Rapidly curable hydrogel based on bioorthogonal reaction, its preparation method and application
A fast curing, bioorthogonal technology, applied in biochemical equipment and methods, microorganisms, animal cells, etc., can solve the problem of increasing cell adhesion and chemotactic host cell migration, increasing seed cell differentiation ability, and low biocompatibility. and other problems, to achieve excellent biocompatibility, improved adhesion and proliferation, and good biocompatibility.
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[0039] As another aspect of the technical solution of the present invention, it relates to a method for preparing a rapidly curable hydrogel based on a bioorthogonal reaction, which includes:
[0040] Modifying trans-cyclooctene to four-arm polyethylene glycol to obtain trans-cyclooctene-modified four-arm polyethylene glycol;
[0041] Condensation reaction between hyaluronic acid and tetrazine to obtain tetrazine-modified hyaluronic acid;
[0042] The trans-cyclooctene-modified four-arm polyethylene glycol and tetrazine-modified hyaluronic acid are uniformly mixed and reacted to obtain a rapidly curable hydrogel based on a bioorthogonal reaction.
[0043] In some embodiments, the preparation method includes: uniformly mixing trans-cyclooctene and four-armed polyethylene glycol, and reacting at 15-30°C for 10-20 hours to obtain trans-cyclooctene-modified four-armed polyethylene glycol ethylene glycol.
[0044] In some more specific embodiments, the preparation method specific...
Embodiment 1
[0085] Step 1: Dissolve trans-cyclooctene in 1% anhydrous N,N-dimethylformamide solution, and add N-methylmorpholine and isobutyl chloroformate to react at 4°C for 20 min.
[0086] Wherein, the molar ratio of N-methylmorpholine to trans-cyclooctene is 1:1, and the molar ratio of isobutyl chloroformate to trans-cyclooctene is 1.5:1.
[0087] Step 2: After the reaction in Step 1 is completed, add four-arm polyethylene glycol and react at 15° C. for 20 h.
[0088] Wherein, the molar ratio of the four-arm polyethylene glycol to trans-cyclooctene is 1:1.5.
[0089] After the reaction in step 2 is completed, precipitate in ether to obtain a white flocculent precipitate, which is collected by centrifugation at 12,000 rpm for 5 minutes, dissolved in water, purified by Sephadex G-15 column, and freeze-dried to obtain trans-cyclooctene-modified Four-arm polyethylene glycol, its structural formula is as shown in formula (2):
[0090]
[0091] Wherein, the value of n is 115.
[0092...
Embodiment 2
[0105] Step 1: Dissolve trans-cyclooctene in 1% anhydrous N,N-dimethylformamide solution, add N-methylmorpholine and isobutyl chloroformate to react on ice for 30min at 8°C. Wherein, the molar ratio of N-methylmorpholine to trans-cyclooctene is 1:1, and the molar ratio of isobutyl chloroformate to trans-cyclooctene is 3:1.
[0106] Step 2: After the reaction of step 1 is completed, four-arm polyethylene glycol is added, and the reaction is carried out at 25° C. for 10 hours. Wherein, the molar ratio of the four-arm polyethylene glycol to trans-cyclooctene is 1:3.
[0107] After the reaction in step 2, precipitate in ether to obtain a white flocculent precipitate, centrifuge at 12,000 rpm for 5 min to collect the precipitate, dissolve the above precipitate with water, and purify it through Sephadex column G-15 to obtain trans-cyclooctene-modified Four-arm polyethylene glycol solution, the structural formula of the four-arm polyethylene glycol modified by trans-cyclooctene is s...
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