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Fluorescent probe for detecting high-concentration gamma-Glutamyl Transpeptidase and preparation method thereof

A technology of glutamyl transpeptidase and fluorescent probe, which is applied in the field of analytical chemistry, and achieves the effects of low preparation cost, easy promotion, and simple synthesis process

Active Publication Date: 2018-11-27
川北医学院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the steric hindrance caused by the bulky substituent on the boron central atom, triarylboron exhibits higher selectivity to fluoride ions, so triarylboron fluorescent derivatives are used in the design of F ion fluorescent probes , but this F ion fluorescent probe can generally only be applied in organic solvents
However, there are no reports in the literature on the design of bioluminescent probes for the application of triaryl borons in GGT detection.
[0009] In addition, almost all fluorescent probes reported for GGT detection can only be used for detection within the normal GGT concentration range of the human body.

Method used

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  • Fluorescent probe for detecting high-concentration gamma-Glutamyl Transpeptidase and preparation method thereof
  • Fluorescent probe for detecting high-concentration gamma-Glutamyl Transpeptidase and preparation method thereof
  • Fluorescent probe for detecting high-concentration gamma-Glutamyl Transpeptidase and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Synthesis of TAB-3-GSH

[0056]

[0057] (1) Preparation of Compound 2: Under the protection of nitrogen, 10g (32mmol) of Compound 2 was dissolved in 60mL of dry ether, cooled to -78°C, and 20mL of 1.6M n-butyllithium n-hexane was added dropwise. Hexane solution. The reaction was warmed to room temperature and stirred for 20 min. Then, it was cooled to -78°C again, and 1.25 mL (10 mmol) of boron trifluoride ether was added. The reaction continued at room temperature and stirred overnight. The solvent was spin-dried, and further purified by silica gel column chromatography to obtain 4.0 g of white solid with a yield of 71%.

[0058] (2) Preparation of compound 3: Put 595 mg (3.2 mmol) of N-butyl ester piperazine, 560 mg (1 mmol) of compound 2, 864 mg (9 mmol) of sodium tert-butyl alkoxide, and 27 mg (0.12 mmol) of palladium acetate into three mouths In the bottle, pump three times on a double-row tube, under the protection of nitrogen, add 50 mL of toluene, and then add 2...

Embodiment 2

[0063] Synthesis of TAB-3-Cys-Gly

[0064]

[0065] (1) Preparation of Compound 2: Under the protection of nitrogen, 10g (32mmol) of Compound 2 was dissolved in 60mL of dry ether, cooled to -78°C, and 20mL of 1.6M n-butyllithium n-hexane was added dropwise. Hexane solution. The reaction was warmed to room temperature and stirred for 20 min. Then, it was cooled to -78°C again, and 1.25 mL (10 mmol) of boron trifluoride ether was added. The reaction continued at room temperature and stirred overnight. The solvent was spin-dried, and further purified by silica gel column chromatography to obtain 4.0 g of white solid with a yield of 71%.

[0066] (2) Preparation of compound 3: Put 595 mg (3.2 mmol) of N-butyl ester piperazine, 560 mg (1 mmol) of compound 2, 864 mg (9 mmol) of sodium tert-butyl alkoxide, and 27 mg (0.12 mmol) of palladium acetate into three mouths In the bottle, pump three times on a double-row tube, under the protection of nitrogen, add 50 mL of toluene, and then a...

Embodiment 3

[0071] Synthesis of TAB-3-Cys

[0072]

[0073] (1) Preparation of Compound 2: Under the protection of nitrogen, 10g (32mmol) of Compound 2 was dissolved in 60mL of dry ether, cooled to -78°C, and 20mL of 1.6M n-butyllithium n-hexane was added dropwise. Hexane solution. The reaction was warmed to room temperature and stirred for 20 min. Then, it was cooled to -78°C again, and 1.25 mL (10 mmol) of boron trifluoride ether was added. The reaction continued at room temperature and stirred overnight. The solvent was spin-dried, and further purified by silica gel column chromatography to obtain 4.0 g of white solid with a yield of 71%.

[0074] (2) Preparation of compound 3: Put 595 mg (3.2 mmol) of N-butyl ester piperazine, 560 mg (1 mmol) of compound 2, 864 mg (9 mmol) of sodium tert-butyl alkoxide, and 27 mg (0.12 mmol) of palladium acetate into three mouths In the bottle, pump three times on a double-row tube, under the protection of nitrogen, add 50 mL of toluene, and then add 2...

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Abstract

The invention provides a fluorescent probe for detecting high-concentration gamma-Glutamyl Transpeptidase, which solves the problem of selective response to abnormally high-concentration gamma-Glutamyl Transpeptidase in vivo. The fluorescent probe of the invention starts to produce obvious fluorescence changes after the gamma-Glutamyl Transpeptidase is higher than the normal concentration of humanbody, and as the concentration of gamma-Glutamyl Transpeptidase increases, the fluorescent probe solution of the invention produces large fluorescence enhancement and obvious color change. At the same time, after the fluorescent probe of the invention reacts with gamma-Glutamyl Transpeptidase, the permeability of the cell membrane is greatly enhanced, and when applied to cell imaging, the fluorescent probe can selectively image ovarian cancer cells with high expression of gamma-Glutamyl Transpeptidase. According to the invention, the synthesis process is simple and feasible, the raw materialsare cheap and easy to obtain, the preparation cost is low, and the preparation method is easy to popularize.

Description

Technical field [0001] The invention relates to a novel fluorescent probe for detecting γ-glutamyl transpeptidase and a preparation method thereof, in particular to a fluorescent probe for detecting high-concentration γ-glutamyl transpeptidase and preparation method thereof The method belongs to the technical field of analytical chemistry. Background technique [0002] Gamma-glutamyl transpeptidase (GGT) is an enzyme that exists on the surface of cells and plays an important role in many physiological processes. According to reports, in adult women and adult men, the normal concentration of GGT is 5-55U / L and 15-85U / L, respectively. In some liver and gallbladder diseases, the GGT concentration level can rise to more than 10 times the normal concentration. GGT is also overexpressed in a variety of human tumor cells, such as ovarian cancer, cervical cancer and liver cancer. Therefore, the detection of GGT concentration has important clinical diagnostic value in the evaluation of...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F5/02C07K5/037C07K1/02A61K49/00
CPCA61K49/0021C07F5/027C07K5/0215C07K19/00C09K11/06C09K2211/1007C09K2211/1044Y02P20/55
Inventor 刘军张小明沈成仪
Owner 川北医学院
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