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Glucose-like peptide and preparation method thereof as well as injectable hydrogel

A hydrogel and injectable technology, which is applied in pharmaceutical formulations, medical preparations of non-active ingredients, medical science, etc., can solve the problems of hydrogels that do not have biological activity, are difficult to modify, and have poor stability

Active Publication Date: 2014-07-23
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the injectable hydrogels prepared by the prior art have defects such as poor stability, low mechanical strength, and difficulty in modification. role, thus limiting its application in the biomedical field

Method used

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  • Glucose-like peptide and preparation method thereof as well as injectable hydrogel
  • Glucose-like peptide and preparation method thereof as well as injectable hydrogel
  • Glucose-like peptide and preparation method thereof as well as injectable hydrogel

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preparation example Construction

[0056] The present invention also provides a method for preparing the above-mentioned glycopeptides with the structure of formula (I), comprising: adding one or more of the compounds with the structures shown in formula (V-1) to formula (V-3) 1. The compound with the structure of formula (IV) and the compound with the structure of formula (VI) are mixed with an organic solvent, and reacted under the action of a catalyst to obtain the glycopeptide with the structure of formula (I).

[0057]

[0058]

[0059] Among them, x, y, z and n are the degree of polymerization; 0≤x≤300; 15≤y≤800; 3≤z≤200; and 30≤x+y+z≤1000; n=x+y+z; The x, y, and z are the same as those described above, and will not be repeated here.

[0060] -R 1 It has one of the structures shown in the following formula (II-1) ~ formula (II-3):

[0061]

[0062] -R 2 It has the structure shown in the following formula (III):

[0063]

[0064] The present invention does not limit the sources of all raw m...

Embodiment 1

[0086] 1.1 In an ice-water bath, mix 20g of L-glutamic acid and 30ml of propynyl alcohol, mix and add 8ml of concentrated sulfuric acid dropwise under stirring conditions, after the dropwise addition, react at room temperature for 12-24h; after the reaction, add 27g of sodium bicarbonate aqueous solution Neutralize the reaction, filter and drain to obtain a crude product, which is recrystallized with 150ml of water to obtain γ-propargyl-L-glutamate.

[0087] 1.2 Add 100ml of dried tetrahydrofuran to a dry reaction flask, and continue to add 7.4g of γ-propargyl-L-glutamate obtained in 1.1 and 4g of triphosgene under a nitrogen atmosphere, and react at 55°C for 0.5 ~1h, after the reaction solution is clarified, stir at room temperature for 30min, then precipitate with cold petroleum ether; pour off the supernatant, dissolve the viscous substance in the lower layer with ethyl acetate, wash with cold water three times, and dry the organic phase with anhydrous magnesium sulfate over...

Embodiment 2

[0090] 2.1 Mix 2g of the compound of formula (IV) obtained in Example 1, 6.0g of the compound of formula (V-1) 2-azidoethyl-O-α-D-mannose with 0.15g of the compound of formula The compound of structure (VI) N-(3-azidopropyl) p-hydroxyphenylpropanamide was dissolved in 40ml of dimethyl sulfoxide, then bubbled with nitrogen for 30min to remove dissolved oxygen, and then added 0.3g of cuprous bromide With 0.5ml of pentamethyldivinyldiamine, continue bubbling for 5min, seal it, and react under nitrogen atmosphere at 25°C for three days. Distilled water was dialyzed for three days, and the glycopeptide with the structure of formula (I) was obtained after freeze-drying.

[0091] 2.2 Prepare the glycopeptide with the structure of formula (I) obtained in 2.1 into a phosphate buffer solution with a mass concentration of 6%-20% as the first mixed solution; prepare hydrogen peroxide into 2.45-49mmol / L phosphoric acid The salt buffer solution is the third mixed solution; the phosphate bu...

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Abstract

The invention provides a glucose-like peptide and a preparation method thereof as well as injectable hydrogel. The preparation method comprises the following steps: mixing one or more compounds with the structures shown as formulas (V-1) to (V-3), a compound with the structure of a formula (IV), a compound with the structure of a formula (VI) and an organic solvent, and reacting in the presence of a catalyst to obtain the glucose-like peptide with the structure of the formula (I). Compared with an existing natural polymer, the glucose-like peptide has the advantages that the compound with the structure of the formula (IV) serves as a main chain, the glucose-like peptide has a secondary structure similar to that of natural proteins or polypeptides and also has high biocompatibility and biodegradability; the glucose-like peptide can simulate the structure of protein polysaccharides in an extracellular matrix; the glucose-like peptide contains a phenol structure, different grafting rates can be regulated, a cross-linked network can be formed under the effects of horse radish peroxidase and hydrogen peroxide, the reaction condition is mild, the reaction rate is easily controlled, and the hydrogel with controllable performance can be prepared.

Description

technical field [0001] The invention belongs to the technical fields of biotechnology, biomedical materials and tissue engineering, and in particular relates to a glycopeptide, a preparation method thereof, and an injectable hydrogel. Background technique [0002] Carbohydrates play a pivotal role in nature and play important roles in many biological functions, including cell-cell recognition, immune response, hormone activity and inflammation. Glycoproteins are proteins formed by the covalent combination of sugar molecules and protein molecules. This glycosylation modification makes the properties and functions of protein molecules more abundant and diverse, especially for the recognition of cell signals. Combining various glycosaminoglycans with different core proteins can also form a type of carbohydrate complex, which is proteoglycan, which mainly exists in the extracellular matrix of higher animals, and some also exist in the cell membrane, which is the structure of cel...

Claims

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Application Information

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IPC IPC(8): C08G69/48C08L77/02A61K47/34A61K9/06A61L31/06A61L31/14
Inventor 贺超良任凯旋成一龙肖春生李杲陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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