Construction of Cysteine Fluorescent Probes and Their Applications in Pathological Examination

doi:10.6023/cjoc202410024

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (7): 2335-2349.DOI: 10.6023/cjoc202410024 Previous Articles Next Articles

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半胱氨酸荧光探针的构建及其在病理学检验中的应用

李兆周^a^,^†, 谢亚芳^a^,^†, 陶健^b, 魏雪冰^a, 黎乐乐^a, 李亚娟^a, 唐嘉敏^a, 牛华伟^a^,^*(), 陈秀金^a, 高红丽^a, 李芳^a, 于慧春^a, 袁云霞^a, 古绍彬^a, 康怀彬^a, 孙晓菲^a, 任国艳^a, 吴影^a

^a 河南科技大学食品与生物工程学院河南省绿色食品加工与质量安全控制国际联合实验室/食品加工与安全国家级安全教育示范中心河南洛阳 471000
^b 河南省食品和盐业检验技术研究院国家市场监督管理总局重点实验室(食品安全快速检测与智慧监管技术) 郑州 450003

收稿日期:2024-10-30 修回日期:2025-01-03 发布日期:2025-02-07
作者简介:
^† 共同第一作者
基金资助:
洛阳市公益性行业科研专项项目(2202021A); 河南省科技攻关项目(242102411001); 河南省优秀青年科学基金(202300410121); 国家自然科学基金(31701694); 国家自然科学基金(U1504330); 河南科技大学横向技术开发委托项目(20240139); 河南科技大学横向技术开发委托项目(20230120)

Construction of Cysteine Fluorescent Probes and Their Applications in Pathological Examination

Zhaozhou Li^a, Yafang Xie^a, Jian Tao^b, Xuebing Wei^a, Lele Li^a, Yajuan Li^a, Jiamin Tang^a, Huawei Niu^a^,^*(), Xiujin Chen^a, Hongli Gao^a, Fang Li^a, Huichun Yu^a, Yunxia Yuan^a, Shaobin Gu^a, Huaibin Kang^a, Xiaofei Sun^a, Guoyan Ren^a, Ying Wu^a

^a Henan International Joint Laboratory of Green Food Processing and Quality and Safety Control/National Safety Education Demonstration Center for Food Processing and Safety, College of Food and Biological Engineering, Henan University of Science and Technology, Luoyang, Henan 471000
^b Key Laboratory of Rapid Detection and Smart Supervision Technology for Food Safety, State Administration for Market Regulation/Henan Institute of Food and Salt Industry Inspection Technology, Zhengzhou 450003

Received:2024-10-30 Revised:2025-01-03 Published:2025-02-07
Contact: *E-mail: niuhw0816@126.com
About author:
^† These authors contributed equally to this work
Supported by:
Special Fund for Scientific Research in the Public Interest from Luoyang City(2202021A); Scientific and Technological Research Project of Henan Province(242102411001); Natural Science Foundation of Henan Province(202300410121); National Natural Science Foundation of China(31701694); National Natural Science Foundation of China(U1504330); Entrusted Horizontal Technology Development Project of Henan University of Science and Technology, Henan Province(20240139); Entrusted Horizontal Technology Development Project of Henan University of Science and Technology, Henan Province(20230120)

As a reducing biothiol, cysteine participates in the redox process in cells and plays an important role in maintaining cellular homeostasis and organismal health. Previous studies showed that the occurrence of many diseases was often accompanied by changes in the level of cysteine in the body. Therefore, real-time monitoring of changes in cysteine content in the body is of great significance for the prevention and treatment of diseases. Traditional methods for the detection of cysteine in biological samples have strict test conditions and poor biocompatibility. The fluorescent probe developed based on fluorescence imaging technology possesses the advantages of high specificity, strong tissue penetration and non-invasiveness, and can recognize real-time quantitative monitoring of cysteine in organisms. In this review, the construction strategies, recognition mechanisms and applications of cysteine fluorescent probes in the field of medical testing are summarized, specifically involving Parkinson’s disease, Alzheimer’s disease, liver injury, arthritis, depression and diabetes, and the signal response and biological applications of fluorescent probes in the development of these diseases are analyzed. It will provide more accurate measurement methods and diagnostic methods for human health and disease research, and also provide new ideas and methods for the development of fluorescent probes.

Key words: cysteine, fluorescent probe, construction strategy, pathological examination

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Zhaozhou Li, Yafang Xie, Jian Tao, Xuebing Wei, Lele Li, Yajuan Li, Jiamin Tang, Huawei Niu, Xiujin Chen, Hongli Gao, Fang Li, Huichun Yu, Yunxia Yuan, Shaobin Gu, Huaibin Kang, Xiaofei Sun, Guoyan Ren, Ying Wu. Construction of Cysteine Fluorescent Probes and Their Applications in Pathological Examination[J]. Chinese Journal of Organic Chemistry, 2025, 45(7): 2335-2349.

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Fig. & Tab. 26

Serial number	Construction strategies	Biological applications	Reference
1	With acrylate as the responsive site and naphthalimide as the fluorophore	Targeting the endoplasmic reticulum and recognizing cysteine	[7,8]
2	With coumarin derivatives as the responsive sites	Detecting cysteine in vivo	[9,10]
3	The chlorine atom on the probe is substituted by a thiol group, followed by an intramolecular rearrangement, resulting in fluorescence emission	Enabling cysteine imaging in HepG-2 cells and zebrafish	[11]
4	With thiobenzoate as the responsive site and aminoquinoline dye as the fluorophore	Detecting cysteine production during stress responses	[12]
5	With the disulfide ester moiety as the response site and quinoline derivative as the fluorophore	Detection of cysteine level fluctuations in living cells and zebrafish	[13]
6	Using 2,4-dinitrobenzenesulfonyl group as the response site to react with cysteine	Monitoring Hg^2＋-induced cysteine fluctuations in living cells	[14]
7	Using α,β-unsaturated acetylcarbazole as the fluorescent group, thiol as the response site, and methyl carbitol as the lysosome-targeting group	Detection of endogenous cysteine level changes under oxidative stress in living cells	[15]
8	With the red dye HDM as the fluorescent group and SBD-Cl as the response site	Tracking cysteine fluctuations under Cu^2＋/ H₂O₂-induced redox imbalance	[16]

Table 1. Construction strategies and biological applications of cysteine fluorescent probes

Scheme 1. Structure of fluorescent probe 1 and its mechanism of action

Scheme 2. Structure of fluorescent probe 2 and its mechanism of action

Figure 1. (A) Fluorescence imaging of endogenous Hcy, GSH, and Cys in hippocampal tissues of normal mice and transgenic mice; (B) Confocal fluorescence imaging of endogenous Hcy, GSH and Cys in substantia nigra tissues of normal mice and PD model mice; (C) Fluorescence intensities corresponding to endogenous Hcy, GSH, and Cys in the hippocampus of normal mice and transgenic mice in Figure (A); (D) Fluorescence intensities corresponding to endogenous Hcy, GSH, and Cys in substantia nigra tissues of normal mice and PD model mice in Figure (B); (E) Effect of different concentrations of Hcy/Cys on intracellular reactive oxygen species; (F) Effect of different concentrations of Hcy/Cys on the level of Aβ aggregation in cells; (G) MTT assay to determine cell viability of Hcy/Cys-treated cells at different concentrations after 12 h[32]

Scheme 3. Structure of fluorescent probe 3 and its mechanism of action

Figure 2. Two-photon fluorescence image of PC12 cells: (A) probe 4 treatment group, (B) Cys group, (C) Hcy group, (D) GSH group, (E) Cys and H2O2 groups, (F) Cys and NEM groups, (G) DTT group, (H) DTT and NEM groups; (I) Fluorescence intensity plots corresponding to panels (A)~(D); (J) Fluorescence intensity plots corresponding to (E)~(H) panels[43]

Scheme 4. Structure of fluorescent probe 4 and its mechanism of action

Scheme 5. Structure of fluorescent probe 5 and its mechanism of action

Scheme 6. Structure of fluorescent probe 6 and its mechanism of action

Figure 3. (A) In vivo fluorescence imaging of mice (from top to bottom, images of healthy mice, epileptic mice, and curcumin-treated epileptic mice); (B) Fluorescence intensity of healthy mice, epilepsy mice, and epilepsy mice treated with curcumin in Figure (A); (C) Fluorescence image of mouse isolated brain; (D) Neuronal damage in the hippocampus after administration in epileptic mice[50]

Scheme 7. Structure of fluorescent probe 7 and its mechanism of action

Figure 4. (A) Fluorescence imaging of λ-carrageenan-induced arthritis in mice (normal saline injection on the left and λ-carrageenan injection on the right); (B) Fluorescence intensity of Figure (A)[56]

Scheme 8. Structure of fluorescent probe 8 and its mechanism of action

Scheme 9. Structure of fluorescent probe 9 and its mechanism of action

Scheme 10. Structure of fluorescent probe 10 and its mechanism of action

Figure5. (A) Fluorescence images of Hela cells treated with blank, Cys, H2O2, BSO, BSO＋GSHee and then treated with probes; (B) Fluorescence images of Hela cells pretreated with different concentrations of SAS followed by probes[65]

Scheme 11. Structure of fluorescent probe 11 and its mechanism of action

Figure 6. (A) TP imaging of TPER-Cys and TPER-ONOO in mouse lungs; (B) Fluorescence imaging of TPER-Cys in the lungs of control and pneumonia mice; (C) Relative fluorescence intensity of lung tissue from pneumoniac mice and control mice; (D) Relative fluorescence intensity of lung fibrosis and control mouse lung tissue; (E) Relative activities of GCL and GSS enzymes in mouse lungs; (F) Possible signaling pathways for GSH synthesis in pulmonary fibrosis[70]

Scheme 12. Structure of fluorescent probe 12 and its mechanism of action

Scheme 13. Structure of fluorescent probe 13 and its mechanism of action

Scheme 14. Structure of fluorescent probe 14 and its mechanism of action

Scheme 15. Structure of fluorescent probe 15 and its mechanism of action

Figure 7. (A) Schematic diagram of ALI induced by over ethanol gavage; (B) Schematic diagram of ethanol-induced ALI mice surgically injected; (C) Near-infrared fluorescence imaging of ALI mice in the injection group after 0, 30, and 60 min; (D) Near-infrared imaging of ALI mice in the surgical group after 30 and 60 min; (E) Fluorescence imaging of isolated liver in the gastric perfusion group; (F) Fluorescence imaging of isolated liver in the injection group; (G) Semi-quantitative analysis of near-infrared fluorescence intensity in the gavage group; (H) Semi-quantitative analysis of near-infrared fluorescence intensity in the surgical group[79]

Scheme 16. Structure of fluorescent probe 16 and its mechanism of action

Scheme 17. Structure of fluorescent probe 17 and its mechanism of action

Figure 8. (A) From top to bottom, this is the fluorescence image of the anatomical organs of the control group, the diabetic group, and the treatment group after 1 h of probe action; (B) Fluorescence intensity of the control group, diabetic group, and treatment group in Figure A; (C) HE staining images of liver sections of the control group, diabetic group, and treatment group in Figure A[87]

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半胱氨酸荧光探针的构建及其在病理学检验中的应用

Construction of Cysteine Fluorescent Probes and Their Applications in Pathological Examination

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