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Biguanide probe and preparation method thereof

A compound and labeling technology, applied in the field of biomedicine, can solve problems that need to be studied

Active Publication Date: 2020-03-27
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, current biguanide drug detection probes are still under investigation

Method used

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  • Biguanide probe and preparation method thereof
  • Biguanide probe and preparation method thereof
  • Biguanide probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] In this example, according to figure 1 Synthesis of compound represented by formula VI:

[0059] Step 1: Preparation of Compound I:

[0060] 15.0 g of 2-phenethylamine hydrochloride was added to 500 mL of DCM, 24.5 g of triethylamine and 9.0 g of acetyl chloride were added on ice, and the reaction was stirred on ice for 5 hours. The reaction solution was returned to room temperature and washed with water and brine. The organic phase was dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was purified by chromatography to obtain 13.9 g of compound I as a white solid with a purity of 90%.

[0061] Step 2: Preparation of Compound II:

[0062] 14.7 g of aluminum trichloride was added to 300 mL of nitrobenzene, placed on ice, and 18.8 g of 4-methoxybenzoyl chloride was slowly added dropwise. After stirring on ice for 30 minutes, 12.0 g of compound I was added, heated to 100°C, and the reaction was stirred overnight. The reaction solutio...

Embodiment 2

[0072] Primary mouse liver cells were extracted and seeded into 6-well plates at about 80% confluence before the experiment. Add medium without (negative control group), with different concentrations of metformin, phenformin (positive control group) or with different concentrations of compound VI (experimental group), incubate at 37°C for 30 minutes, then remove the medium and add ice-cold PBS. The cells were washed 3 times, collected, RNA was extracted, reverse transcribed into cDNA, and the gene expression changes of G6PC were detected by qPCR. The result is as figure 2 shown.

[0073] Primary mouse liver cells were extracted and seeded into 6-well plates at about 80% confluence before the experiment. Add medium without (negative control group), with different concentrations of metformin, phenformin (positive control group) or with different concentrations of compound VI (experimental group), incubate at 37°C for 30 minutes, then remove the medium and add ice-cold PBS. W...

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Abstract

The invention provides compounds, a preparation method thereof, an application of the compounds in kit preparation, a method for screening drug targets and a method for determining whether the drug targets exist in a sample. Each compound contains an active group and a potential reporter group, wherein the active group has a structure represented as a formula in the description, and the potential reporter group is alkynyl. The compounds can specifically identify and be bound with in-vivo acting targets of biguanides without affecting cell permeability and facilitate observation, separation and purification of target protein. The compounds further have activity of biguanides, and have great significance on study of the in-vivo acting targets of biguanides as well as structural information such as action modes of drugs and the targets, active sites and the like.

Description

technical field [0001] The present invention relates to the field of biomedicine. Specifically, the present invention relates to biguanide probes and preparation methods thereof. Background technique [0002] Biguanides are a series of compounds derived from galegine (galegine, isopentenidine), containing the biguanide structure. The structural formula is as follows: [0003] [0004] Three biguanide compounds have been developed as diabetes drugs: metformin, phenformin, and buformin, of which phenformin and buformin were withdrawn from the market in the 1970s due to their high risk of lactic acidemia and cardiotoxicity, while metformin It showed very good drug safety and tolerability indicators. Several studies (Gaochao Zhao et al., 2001; Shinichi Ota et al., 2009; Andre Madsen et al., 2015) showed that metformin inhibited mouse hepatogens by activating AMPKα and downregulating the expression of key genes in the gluconeogenesis pathway. Generation of cellular gluconeo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C279/26G01N21/64
CPCC07C279/26G01N21/6428G01N21/6486G01N2021/6439
Inventor 陈立功程丽丽梁宇李月明汪舰郎明
Owner TSINGHUA UNIV