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High-Specific Fluorescence Probe for SO32− Detection and Bioimaging

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Abstract

It is well known that sulfite (SO32−) plays an indispensable role in various physiological processes. Abnormal levels of SO32− can trigger a wide variety of diseases involving respiratory, nervous and cardiovascular systems. Hence, it is necessary to find an efficient approach for detection of SO32−. In this study, a pyrene derivative, (E)-4-(3-oxo-3-(pyren-1-yl)prop-1-en-1-yl)phenyl acrylate (PPA), was designed and synthesized for monitoring SO32−. The probe possessed simple synthetic steps, excellent anti-interference ability and specific response to SO32− in the presence of other substances. The reaction between PPA and SO32− was ascribed to Michael addition and the detection mechanism was confirmed by HRMS spectra analysis and FTIR analysis. Additionally, PPA responded linearly to detect SO32− within the rang of 0–100 μM. The limit of detection was calculated as low as 0.17 μM in accordance with the recommendation of IUPAC (CDL =3sb/m). Notably, PPA was further applied in biological imaging in HepG2 cells, which provided a possibility to monitor SO32− in vivo.

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Data Availability

The data and materials used or analysed during the current study are available from the corresponding author on reasonable request.

References

  1. Li MY, Cui PC, Li K, Feng JH, Zou MM, Yu XQ (2018) Dual-site fluorescent probe for highly selective and sensitive detection of sulfite and biothiols. Chin Chem Lett 29:992–994. https://doi.org/10.1016/j.cclet.2017.11.011

    Article  CAS  Google Scholar 

  2. Zeng LT, Chen TH, Chen BQ, Yuan HQ, Sheng RL, Bao GM (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. https://doi.org/10.1039/c9tb02593f

    Article  CAS  PubMed  Google Scholar 

  3. Zhu YZ, Du W, Zhang MZ, Xu Y, Song LL, Zhang Q, Tian XH, Zhou HP, Wu JY, Tian YP (2017) A series of water-soluble A–π–A’typological indolium derivatives with two-photon properties for rapidly detecting HSO3−/SO32− in living cells. J Mater Chem B 5:3862–3869. https://doi.org/10.1039/c7tb00726d

  4. Yin CX, Li XQ, Yue YK, Chao JB, Zhang YB, Huo FJ (2017) A new fluorescent material and its application in sulfite and bisulfite bioimaging. Sensors Actuators B Chem 246:615–622. https://doi.org/10.1016/j.snb.2017.02.127

    Article  CAS  Google Scholar 

  5. Yang D, He XY, Wu XT, Shi HN, Miao JY, Zhao BX, Lin ZM (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. https://doi.org/10.1039/d0tb00149j

    Article  CAS  PubMed  Google Scholar 

  6. Gao T, Cao XZ, Ge P, Dong J, Yang SQ, Xu H, Wu Y, Gao F, Zeng WB (2017) A self-assembled fluorescent organic nanoprobe and its application for sulfite detection in food samples and living systems. Organic & Biomolecular Chemistry 15:4375–4382. https://doi.org/10.1039/c7ob00580f

    Article  CAS  Google Scholar 

  7. Song GJ, Luo J, Xing XJ, Ma HL, Yang D, Cao XQ, Ge YQ, Zhao BX (2018) A ratiometric fluorescence probe for rapid detection of mitochondrial SO2 derivatives. New J Chem 42:3063–3068. https://doi.org/10.1039/c7nj04021k

  8. Duan C, Zhang JF, Hu YB, Zeng LT, Su DD, Bao GM (2019) A distinctive near-infrared fluorescence turn-on probe for rapid, sensitive and chromogenic detection of sulfite in food. Dyes Pigments 162:459–465. https://doi.org/10.1016/j.dyepig.2018.10.057

    Article  CAS  Google Scholar 

  9. Samanta S, Halder S, Dey P, Manna U, Ramesh A, Das P (2018) A ratiometric fluorogenic probe for the real-time detection of SO32− in aqueous medium: application in a cellulose paper based device and potential to sense SO32− in mitochondria. Analyst 143:250–257. https://doi.org/10.1039/c7an01368j

  10. Cai FZ, Hou B, Zhang SP, Chen H, Ji SC, Shen XC, Liang H (2019) A chromenoquinoline-based two-photon fluorescent probe for the highly specific and fast visualization of sulfur dioxide derivatives in living cells and zebrafish. J Mater Chem B 7:2493–2498. https://doi.org/10.1039/c9tb00179d

    Article  CAS  PubMed  Google Scholar 

  11. Bush RK, Taylor SL, Busse W (1986) A critical evaluation of clinical trials in reactions to sulfites. J Allergy Clin Immunol 78:191–202. https://doi.org/10.1016/0091-6749(86)90012-6

    Article  CAS  PubMed  Google Scholar 

  12. Yang YT, Huo FJ, Zhang JJ, Xie ZH, Chao JB, Yin CX (2012) A novel coumarin-based fluorescent probe for selective detection of bissulfite anions in water and sugar samples. Sensors Actuators B Chem 166:665–670. https://doi.org/10.1016/j.snb.2012.03.034

    Article  CAS  Google Scholar 

  13. Li GY, Chen Y, Wang JQ, Wu JH, Gasser G, Ji LN, Chao H (2015) Direct imaging of biological sulfur dioxide derivatives in vivo using a two-photon phosphorescent probe. Biomaterials 63:128–136. https://doi.org/10.1016/j.biomaterials.2015.06.014

    Article  CAS  PubMed  Google Scholar 

  14. Zeng RF, Lan JS, 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 318:1–8. https://doi.org/10.1016/j.foodchem.2020.126358

    Article  CAS  Google Scholar 

  15. Yang B, Xu J, Zhu HL (2019) Recent progress in the small-molecule fluorescent probes for the detection of sulfur dioxide derivatives (HSO3−/SO32−). Free Radic Biol Med 145:42–60. https://doi.org/10.1016/j.freeradbiomed.2019.09.007

  16. 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. Sensors Actuators B 253:19–26. https://doi.org/10.1016/j.snb.2017.06.072

    Article  CAS  Google Scholar 

  17. Li DY, Tian XW, Li Z, Zhang JH, Yang XB (2019) Preparation of a near-infrared fluorescent probe based on IR-780 for highly selective and sensitive detection of bisulfite−sulfite in food, living cells, and mice. J Agric food Chem 67:3062−3067. https://doi.org/10.1021/acs.jafc.9b00822

  18. Yang X, Feng P, Ma L, Kang T, Hu SL, Hai A, Ke BW, Liu J, Li MY (2020) Biological applications of a turn-on bioluminescent probe for monitoring sulfite oxidase defificiency in vivo. Eur J Med Chem 200:112476. https://doi.org/10.1016/j.ejmech.2020.112476

    Article  CAS  PubMed  Google Scholar 

  19. Macedo AN, Jiwa MIY, Macri J, Belostotsky V, Hill S, Britz-McKibbin P (2013) Strong anion determination in biological fluids by capillary electrophoresis for clinical diagnostics. Anal Chem 85:11112–11120. https://doi.org/10.1021/ac402975q

    Article  CAS  PubMed  Google Scholar 

  20. Chen YH, Wang X, Yang XF, Zhong YG, Li Z, Li H (2015) Development of a ratiometric fluorescent probe for sulfite based on a coumarin–benzopyrylium platform. Sensors Actuators B Chem 206:268–275. https://doi.org/10.1016/j.snb.2014.09.052

    Article  CAS  Google Scholar 

  21. Cheng XH, Jia HZ, Feng J, Qin JG, Li Z (2013) “Reactive” probe for hydrogen sulfite: good ratiometric response and bioimaging application. Sensors Actuators B Chem 184:274–280. https://doi.org/10.1016/j.snb.2013.04.070

    Article  CAS  Google Scholar 

  22. Yang XJ, Zhang CK, Shen LQ, Bao HB, Xu JW, Fang XX, Zhao YX, Yang W (2017) A near-infrared fluorescent probe for sulfide detection. Sensors Actuators B Chem 242:332–337. https://doi.org/10.1016/j.snb.2016.11.064

    Article  CAS  Google Scholar 

  23. Liu Y, Li K, Xie KX, Li LL, Yu KK, Wang X, Yu XQ (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 

  24. Zhu XY, Zhu LM, Liu HW, Hu XX, Peng RZ, Zhang J, Zhang XB, Tan WH (2016) A two-photon fluorescent turn-on probe for imaging of SO2 derivatives in living cells and tissues. Anal Chim Acta 937:136–142. https://doi.org/10.1016/j.aca.2016.07.017

    Article  CAS  PubMed  Google Scholar 

  25. Zhang Q, Zhang Y, Ding SS, Zhang HY, Feng GQ (2015) A near-infrared fluorescent probe for rapid, colorimetric and ratiometric detection of bisulfite in food, serum, and living cells. Sensors Actuators B Chem 211:377–384. https://doi.org/10.1016/j.snb.2015.01.122

    Article  CAS  Google Scholar 

  26. Xu GS, Wu H, Liu XG, Feng RK, Liu ZX (2015) A simple pyrene-pyridinium-based fluorescent probe for colorimetric and ratiometric sensing of sulfite. Dyes Pigments 120:322–327. https://doi.org/10.1016/j.dyepig.2015.04.038

    Article  CAS  Google Scholar 

  27. Song JH, Zhang D, Liu YQ, Zhao YF, Ye Y (2015) A highly sensitive and selective turn-on fluorescent probe for sulfite and its application in biological imaging. New J Chem 39:6284–6288. https://doi.org/10.1039/c5nj00879d

    Article  CAS  Google Scholar 

  28. Liu KY, Chen YL, Sun H, Wang SJ, Kong FG (2018) Construction of a novel near-infrared fluorescent probe with multiple fluorescence emission and its application for SO2 derivative detection in cells and living zebrafish. J Mater Chem B 6:7060–7065. https://doi.org/10.1039/c8tb02030b

    Article  CAS  PubMed  Google Scholar 

  29. Lan JS, Zeng RF, Ding Y, Zhang Y, Zhang T, Wu T (2018) A simple pyrene–hemicyanine fluorescent probe for colorimetric and ratiometric detection of SO2 derivatives in the mitochondria of living cells and zebrafish in vivo. Sensors Actuators B Chem 268:328–337. https://doi.org/10.1016/j.snb.2018.04.047

  30. Möller MN, Denicola A (2018) Diffusion of nitric oxide and oxygen in lipoproteins and membranes studied by pyrene fluorescence quenching. Free Radic Biol Med 128:137–143. https://doi.org/10.1016/j.freeradbiomed.2018.04.553

    Article  CAS  PubMed  Google Scholar 

  31. Yao CX, Kraatz HB, Steer RP (2005) Photophysics of pyrene-labelled compounds of biophysical interest. Photochemical & Photobiological Sciences 4:191–199. https://doi.org/10.1039/b414577c

    Article  CAS  Google Scholar 

  32. Aparin IO, Proskurin GV, Golovin AV, Ustinov AV, Formanovsky AA, Zatsepin TS, Korshun VA (2017) Fine tuning of pyrene excimer fluorescence in molecular beacons by alteration of the monomer structure. J Org Chem 82:10015–10024. https://doi.org/10.1021/acs.joc.7b01451

    Article  CAS  PubMed  Google Scholar 

  33. Chao JB, Wang XL, Liu YM, Zhang YB, Huo FJ, Yin CX, Zhao MG, Sun JY, Xu M (2018) A pyrene-thiophene based fluorescent probe for ratiometric sensing of bisulfite and its application in vivo imaging. Sensors Actuators B Chem 272:195–202. https://doi.org/10.1016/j.snb.2018.05.058

    Article  CAS  Google Scholar 

  34. Rani BK, John SA (2016) A novel pyrene based fluorescent probe for selective detection of cysteine in presence of other bio-thiols in living cells. Biosens Bioelectron 83:237–242. https://doi.org/10.1016/j.bios.2016.04.013

    Article  CAS  PubMed  Google Scholar 

  35. Liu T, Huang ZJ, Feng RH, Ou ZQ, Wang S, Yang LT, Ma LJ (2019) An intermolecular pyrene excimer-based ratiometric fluorescent probes for extremely acidic pH and its applications. Dyes Pigments 174:108102. https://doi.org/10.1016/j.dyepig.2019.108102

    Article  CAS  Google Scholar 

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Funding

The work was supported by the National Natural Science Foundation of China (No. 21472118, 21672131), the Program for the Top Young and Middle-aged Innovative Talents of Higher Learning Institutions of Shanxi (No. 2013802), Talents Support Program of Shanxi Province (No. 2014401), Shanxi Province Outstanding Youth Fund (No. 2014021002), Natural Science Foundation of Shanxi Province of China (No. 201701D121018).

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Authors and Affiliations

  1. Scientific Instrument Center, Shanxi University, Taiyuan, 030006, People’s Republic of China

    Jianbin Chao, Jiamin Zhao, Ming Li & Yuexiang Duan

  2. School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006, People’s Republic of China

    Jiamin Zhao, Ming Li & Yuexiang Duan

  3. Research Institute of Applied Chemistry, Shanxi University, Taiyuan, 030006, People’s Republic of China

    Yongbin Zhang & Fangjun Huo

  4. Institute of Molecular Science, Shanxi University, Taiyuan, 030006, People’s Republic of China

    Caixia Yin

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  1. Jianbin Chao
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Contributions

Jianbin Chao,Yongbin Zhang: contributed to the conception of the study;

Jiamin Zhao: performed the experiment;Jianbin Chao, Jiamin Zhao: contributed significantly to analysis and manuscript preparation;Jiamin Zhao: performed the data analyses and wrote the manuscript;Fangjun Huo, Caixia Yin, Ming Li, Yuexiang Duan: helped perform the analysis with constructive discussions.

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Correspondence to Jianbin Chao.

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Cite this article

Chao, J., Zhao, J., Zhang, Y. et al. High-Specific Fluorescence Probe for SO32− Detection and Bioimaging. J Fluoresc 31, 363–371 (2021). https://doi.org/10.1007/s10895-020-02662-4

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  • DOI: https://doi.org/10.1007/s10895-020-02662-4

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