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Application of 4-methyl-5,6-dihydropyran-2ketone in preparing anti-hepatic fibrosis and anti-hepatoma drugs

An anti-hepatic fibrosis and dihydropyran technology, applied in the direction of anti-tumor drugs, drug combinations, digestive system, etc., can solve problems such as poor prognosis and limited treatment options

Active Publication Date: 2019-10-18
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Surgery is the most commonly used treatment for liver cancer, but it is affected by various factors such as tumor size, location, and malignancy, and when liver cancer is discovered, it has generally developed to the middle and late stages, and only a small number of patients can be treated with surgery. Liver cancer patients have very limited treatment options and poor prognosis

Method used

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  • Application of 4-methyl-5,6-dihydropyran-2ketone in preparing anti-hepatic fibrosis and anti-hepatoma drugs
  • Application of 4-methyl-5,6-dihydropyran-2ketone in preparing anti-hepatic fibrosis and anti-hepatoma drugs
  • Application of 4-methyl-5,6-dihydropyran-2ketone in preparing anti-hepatic fibrosis and anti-hepatoma drugs

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preparation example Construction

[0027] The present invention has no special requirements on the source of the 4-methyl-5,6-dihydropyran-2-one, use commercially available 4-methyl-5,6-dihydropyran-2-one or Can be prepared. When it is necessary to prepare 4-methyl-5,6-dihydropyran-2-one by itself, the preparation method of 4-methyl-5,6-dihydropyran-2-one preferably includes the following steps:

[0028] Under the action of a catalyst, the mevalonolactone is eliminated to obtain 4-methyl-5,6-dihydropyran-2-one.

[0029] In the present invention, the catalyst is preferably p-toluenesulfonic acid monohydrate; the mass ratio of the mevalonolactone to the catalyst is preferably 20:1; in the present invention, the solvent used in the elimination reaction is preferably Toluene, the present invention has no special requirements on the amount of the solvent, as long as the mevalonolactone and the catalyst can be dissolved. In the present invention, the temperature of the elimination reaction is preferably the reflux ...

Embodiment 1

[0042] Example 1 4-Methyl-5,6-dihydropyran-2one has no toxicity to LX2 cells

[0043] Using different concentrations of 4-methyl-5,6-dihydropyran-2-one (hereinafter referred to as C8) (50, 100, 150, 200, 300 μmol L -1 ) Treat human hepatic stellate cells LX2 in the logarithmic growth phase for 24 hours, and use the sulforhodamine B protein staining (SRB) colorimetric method to detect the effect of the compound on cell proliferation. The specific operation method is as follows:

[0044] (1) Cell plating: cells in the logarithmic growth phase were seeded in 96-well culture plates, at 37°C, 5% CO 2 Cultivate under the condition for 24h;

[0045] (2) Administration: After the cells adhere to the wall, the original medium is discarded, and the compound stock solution is prepared into a gradient concentration with the medium, and the blank control group, the vehicle control group, and the administration group are respectively set up, and each concentration is set to 3 Duplicate we...

Embodiment 2

[0052] Example 2 4-methyl-5,6-dihydropyran-2one inhibits the activity of COL1A1 promoter in hepatic stellate cells

[0053] The most important feature of liver fibrosis is the overexpression of collagen, especially type I collagen α1 (COL1A1). High expression is manifested at the transcriptional level. If the promoter activity can be inhibited, collagen production can be inhibited, thereby inhibiting liver fibrosis. Therefore, the effect of 4-methyl-5,6-dihydropyran-2one on the activity of collagen promoter was used as an index to initially judge the anti-hepatic fibrosis effect of potential drugs.

[0054] Using a high-throughput anti-hepatic fibrosis screening model based on the COL1A1 promoter, a single luciferase gene reporter assay system was used to detect different concentrations of 4-methyl-5,6-dihydropyran-2-one (3, 20, 50 and 100μmol·L -1 ) and positive control 25 μmol L -1 Indicate the impact of gallocatechin gallate (EGCG) on the activity of the COL1A1 promoter...

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Abstract

The invention provides application of 4-methyl-5,6-dihydropyran-2ketone in preparing anti-hepatic fibrosis and anti-hepatoma drugs, and belongs to the technical field of anti-hepatic fibrosis and anti-hepatoma drugs. It is found that the 4-methyl-5,6-dihydropyran-2ketone has good anti-hepatic fibrosis activity and activity for inhibiting the hepatoma carcinoma cell migration, and can be used for preparing the anti-hepatic fibrosis and anti-hepatoma drugs. Embodiment results show that the 4-methyl-5,6-dihydropyran-2ketone can inhibit the activity of type I collagen alpha 1 promoter, reduce theexpression of hepatic fibrosis markers such as COL1A1 and ACTA3 in hepatic stellate cells LX-2, improve the liver tissue pathological structure and hepatic fibrosis degree in BDL mice, and inhibit themigration of hepatoma carcinoma cells HepG2.

Description

technical field [0001] The invention relates to the technical field of anti-hepatic fibrosis and liver cancer drugs, in particular to the application of 4-methyl-5,6-dihydropyran-2one in the preparation of anti-hepatic fibrosis and anti-liver cancer drugs. Background technique [0002] Chronic liver disease is a worldwide disease that seriously endangers human health. Various factors such as viral infection (HBV HCV), poison (aflatoxin), alcohol, and congenital metabolic defects can cause chronic liver disease. Hepatic fibrosis is a compensatory response in the tissue repair process secondary to liver injury and inflammation caused by various chronic factors. Further development of hepatic fibrosis can lead to liver cirrhosis, liver failure and liver cancer. Studies have found that liver fibrosis is a reversible disease. If effective treatment can be given at this stage, it will be of great significance to the treatment of chronic hepatitis and the prevention of severe fatal...

Claims

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Application Information

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IPC IPC(8): A61K31/351A61P1/16A61P35/00
CPCA61K31/351A61P1/16A61P35/00
Inventor 何红伟陈明华牛伟晓张娜葛茂旭路振宁鲍云洋
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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