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

doi:10.6023/cjoc202507024

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (2): 586-593.DOI: 10.6023/cjoc202507024 Previous Articles Next Articles

ARTICLES

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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Abstract

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

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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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Fig. & Tab. 7

Scheme 1. Synthesis process of probe PTD

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)

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

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

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

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

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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