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Fluorescent probe for detecting glutathione in blood, and synthesis method and application thereof

A technology of glutathione and fluorescent probes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of non-specific recognition of GSH, achieve specific recognition ability, fast response speed, selective sex high effect

Active Publication Date: 2017-06-20
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At the same time, the organism is also rich in other sulfhydryl-containing biomolecules, such as cysteine ​​(Cys) and homocysteine ​​(Hcy), their structures are similar to GSH, and the sulfhydryl groups they contain can also be similar to probe molecules. response, making the probe appear to be non-specific for GSH recognition

Method used

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  • Fluorescent probe for detecting glutathione in blood, and synthesis method and application thereof
  • Fluorescent probe for detecting glutathione in blood, and synthesis method and application thereof
  • Fluorescent probe for detecting glutathione in blood, and synthesis method and application thereof

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Embodiment 1

[0028] The following examples will further illustrate the present invention, but do not limit the present invention thereby. Example 1: Preparation of a fluorescent probe for detecting GSH in blood, the basic synthesis method is as follows:

[0029] In a 50mL single-necked bottle, add rhodamine fluorescein precursor compound (0.2mmol) and 2,4-dinitrobromobenzene 63mg (0.25mmol), add acetonitrile 10mL, triethylamine 0.5mL, heat and reflux at 80°C for 6h, after cooling Add 4 times the volume of dichloromethane, then extract 3 times with saturated saline, dry, filter, spin dry the solvent, pass through a silica gel column at room temperature, and elute under the condition of dichloromethane: anhydrous methanol = 20:1 The product was obtained in 70% yield.

[0030] The hydrogen spectrum and carbon spectrum data of the probe molecule are as follows: 1 H NMR (400MHz, CDCl3) δ8.85 (d, J = 4Hz, 1H), 8.36 (dd, J = 9.2, 2.4Hz, 1H), 8.03 (d, J = 7.6Hz, 1H), 7.68 (t, J=7.2Hz, 1H), 7.62...

Embodiment 2

[0031] Embodiment 2: the response situation of the fluorescent probe prepared in embodiment 1 to GSH in the presence of GST

[0032] The probe was dissolved in DMSO solution to prepare 10 -3 Stock solution of M, in 4 mL, 20 mM pH=7.4

[0033] 1 μM probe, mixed solution of probe (1 μM) and GSH (5 μM), mixed solution of probe (1 μM) and GST (1 μM), probe (1 μM), GSH (5 μM) and GST were respectively configured in the PBS solution (1μM) mixed solution, measure the fluorescence to get Figure 5 .

[0034] Figure 5 In the presence of only the probe (1 μM), it showed weak fluorescence, and when only GSH (5 μM) was added to the probe solution, the fluorescence was only slightly enhanced. However, when GSH is added in the presence of 1 μM GST, the fluorescence is significantly enhanced, the enhancement is about 35 times, and the emission wavelength is in the near-infrared region (~700nm).

Embodiment 3

[0035] Embodiment 3: the selectivity of the fluorescent probe prepared in embodiment 1

[0036] Add 1 μM probe and 1 μM GST to 4 mL of 20 mM PBS solution with pH=7.4, then add 5 μM of 20 kinds of amino acids and GSH respectively, and measure the fluorescence to obtain Figure 6 , the results showed that the fluorescence was significantly enhanced only after the addition of GSH, indicating that this probe can specifically recognize GSH.

[0037] Add 1 μM probe, 1 μM GST to 4 mL, 20 mM PBS solution with pH=7.4, then add 5 μM GSH, Cys and Hcy respectively, and measure the fluorescence intensity to obtain Figure 7 . The results showed that the fluorescence was significantly enhanced only when GSH was added, which proved that the probe did not respond to the biosulfhydryl compounds Cys and Hcy that existed in large quantities in the organism, and further proved the selective recognition ability of the probe to GSH.

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Abstract

The invention discloses a fluorescent probe for detecting the content of glutathione (GSH) in blood, and a synthesis method and an application thereof. The synthesis steps of the probe are simple, and the light stability is good. In the detection process, the fluorescent probe firstly as a substrate is combined with glutathione S-transferase (GST), and undergoes a reaction with another specific substrate GSH of the GST to produce fluorescence, the fluorescence is enhanced by about 35 times, and the maximum emission wavelength is at the near infrared region (beyond 700 nm). Compared with conventional GSH fluorescent probes, the probe can specifically detect the content of the GSH in a complex system, and has the advantages of wide dynamic response window, high efficiency and the like. The probe realizes the specific and high-efficiency identification on the GSH in the complex environment, and has extremely important application value in the biological and medical fields.

Description

technical field [0001] The invention belongs to the field of biological analysis and detection, and in particular relates to a fluorescent probe for detecting GSH in blood, its synthesis method and application. Background technique [0002] Reduced glutathione (GSH) is the main non-protein sulfhydryl compound in organisms, and is an important molecule to maintain the normal operation of the body. Its existence can not only prevent aging, cancer, heart disease, senile dementia and other diseases, but also an important criterion for evaluating Parkinson's disease and Alzheimer's disease. In the body's metabolic process, GSH plays a role in fighting oxidative stress and detoxifying exogenous compounds. Studies have shown that the liver, an important organ of metabolism, contains a large amount of GSH, and changes in the concentration of GSH in liver cells will affect the activity of mitochondrial membrane transport proteins, thereby affecting liver function. Compared with the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/052C09K11/06G01N21/64
CPCC07D491/052C09K11/06C09K2211/1007C09K2211/1044C09K2211/1088G01N21/6428
Inventor 徐兆超苗露冯薇
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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