Tetramethylpyrazine derivatives modified silk fibroin protein fiber anti-coagulant material and its preparation method

A technology of silk fibroin and ligustrazine, applied in the field of biomedical materials

Inactive Publication Date: 2007-10-17
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chemical modification of silk fibroin fibers with ligustrazine derivatives without initiators has not been reported

Method used

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  • Tetramethylpyrazine derivatives modified silk fibroin protein fiber anti-coagulant material and its preparation method
  • Tetramethylpyrazine derivatives modified silk fibroin protein fiber anti-coagulant material and its preparation method
  • Tetramethylpyrazine derivatives modified silk fibroin protein fiber anti-coagulant material and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0021] (1) Preparation of 2,5-diacryloyloxymethylene-3,6-dimethylpyrazine (PZOE2)

[0022] Synthesize 2,5-dimethylol-3,6-dimethylpyrazine (TMPD2) according to literature (see Chinese patent, application number 200410042876.9[2]), with a melting point of 76-83°C. Then in a 100ml round bottom flask, 1.23g TMPD2 was dissolved in a mixed solution of 15ml DMF and 1.36ml pyridine, 1.2ml acryloyl chloride was dissolved in 15ml DMF, and was added dropwise into the flask from a constant pressure funnel, and the dropwise addition was completed in one hour. The reaction was continued for 24 hours and left to stand for 48 hours. After filtration, the reaction solution was poured into a large amount of glacial ether, and a pale yellow precipitate appeared, which was collected after centrifugation to obtain an orange-red substance. The remaining ether was evaporated at room temperature. Obtain 2,5-diacryloyloxymethylene-3,6-dimethylpyrazine, FTIR (KBr): 1731cm -1 (C=O, ester carbonyl), 1...

preparation example 2

[0031] (1) Preparation of 2-acryloyloxymethylene-5-hydroxymethyl-3,6-dimethylpyrazine (PZOHOE)

[0032] In a 100ml round bottom flask, dissolve 1.23g TMPD2 in a mixed solution of 15ml DMF and 0.7ml pyridine, and dissolve 0.7ml acryloyl chloride in 15ml DMF, and drop them into the flask from a constant pressure funnel. After one hour, continue the reaction 24 hours, let stand for 48 hours. After filtration, the reaction solution was poured into a large amount of glacial ether, and a pale yellow precipitate appeared, which was collected after centrifugation to obtain an orange-red substance. The remaining ether was evaporated at room temperature. Obtain 2-acryloyloxymethylene-5-hydroxymethyl-3,6-dimethylpyrazine, FTIR (KBr): 1735cm -1 (C=O, ester carbonyl), 1489cm -1 (-N=C-, pyrazine ring), at 1172cm -1 (C-O-C).

[0033] (2) Preparation of silk fibroin fibers.

[0034] Repeat the steps of Preparation Example 1

[0035] (3) Chemical modification of silk fibroin fibers

[...

preparation example 3

[0040] (1) Preparation of 2-acryloyloxymethylene-3,5,6-trimethylpyrazine (PZOE)

[0041] Synthesize 2-hydroxymethyl-3,5,6-trimethyl according to the literature (see "Research on the Structure Modification of Ligustrazine and Its Anticoagulant Property" Beijing Institute of Technology Master's Degree Thesis (2004): Author: Xia Chengjian [3]) Pyrazine (TMPD1), melting point 70~72℃. Dissolve 0.91g TMPD1 in a mixed solution of 11.5ml DMF and 0.485ml pyridine, dissolve 0.487ml acryloyl chloride in 11.5ml DMF, and drop them into the flask from a constant pressure funnel; after one hour, continue to react for 24 hours, Set 48h. After filtration, the reaction solution was poured into a large amount of glacial ether, and a pale yellow precipitate appeared, which was collected after centrifugation to obtain an orange-red substance. The remaining ether was evaporated at room temperature. Obtained 2-methacrylate-5-hydroxymethyl-3,6-dimethylpyrazine, FTIR (KBr): 1731cm -1 (C=O, ester c...

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Abstract

Disclosed are three kinds of ligustrazine derivatives including 2,5-diacryloyl oxymethylene-3,6- dimethylpyrazine, 2-acryloyl oxymethylene-5-methyol-3,6- dimethylpyrazine, and 2- acryloyl oxymethylene-3,5,6- trimethylpyrazine, and three kinds of anticoagulation material modified from three kinds of ligustrazines and obtained on the surface of silk protein fiber by graft polymerization. The invention also provides synthesis of the ligustrazine derivatives and preparation method of the coagulation materials which comprises the steps of transforming the lateral chain of ligustrazine into a ligustrazine derivative with double bond active group and initiating graft polymerization by free radical on the surface of silk protein fiber. The anticoagulation activity of silk protein applied in the biomedical material field is improved and the application field is expanded.

Description

technical field [0001] The invention relates to research on three derivatives of ligustrazine, an active ingredient of Chinese herbal medicine, modified polymer silk fibroin fiber and a preparation method thereof, and relates to the field of biomedical materials. Background technique [0002] Silk fibroin is a natural polymer material and the main component of silk. Due to its good biocompatibility, it is widely used in the fields of biomedical materials such as enzyme immobilization technology, cell culture substrate, artificial skin, and drug sustained release materials. However, unmodified silk fibroin cannot meet the requirements of the environment in direct contact with blood. Chinese herbal medicine is a treasure of Chinese culture, and its application has a history of thousands of years. Clinical treatment and pharmacological studies have shown that Ligustrazine, an active ingredient of the Chinese herbal medicine Ligusticum Chuanxiong for promoting blood circulatio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61P7/02C12N11/04A61L27/60A61K31/4965A61K47/64
Inventor 王松连小洁朱鹤孙
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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