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γ-glutamyl transpeptidase biological probe and its preparation method and application

A technology of reaction and application, applied in the field of γ-glutamyl transpeptidase biological probe and its preparation and application, can solve the problems of high detection cost, large consumption of organic solvent, large environmental pollution, etc., and achieves good selectivity and high efficiency. Sensitivity, fewer synthesis steps, and shorter reaction times

Active Publication Date: 2020-11-24
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, among these analysis methods, the detection accuracy of the colorimetric method is low, and the use of high-performance liquid chromatography requires a large amount of organic solvents, which causes great environmental pollution, high detection costs, and is difficult to achieve trace detection; Dependence on photobleaching and autofluorescence, which can not be ignored, also limits its further application.

Method used

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  • γ-glutamyl transpeptidase biological probe and its preparation method and application
  • γ-glutamyl transpeptidase biological probe and its preparation method and application
  • γ-glutamyl transpeptidase biological probe and its preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0059] Preparation of compound (1)

[0060]

[0061] Under argon protection, N-BOC-L-glutamic acid-1-tert-butyl ester (3.3mmol, 1.01g) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide Hydrochloride (3.3mmol, 632.6mg) was dissolved in 6ml of dichloromethane, and a solution of 4-aminobenzyl alcohol (3.0mmol, 369mg) dissolved in 4mL of dichloromethane was slowly added dropwise at 0°C, and stirred at room temperature for 1.5h . After the reaction was completed, the organic phase was spin-dried, and the crude product was passed through a silica gel column with a developing solvent of ethyl acetate / petroleum ether / methanol to obtain a white solid (945mg, 78%). ESI (C 21 h 32 N 2 o 6 ):[M+23] + = 431.4. 1 H-NMR (400MHz, CD 4 O), δ: 7.54(d, J=8.4, 2H), 7.31(d, J=8.4, 2H), 4.57(s, 2H), 4.05-4.01(m, 1H), 2.46(t, J=7.6 ,2H),2.23-2.15(m,1H),2.03-1.94(m,1H),1.49(s,9H),1.45(s,9H).

Embodiment 2

[0063] Preparation of compound (2)

[0064]

[0065] Under argon protection, compound 1 (1.16mmol, 500mg) and triethylamine (1.27mmol, 0.3ml) were dissolved in 10ml of dichloromethane, and p- Tosyl chloride (2.52mmol, 480mg), continued stirring for 2.5h. After the reaction was completed, the organic phase was spin-dried, and the crude product was passed through a silica gel column with the developer ethyl acetate / petroleum ether to obtain a white solid intermediate (690 mg, 46%). Under argon protection, the intermediate product (1.2mmol, 660mg), 2-cyano-6-hydroxybenzothiazole (1.4mmol, 246.7mg), potassium carbonate (7.1mmol, 981.3mg), sodium iodide (0.4 mmol, 59.9mg) was dissolved in 12mL of acetonitrile and reacted at 85°C for 5h. After the reaction was completed, the reaction solution was filtered, the organic phase was extracted with dichloromethane, and the organic phase was spin-dried, and the crude product was passed through a silica gel column with a developer ethy...

Embodiment 3

[0067] Preparation of compound (3)

[0068]

[0069] Under argon protection, compound 2 (0.42mmol, 240mg) was dissolved in a mixed solvent of 5ml methanol and dichloromethane (v / v=1:1), and added with a mixed solvent of 5ml methanol and deionized water (v / v=1:1) solution of dissolved D-cysteine ​​hydrochloride (0.45 mmol, 55 mg) and potassium carbonate (0.45 mmol, 62 mg). React at room temperature for 20 minutes. After the reaction, the organic solvent was spin-dried, an equal volume of water was added, and the pH was adjusted to about 2-3 with 1M hydrochloric acid solution. The crude product obtained was a yellow solid. The crude product was recrystallized from methanol to give a slightly yellow product (100 mg, 53.9%). ESI (C 32 h 38 N 4 o 8 S 2 ):[M-1] — = 669.8. 1 H-NMR (300MHz, DMSO), δ: 9.96(s, 1H), 8.04(d, J=9.0Hz, 1H), 7.84(s, 1H), 7.60(d, J=8.3Hz, 2H), 7.40 (d, J=8.4Hz, 2H), 7.30–7.19(m, 1H), 7.13(d, J=7.4Hz, 1H), 5.39(t, J=9.0Hz, 1H), 5.12(s, 2H) ,4.0...

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Abstract

The present invention relates to a gamma-glutamyltranspeptidase detection bioluminescent probe structure represented by general formulas (IA) and (IB), a preparation method and applications thereof. According to the present invention, a class of the gamma-glutamyltranspeptidase detection bioluminescent probes are synthesized by chemically modifying luciferin-like substances and linking with a gamma-glutamyl group having GGT reaction specificity, and have extremely high sensitivity and extremely high selectivity to the GGT in cells and blood; and the gamma-glutamyltranspeptidase bioluminescentprobe has advantages of simple operation, efficient specificity, rapidness, sensitivity and the like, and is suitable for popularization and application. The formulas (IA) and (IB) are defined in thespecification.

Description

technical field [0001] The invention discloses the structure, preparation method and application of a class of bioluminescence probes for gamma-glutamyl transpeptidase detection. Background technique [0002] γ-Glutamyl transpeptidase (GGT) widely exists in organisms and is one of the key enzymes in glutathione (GSH) metabolism. GGT has three catalytic functions: transpeptide, autotranspeptide, and hydrolysis. By specifically catalyzing the transfer of γ-glutamyl groups, it participates in the cycle of glutathione and the transmembrane transport of amino acids. As a cell membrane-bound enzyme, GGT plays an important role in a series of important physiological processes. According to reports, abnormal GGT content in the body is usually associated with some major physiological diseases such as tumors, diabetes, and liver or gallbladder lesions. Therefore, the rapid detection of the level of GGT in cells and serum is of great significance in life science and medical clinical ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/62G01N21/64
CPCC07D277/62G01N21/6486
Inventor 杨国强李双胡睿杨晨临张欣王双青
Owner INST OF CHEM CHINESE ACAD OF SCI
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