huber C (1996) A coulometer for determination of residual sulfite following the dechlorination of water. Anal Chim Acta 332:155–160. https://doi.org/10.1016/0003-2670(96)00156-0

    Article  CAS  Google Scholar 

  22. Isaac A, Livingstone C, Wain A, Compton R, Davis J (2006) Electroanalytical methods for the determination of sulfite in food and beverages. TrAC Trends Anal Chem 25:589–598. https://doi.org/10.1016/j.trac.2006.04.001

    Article  CAS  Google Scholar 

  23. Lu J, Niu L, Yang Q (2020) Fluorescent probe for simultaneous discrimination of GSH, Cys, and SO2 derivatives. Anal Chem 92:10800–10806. https://doi.org/10.1021/acs.analchem.0c02255

    Article  CAS  Google Scholar 

  24. Sun W, Li N, Li Z, Yuan Y, Miao J, Zhao B, Lin Z (2020) A mitochondria-targeted ratiometric fluorescence probe for detection of SO2 derivatives in living cells. Dyes Pigments 182:108658. https://doi.org/10.1016/j.dyepig.2020.108658

    Article  CAS  Google Scholar 

  25. Wang L, Zhao L, Xu Z, Ma Y, Wang X, Sun Q, Liu H (2020) Rapid detection of SO2 in living cells and zebrafish by using an efficient near-infrared ratiometric fluorescent probe with large emission shift. Microchem J 160:105703. https://doi.org/10.1016/j.microc.2020.105703

    Article  CAS  Google Scholar 

  26. Li J, Li X, Jia J, Chen X, Lv Y, Guo Y, Li J (2019) A ratiometric near-infrared fluorescence strategy based on spiropyran in situ switching for tracking dynamic changes of live-cell lysosomal pH. Dyes Pigments 166:433–442. https://doi.org/10.1016/j.dyepig.2019.03.060

    Article  CAS  Google Scholar 

  27. Zhang LJ, Wang ZY, Liu JT, Miao JY, Zhao BX (2017) A rational design of ratiometric fluorescent probes based on new ICT/FRET platform and imaging of endogenous sulfite in living cells. Sens Actuators B Chem 253:19–26. https://doi.org/10.1016/j.snb.2017.06.072

    Article  CAS  Google Scholar 

  28. Wan Q, Chen S, Shi W, Li L, Ma H (2014) Lysosomal pH rise during heat shock monitored by a lysosome-targeting near‐infrared ratiometric fluorescent probe. Angew Chem Int Ed 53:1–6. https://doi.org/10.1002/ange.201405742

    Article  Google Scholar 

  29. Li Z, He X, Wang Z, Yang R, Shi W, Ma H (2015) In vivo imaging and detection of nitroreductase in zebrafish by a new near-infrared fluorescence off–on probe. Biosens Bioelectron 63:112–116. https://doi.org/10.1016/j.bios.2014.07.024

    Article  CAS  PubMed  Google Scholar 

  30. Mishra A, Behera R, Behera P, Behera P, Behera G (2000) Cyanines during the 1990s: A review. Chem Rev 100:1973–2011. https://doi.org/10.1021/cr990402t

    Article  CAS  PubMed  Google Scholar 

  31. Zhao X, Yin G, Jin D, Yan X, Li Y, Chen L (2015) A sensitive colorimetric and ratiometric chemosensor for trivalent metal cations. J Fluoresc 25:327–333. https://doi.org/10.1007/s10895-015-1513-5

    Article  CAS  PubMed  Google Scholar 

  32. Jin D, Zhao X, Li Y, Yan X, Chen L (2016) A novel near-infrared colorimetric probe for fluoride anions based on a heptamethine dye. Anal Methods 8:6452–6457. https://doi.org/10.1039/C6AY01312K

    Article  CAS  Google Scholar 

  33. Ye Z, Duan C, Sheng R, Xua J, Wang H, Zeng L (2018) A novel colorimetric and ratiometric fluorescent probe for visualizing SO2 derivatives in environment and living cells. Talanta 176:389–396. https://doi.org/10.1016/j.talanta.2017.08.054

    Article  CAS  PubMed  Google Scholar 

  34. Liu Y, Li K, Xie K, Li L, Yu K, Wang X, Yu X (2016) A water-soluble and fast-response mitochondria-targeted fluorescent probe for colorimetric and ratiometric sensing of endogenously generated SO2 derivatives in living cells. Chem Commun 52:3430–3433. https://doi.org/10.1039/C5CC10505F

    Article  CAS  Google Scholar 

  35. Liu Y, Li K, Wu M, Liu Y, Xie Y, Yu X (2015) A mitochondria-targeted colorimetric and ratiometric fluorescent probe for biological SO2 derivatives in living cells. Chem Commun 51:10236–10239. https://doi.org/10.1039/C5CC03055B

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This study was supported by the Open Fund of Key Laboratory of Road Structure and Material of Ministry of Transport (kfj170301), Hunan Provincial Natural Science Foundation of China (2019JJ40295), Changsha University of Science and Technology Postgraduate Research and Innovation Project (CX2019SS31) and Key Project of Hunan Provincial Education Department of China (17A002).

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Authors and Affiliations

  1. School of Chemistry and Food Engineering, Key Laboratory of Road Structure and Material of Ministry of Transport, Changsha University of Science and Technology, Changsha, Hunan, 410114, China

    Jinyan Shang, Kangni Chen & Heping Li

  2. School of Hydraulic Engineering, Changsha University of Science and Technology, Changsha, Hunan, 410114, China

    Yanbo Li

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  1. Jinyan Shang
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  4. Heping Li
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Contributions

Jinyan Shang is involved in synthesis and performance analysis, and Yanbo Li, Kangni Chen and Heping Li are involved in performance testing. The first draft of the manuscript was written by Jinyan Shang and all authors read and approved the final manuscript.

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Correspondence to Heping Li.

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Shang, J., Li, Y., Chen, K. et al. Synthesis and Properties of a Water‐soluble Fluorescent Probe Based on ICT System for Detection of Ultra‐trace SO2 Derivatives. J Fluoresc 31, 755–761 (2021). https://doi.org/10.1007/s10895-021-02702-7

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