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Broad-spectrum reactive oxygen species scavenging material and preparation method and application thereof

A technology of active oxygen species and active oxygen, applied in the field of medicine, can solve problems such as unsatisfactory treatment results, achieve good in vivo biocompatibility, simple preparation method, and low cost

Active Publication Date: 2018-11-13
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, relevant clinical trials have shown that a single type of active oxygen scavenging may lead to unsatisfactory treatment results [21]

Method used

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  • Broad-spectrum reactive oxygen species scavenging material and preparation method and application thereof
  • Broad-spectrum reactive oxygen species scavenging material and preparation method and application thereof
  • Broad-spectrum reactive oxygen species scavenging material and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044] Under nitrogen protection, 10mmol 4-hydroxy-2,2,6,6-tetramethylpiperidine nitroxide and 20mmol N,N'-carbonyldiimidazole were reacted in 20mL anhydrous dichloromethane to obtain imidazole carbonyloxy -2,2,6,6-tetramethylpiperidine nitrogen oxide; in the presence of 9mmol 4-dimethylaminopyridine, 2mmolα-cyclodextrin and 6mmol imidazolecarbonyloxy-2,2,6,6-tetra Methyl piperidine nitroxide was reacted in 20 mL of dimethyl sulfoxide at 30°C. After 24 hours, the modified 2,2, Cyclodextrin material of 6,6-tetramethylpiperidine oxynitride.

[0045] Under nitrogen protection, 5mmol 3-hydroxymethyl phenylboronic acid pinacol ester and 10mmol N, N'-carbonyldiimidazole were reacted in 20mL anhydrous chloroform to obtain 3-imidazole carbonyloxy-phenylboronic acid pinacol ester; 9mmol 4 - In the presence of dimethylaminopyridine, 0.3mmol of cyclodextrin material modified with 2,2,6,6-tetramethylpiperidine nitroxide was mixed with 6mmol of 3-imidazolecarbonyloxy-phenylboronic acid pi...

Embodiment 2

[0049] Under nitrogen protection, 10mmol 4-amino-2,2,6,6-tetramethylpiperidine nitrogen oxide and 15mmol N,N'-carbonyldiimidazole were reacted in 15mL anhydrous chloroform to obtain imidazolecarbonylamino-2, 2,6,6-tetramethylpiperidine nitroxide; in the presence of 8 mmol N,N'-dicyclohexylcarbodiimide, 3 mmol β-cyclodextrin and 8 mmol imidazole carbonyloxy-2,2,6,6 -Tetramethylpiperidine nitroxide was reacted in 40mL N,N'-dimethylformamide at 40°C. After 12 hours, it was precipitated in 200mL methanol / ether (1:5), collected by centrifugation, and dried in vacuo A cyclodextrin material modified with 2,2,6,6-tetramethylpiperidine oxynitride was obtained.

[0050] Under nitrogen protection, 5mmol 4-hydroxymethylbenzeneboronic acid pinacol ester and 15mmol N, N'-carbonyldiimidazole were reacted in 30mL anhydrous dichloromethane to obtain 4-imidazolecarbonyloxy-phenylboronic acid pinacol ester; In the presence of 8mmol of N,N'-dicyclohexylcarbodiimide, 0.5mmol of cyclodextrin mater...

Embodiment 3

[0054] Under nitrogen protection, react 10mmol 4-hydroxy-2,2,6,6-tetramethylpiperidine nitroxide with 30mmol N,N'-carbonyldiimidazole in 20mL anhydrous tetrahydrofuran to obtain imidazolecarbonyloxy-2 ,2,6,6-tetramethylpiperidine nitroxide; in the presence of 5mmol N,N'-diisopropylcarbodiimide, 1mmolγ-cyclodextrin and 30mmol imidazolecarbonyloxy-2,2, 6,6-tetramethylpiperidine nitrogen oxide was reacted in 50mL N,N'-dimethylacetamide at 50°C, and after 8 hours, it was collected by precipitation in 50mL methanol / ether (1:1) and centrifuged and vacuum drying to obtain a cyclodextrin material modified with 2,2,6,6-tetramethylpiperidine nitrogen oxide.

[0055] Under nitrogen protection, 8mmol 3-hydroxymethylbenzeneboronic acid pinacol ester and 20mmol N, N'-carbonyldiimidazole were reacted in 25mL anhydrous ethyl acetate to obtain 3-imidazolecarbonyloxy-phenylboronic acid pinacol ester; In the presence of 5mmol of N,N'-diisopropylcarbodiimide, 0.1mmol of cyclodextrin material mod...

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Abstract

The invention discloses a broad-spectrum reactive oxygen species scavenging material and a preparation method and application of the broad-spectrum reactive oxygen species scavenging material. The chemical structure of the broad-spectrum reactive oxygen species scavenging material is as shown in the formula. The broad-spectrum reactive oxygen species scavenging material can effectively remove multiple reactive oxygen species (hydrogen peroxide, hypochlorite, superoxide anions and hydroxyl radicals) simultaneously. The broad-spectrum reactive oxygen species scavenging material is rapidly hydrolyzed in the presence of lower concentration of H2O2, and stable in other aqueous solutions, furthermore, low-dose materials are capable of scavenging large amounts of free radicals, so that the broad-spectrum reactive oxygen species scavenging material can be used for preparing medicines for treating diseases related to inflammation or oxidative stress injuries.

Description

technical field [0001] The invention relates to the field of medicine, in particular to the composition and preparation method of a broad-spectrum reactive oxygen species scavenging material and its application in preventing and treating inflammation-related diseases. Background technique [0002] Inflammation is an automatic defensive response produced by the body based on different stimuli [1] . In general, local and systemic inflammatory responses eliminate infection and promote repair and healing of damaged tissue. However, excessive and uncontrolled acute or chronic inflammatory responses can lead to a series of diseases, including rheumatoid arthritis, chronic pulmonary obstruction, hepatitis, diabetes, cardiovascular and cerebrovascular diseases, and neurodegenerative diseases, etc. [2-4] . Therefore, anti-inflammation is very important for the treatment of this series of diseases. Two classes of drugs, glucocorticoids and non-steroidal anti-inflammatory drugs, ha...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16A61K31/724A61P29/00A61P11/00A61P11/06A61P1/16A61P1/00A61P9/10
CPCA61K31/724A61P1/00A61P1/16A61P9/10A61P11/00A61P11/06A61P29/00C08B37/0012
Inventor 张建祥胡厚源李兰兰窦寅王玉泉张定林
Owner ARMY MEDICAL UNIV