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Biguanide probes and preparation method thereof

A technology of compounds and reporter groups, which can be used in the field of biomedicine and can solve problems to be studied.

Active Publication Date: 2017-11-28
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 probes and preparation method thereof
  • Biguanide probes and preparation method thereof
  • Biguanide probes and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] In this example, according to figure 1 Synthetic compound shown in formula VI:

[0059] The first step: the preparation of compound I:

[0060] 15.0 g of 2-phenylethylamine 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, washed with water and brine. The organic phase was dried with anhydrous sodium sulfate, and concentrated to obtain a crude product, which was purified by chromatography to obtain 13.9 g of white solid compound I with a purity of 90%.

[0061] The second step: the preparation of compound II:

[0062] Add 14.7g of aluminum trichloride to 300mL of nitrobenzene, place on ice, and slowly drop into 18.8g of 4-methoxybenzoyl chloride. After stirring on ice for 30 minutes, 12.0 g of compound I was added, heated to 100° C., and stirred overnight. After the reaction solution was naturally c...

Embodiment 2

[0072] The mouse liver primary cells were extracted and seeded into a 6-well plate, with a confluence of about 80% 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 wash with ice-cold PBS The cells were washed 3 times, the cells were 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] The mouse liver primary cells were extracted and seeded into a 6-well plate, with a confluence of about 80% 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, t...

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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 invention relates to the field of biomedicine. Specifically, the present invention relates to biguanide probes and methods for their preparation. Background technique [0002] Biguanides are a series of compounds derived from galegine (prenylguanidine) and containing a biguanide structure. The structural formula is as follows: [0003] [0004] Three biguanide compounds have been developed as diabetes drugs: metformin, phenformin and buformin, among which phenformin and buformin were withdrawn from the market in the 1970s due to the high risk of lactic acidemia and cardiotoxicity, and metformin Showed very good indicators of drug safety and tolerability. A number of studies (Gaochao Zhao et al., 2001; Shinichi Ota et al., 2009; Andre Madsen et al., 2015) have shown that metformin inhibits the expression of key genes in the gluconeogenesis pathway by activating AMPKα and inhibiting the expression of hepatic Gluconeogenesis of generational cell...

Claims

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Application Information

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Patent Type & Authority Applications(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