Near-infrared and multifunctional fluorescent probe enabled by cyanopyridine cyanine dye for bisulfite recognition and biological imaging

• Published in: Journal of hazardous materials Vol. 477; p. 135369
• Main Authors: Gu, Shangcong, Huang, Yan, Li, Xinxin, Xin, Haotian, Mu, Haoran, Zhang, Yan, Li, Keyi, Yang, Guiyi, Zhao, Songfang, Cao, Duxia
• Format: Journal Article
• Language: English
• Published: Netherlands Elsevier B.V 15-09-2024
• Subjects: Carbocyanines - chemistry; Cell imaging; Cyanine dye; Food Analysis; Food inspection; HeLa Cells; Humans; Hydrogels - chemistry; Limit of Detection; Molecular Structure; Near-infrared fluorescence; Photochemical Processes; Pyridines - chemistry; Spectrometry, Fluorescence - methods; Spectroscopy, Near-Infrared - methods; Sulfites - analysis; Sulfites - chemistry; Food inspection; Cell imaging; Cyanine dye; Near-infrared fluorescence
• ISSN: 0304-3894; 1873-3336; 1873-3336
• DOI: 10.1016/j.jhazmat.2024.135369

SO2 derivatives, sulfite/bisulfite, are widely employed in both the food processing and drug synthesis industries. Despite their widespread application, excessive levels of sulfite/bisulfite can negatively impact human health. Most probes for detecting sulfite/bisulfite are restricted by their fluorescence within the visible spectrum range and poor solubility in aqueous solution, which limit their use in food testing and biological imaging. Herein, a near-infrared probe comprising of the cyanopyridine cyanine skeleton, 4-((Z)−2-((E)−2-chloro-3-(2-cyano-2-(1-methylpyridine-4(1H)-ylidene)ethylidene)cyclohex-1-en-1-yl)−1-cyanovinyl)−1-methylpyridin-1-ium (abbreviated as CCP), was developed. This probe enables precise quantification of bisulfite (HSO3-) in almost pure buffered solutions, showing a near-infrared fluorescence emission at 784 nm with an impressively low detection limit of 0.32 μM. The probe stands out for its exceptional selectivity, minimal susceptibility to interference, and strong adaptability. The probe CCP utilizes the CC bond to trigger a near-infrared fluorescence quenching reaction with HSO3- via nucleophilic addition, which effectively disrupts the large delocalization within the molecule for accurate HSO3- identification. Moreover, the probe has been successfully applied in detecting HSO3- in various food products and living cells, simplifying the measurement of HSO3- content in water samples. This advancement not only enhances the analytical capabilities but also contributes to ensuring food safety and environmental protection.
SO2 derivatives including sulfite/bisulfite, serving dual roles as preservatives and antioxidants, have widespread application across various sectors including food preservation, water sanitation, and the pharmaceutical industry. Despite their widespread application, excessive levels of sulfite/bisulfite can affect human health. Developing methods for precisely and sensitively detecting sulfite/bisulfite in food products and biological samples is important for ensuring food safety and environmental protection. Here, a sensitive near-infrared and multifunctional fluorescent probe in a 99.9 % buffered solution, along with water gel encapsulation, has been successfully applied for the detection of bisulfite in food, authentic water samples, and biological cells.
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•A near-infrared fluorescent probe of cyanine dye for bisulfite was developed.•NIR emission reduces background fluorescence, making it suitable for cell imaging.•The probe can accurately quantifies bisulfites in 99.9 % HEPES with high sensitivity.•Hydrogel embedded probe is used for real water sample detection.