基于苯并吡喃点亮型硫化氢荧光探针在食品检测中的应用与细胞成像
收稿日期: 2023-11-14
修回日期: 2024-01-14
网络出版日期: 2024-02-20
基金资助
辽宁省教育厅科研基金(LJKMZ20221480); 北京工商大学中国轻工业酿酒分子工程重点实验室开放课题(BME-202202); 渤海大学海洋研究所开放(BDHYYJY2023008)
Application and Cell Imaging of Turn-On Fluorescent Probe for Hydrogen Sulfide Based on Benzopyran in Food Samples
Received date: 2023-11-14
Revised date: 2024-01-14
Online published: 2024-02-20
Supported by
Scientific Research Fund of Liaoning Provincial Education Department(LJKMZ20221480); Open Project Program of the Key Laboratory of Brewing Molecular Engineering of China Light Industry(BME-202202); Open Project of Institute of Ocean of Bohai University(BDHYYJY2023008)
硫化氢(H2S)不仅参与人体生理调节, 也对酒的风味和口感有影响. 合成了一种2,4-二硝基苯修饰的苯并吡喃衍生物(DCM-dip), 该化合物在二甲基亚砜(DMSO)/磷酸缓冲溶液(PBS) (V:V=8:2, pH=8)溶液中没有荧光, H2S与其发生硫解反应释放出具有荧光的中间体, 进而实现荧光点亮识别H2S. DCM-dip识别H2S的响应时间为20 min, 检测限为2.82 μmol/L, pH适用范围为8~11, 且具有较大的斯托克斯位移(123 nm), 避免了背景干扰. 应用研究表明, DCM-dip可用于红酒、啤酒样品中检测H2S, 可对活细胞中H2S进行荧光成像.
刘琳 , 陈琳 , 胡晓玲 , 钟克利 , 张璟琳 , 汤立军 . 基于苯并吡喃点亮型硫化氢荧光探针在食品检测中的应用与细胞成像[J]. 有机化学, 2024 , 44(6) : 2027 -2032 . DOI: 10.6023/cjoc202311014
Hydrogen sulfide (H2S) is not only involved in the physiological regulation of human body, but also has an impact on the flavor and taste of wine. Therefore, a benzopyran derivative modified by 2,4-dinitrobenzene (DCM-dip) was synthesized, which had no fluorescence in dimethyl sulfoxide (DMSO)/phosphate buffered saline (PBS) (V:V=8:2, pH=8) solution. DCM-dip underwent a thiolysis reaction with H2S to release the intermediate with fluorescence, which showed a fluorescence turn-on response for recognition of H2S. DCM-dip recognized H2S with a response time of 20 min, a detection limit of 2.82 μmol/L, pH application range of 8~11 and a large Stokes shift (123 nm), avoiding background interference. The application research indicates that DCM-dip can be used to detect H2S in red wine and beer samples, and image for H2S in living cells.
Key words： benzopyran; turn-on; hydrogen sulfide; fluorescent probe; food sample
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