NIR fluorescent probe based on benzopyran derivative for highly sensitive detection of SO2 derivative and bioimaging

doi:10.6023/cjoc202510002

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基于苯并吡喃衍生物的近红外荧光探针用于二氧化硫衍生物的高灵敏检测与生物成像

刘琳^a, 周璐璐^a, 梁天宇^a, 钟克利^*,a, 燕小梅^b, 汤立军^*,a

^a渤海大学化学学院,锦州 121013
^b大连医科大学检验医学院大连 116044

收稿日期:2025-10-07 修回日期:2025-12-18
基金资助:
国家自然科学基金（No.22278038）、渤海大学海洋研究所开放项目（No.BDHYYJY2025003, BDHYYJY2025008）、辽宁省教育厅科研基金项目（Nos.JTTMS1618）资助

NIR fluorescent probe based on benzopyran derivative for highly sensitive detection of SO₂ derivative and bioimaging

Liu Lin^a, Zhou Lulu^a, Liang Tianyu^a, Zhong Keli^*,a, Yan Xiaomei^b, Tang Lijun^*,a

^aCollege of Chemistry, Bohai University, Jinzhou 121013
^bCollege of Laboratory Medicine, Dalian Medical University, Dalian, 116044

Received:2025-10-07 Revised:2025-12-18
Contact: *E-mail: zhongkeli2000@bhu.edu.cn (K. Zhong); ljtang@bhu.edu.cn (L. Tang).
Supported by:
National Natural Science Foundation of China (No.22278038); the Open Fund of Institute of Ocean Research of Bohai University (No.BDHYYJY2025003, BDHYYJY2025008); Scientific Research Project of Liaoning Provincial Department of Education (Nos.JTTMS1618)

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Abstract

A novel near-infrared fluorescent probe DCA-Tcf is developed for the detection of sulfur dioxide derivatives (HSO₃^-/SO₃^2-) in biological systems and food samples in this paper. Utilizing 6-(diethylamino)-1,2-dihydrocyclopentene[b]benzopyran as the fluorophore, and incorporating electron-withdrawing groups, the emission wavelength of the probe is red-shifted to 809 nm, which surpasses the typical 800 nm barrier for small-molecule probes. The emission wavelength (809 nm) can effectively enhance the tissue penetration depth and reduce the background fluorescence interference, making this probe more advantageous in biological imaging applications. Probe DCA-Tcf exhibits high selectivity, rapid response within 40 seconds, and a detection limit as low as 0.509 μM toward HSO₃^-/SO₃^2-. DCA-Tcf has been successfully applied to the detection of HSO₃^- in real water and sugar samples, and demonstrates promising potential for application in fluorescence imaging of living cells. The DCA-Tcf developed in this study can become a powerful tool in the fields of food safety detection and bioimaging.

Key words: NIR emission, Fluorescent probe, Sulfur dioxide derivatives, bioimaging, Food samples

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Liu Lin, Zhou Lulu, Liang Tianyu, Zhong Keli, Yan Xiaomei, Tang Lijun. NIR fluorescent probe based on benzopyran derivative for highly sensitive detection of SO₂ derivative and bioimaging[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202510002.

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基于苯并吡喃衍生物的近红外荧光探针用于二氧化硫衍生物的高灵敏检测与生物成像

NIR fluorescent probe based on benzopyran derivative for highly sensitive detection of SO₂ derivative and bioimaging

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