基于“OFF-ON”型荧光探针的智能一体化平台在三文鱼肉新鲜度监测中的应用

doi:10.6023/cjoc202507024

有机化学 ›› 2026, Vol. 46 ›› Issue (2): 586-593.DOI: 10.6023/cjoc202507024 上一篇下一篇

研究论文

基于“OFF-ON”型荧光探针的智能一体化平台在三文鱼肉新鲜度监测中的应用

孙小飞^a^,^b^,^c^,^d, 张海媛^a, 李娟^a, 马骥^c, 王若溪^a, 钟克利^b, 李学鹏^a, 梁天宇^b, 汤立军^a^,^b^,^*(), 励建荣^a^,^*()

^a 渤海大学食品科学与工程学院海洋研究院生鲜农产品贮藏加工及安全控制技术国家地方联合工程研究中心辽宁锦州 121013
^b 渤海大学化学与材料工程学院辽宁锦州 121013
^c 佛山大学广东省食品智能制造重点实验室广东佛山 528225
^d 新加坡国立大学理学院食品科学与技术系新加坡 117542

收稿日期:2025-07-19 修回日期:2025-09-07 发布日期:2025-10-14
通讯作者: 汤立军, 励建荣
基金资助:
国家自然科学基金青年科学基金(32201948); 广东省食品智能制造重点实验室开放基金(2022B1212010015); 广东省食品智能制造重点实验室开放基金(GPKLIFM-KF-202410); 国家留学基金管理委员会和辽宁省教育厅地方合作项目地方创新子项目(202308210400); 广东省水产品加工与安全重点实验室开放基金(GDPKLAPPS2404); 及辽宁省教育厅(LJ212510167023)

Application of an Intelligent Integrated Platform Based on “OFF-ON” Fluorescent Probe in Salmon Freshness Monitoring

Xiaofei Sun^a^,^b^,^c^,^d, Haiyuan Zhang^a, Juan Li^a, Ji Ma^c, Ruoxi Wang^a, Keli Zhong^b, Xuepeng Li^a, Tianyu Liang^b, Lijun Tang^a^,^b^,^*(), Jianrong Li^a^,^*()

^a National and Local Joint Engineering Research Center for Storage, Processing and Safety Control Technology of Fresh Agricultural Products, Institute of Oceanography, College of Food Science and Engineering, Bohai University, Jinzhou, Liaoning 121013
^b College of Chemistry and Materials Engineering, Bohai University, Jinzhou, Liaoning 121013
^c Guangdong Provincial Key Laboratory of Food Intelligent Manufacturing, Foshan University, Foshan, Guangdong 528225
^d Department of Food Science and Technology, College of Science, National University of Singapore, Singapore 117542

Received:2025-07-19 Revised:2025-09-07 Published:2025-10-14
Contact: Lijun Tang, Jianrong Li
Supported by:
National Natural Science Foundation of China for Young Scientists(32201948); Open Fund of Guangdong Provincial Key Laboratory of Food Intelligent Manufacturing(2022B1212010015); Open Fund of Guangdong Provincial Key Laboratory of Food Intelligent Manufacturing(GPKLIFM-KF-202410); Local Innovative Sub-project of the Local Cooperation Project of the National Scholarship Council of China and Liaoning Provincial Department of Education(202308210400); Guangdong Provincial Open Fund for Key Laboratory of Aquatic Product Processing and Safety(GDPKLAPPS2404); Scientific Research Fund of Liaoning Provincial Education Department(LJ212510167023)

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摘要/Abstract

鱼肉新鲜度与食品安全和人类健康密切相关, 因此, 开发一种快速、简便、无损且直观的鱼肉新鲜度检测方法具有重要意义. 以噻吩醛和2,4-噻唑烷二酮为原料, 通过Knoevenagel缩合反应成功合成了一种“OFF-ON”型荧光探针. 该探针在溶液体系中展现出对胺类物质的比色和荧光双通道识别功能, 具有响应速度快(3 s)及灵敏度高(1.20 μmol/L)等优点. 将探针负载在滤纸片上, 所制备的指示标签能够对三文鱼肉的新鲜度呈现比色和荧光双通道响应, 标签的日光颜色由橙色变为土黄色, 荧光由亮橙色变为肉粉色. 借助智能手机软件和指示标签构建的智能一体化检测平台, 可以自动输出三文鱼肉的总挥发性盐基氮(total volatile basic nitrogen, TVB-N)值, 其准确性和可靠性在室温条件下经由中国国家标准方法证实. 本研究有望为便携式智能化检测领域提供新的思路, 同时也为商家、消费者和监管者提供一种评估鱼肉新鲜度的智能读取新型工具.

关键词: 荧光探针, 指示标签, 智能一体化平台, 新鲜度

Fish freshness is closely related to food safety and human health. Therefore, it is of great significance to develop a rapid, simple, non-destructive and intuitive fish freshness detection method. Herein, an “OFF-ON” fluorescent probe was successfully synthesized by using thiophenealdehyde and 2,4-thiazolidinedione through Knoevenagel condensation. The probehad dual recognition capability of colorimetric and fluorescence for amines in solution, with high sensitivity (1.20 μmol/L) and fast response speed (3 s). The prepared probe-loaded indicator label exhibited dual-channel response to the salmon freshness, with the daylight color changing from orange to earth-yellow and the fluorescence shifting from bright orange to flesh pink. By utilizing smartphone software and the indicator label, an intelligent integrated detection platform was constructed, which could automatically output the total volatile basic nitrogen (TVB-N) value of salmon. Under room temperature condition, its accuracy and reliability were confirmed by the Chinese national standard method. This study is expected to provide new ideas for the field of portable intelligent detection and offer a smart detection tool to merchants and consumers for assessing fish freshness.

Key words: fluorescent probe, indicator label, intelligent integrated platform, freshness

引用此文

孙小飞, 张海媛, 李娟, 马骥, 王若溪, 钟克利, 李学鹏, 梁天宇, 汤立军, 励建荣. 基于“OFF-ON”型荧光探针的智能一体化平台在三文鱼肉新鲜度监测中的应用[J]. 有机化学, 2026, 46(2): 586-593.

Xiaofei Sun, Haiyuan Zhang, Juan Li, Ji Ma, Ruoxi Wang, Keli Zhong, Xuepeng Li, Tianyu Liang, Lijun Tang, Jianrong Li. Application of an Intelligent Integrated Platform Based on “OFF-ON” Fluorescent Probe in Salmon Freshness Monitoring[J]. Chinese Journal of Organic Chemistry, 2026, 46(2): 586-593.

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图/表 7

图式1. 探针PTD的合成过程

Scheme 1. Synthesis process of probe PTD

图1. (a) PTD溶液中加入不同胺的紫外-可见吸收光谱[内插图为日光颜色变化, 1: 色胺, 2: 氨水, 3: 二甲胺, 4: 三乙胺, 5: 乙胺, 6: 精胺, 7: 尸胺, 8: 酪胺, 9: 2-苯乙胺, 10: 二乙胺, 11: 三甲胺, 12: 腐胺(Put), 13: 苯胺)]; (b) PTD溶液中加入不同胺的荧光光谱(内插图为荧光变化); (c) PTD溶液中加入不同浓度腐胺后的荧光光谱[内插图为625 nm 波长下腐胺浓度(0~300 μmol/L)与荧光强度的线性关系图]

Figure 1. (a) Ultraviolet-visible absorption spectra of different amines added to PTD solution (Inset: color changes of sunlight, 1: tryptamine, 2: ammonia water, 3: dimethylamine, 4: triethylamine, 5: ethylamine, 6: spermatine, 7: cothiamine, 8: tyramine, 9: 2-phenyl- ethylamine, 10: diethylamine, 11: trimethylamine, 12: putrescine (Put), 13: aniline); (b) fluorescence spectra of different amines added to PTD solution (Inset: fluorescence changes); (c) fluorescence spectra of PTD solution after adding different concentrations of putsamine (Inset: linear relationship graph between the concentration of putsamine (0~300 μmol/L) and fluorescence intensity at a wavelength of 625 nm)

图2. (a) PTD对腐胺的时间响应及(b) PTD在不同pH下荧光强度变化

Figure 2. (a) Time response of PTD to put and (b) variation of fluorescence intensity of PTD at different pH values

图3. (a) PTD对Put的响应机理; (b) PTD＋Put与PTD＋NaOH的紫外光谱对比图; (c) PTD＋Put与PTD＋NaOH的荧光光谱对比图

Figure 3. (a) Response mechanism of PTD to put; (b) UV spectra comparison chart of PTD＋Put and PTD＋NaOH; (c) Comparison chart of fluorescence spectra of PTD＋Put and PTD＋NaOH

图4. (a)指示标签对不同胺的比色和荧光变化; (b)风味物质对指示标签的影响; (c)温度对指示标签的影响

Figure 4. (a) Indicate the colorimetric and fluorescence changes of the label to different amines; (b) Influence of flavor substances on indication labels; (c) Influence of temperature on indicating labels

图5. (a)三文鱼肉TVB-N值和pH值; (b)三文鱼肉TVC值和TBA值; (c)指示标签随时间和TVB-N变化的比色和荧光变化

Figure 5. (a) TVB-N value and pH value of salmon meat; (b) TVC value and TBA value of salmon meat; (c) Colorimetric and fluorescent changes of the indicator label with time and TVB-N variations

图6. (a)智能手机VE软件示意图、智能手机的RGB提取功能及PTD指示标签的R/(B＋G)值与三文鱼肉TVB-N含量的线性关系; (b)在25 ℃条件下智能手机软件提取三个时间节点的R/(B＋G)值; (c)由图b得到的R/(B＋G)值自动输出相应的TVB-N值, 并与国标法测出的TVB-N值(括号内的数值)进行对比验证

Figure 6. (a) Schematic diagram of the VE software of the smart phone, RGB extraction function of the smart phone, and the linear relationship between the R/(B＋G) value of the PTD indication label and the TVB-N content of salmon meat; (b) Under the condition of 25 ℃, the R/(B＋G) values of the three time nodes extracted by the smart phone software; (c) TVB‑N values automatically output from the R/(B+G) values obtained from Figure B and compared and verified with those determined by the national standard method (the values in parentheses)

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基于“OFF-ON”型荧光探针的智能一体化平台在三文鱼肉新鲜度监测中的应用

Application of an Intelligent Integrated Platform Based on “OFF-ON” Fluorescent Probe in Salmon Freshness Monitoring

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