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A kind of azide modification method of heparin, azide heparin and application

A modification method, a technology for nitriding heparin, applied in the field of biological materials, can solve the problems of increasing the material synthesis process and cost, etc.

Active Publication Date: 2019-04-09
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of method requires that biological materials must contain active groups (amino or carboxyl groups), while the vast majority of clinical cardiovascular materials are inert materials, lacking the above-mentioned active groups, and often require surface treatment methods, such as low-temperature plasma, Corona discharge and chemical corrosion and other methods, which further increase the synthesis process and cost of materials

Method used

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  • A kind of azide modification method of heparin, azide heparin and application
  • A kind of azide modification method of heparin, azide heparin and application
  • A kind of azide modification method of heparin, azide heparin and application

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Add 0.815g of p-azidobenzoic acid, 0.958g of EDC.HCl, 0.575g of NHS in sequence to a container with 20ml of dimethyl sulfoxide (DMSO, containing water), stir well and then adjust with 0.1M dilute hydrochloric acid solution After the pH reaches 4.7, place it in a 4°C environment with magnetic stirring, avoid light reaction (to prevent the azide group from being decomposed by light) for 4 hours; add 10ml (0.1g / ml) of heparin sodium (molecular weight: 12000) After adjusting the pH of the NaOH solution to 7.4, place it in an environment at 4°C and avoid light for 6 hours; finally, pour the reaction solution into a dialysis bag (3.5K), dialyze it with water until there is no azido-terebenzoic acid, filter it, and put the reaction solution in Freeze-dry at -25°C to obtain the product, ie heparin azide, with an azide group content of 8.8‰ (g / g) and a yield of 95%.

[0036] The infrared absorption spectrum of the heparin azide synthesized in this embodiment is as follows: figu...

Embodiment 2

[0038] Add 0.955g of 3-(4-azidophenyl)propionic acid, 1.916g of EDC.HCl, and 2.170g of sulfo-NHS in sequence to a container containing 20ml of dimethylformamide (DMF, containing water), and stir thoroughly After adjusting the pH to 4.7 with 0.1M dilute hydrochloric acid solution, place it in a 6°C environment with magnetic stirring, and react in the dark for 4 hours, add 10ml (0.05g / ml) of heparin lithium (molecular weight: 20000) aqueous solution, and use 0.01M NaOH After the pH of the solution was adjusted to 7.4, it was placed in a 6°C environment and protected from light for 6 hours; finally, the reaction solution was poured into a dialysis bag (3.5K) and dialyzed with water until there was no 3-(4-azidophenyl)propionic acid. After filtering, the reaction solution was freeze-dried at -25°C to obtain the product, namely heparin azide, with an azide group content of 5.5‰ and a yield of 90%.

Embodiment 3

[0040] Add 0.155g of 4-azidobutanoic acid, 0.258g of EDC.HCl, and 0.345g of sulfo-NHS to a container containing 40ml of dimethyl sulfoxide (DMSO, containing water) in sequence. After adjusting the pH of the dilute hydrochloric acid solution to 5.0, place it in a 10°C environment with magnetic stirring, and react in the dark for 6 hours; add 10ml (0.1g / ml) of heparin calcium (molecular weight: 20000) aqueous solution, and use 0.01M NaOH solution to adjust the pH to After 7.4, place it in a 10°C environment to avoid light for 6 hours; finally, pour the reaction solution into a dialysis bag (3.5K), dialyze with water until there is no 4-azidobutyric acid, filter, and store the reaction solution at -30°C After lyophilization, the product, namely heparin azide, was obtained. The azide group content of the product was 2.0‰, and the yield of the product was 85%.

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Abstract

The invention belongs to the technical field of biological materials, discloses an azidation modifying method for heparin, azidated heparin and application of the azidated heparin. The method comprises the following steps: (1) activating azide containing carboxyl by virtue of an activating agent, so as to obtain activated azide, wherein the activating conditions are as follows: reacting at a temperature from 0 to the room temperature for 1-14 hours; and (2) adding a heparinate solution into the activated azide obtained in the step (1), adjusting the pH to 7-9, reacting at a temperature from 0 to the room temperature, carrying out dialysis to remove micromolecules, and drying, so as to obtain the azidated heparin. The method is simple, and azide groups are successfully modified to heparin molecular chains so as to generate the azidated heparin. The azidated heparin can be used for well modifying the biological materials and introducing heparin into the biological materials in a chemical bond manner, so that the application field of the heparin is extended.

Description

technical field [0001] The invention belongs to the technical field of biological materials, and relates to the modification of heparin, in particular to the azide modification and modification of heparin, the modified azide heparin and the use of the azide heparin for modifying biological materials. Background technique [0002] Biomaterials are widely used in clinical applications such as vascular catheters, heart valves, and hemodialysis. However, when biomaterials come into contact with blood, they will quickly adsorb a layer of plasma proteins; poor blood compatibility will cause protein conformation changes. The conformationally transformed protein interacts with platelet membrane surface receptors, activates platelets, and eventually induces thrombus. The surface anticoagulation treatment of related materials is of great significance. Heparin is a major clinical anticoagulant drug and an important anticoagulant material modification reagent. The introduction of hepar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/10
CPCC08B37/0003C08B37/0075
Inventor 吴刚刘章拴
Owner SOUTH CHINA UNIV OF TECH
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