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采用新型罗丹明-咪唑偶联物对食品样品中腐胺和尸胺的痕量检测及其生物学性质评价。

Trace level detection of putrescine and cadaverine in food samples using a novel rhodanine-imidazole dyad and evaluation of its biological properties.

机构信息

Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore 632014, Tamil Nadu, India.

Department of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore 632014, Tamil Nadu, India.

出版信息

J Hazard Mater. 2024 Dec 5;480:136445. doi: 10.1016/j.jhazmat.2024.136445. Epub 2024 Nov 9.

Abstract

Biogenic amines are important indicators of food spoilage and quality. Food safety is significantly influenced by biogenic amines such as Putrescine and Cadaverine, produced by microbes during food spoilage. Herein, a colorimetric probe for detecting Putrescine and Cadaverine based on a chemo-dosimeter strategy has been proposed. The probe L irreversibly binds with Putrescine and Cadaverine through an aza-Michael addition reaction in which the dicyanomethyl group of the probe is substituted by the primary amine group from the biogenic amines. This chemical reaction rapidly changes color from colorless to pale green. The probe could detect Putrescine and Cadaverine in trace levels of 52 nM and 18 nM, without much interference from other common biogenic amines. The binding mechanism of probe L with biogenic amines was confirmed using H NMR, IR, and DFT studies. The detection procedure is made portable and affordable by using a smartphone camera to capture colorimetric changes and convert them into RGB coordinates. Test paper strips coated with the probe were developed to illustrate its real-world analytical application. The potential application of probe L in real samples was demonstrated using in-vivo models of Prawn and Beef using test paper strips. Probe L showed satisfactory performance for detecting Putrescine and Cadaverine in the vapor phase.

摘要

生物胺是食品变质和质量的重要指标。食品安全受到生物胺的显著影响,例如腐胺和尸胺,这些物质是微生物在食品变质过程中产生的。本文提出了一种基于化学计量策略的用于检测腐胺和尸胺的比色探针。探针 L 通过氮杂迈克尔加成反应与腐胺和尸胺不可逆结合,其中探针的二氰甲基基团被生物胺的伯胺基取代。这种化学反应会迅速使颜色从无色变为淡绿色。探针可以检测痕量的 52 nM 和 18 nM 的腐胺和尸胺,而不会受到其他常见生物胺的干扰。使用 H NMR、IR 和 DFT 研究证实了探针 L 与生物胺的结合机制。使用智能手机摄像头捕捉比色变化并将其转换为 RGB 坐标,使检测过程变得便携且经济实惠。开发了涂有探针的试纸条以说明其在实际分析中的应用。使用 Prawn 和 Beef 的体内模型,通过试纸条证明了探针 L 在实际样品中的潜在应用。探针 L 在检测气相中的腐胺和尸胺方面表现出令人满意的性能。

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