Application and Cell Imaging of Turn-On Fluorescent Probe for Hydrogen Sulfide Based on Benzopyran in Food Samples

doi:10.6023/cjoc202311014

Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (6): 2027-2032.DOI: 10.6023/cjoc202311014 Previous Articles Next Articles

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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

刘琳^a,†, 陈琳^b,†, 胡晓玲^a, 钟克利^a^,^*(), 张璟琳^c^,^*(), 汤立军^a

a 渤海大学化学与材料工程学院辽宁锦州 121013
b 辽宁省检验检测认证中心沈阳 110000
c 北京工商大学中国轻工业酿酒分子工程重点实验室北京 100048

收稿日期:2023-11-14 修回日期:2024-01-14 发布日期:2024-02-19
作者简介:
^†共同第一作者
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

Lin Liu^a,†, Lin Chen^b,†, Xiaoling Hu^a, Keli Zhong^a,*(), Jinglin Zhang^c,*(), Lijun Tang^a

a College of Chemistry and Material Engineering, Bohai University, Jinzhou, Liaoning 121013
b Liaoning Inspection, Examination & Certification Centre, Shenyang 110000
c Key Laboratory of Brewing Molecular Engineering of China Light Industry, Beijing Technology and Business University, Beijing 100048

Received:2023-11-14 Revised:2024-01-14 Published:2024-02-19
Contact: * E-mail: zhongkeli2000@bhu.edu.cn; zhangjinglin@btbu.edu.cn
About author:
^†These authors contributed equally to this work.
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)

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Abstract

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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Lin Liu, Lin Chen, Xiaoling Hu, Keli Zhong, Jinglin Zhang, Lijun Tang. Application and Cell Imaging of Turn-On Fluorescent Probe for Hydrogen Sulfide Based on Benzopyran in Food Samples[J]. Chinese Journal of Organic Chemistry, 2024, 44(6): 2027-2032.

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Fig. & Tab. 8

Scheme 1. Synthesis of DCM-dip

Figure 1. (a) Fluorescence spectra changes of DCM-dip (10 μmol/L) after adding various analytes (610 μmol/L) in DMSO/ PBS (V:V=8:2, pH=8) solution (λex=400 nm) and (b) fluorescence changes of various anions added to DCM-dip 1: F–, 2: Cl–, 3: Br–, 4: $\mathrm{HPO}_{4}^{2-}$, 5: $\mathrm{SO}_{4}^{2-}$, 6: $\mathrm{N}_{3}^{-}$, 7: SCN–, 8: I–, 9: $\mathrm{S}_{2} \mathrm{O}_{3}^{-}$, 10: $\mathrm{CO}_{3}^{2-}$, 11: CH3COO–, 12: PPi, 13: $\mathrm{C}_{2} \mathrm{O}_{4}^{2-}$, 14: $\mathrm{HCO}_{3}^{-}$, 15: $\mathrm{NO}_{2}^{-}$, 16: $\mathrm{S}_{2} \mathrm{O}_{3}^{2-}$, 17: HS–

Figure 2. Fluorescence spectra changes of DCM-dip (10 μmol/L) with addition of different concentrations of HS– (0~610 μmol/L) in DMSO/PBS (V:V=8:2, pH=8) solution (λex=400 nm) Insert: the linear relationship between the concentration of HS– and the fluorescence intensity of DCM-dip (523 nm).

Figure 3. Fluorescence intensity (523 nm) changes of DCM-dip (10 μmol/L) containing various anions (610 μmol/L) in the DMSO/PBS (V:V=8:2, pH=8) solution before and after addtion of HS– (λex=400 nm)

Figure 4. Mechanism of DCM-dip recognition of H2S and application of DCM-dip

Figure 5. Fluorescence intensity changes of DCM-dip (10 μmol/L) upon adding HS– (70~120 μmol/L) in (a) red wine and (b) beer samples

Sample	Added/(μmol/L)	Found/(μmol/L)	Recovery/%	RSD/% (n=3)
Red wine 1	70 80 90	70.06 79.69 90.69	100.0 99.6 100.7	0.62 0.76 0.66
Red wine 2	70 80 90	72.87 79.72 91.33	104.1 99.6 101.4	0.52 0.46 0.80
Beer 1	80 90 100	80.50 90.59 100.21	100.6 100.6 100.2	0.85 2.13 0.65
Beer 2	80 90 100	79.71 90.21 100.99	99.6 100.2 100.9	0.42 0.45 0.65

Table 1. Data of HS– concentrations detected by DCM-dip in red wines and beer samples

Figure 6. Bright-field (left) and dark field (right) image of MCF-7 cells which were incubated for 30 min after addition of DCM-dip (10 μmol/L) and then incubated for another 30 min after addition of HS– (100, 200, 500, 1000 μmol/L) at 37 ℃ [λex=458 nm, green channel (510~550 nm)]

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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

Application and Cell Imaging of Turn-On Fluorescent Probe for Hydrogen Sulfide Based on Benzopyran in Food Samples

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