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Hydrogel capable of being rapidly cured based on reverse Diels-Alder reaction as well as preparation method and application thereof

A hydrogel and reaction technology, applied in biochemical equipment and methods, 3D culture, microorganisms, etc., can solve problems such as cell damage, and achieve the effects of low toxicity, good biocompatibility, and simple preparation methods

Active Publication Date: 2020-12-25
SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The hydrogel prepared by this method has the advantages of good stability, but the traditional chemical method will introduce chemical cross-linking agents during the reaction process, which may cause certain damage to the cells

Method used

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  • Hydrogel capable of being rapidly cured based on reverse Diels-Alder reaction as well as preparation method and application thereof
  • Hydrogel capable of being rapidly cured based on reverse Diels-Alder reaction as well as preparation method and application thereof
  • Hydrogel capable of being rapidly cured based on reverse Diels-Alder reaction as well as preparation method and application thereof

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preparation example Construction

[0053] In some embodiments, the preparation method includes: mixing four-armed polyethylene glycol and a condensing agent in a first solvent to obtain a first mixed system, and then reacting the first mixed system at 0-8°C for 10-30 minutes ; Then add 3-(4-benzylamino)-1,2,4,5-tetrazine to form a second mixed system, and then react the second mixed system at 15~30°C for 10~20h to obtain tetrazine-modified Four-armed polyethylene glycol; preferably, the first solvent includes dichloromethane.

[0054] Further, the condensing agent includes benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate and N,N-diisopropylethylamine.

[0055] Further, the molar ratio of the condensing agent to four-arm polyethylene glycol is 1-3:1.

[0056] Further, the molar ratio of the four-arm polyethylene glycol to 3-(4-benzylamino)-1,2,4,5-tetrazine is 1:1-3.

[0057] Further, the preparation method further includes: after the reaction of the second mixed system is completed, addi...

Embodiment 1

[0070] Step 1: Add 4armPEG-COOH (M w =10000) was dissolved in dichloromethane, then added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate and N,N-diisopropylethylamine, ice bath After activating for 15 minutes, add 3-(4-benzylamino)-1,2,4,5-tetrazine and react overnight.

[0071] Among them, the carboxyl group on 4armPEG-COOH, 3-(4-benzylamino)-1,2,4,5-tetrazine, 1H-benzotriazol-1-yloxytripyrrolidinylphosphonium hexafluorophosphate And the reaction molar ratio of N,N-diisopropylethylamine is 1:1.2:2.5:2.5.

[0072] After the reaction in step 1 is completed, precipitate in ether to obtain a pink precipitate, centrifuge at 7000rpm for 5 minutes to collect the precipitate, dissolve the above precipitate in water, purify it through a G15 Sephadex column, and finally freeze-dry to obtain a tetrazine-modified PEG, tetrazine-modified PEG. The PEG structural formula modified by oxazine is shown in formula (1):

[0073]

[0074] Step 2: sodium hyaluronate (...

Embodiment 2

[0084] Step 1: Add 4armPEG-COOH (M w =10000) was dissolved in dichloromethane, then added isobutyl chloroformate and N-methylmorpholine, activated at 4°C for 30min, and then added 3-(4-benzylamino)-1,2,4,5- Tetrazine, overnight reaction.

[0085] Among them, the carboxyl group on 4armPEG-COOH, 3-(4-benzylamino)-1,2,4,5-tetrazine, 1H-benzotriazol-1-yloxytripyrrolidinylphosphonium hexafluorophosphate And the reaction molar ratio of N,N-diisopropylethylamine is 1:2:3:3.

[0086] After the reaction in step 1, precipitate in ether to obtain a pink precipitate, centrifuge at 8000 rpm for 5 min to collect the precipitate, dissolve the above precipitate in water, purify it through a G-15 Sephadex column, and finally freeze-dry to obtain the tetrazine-modified tetrazine Arm polyethylene glycol, tetrazine-modified four-arm polyethylene glycol structural formula as shown in formula (1):

[0087]

[0088] Step 2: sodium hyaluronate (M w =36KDa) was dissolved in MES buffer solution ...

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Abstract

The invention provides hydrogel capable of being rapidly cured based on reverse Diels-Alder reaction as well as a preparation method and application thereof. The preparation method comprises the following steps of modifying 3-(4-benzylamino)-1, 2, 4, 5-tetrazine onto four-arm polyethylene glycol to obtain four-arm polyethylene glycol modified by tetrazine, carrying out condensation reaction on hyaluronic acid and 5-norbornene-2-methylamine to obtain norbornene modified hyaluronic acid, carrying out reverse Diels-Alder reaction on tetrazine modified four-arm polyethylene glycol and norbornene modified hyaluronic acid to obtain the hydrogel capable of being quickly cured. The hydrogel capable of being rapidly cured, which is obtained on the basis of the reverse Diels-Alder reaction, is shortin curing time, good in biocompatibility and low in toxicity, a three-dimensional living environment can be provided for cells, and the adhesion and proliferation of stem cells on a three-dimensionalbracket are improved.

Description

technical field [0001] The invention relates to a rapidly curable hydrogel, in particular to a rapidly curable hydrogel based on reverse Diels-Alder reaction for three-dimensional culture of stem cells, a preparation method and application thereof, and belongs to the technical field of tissue engineering material preparation. Background technique [0002] With the development of science and technology, tissue engineering has become an important means of repairing damaged tissues. Tissue engineering is the application of the principles and technologies of life science and engineering. On the basis of a correct understanding of the relationship between the tissue structure and function of mammals in both normal and pathological states, research and development are used to repair, maintain, and promote various tissues in the human body. Or an emerging discipline of biological substitutes for function and morphology after organ damage. Tissue engineering includes three basic el...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/075C08L5/08C08L71/02C08B37/08C08G65/333C12N5/00
CPCC08J3/075C08B37/0072C08G65/33396C12N5/0062C08J2305/08C08J2471/02C08J2405/08C08J2371/02C12N2513/00C12N2533/30
Inventor 裴仁军昝悦刘敏
Owner SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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