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化学进展 2022, Vol. 34 Issue (5): 1136-1152 DOI: 10.7536/PC210537 前一篇   后一篇

• 综述 •

检测谷胱甘肽的荧光探针

颜范勇*(), 臧悦言, 章宇扬, 李想, 王瑞杰, 卢贞彤   

  1. 天津工业大学化学工程与技术学院 分离膜与膜过程国家重点实验室/分离膜科学与技术国家国际联合研究中心 天津 300387
  • 收稿日期:2021-05-24 修回日期:2021-06-28 出版日期:2022-05-24 发布日期:2021-07-29
  • 通讯作者: 颜范勇
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The Fluorescent Probe for Detecting Glutathione

Fanyong Yan(), Yueyan Zang, Yuyang Zhang, Xiang Li, Ruijie Wang, Zhentong Lu   

  1. State Key Laboratory of Separation Membrane and Membrane Processes/National International Joint Research Center for Separation Membrane Science and Technology, School of Chemical Engineering and Technology, Tiangong University,Tianjin 300387, China
  • Received:2021-05-24 Revised:2021-06-28 Online:2022-05-24 Published:2021-07-29
  • Contact: Fanyong Yan

谷胱甘肽作为细胞中最丰富的非蛋白巯基化合物,对维持人体正常生理活动有着重要作用。因此,能够高效灵敏检测谷胱甘肽意义重大。荧光探针法具有操作方便、特异性优良和灵敏度高等优点,成为目前检测生物样品中谷胱甘肽的主要手段。荧光探针法的成功应用还得益于谷胱甘肽的特殊结构特征,如巯基的亲核性、还原性、对金属离子高亲合力以及氨基的协同反应能力。本文针对近五年来特异性检测谷胱甘肽的荧光探针进行总结,将其分为有机荧光探针和无机荧光探针两大类,并结合香豆素、BODIPY、罗丹明、花菁、苯并噻唑、萘酰亚胺、金属有机骨架、半导体量子点、碳点、金属纳米颗粒、二氧化锰纳米片、石墨烯量子点等有机/无机荧光探针的结构特征,综述了迈克尔加成反应、亲核取代、还原反应以及硫醇诱导的2,4-二硝基苯磺酰基的断裂反应与络合反应等传感机理。同时,对探针的设计策略、谷胱甘肽的响应模式及其在实际中的应用进行了阐述和分析,以期为新型谷胱甘肽荧光探针的构建提供新的思路。

关键词： 谷胱甘肽, 荧光探针, 检测, 有机, 无机

As the most abundant non-protein sulfhydryl compound in cells, glutathione plays an important role in maintaining normal physiological activities of the human body. Therefore, it is of great significance to be able to detect glutathione efficiently and sensitively. Fluorescent probe method has become the main method for the determination of glutathione in biological samples due to its advantages of convenient operation, excellent specificity and high sensitivity. The successful application of fluorescent probe method is also attributed to the special structural features of GSH, such as the nucleophilicity of sulfhydryl groups, reduction, high affinity for metal ions and the synergistic reaction ability of amino groups. Based on the classification of the probe structure, the fluorescent probes that can specifically detect glutathione in the past five years are divided into two categories: organic fluorescent probes and inorganic fluorescent probes. According to the structural characteristics of coumarin, BODIPY, rhodamine, cyanine, benzothiazole, naphthalimide, metal-organic framework, semiconductor quantum dots, carbon dots, metal nano, manganese dioxide nanosheet, graphene quantum dots, etc., organic fluorescent probes/inorganic fluorescent probes, the sensing mechanisms of Michael addition reaction, nucleophilic substitution, reduction reaction, and thiol-induced breakage reaction and complexation reaction of 2,4-dinitrobenzenesulfonyl are reviewed. Meanwhile, the design strategy, response model for glutathione and practical application of the probes are described and analyzed. We really look forward to providing a new idea for the construction of a new glutathione fluorescent probe.

Contents

1 Introduction

2 Organic small molecule fluorescent probes for GSH

2.1 Coumarin-based fluorescent probes for GSH

2.2 BODIPY-based fluorescent probes for GSH

2.3 Rhodamine-based fluorescent probes for GSH

2.4 Cyanine-based fluorescent probes for GSH

2.5 Benzothiazole-based fluorescent probes for GSH

2.6 Naphthalimide-based fluorescent probes for GSH

2.7 Metal-organic framework-based fluorescent probes for GSH

2.8 Other organic fluorescent probes for GSH

3 Inorganic nano-fluorescent probes for GSH

3.1 Semiconductor quantum dots for GSH

3.2 Carbon dots for GSH

3.3 Metal nano-fluorescent probes for GSH

3.4 Manganese dioxide nanosheet-based fluorescent probes for GSH

4 Conclusion and outlook

Key words: glutathione, fluorescent probe, detect, organic, inorganic
()
图1 基于迈克尔加成的香豆素类荧光探针对GSH的检测机理
Fig. 1 The detection mechanism of Coumarin-based fluorescent probe based on Michael addition for GSH
图2 探针G-1对GSH的检测机理[20]
Fig. 2 The detection mechanism of probe G-1 for GSH[20]
图3 探针G-2、G-3对GSH的检测机理[21,22]
Fig. 3 The detection mechanism of probe G-2 and G-3for GSH[21,22]
图4 基于亲核取代的香豆素类荧光探针对GSH的检测机理
Fig. 4 The detection mechanism of nucleophilic substituted glutathione-coumarin-based fluorescent probe
图5 探针G-4、G-5对GSH的检测机理[23,24]
Fig. 5 The detection mechanism of probe G-4 and G-5 for GSH[23,24]
图6 探针G-6对GSH的检测机理[25]
Fig. 6 The detection mechanism of probe G-6 for GSH[25]
图7 探针G-7对GSH的检测机理[26]
Fig. 7 The detection mechanism of probe G-7 for GSH[26]
图8 基于脱金属反应的香豆素类荧光探针对GSH的检测机理
Fig. 8 The detection mechanism of Coumarin-based fluorescent probe based on demetallization reaction for GSH
图9 探针G-8、G-9对GSH的检测机理[27,28]
Fig. 9 The detection mechanism of probe G-8 and G-9 for GSH[27,28]
图10 基于芳环取代的BODIPY类荧光探针对GSH的检测机理
Fig. 10 The detection mechanism of BODIPY-based fluorescent probe based on aromatic ring substitution for GSH
图11 探针G-10对GSH的检测机理[29]
Fig. 11 The detection mechanism of probe G-10 for GSH[29]
图12 探针G-11对GSH的检测机理[30]
Fig. 12 The detection mechanism of probe G-11 for GSH[30]
图13 探针G-12对GSH的检测机理[31]
Fig. 13 The detection mechanism of probe G-12 for GSH[31]
图14 以—SH切断思路为设计策略的BODIPY类荧光探针对GSH的检测机理
Fig. 14 The detection mechanism of BODIPY-based fluorescent probe with sulfhydryl cutting as design strategy for GSH
图15 探针G-13对GSH的检测机理[32]
Fig. 15 The detection mechanism of probe G-13 for GSH[32]
图16 探针G-14对GSH的检测机理[33]
Fig. 16 The detection mechanism of probe G-14 for GSH[33]
图17 罗丹明类荧光探针对GSH的检测机理
Fig. 17 The detection mechanism of Rhodamine-based fluorescent probes for GSH
图18 探针G-15对GSH的检测机理[34]
Fig. 18 The detection mechanism of probe G-15 for GSH[34]
图19 探针G-16对GSH的检测机理[35]
Fig. 19 The detection mechanism of probe G-16 for GSH[35]
图20 探针G-17、G-18对GSH的检测机理[36,37]
Fig. 20 The detection mechanism of probe G-17 and G-18 for GSH[36,37]
图21 以硫醚键、醚键为识别位点的花菁类荧光探针对GSH的检测机理
Fig. 21 The detection mechanism of Cyanine-based fluorescent probe with thioether bond and ether bond as recognition site for GSH
图22 探针G-19、G-20对GSH的检测[38]
Fig. 22 The detection mechanism of probe G-19 and G-20 for GSH[38]
图23 探针G-21对GSH的检测机理[39]
Fig. 23 The detection mechanism of probe G-21 for GSH[39]
图24 苯并噻唑类荧光探针对GSH的检测机理
Fig. 24 The detection mechanism of Benzothiazole-based fluorescent probes for GSH
图25 探针G-22、G-23对GSH的检测机理[40,41]
Fig. 25 The detection mechanism of probe G-22 and G-23 for GSH[40,41]
图26 探针G-24对GSH的检测机理[42]
Fig. 26 The detection mechanism of probe G-24 for GSH[42]
图27 萘酰亚胺类荧光探针对GSH的检测机理
Fig. 27 The detection mechanism of Naphthalimide-based fluorescent probes for GSH
图28 探针G-25、G-26对GSH的检测机理[43]
Fig. 28 The detection mechanism of probe G-25 and G-26 for GSH[43]
图29 探针G-27对GSH的检测机理[44]
Fig. 29 The detection mechanism of probe G-27 for GSH[44]
图30 探针G-28对GSH的检测机理[45]
Fig. 30 The detection mechanism of probe G-28 for GSH[45]
图31 探针G-29对GSH的检测机理[46]
Fig. 31 The detection mechanism of probe G-29 for GSH[46]
图32 探针G-30对GSH的检测机理[47]
Fig. 32 The detection mechanism of probe G-30 for GSH[47]
图33 探针G-31对GSH的检测机理[48]
Fig. 33 The detection mechanism of probe G-31 for GSH[48]
图34 探针G-32对GSH的检测机理[49]
Fig. 34 The detection mechanism of probe G-32 for GSH[49]
图35 探针G-33对GSH的检测机理[50]
Fig. 35 The detection mechanism of probe G-33 for GSH[50]
图36 基于二硫键-硫醇交换反应的探针对GSH的检测机理
Fig. 36 The detection mechanism of probe based on disulfide bond-mercaptan exchange reactions for GSH
图37 探针G-35对GSH的检测机理[52]
Fig. 37 The detection mechanism of probe G-35 for GSH[52]
图38 探针G-36对GSH的检测机理[53]
Fig. 38 The detection mechanism of probe G-36 for GSH[53]
图39 探针G-37对GSH的检测机理[54]
Fig. 39 The detection mechanism of probe G-37 for GSH[54]
图40 探针G-38对GSH的检测机理[55]
Fig. 40 The detection mechanism of probe G-38 for GSH[55]
图41 探针G-40对GSH的检测机理[57]
Fig. 41 The detection mechanism of probe G-40 for GSH[57]
图42 探针G-41对GSH的检测机理[58]
Fig. 42 The detection mechanism of probe G-41 for GSH[58]
图43 探针G-45对GSH的检测机理[63]
Fig. 43 The detection mechanism of probe G-45 for GSH[63]
图44 探针G-46对GSH的检测机理[64]
Fig. 44 The detection mechanism of probe G-46 for GSH[64]
图45 探针G-49对GSH的检测机理[66,67]
Fig. 45 The detection mechanism of probe G-49 for GSH[66,67]
图46 探针G-51对GSH的检测机理[69]
Fig. 46 The detection mechanism of probe G-51 for GSH[69]
图47 探针G-52对GSH的检测机理[70]
Fig. 47 The detection mechanism of probe G-52 for GSH[70]
图48 探针G-53对GSH的检测机理[71]
Fig. 48 The detection mechanism of probe G-53 for GSH[71]
图49 探针G-55对GSH的检测机理[73]
Fig. 49 The detection mechanism of probe G-55 for GSH[73]
表1 谷胱甘肽探针的传感性能及应用比较
Table 1 Comparison of GSH Probe Sensing Performance and Applications
Probe Fluorophore Detection limit (μmol·L-1) Detection range (μmol·L-1) Application ref
G-6 Coumarin 90 0~15 000 tumor margin recognition 25
G-9 Coumarin 0.12 / endogenous GSH 28
G-12 BODIPY 0.056 0~100 RAW 264.7 cells 31
G-14 BODIPY 1.07 / cervical cancer cell 33
G-16 Rhodamine 0.17 5~50 cell redox state 35
G-18 Rhodamine 0.07 1~3 human serum samples 37
G-20 Cyanine 0.33 0~100 identification and
sequence detection		 38
G-23 Benzothiazole 0.33 0~1000 living cells and zebrafish 41
G-27 Naphthalimide 0.10 2~150 tracer lysosomes 44
G-29 Metal-organic framework 97.5 500~10 000 clinical medicine 46
G-30 Metal-organic framework 0.57 1~70 human serum samples 47
G-38 Semiconductor quantum dots 0.92 1.95~104 indirect fluorometry 55
G-47 Carbon dots 0.076 5~32 H1299 cells 64
G-49 Carbon dots 1.53 10~2000 tumor targeted 67
G-50 Metal nano-fluorescent probes / 0~200 HeLa cells 68
G-55 Manganese dioxide nanosheet 0.22 0.5~20 pH and GSH dual sensing 73
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摘要

检测谷胱甘肽的荧光探针