半胱氨酸荧光探针的构建及其在病理学检验中的应用

doi:10.6023/cjoc202410024

有机化学 ›› 2025, Vol. 45 ›› Issue (7): 2335-2349.DOI: 10.6023/cjoc202410024 上一篇下一篇

综述与进展

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)

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摘要/Abstract

半胱氨酸作为还原性生物硫醇, 参与细胞内的氧化还原过程, 在维持细胞稳态及生物体健康的过程中起着重要作用. 研究表明, 多种疾病的发生常伴随体内半胱氨酸含量的变化. 因此, 实时监测体内半胱氨酸含量的变化对于疾病的防治具有重要意义. 传统生物样品中半胱氨酸的检测方法, 测试条件要求高、生物相容性较差. 基于荧光成像技术研发的荧光探针, 具有特异性高、组织穿透性强、无创性等优点, 可以实现实时定量监测生物体内的半胱氨酸. 本综述总结了半胱氨酸荧光探针的构建策略、识别机理及其在医学检验领域中的应用, 具体涉及到帕金森、阿尔兹海默病、肝脏损伤、关节炎、抑郁症和糖尿病等疾病, 分析了在这些疾病发展过程中, 荧光探针的信号响应及生物学应用, 为人类健康和疾病研究提供更加精确的测定方法及诊断手段, 同时也为荧光探针的开发提供新的思路和方法.

关键词: 半胱氨酸, 荧光探针, 构建策略, 病理学检验

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

引用此文

李兆周, 谢亚芳, 陶健, 魏雪冰, 黎乐乐, 李亚娟, 唐嘉敏, 牛华伟, 陈秀金, 高红丽, 李芳, 于慧春, 袁云霞, 古绍彬, 康怀彬, 孙晓菲, 任国艳, 吴影. 半胱氨酸荧光探针的构建及其在病理学检验中的应用[J]. 有机化学, 2025, 45(7): 2335-2349.

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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图/表 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]

表1. 半胱氨酸荧光探针的构建策略与生物应用

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

图式1. 荧光探针1的结构及其作用机理

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

图式2. 荧光探针2的结构及其作用机理

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

图1. (A)正常小鼠和转基因小鼠海马组织内源性Hcy、GSH和Cys的荧光成像; (B)正常小鼠和PD模型小鼠黑质组织内源性Hcy、GSH和Cys的共聚焦荧光成像; (C)图(A)中正常小鼠和转基因小鼠海马组织内源性Hcy、GSH和Cys对应的荧光强度; (D)图(B)中正常小鼠和PD模型小鼠黑质组织内源性Hcy、GSH和Cys对应的荧光强度; (E)不同浓度Hcy/Cys对细胞内活性氧的影响; (F)不同浓度Hcy/Cys对细胞Aβ聚集水平的影响; (G) MTT法测定不同浓度Hcy/Cys处理细胞1 h后的细胞活力[32]

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]

图式3. 荧光探针3的结构及其作用机理

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

图2. PC12细胞的双光子荧光图像: (A)探针4处理组, (B) Cys组, (C) Hcy组, (D) GSH组, (E) Cys和H2O2组, (F) Cys和NEM组, (G) DTT组, (H) DTT和NEM组; (I)图(A)~(D)对应的荧光强度图; (J)图(E)~(H)对应的荧光强度图[43]

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]

图式4. 荧光探针4的结构及其作用机理

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

图式5. 荧光探针5的结构及其作用机理

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

图式6. 荧光探针6的结构及其作用机理

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

图3. (A)小鼠体内荧光成像(从上到下依次为健康小鼠、癫痫小鼠和姜黄素治疗的癫痫小鼠图像); (B)图(A)中健康小鼠、癫痫小鼠和姜黄素治疗的癫痫小鼠对应的荧光强度; (C)小鼠分离脑的荧光图像; (D)癫痫小鼠给药后海马区神经元损伤[50]

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]

图式7. 荧光探针7的结构及其作用机理

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

图4. (A) λ-卡拉胶诱导小鼠关节炎的荧光成像(左边注射生理盐水, 右边注射λ-卡拉胶); (B)图(A)中对应的荧光强度[56]

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]

图式8. 荧光探针8的结构及其作用机制

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

图式9. 荧光探针9的结构及其作用机理

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

图式10. 荧光探针10的结构及其作用机理

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

图5. (A)空白、Cys、H2O2、BSO、BSO＋GSHee处理再用探针处理的Hela细胞荧光图像; (B)不同浓度的SAS预处理再用探针处理的Hela细胞荧光图像[65]

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]

图式11. 荧光探针11的结构及其作用机理

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

图6. (A)小鼠肺部TPER-Cys和TPER-ONOO的TP成像; (B)对照组和肺炎小鼠肺部TPER-Cys的荧光成像; (C)肺炎小鼠和对照小鼠肺组织的相对荧光强度; (D)肺纤维化和对照小鼠肺组织的相对荧光强度; (E)小鼠肺中GCL和GSS酶的相对活性; (F)肺纤维化中GSH合成的可能信号通路[70]

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]

图式12. 荧光探针12的结构及其作用机理

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

图式13. 荧光探针13的结构及其作用机理

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

图式14. 荧光探针14的结构及其作用机理

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

图式15. 荧光探针15的结构及其作用机理

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

图7. (A)过量乙醇灌胃诱导ALI小鼠的示意图; (B)手术注射乙醇诱导ALI小鼠的示意图; (C)注射组ALI小鼠在0、30、60 min后的近红外荧光成像; (D)手术组ALI小鼠30、60 min后的近红外成像; (E)灌胃组离体肝脏荧光成像; (F)注射组离体肝脏的荧光成像; (G)灌胃组近红外荧光强度的半定量分析; (H)手术组近红外荧光强度的半定量分析[79]

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]

图式16. 荧光探针16的结构及其作用机理

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

图式17. 荧光探针17的结构及其作用机理

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

图8. (A)从上到下以此为对照组、糖尿病组、和治疗组小鼠在探针作用1 h后解剖器官的荧光图像; (B)图(A)中对照组、糖尿病组和治疗组对应的荧光强度; (C)图(A)中对照组、糖尿病组和治疗组肝脏切片的HE染色图片[87]

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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