Synthesis of a Turn-On Fluorescent Probe for Hydrogen Sulfide and Its Application in Red Wine and Living Cells

doi:10.6023/cjoc202207011

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 308-312.DOI: 10.6023/cjoc202207011 Previous Articles Next Articles

一种点亮型硫化氢荧光探针的合成及其在红酒和细胞中的应用

杨雅馨^†^,^a, 陈琳^†^,^c, 胡晓玲^a, 钟克利^a^,^*(), 李世迪^d, 燕小梅^d, 张璟琳^b^,^*(), 汤立军^a

a 渤海大学化学与材料工程学院辽宁锦州 121013
b 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
c 辽宁省检验检测认证中心沈阳 110000
d 大连医科大学检验医学院辽宁大连 116044

收稿日期:2022-07-05 修回日期:2022-08-07 发布日期:2022-09-08
通讯作者: 钟克利, 张璟琳
作者简介:
^† 共同第一作者
基金资助:
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); 国家自然科学基金(22278038); 辽宁省自然科学基金指导计划(2020-MS-289); 辽宁省自然科学基金指导计划(20180551195)

Synthesis of a Turn-On Fluorescent Probe for Hydrogen Sulfide and Its Application in Red Wine and Living Cells

Yaxin Yang^†^,^a, Lin Chen^†^,^c, Xiaoling Hu^a, Keli Zhong^a(), Shidi Li^d, Xiaomei Yan^d, Jinglin Zhang^b(), Lijun Tang^a

a College of Chemistry and Material Engineering, Bohai University, Jinzhou, Liaoning 121013
b Key Laboratory of Brewing Molecular Engineering, China Light Industry, Beijing 100048
c Liaoning Inspection, Examination & Certification Centre, Shenyang 121013
d College of Laboratory Medicine, Dalian Medical University, Dalian, Liaoning 116044

Received:2022-07-05 Revised:2022-08-07 Published:2022-09-08
Contact: Keli Zhong, Jinglin Zhang
About author:
^† These authors contributed equally to this work.
Supported by:
Open Project Program of the Key Laboratory of Brewing Molecular Engineering of China Light Industry(BME-202202); National Natural Science Foundation of China(22278038); Natural Science Foundation of Liaoning Province(2020-MS-289); Natural Science Foundation of Liaoning Province(20180551195)

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Abstract

In this paper, a novel triphenylamine derivative (Tdip) was synthesized. Tdip can recognize hydrogen sulfide (H₂S) with turn-on fluorescence response through tandem reaction triggered by HS^– to release precursor compound, which produces a strong fluorescent signal. Tdip displayed good selectivity and anti-interference ability toward H₂S, a large Stokes shift (146 nm), a pH range of 8~13, and a low detection limit (2.24 μmol/L). In addition, Tdip can detect H₂S in actual red wine samples and image H₂S in living cells.

Key words: hydrogen sulfide, turn-on, fluorescent probe, food sample, fluorescence imaging

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Yaxin Yang, Lin Chen, Xiaoling Hu, Keli Zhong, Shidi Li, Xiaomei Yan, Jinglin Zhang, Lijun Tang. Synthesis of a Turn-On Fluorescent Probe for Hydrogen Sulfide and Its Application in Red Wine and Living Cells[J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 308-312.

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Scheme 1. Synthesis, possible mechanism of sensing HS– and application of Tdip

Figure 1. Fluorescence spectrum of Tdip (10 μmol/L) in DMSO/PBS (V∶V=7∶3, pH=7.4) solution upon addition of various anions (λex=350 nm)

Figure 2. Fluorescence spectrum of Tdip (10 μmol/L) in DMSO/PBS (V∶V=7∶3, pH=7.4) solution upon addition different amounts of HS– (0~340 μmol/L) (λex=350 nm) (Insert: detection limit of Tdip recognition of HS–)

Figure 3. Fluorescence intensity (496 nm) changes of Tdip solution (10 μmol/L) in the presence of various anions (340 μmol/L) and further addition of HS– (340 μmol/L)

Figure 4. (a) Fluorescence spectra of TN, Tdip and Tdip+HS– in DMSO/PBS (V∶V=7∶3, pH=7.4) solution, and (b) TLC of TN and Tdip+HS–

Figure 5. Fluorescence intensities (496 nm) changes of Tdip (10 μmol/L) upon adding HS– (50~100 μmol/L) in red wine samples

Sample	Added/ (μmol•L^–1)	Found/ (μmol•L^–1)	Recovery/%	RSD (n=3)
Red wine 1	50 60 70	49.81 62.18 71.44	99.6 103.6 102.1	0.11 0.64 0.33
Red wine 2	50 60 70	49.58 59.20 73.45	99.2 98.7 104.9	0.52 0.46 0.80

Table 1. Detection results of HS– in red wine samples

Figure 6. Fluorescence images of Tdip for HS– in MCF-7 cells The cells were only incubated with Tdip (10 μmol/L) for 30 min, then HS– (0, 10, 100, 200, 500 μmol/L) were added into the cells, and further incubated for 30 min. Images from left to right: bright field and fluorescence field.

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一种点亮型硫化氢荧光探针的合成及其在红酒和细胞中的应用

Synthesis of a Turn-On Fluorescent Probe for Hydrogen Sulfide and Its Application in Red Wine and Living Cells

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