Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 70, Issue 35, Pages 10899-10906Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.2c04571
Keywords
near-infrared; colorimetric; fluorescent probe; food sample; bisulfite/sulfite
Funding
- Open Project Program of the Key Laboratory of Brewing Molecular Engineering of China Light Industry [BME-202202]
- National Natural Science Foundation of China [21878023]
- Natural Science Foundation of Liaoning Province [2020-MS-289, 20180551195]
- Scientific Research Fund of Liaoning Provincial Education Department [LJKQZ2021135]
- Open Fund of the State Key Laboratory of Molecular Reaction Dynamics in DICP, CAS [SKLMRD-K202123]
- Program for Distin- guished Professor of Liaoning Province
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In this study, a benzopyran-benzothiazole derivative (probe DCA-Btl) was designed and synthesized to selectively recognize HSO3-/SO32- in food samples. The compound showed both colorimetric and fluorescence response, and had a large Stokes shift, good anti-interference ability, and low cytotoxicity. The results demonstrated that DCA-Btl could effectively detect HSO3-/SO32- in food samples and fluorescently image HSO3- in living cells.
Despite their status of being widely used as food additives, bisulfite (HSO3-)/sulfite (SO32-) can pose serious health risks when they are excessively added. Therefore, it is vital to develop a new method for detecting HSO3-/SO32- in foodstuff. In this paper, a benzopyran-benzothiazole derivative (probe DCA-Btl) with near-infrared emission was designed and synthesized by constructing a push-pull electronic system. DCA-Btl can selectively recognize HSO3-/SO32- via a colorimetric and fluorescence dual channel in DMF/PBS (1:1, v/v, pH = 8.4), and the emission wavelength of DCA-Btl can reach 710 nm. The fluorescence quenching of DCA-Btl after recognition of HSO3- is attributed to the photoinduced electron transfer (PET) process of the adduct DCA-Btl-HSO3- as evaluated by the DFT/TD-DFT method. In addition, DCA-Btl has many advantages, including a large Stokes shift (95 nm), good anti-interference ability, and little cytotoxicity. What's more, DCA-Btl has been successfully applied for the detection of HSO3-/SO32- in actual water samples and food samples such as sugar, red wine, and biscuits with satisfying results, as well as for fluorescent imaging of HSO3- in living MCF-7 cells.
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