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.
Graphical abstract
Similar content being viewed by others
Data Availability
All data generated or analysed during this study are included in this published article and its supplementary information files.
Code Availability
All data were obtained using word, origin and chemBioDraw.
References
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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).
Author information
Authors and Affiliations
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.
Corresponding authors
Ethics declarations
Conflicts of Interest
The authors declare that they have no conflict of interest.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Supplementary Information
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-021-02794-1