Preparation method and use of tripterine-chitosan oligosaccharide coupled drug

A technology of tripterine and chitosan oligosaccharides, which is applied in the field of medicine, can solve the problems of short biological half-life, poor water solubility, and large toxic and side effects of tripterine, and achieve weight loss, mild reaction conditions, and good water solubility.

Inactive Publication Date: 2021-04-09
HENAN UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the above situation, in order to solve the defects of the prior art, the purpose of the present invention is to provide a preparation method and application of tripterylide-chitooligosaccharide conjugated drug, which can effectively solve the problem of tripteryglide's large toxic and side effects, water-soluble Problems of poor sex and short biological half-life

Method used

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  • Preparation method and use of tripterine-chitosan oligosaccharide coupled drug
  • Preparation method and use of tripterine-chitosan oligosaccharide coupled drug
  • Preparation method and use of tripterine-chitosan oligosaccharide coupled drug

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Embodiment 1

[0025] The synthetic steps of tripterine-chitooligosaccharide conjugated drug one (CEL-CSO1) are:

[0026] 1) Activate tripterine

[0027] Weigh 100mg (0.22mmol) tripterine and dissolve in 3mL DMSO, then add 64mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC , 0.33mmol) and 45mg of 1-hydroxybenzotriazole (HOBt, 0.33mmol), stirred and activated at 25°C for 6h. 1), then the mobile phase was spin-dried to obtain 88.7mg solid product (71%);

[0028] 2) Synthesis of conjugated drug CEL-CSO1

[0029] Weigh 800 mg chitosan oligosaccharide (MW=1000) and dissolve it in dimethyl sulfoxide at 55°C, cool to 25°C after dissolving, add activated tripterine drop by drop, stir at 25°C for 24 hours, transfer the reaction solution into In a dialysis bag with a molecular weight cut-off of 500 Da, low-temperature dialysis was performed with double-distilled water for 24 hours, and the water was changed every 6 hours. The liquid in the bag was collected and freeze-dried to ob...

Embodiment 2

[0031] Tripterine-chitooligosaccharide conjugated drug two (CEL-CSO3) synthesis steps are:

[0032] 1) Activate tripterine

[0033] Weigh 100mg (0.22mmol) tripterine and dissolve in 3mL DMSO, then add 64mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC , 0.33mmol) and 45mg 1-hydroxybenzotriazole (HOBt, 0.33mmol), stirred and activated at 25°C for 6h, after the reaction was completed, the sample was wet-loaded and purified by silica gel chromatography (mobile phase CH2Cl2 / CH3OH, 30:1 ~20:1), then the mobile phase was spin-dried to give 88.7 mg of solid product (71%).

[0034] 2) Synthesis of coupled drug CEL-CSO3

[0035] Weigh 800 mg chitosan oligosaccharide (MW=3000) and dissolve it in dimethyl sulfoxide at 55°C, cool to 25°C after dissolving, add activated tripterine dropwise, stir at 25°C for 24h, and dissolve the reaction solution Transfer it into a dialysis bag with a molecular weight cut-off of 500 Da, dialyze with double distilled water at low tempe...

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Abstract

The invention relates to a preparation method and use of a tripterine-chitosan oligosaccharide coupled drug. The preparation method can effectively solve problems of large toxic and side effects, poor water solubility and a short biological half-life period of tripterine. A technical scheme to be solved is as follows: the tripterine-chitosan oligosaccharide coupled drug has a structural formula as follows, wherein, a molecular weight of chitosan oligosaccharide (CSO) is 320-3,200 Da, the acetyl content z is 0.1-0.8 (%), and x+y+z is 1-20. The preparation method has mild reaction conditions, strong controllability and high yield, water solubility of a final product is good, the prepared coupled drug has a good toxicity-reducing effect and the preparation method of the tripterine-chitosan oligosaccharide coupled drug is an innovation.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a preparation method and application of tripterine-chitooligosaccharide coupled medicine. Background technique [0002] Tripterygium wilfordii (CEL), also known as celastrol, is mainly a quinonemethyl triterpenoid compound extracted from the root of Tripterygium wilfordii, which has a wide range of anti-cancer, anti-inflammatory, and weight-loss effects. It is clinically , tripterine is widely used in the treatment of rheumatoid arthritis, systemic lupus erythematosus and chronic nephritis and other diseases, and can exert anti-inflammatory and anti-tumor effects through various channels. In the study, it was found that tripterine can also significantly reduce the weight of obese mice (DIO). It was found that tripterine is a leptin sensitizer, which reduces body weight by increasing the sensitivity of leptin. Tripterygium has become the most effective weight-loss drug reported so far, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/61A61K31/56A61P29/00A61P3/04A61P35/00C08B37/08
CPCA61K47/61A61K31/56A61P29/00A61P3/04A61P35/00C08B37/003
Inventor 曾华辉田启康武香香朱鑫闫敏王培智
Owner HENAN UNIV OF CHINESE MEDICINE
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