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An HBT-Based Near-Infrared Fluorescent Probe for Colorimetric and Ratiometric Detection of Bisulfite and its Application in Living Cells

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Abstract

In this paper, a new type of ratiometric fluorescent probe HBT-TCF with large emission shift (up to 200 nm) has been developed for sensing HSO3 based on Michael-type addition reaction. The probe could fast recognize of HSO3 within 3 min in PBS buffer solution. The detection limit of the probe for HSO3 is as low as 101 nM. Meanwhile, the sensing mechanism is confirmed by NMR, LCMS. In addition, the probe can be applied to detect HSO3 in living cells.

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References

  1. Meng Z, Qin G, Zhang B, Bai J (2004) DNA damaging effects of sulfur dioxide derivatives in cells from various organs of mice. Mutagenesis 19:465–468

    Article  CAS  PubMed  Google Scholar 

  2. Shi X (1994) Generation of SO3 and OH radicals in SO3 2− reactions with inorganic environmental pollutants and its implications to SO3 2− toxicity. J Inorg Biochem 56:155–165

    Article  CAS  PubMed  Google Scholar 

  3. Stipanuk MH, Ueki I (2011) Dealing with methionine/homocysteine sulfur: cysteine metabolism to taurine and inorganic sulfur. J Inherit Metab Dis 34:17–32

    Article  CAS  PubMed  Google Scholar 

  4. Mathew ND, Schlipalius DI, Ebert PR (2011) Sulfurous gases as biological messengers and toxins: comparative genetics of their metabolism in model organisms. J Toxicol 2011:14

    Article  Google Scholar 

  5. Luo L, Chen S, Jin H, Tang C, Du J (2011) Endogenous generation of sulfur dioxide in rat tissues. Biochem Biophys Res Commun 415:61–67

    Article  CAS  PubMed  Google Scholar 

  6. Meng Z, Yang Z, Li J, Zhang Q (2012) The vasorelaxant effect and its mechanisms of sodium bisulfite as a sulfur dioxide donor. Chemosphere 89:579–584

    Article  CAS  PubMed  Google Scholar 

  7. Wang XB, Huang XM, Ochs T, Li XY, Jin HF, Tang CS, Du JB (2011) Effect of sulfur dioxide preconditioning on rat myocardial ischemia/reperfusion injury by inducing endoplasmic reticulum stress. Basic Res Cardiol 106:865–878

    Article  CAS  PubMed  Google Scholar 

  8. Du SX, Jin HF, Bu DF, Zhao X, Geng B, Tang CS, Du JB (2008) Endogenously generated sulfur dioxide and its vasorelaxant effect in rats. Acta Pharmacol Sin 29:923–930

    Article  CAS  PubMed  Google Scholar 

  9. Reist M, Jenner P, Halliwell B (1998) Sulphite enhances peroxynitrite-dependent α1-antiproteinase inactivation. A mechanism of lung injury by sulphur dioxide? FEBS Lett 423:231–234

    Article  CAS  PubMed  Google Scholar 

  10. Pundir CS, Rawal R (2013) Determination of sulfite with emphasis on biosensing methods: a review. Anal Bioanal Chem 405:3049–3062

    Article  CAS  PubMed  Google Scholar 

  11. Xu Z, Xu L (2016) Fluorescent probes for the selective detection of chemical species inside mitochondria. Chem Commun 52:1094–1119

    Article  CAS  Google Scholar 

  12. Zhang H, Xue S, Feng G (2016) A colorimetric and near-infrared fluorescent turn-on probe for rapid detection of sulfite. Sensors Actuat B-Chem 231:752–758

    Article  CAS  Google Scholar 

  13. Liu C, Wu H, Yang W, Zhang X (2014) A simple levulinate-based ratiometric fluorescent probe for sulfite with a large emission shift. Anal Sci 30:589–593

  14. Hou P, Chen S, Voitchovsky K, Song X (2014) A colorimetric and ratiometric fluorescent probe for sulfite based on an intramolecular cleavage mechanism. Luminescence 29:749–753

    Article  CAS  PubMed  Google Scholar 

  15. Ma X, Liu C, Shan Q, Wei G, Wei D, Du Y (2013) A fluorescein-based probe with high selectivity and sensitivity for sulfite detection in aqueous solution. Sensors Actuat B-Chem 188:1196–1200

    Article  CAS  Google Scholar 

  16. Chen S, Hou P, Wang J, Song X (2012) A highly sulfite-selective ratiometric fluorescent probe based on ESIPT. RSC Adv 2:10869–10873

    Article  CAS  Google Scholar 

  17. Gu X, Liu C, Zhu YC, Zhu YZ (2011) A boron-dipyrromethene-based fluorescent probe for colorimetric and ratiometric detection of sulfite. J Agric Food Chem 59:11935–11939

  18. Choi MG, Hwang J, Eor S, Chang SK (2010) Chromogenic and fluorogenic signaling of sulfite by selective deprotection of resorufin levulinate. Org Lett 12:5624–5627

  19. Liu X, Yang Q, Chen W, Mo L, Chen S, Kang J, Song X (2015) A ratiometric fluorescent probe for rapid, sensitive and selective detection of sulfur dioxide with large stokes shifts by single wavelength excitation. Org Biomol Chem 13:8663–8668

    Article  CAS  PubMed  Google Scholar 

  20. Yu C, Luo M, Zeng F, Wu S (2012) A fast-responding fluorescent turn-on sensor for sensitive and selective detection of sulfite anions. Anal Methods 4:2638–2640

    Article  CAS  Google Scholar 

  21. Yang J, Li K, Hou JT, Li LL, Lu CY, Xie YM, Wang X, Yu XQ (2016) Novel tumor-specific and mitochondria-targeted near-infrared-emission fluorescent probe for SO2 derivatives in living cells. ACS Sensors 1:166–172

    Article  CAS  Google Scholar 

  22. Xu J, Pan J, Jiang X, Qin C, Zeng L, Zhang H, Zhang JF (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

  23. Wu WL, Wang ZY, Dai X, Miao JY, Zhao BX (2016) An effective colorimetric and ratiometric fluorescent probe based FRET with a large stokes shift for bisulfite. Sci Rep 6:25315

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. Wang G, Chen H, Chen X, Xie Y (2016) A novel carbazole-based mitochondria-targeted ratiometric fluorescent probe for bisulfite in living cells. RSC Adv 6:18662–18666

    Article  CAS  Google Scholar 

  25. Li H, Yao Q, Fan J, Hu C, Xu F, Du J, Wang J, Peng XJ (2016) A fluorescent probe for ratiometric imaging of SO2 derivatives in mitochondria of living cells. Ind Eng Chem Res 55:1477–1483

  26. Zhu L, Xu J, Sun Z, Fu B, Qin C, Zeng L, Hu X (2015) A twisted intramolecular charge transfer probe for rapid and specific detection of trace biological SO2 derivatives and bio-imaging applications. Chem Commun 51:1154–1156

    Article  CAS  Google Scholar 

  27. Zhang Q, Zhang Y, Ding S, Zhang H, Feng G (2015) A near-infrared fluorescent probe for rapid, colorimetric and ratiometric detection of bisulfite in food, serum, and living cells. Sensors Actuat B-Chem 211:377–384

    Article  CAS  Google Scholar 

  28. Xu W, Teoh CL, Peng J, Su D, Yuan L, Chang YT (2015) A mitochondria-targeted ratiometric fluorescent probe to monitor endogenously generated sulfur dioxide derivatives in living cells. Biomaterials 56:1–9

    Article  CAS  PubMed  Google Scholar 

  29. Xu G, Wu H, Liu X, Feng R, Liu Z (2015) A simple pyrene-pyridinium-based fluorescent probe for colorimetric and ratiometric sensing of sulfite. Dyes Pigments 120:322–327

    Article  CAS  Google Scholar 

  30. Liu Y, Li K, Wu MY, Liu YH, Xie YM, Yu XQ (2015) A mitochondria-targeted colorimetric and ratiometric fluorescent probe for biological SO2 derivatives in living cells. Chem Commun 51:10236–10239

  31. Dai X, Zhang T, Du ZF, Cao XJ, Chen MY, Hu SW, Miao JY, Zhao BX (2015) An effective colorimetric and ratiometric fluorescent probe for bisulfite in aqueous solution. Anal Chim Acta 888:138–145

    Article  CAS  PubMed  Google Scholar 

  32. Chen Y, Wang X, Yang XF, Zhong Y, Li Z, Li H (2015) Development of a ratiometric fluorescent probe for sulfite based on a coumarin–benzopyrylium platform. Sensors Actuat B-Chem 206:268–275

    Article  CAS  Google Scholar 

  33. Chen W, Liu X, Chen S, Son X, Kang J (2015) A real-time colorimetric and ratiometric fluorescent probe for rapid detection of SO2 derivatives in living cells based on a near-infrared benzopyrylium dye. RSC Adv 5:25409–25415

    Article  CAS  Google Scholar 

  34. Zhang Y, Guan L, Yu H, Yan Y, Du L, Liu Y, Sun M, Huang D, Wang S (2016) Reversible fluorescent probe for selective detection and cell imaging of oxidative stress indicator bisulfite. Anal Chem 88:4426–4431

    Article  CAS  PubMed  Google Scholar 

  35. Zhang H, Huang Z, Feng G (2016) Colorimetric and ratiometric fluorescent detection of bisulfite by a new HBT-hemicyanine hybrid. Anal Chim Acta 920:72–79

    Article  CAS  PubMed  Google Scholar 

  36. Wu MY, Li K, Li CY, Hou JT, Yu XQ (2014) A water-soluble near-infrared probe for colorimetric and ratiometric sensing of SO2 derivatives in living cells. Chem Commun 50:183–185

    Article  CAS  Google Scholar 

  37. Lv YL, Liu P, Ding H, Wu Y, Yan YL, Liu H, Wang X, Huang F, Zhao YS, Tian ZY Conjugated polymer-based hybrid nanoparticles with two-photon excitation and near-infrared emission features for fluorescence bioimaging within the biological window. ACS Appl Mater Inter 7:20640–20648

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Acknowledgment

This work was supported by the Key Project of the Education Department of Hubei Province (No. Q2015010).

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Correspondence to Heng Liu.

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Sun, Y., Chen, Z., Chen, F. et al. An HBT-Based Near-Infrared Fluorescent Probe for Colorimetric and Ratiometric Detection of Bisulfite and its Application in Living Cells. J Fluoresc 27, 1405–1411 (2017). https://doi.org/10.1007/s10895-017-2077-3

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  • DOI: https://doi.org/10.1007/s10895-017-2077-3

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