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A kind of fluorescent probe for detecting gsh with high specificity and its application

A fluorescent probe, high specificity technology, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve problems such as failure to distinguish, and achieve the effect of simple method, low toxicity and good linearity

Active Publication Date: 2022-07-01
THE AFFILIATED HOSPITAL OF SOUTHWEST MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for the currently reported GSH fluorescent probes, most of them detect sulfhydryl groups, and fail to distinguish GSH, CYS (cysteine) and HCYS (homocysteine)

Method used

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  • A kind of fluorescent probe for detecting gsh with high specificity and its application
  • A kind of fluorescent probe for detecting gsh with high specificity and its application
  • A kind of fluorescent probe for detecting gsh with high specificity and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] A fluorescent probe for the detection of GSH with high specificity, such as figure 1 As shown, the fluorescent probe is a 3-benzothiazolyl-coumarin-7-phenol ester derivative, wherein R 1 is methyl, R 2 for the chlorine atom. like figure 2 As shown, the fluorescent probe uses 3-benzothiazolyl-7-hydroxycoumarin compounds as raw materials, and obtains 3-benzothiazolyl-coumarin-7-phenol ester derivatives through esterification . Using 3-benzothiazolyl-7-hydroxycoumarin as raw material, and esterification with 2-chloroacetic acid to obtain 2-chloroacetic acid 3-benzothiazolyl-coumarin-7-phenol ester. like image 3 , Image 6 As shown, we have successfully prepared 3-benzothiazolyl-coumarin-7-phenol 2-chloroacetate.

[0050] Compounds with coumarin core structure all have good fluorescence emission spectrum characteristics (450-650nm). In the present invention, coumarin and benzothiazole are connected as a new type of fluorescent probe, through the generation and quen...

Embodiment 2

[0052] A fluorescent probe for the detection of GSH with high specificity, such as figure 1 As shown, the fluorescent probe is a 3-benzothiazolyl-coumarin-7-phenol ester derivative, wherein R 1 is methyl, R 2 for the chlorine atom. like figure 2 As shown, the fluorescent probe uses 3-benzothiazolyl-7-hydroxycoumarin compounds as raw materials, and obtains 3-benzothiazolyl-coumarin-7-phenol ester derivatives through esterification . 3-benzothiazolyl-7-hydroxycoumarin is used as raw material, and 3-chloropropionic acid 3-benzothiazolyl-coumarin-7-phenol ester is obtained by esterification reaction with 3-chloropropionic acid. like Figure 4 , Figure 7 As shown, we have successfully prepared 3-benzothiazolyl-coumarin-7-phenol 3-chloropropanoate.

[0053] Compounds with coumarin core structure all have good fluorescence emission spectrum characteristics (450-650nm). In the present invention, coumarin and benzothiazole are connected as a new type of fluorescent probe, thro...

Embodiment 3

[0055] A fluorescent probe for the detection of GSH with high specificity, such as figure 1 As shown, the fluorescent probe is a 3-benzothiazolyl-coumarin-7-phenol ester derivative, wherein R 1 is methyl, R 2 for the chlorine atom. like figure 2 As shown, the fluorescent probe uses 3-benzothiazolyl-7-hydroxycoumarin compounds as raw materials, and obtains 3-benzothiazolyl-coumarin-7-phenol ester derivatives through esterification . 3-benzothiazolyl-7-hydroxycoumarin is used as raw material, and 3-bromopropionic acid 3-benzothiazolyl-coumarin-7-phenol ester is obtained by esterification with 3-bromopropionic acid. like Figure 5 , Figure 8 As shown, we have successfully prepared 3-benzothiazolyl-coumarin-7-phenol 3-bromopropanoate.

[0056] Compounds with coumarin core structure all have good fluorescence emission spectrum characteristics (450-650nm). In the present invention, coumarin and benzothiazole are connected as a new type of fluorescent probe, through the gene...

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Abstract

The invention discloses a fluorescent probe for detecting GSH with high specificity and an application thereof. The fluorescent probe is a 3-benzothiazolyl-coumarin-7-phenol ester derivative; the fluorescent probe is used as a GSH detector. A specific probe, the ester bond of the fluorescent probe can recognize the sulfhydryl group in GSH, and generate a substitute with fluorescent properties, which is an off-on type fluorescent reaction. The invention connects coumarin and benzothiazole as a new type of fluorescent probe, and realizes detection through the generation and quenching of fluorescence, and has high detection sensitivity. The cytotoxicity of the fluorescent probe provided by the present invention is low, the structure of the fluorescent probe uses coumarin as the mother nucleus, and the toxic effect on cells is small, and has good biocompatibility, and can be widely used in living cells , tissue in vivo. The detection process of the fluorescent probe in the present invention is not easily interfered by the biological system matrix and impurities, and can be used for quantitative determination of GSH in various biological systems.

Description

technical field [0001] The invention belongs to the technical field of fine chemical industry, and in particular relates to a fluorescent probe for detecting GSH with high specificity and its application. Background technique [0002] GSH is a tripeptide containing sulfhydryl, amino and γ-amide bonds that widely exists in various biological cells. It is mainly composed of glutamic acid, cysteine ​​and glycine. This specific structure makes it an important antibody in the body. Oxidants and free radical scavengers, responsible for protecting proteins and other biological macromolecules, reducing the invasion of various biological macromolecules and damage to biological membranes by free radicals, maintaining the integrity of red blood cell membranes, as well as DNA biosynthesis and cellular immunity, etc. physiological function. In addition, GSH can be combined with toxic compounds, heavy metal ions or carcinogens that enter the human body, and promote their excretion from t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/04C09K11/06G01N21/64
Inventor 梁思成李昊刘增金吕沐瀚吴建明齐晓怡邓明明
Owner THE AFFILIATED HOSPITAL OF SOUTHWEST MEDICAL UNIV