Reaction-Based Ratiometric and Colorimetric Chemosensor for Bioimaging of Biosulfite in Live Cells, Zebrafish, and Food Samples

Abstract

In this work, a reaction-based ratiometric and colorimetric sensor was designed and synthesized for probing bisulfite (HSO3 –) by coupling coumarin (CM) with barbituric (BA) moiety. Further tests have shown that CM–BA has high selectivity and sensitivity for the recognition of HSO3 –, which can be applied for the detection of HSO3 – in environmental and biological systems very effectively. The fluorescence intensity ratios (F 462/F 568) exhibited an outstanding HSO3 –-dependent response with ultrafast response time (within 20 s) and a lower detection limit (105 nM). Meanwhile, the color of the CM–BA solution changed from green to colorless during the recognition process, and its fluorescence changed from green to blue. The mechanism of response is confirmed by the density functional theory (DFT) model. In summary, CM–BA has demonstrated low toxicity and good permeability, which can be applied for imaging HSO3 – in cells and zebrafish safely and effectively. Besides, this novel sensor CM–BA successfully realized the quantification of the concentration of HSO3 – in paper strips and food samples.

Carbazole-based near-infrared-emitting fluorescence probe for the detection of bisulfite in live animals and real food samples

“…[1][2][3] HSO 3 À inhibits enzymatic reactions to prevent spoilage caused by foodstuff oxidation and microbial growth, and it also prevents the inactivation of epinephrine drugs. [4][5][6][7][8][9] Accumulated research data indicate that HSO 3 À , as a derivative of a biological signal molecule (SO 2 ), also participates in a large number of physiological and pathological processes in organisms, such as regulating cardiovascular function, anti-atherosclerosis, maintaining intracellular redox homeostasis, anti-hypertension, and so on. [10][11][12][13] Nevertheless, human health is seriously affected by the excessive intake and abnormal expression of HSO 3 À , which leads to a decline in antioxidant capacity and cardiovascular diseases including spontaneous hypertension, myocardial ischemia, lung cancer, hypoxic pulmonary hypertension and neurological diseases.…”

Determination of bisulfite in food using the Etch-Cu-HCF nanozyme with enhanced polyphenol oxidase-like activity

“…To date, many analytical methods have been used for the detection of sulfur dioxide and its two derivatives, such as mass spectrometry, 12 electrochemistry, 13,14 chromatographic methods, 15 and fluorescence methods. [16][17][18][19][20][21] However, these methods have many limitations in applications, such as the need for expensive instrumentation or materials and complex sample preparation processes. Among the methods reported previously, the enzyme-based colorimetric method is easy to operate and has successfully attracted the interest of researchers; however, natural enzymes are expensive to produce and can easily lose their activity.…”

Ultrafast Detection of Sulfur Dioxide Derivatives by a Distinctive “Dual-Positive-Ion” Platform that Features a Doubly Activated but Irreversible Michael Addition Site

“…To date, various analytical methods for detecting SO 2 , such as chromatography, titration, and electrochemistry, have been developed but are biologically incompatible and difficult to achieve in situ detection of SO 2 in a real-time manner . In contrast, fluorescent imaging has emerged as a powerful tool for monitoring biomolecules in intact living systems with high sensitivity, temporal–spatial resolution, and noninvasiveness. − Therefore, many reaction-based fluorescent probes for SO 2 have been explored based on the selective nucleophilic reaction with the aldehyde group − and the CN double bond, , and Michael addition or 1,2-addition reaction with the CC double bond. − Nevertheless, most of them suffer from several drawbacks. First, their response times are long, of a minute or even hour scale (Tables S1 and S2), making them unsuitable to realize real-time monitoring of SO 2 .…”