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Injectable hyaluronic acid/polyethylene glycol hydrogel and its preparation method and application

A technology of polyethylene glycol and hyaluronic acid, which can be used in pharmaceutical formulations, prostheses, drug delivery, etc. It can solve the problems of poor plasticity and durability, and achieve good mechanical properties, low cytotoxicity, and high yield.

Active Publication Date: 2019-02-26
深圳浦瑞健康科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to provide a preparation method and application of injectable hyaluronic acid / polyethylene glycol hydrogel, so as to overcome the defects of poor plasticity and durability of existing hyaluronic acid injections

Method used

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  • Injectable hyaluronic acid/polyethylene glycol hydrogel and its preparation method and application
  • Injectable hyaluronic acid/polyethylene glycol hydrogel and its preparation method and application
  • Injectable hyaluronic acid/polyethylene glycol hydrogel and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Synthesis of azide-modified polyethylene glycol

[0040] (1) Synthesis of terminal diepoxy PEG

[0041] Terminated Diepoxide PEG

[0042] 20.2g PEG (M n =6000) was placed in a 500mL flask, vacuum-dried with an oil pump for 3h under the condition of heating in an oil bath at 120°C, and then added 200mL of anhydrous tetrahydrofuran, dissolved until clear and transparent, and then added 1.35g of sodium hydride. After stirring overnight at room temperature, 5.3 mL of epichlorohydrin was added, reacted at room temperature for 20 h, and then filtered. The filtrate was concentrated and precipitated in ether, and the resulting solid was vacuum-dried to obtain 19.0 g of white solid-terminated diepoxy PEG with a yield of 94%. 1 H NMR (400MHz, CDCl 3 ,TMS):δ3.57-3.74(m,CH 2 of PEG chain), 3.39(m,2H), 3.1(m,2H), 2.72(m,2H), 2.54(m,2H); 13 CNMR (100MHz, CDCl 3 , TMS), δ70.5, 72.8, 50.4, 44.2.

[0043] (2) Synthesis of terminal tetrahydroxy PEG

[0044] Tetrahydr...

Embodiment 2

[0052] Example 2: Synthesis of Cyclooctyne Modified Hyaluronic Acid

[0053] (1) Synthesis of N-(2-((Z)-2-bromocyclooct-2-enyloxy)ethyl)trifluoroacetamide

[0054] N-(2-((Z)-2-bromocyclooct-2-enyloxy)ethyl)trifluoroacetamide

[0055] First, 4.31g of silver trifluoromethanesulfonate was placed in a 50mL three-necked flask, which was evacuated and filled with argon three times; under the protection of argon, 8mL of toluene was injected into the flask, and then 10.81g of N-(2-hydroxyethyl)trifluoro A mixed solution of acetamide and 1.50 g of 8,8-dibromobicyclo[5.1.0]octane was added dropwise into the flask while stirring. After one day of reaction in the dark, 50 mL of saturated brine was added to quench the reaction, suction filtered, and the filtrate was extracted with dichloromethane (50 mL×3), the organic phases were combined and dried over anhydrous sodium sulfate, filtered, and the solvent was spin-dried to obtain 5.14 g of crude product. The crude product was subjected...

Embodiment 3

[0062] Embodiment 3: SPAAC reaction prepares hydrogel

[0063] The azide-modified polyethylene glycol prepared in Example 1 and the cyclooctyne-modified hyaluronic acid prepared in Example 2 were respectively dissolved in PBS buffer solution with pH = 7.4, and the concentration range of cyclooctine was 1wt%-10wt%. Alkyne-modified hyaluronic acid solution and azide-modified polyethylene glycol solution whose concentration was changed according to the molar amount of alkyne functional group. Mix the cyclooctyne-modified hyaluronic acid solution and the azide-modified polyethylene glycol solution, vortex for half a minute, put it in a constant temperature water bath at 37°C, and let it stand for 3-50 minutes to obtain different concentrations and molar ratios of alkynyl / alkyne groups. Azide = 1:0.5, 1:1, 1:2, 1:3 hydrogels. figure 1 It is a comparison picture of the hydrogel before and after.

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Abstract

The invention discloses injectable hyaluronic acid / polyethylene glycol hydrogel as well as a preparation method and application thereof, and belongs to the fields of plastic and cosmetic biological materials. The method is characterized in that a cyclooctyne-modified hyaluronic acid (HA) solution is mixed with a nitrine-modified polyethylene glycol (PEG) solution, a hydrogel precursor solution with favorable flowability is formed, and the hydrogel precursor solution can be quickly cross-linked through a ring tension promoted click chemical reaction to form the hydrogel after being injected into a body, so as to play roles in water retention, plastic and the like. The preparation process of the material is simple; the additional addition of a cross-linking agent is not needed; the heating is not needed; the ultraviolet treatment or the radiation and the like are not needed; one-step cross-linking is adopted; the injectable hyaluronic acid / polyethylene glycol hydrogel is non-toxic and has no stimulation; therefore, the made hydrogel is good in biocompatibility, and is insignificant in inflammatory reaction. Meanwhile, the gel is slower in degradation speed, and is excellent in mechanical performance; therefore, the material is good in durability and molding performance, is quite applicably used as a face-lifting filling material in the fields of wrinkle resisting, breast enlargement, nose augmentation, filling-padding and the like.

Description

technical field [0001] The invention relates to a preparation method and application of an injectable hyaluronic acid / polyethylene glycol hydrogel, belonging to the field of plastic and cosmetic materials. Background technique [0002] Injection cosmetology is a large class of plastic surgery methods that use injection methods to inject biomaterials or synthetic biocompatible materials into the dermis or subcutaneously to reduce skin wrinkles or shape through different mechanisms of action. This method does not require surgery, is painless, has quick results, has no side effects, is safe and reliable, and is well received by everyone. Among the most common cosmetic fillers are autologous fat, hyaluronic acid (also known as hyaluronic acid, HA) and collagen. The safety of autologous fat is better, but due to the limited survival of fat, it is difficult to achieve the desired effect. Collagen will be absorbed by the body, so the maintenance time is short, and there will be s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08C08G65/00C08G81/00A61L27/60A61L27/52A61L27/18
CPCA61L27/18A61L27/52A61L27/60A61L2400/06C08B37/0072C08G65/00C08G81/00C08J2387/00C08L87/00
Inventor 钟振林付双梨
Owner 深圳浦瑞健康科技有限公司
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