Injectable high-strength chitin-based hydrogel, and preparation method and application thereof

A hydrogel and chitin technology, applied in the field of biomedical materials and tissue engineering, to achieve wide application prospects, good biocompatibility, easy to obtain or prepare effects

Active Publication Date: 2018-01-09
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, to date, there has been no report of the formation of enamine bond-crosslinked injectable high-strength hydrogels via a spontaneous amine-yne ​​click reaction.

Method used

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  • Injectable high-strength chitin-based hydrogel, and preparation method and application thereof
  • Injectable high-strength chitin-based hydrogel, and preparation method and application thereof
  • Injectable high-strength chitin-based hydrogel, and preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0042] Preparation of Hydrophilic Polymer A

[0043] (1) Synthesis of linear diester alkyne-terminated PEG (DA-PEG)

[0044]

[0045] Weigh 10.0 grams of PEG (M n =2000) and 1.05 gram of propiolic acid were placed in a 250mL round-bottomed flask, 150mL of dried toluene solution was added as a solvent, and 0.57 gram of p-toluenesulfonic acid was added as a catalyst under magnetic stirring, and the oil bath was heated to 140°C , condensed and refluxed, the whole system reacted for 48h and then cooled to room temperature. The product mixed solution was concentrated and precipitated in ether, and the collected crude product was recrystallized and dried to obtain 9.33 g of light yellow solid as linear diester alkyne terminal PEG (DA-PEG), with a yield of 88.6%. 1 H NMR (500MHz, CDCl 3 , δ): 4.3(m, COOC H 2 ), 3.7 (m, COOCH 2 C H 2 O), 3.6(m, PEG main chain OC H 2 C H 2 O), 3.0 (s, C H ≡CCOO). By choosing linear PEGs with different molecular weights as raw materials...

Embodiment 1

[0055] Preparation of DA-PEG / CM-Chitosan hydrogel by spontaneous amine-alkyne click reaction.

[0056] DA-PEG (PEG molecular weight 2000) and carboxymethyl chitosan (CM-Chitosan, weight average molecular weight 74kDa, deacetylation degree 0.96, carboxymethyl substitution degree 0.96) were dissolved in 0.15M pH 7.4 A solution of 20wt% DA-PEG and 3wt% CM-Chitosan was prepared in PBS buffer. Take 0.137g of DA-PEG solution, 1g of CM-Chitosan solution and 0.04g of PBS buffer and mix them uniformly for half a minute, then place them in a constant temperature water bath at 37°C for 0.5-6h to obtain the alkynyl / amino group The molar ratio is 0.28, the CM-Chitosan concentration is 2.5wt% hydrogel, and it does not flow, which is recorded as 0.28-2.5% DA-PEG / CM-Chitosan hydrogel.

[0057] figure 1 It is the infrared spectrum of 0.28-2.5% DA-PEG / CM-Chitosan hydrogel and its corresponding precursors DA-PEG and CM-Chitosan, from which it can be seen that the alkynyl C of DA-PEG in the hyd...

Embodiment 2

[0062] Preparation of DA-PEG / CM-Chitosan hydrogel by spontaneous amine-alkyne click reaction.

[0063] DA-PEG (PEG molecular weight 6000) and carboxymethyl chitosan (CM-Chitosan, molecular weight 74kDa, deacetylation degree 0.96, carboxymethyl substitution degree 0.96) were dissolved in 0.15M PBS at pH 7.4 In the buffer solution, a solution of 25wt% DA-PEG and 2wt% CM-Chitosan was prepared. Take 0.15g of DA-PEG solution, 1g of CM-Chitosan solution and 0.18g of PBS buffer and mix them uniformly for half a minute, then place them in a constant temperature water bath at 37°C for 8h, and the molar ratio of alkynyl / amino group is 0.2 , 0.2-1.5% DA-PEG / CM-Chitosan hydrogel with a CM-Chitosan concentration of 1.5 wt%. This example demonstrates that varying the molecular weight and concentration of PEG does not affect the preparation of injectable hydrogels. A series of DA-PEG / CM-Chitosan hydrogels can be obtained by changing the molar feed ratio (0.05-5) of the alkynyl group / amino ...

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Abstract

The invention provides a preparation method of an injectable high-strength chitin-based hydrogel product. The preparation method comprises the following steps: preparing binary or polybasic alkynyl modified hydrophilic polymer A, preparing an amino-containing chitin derivative B, mixing an aqueous solutions of A and B to form an injectable hydrogel precursor solution, and forming high-strenght hydrogel in situ under the physiological condition. The injectable hydrogel is prepared in situ under the physiological condition by utilizing spontaneous amine-alkyne click reaction and performing chemical crosslinking by forming enamine bond, any micromolecular catalysts, initiators or crosslinking agents are not needed, heating, ultraviolet or radiation is not needed, no toxicity and no irritationare realized, and any aftertreatment is not needed. In-situ physical crosslinking rapid formation is conducted by using a temperature-sensitive chitin derivative, and in-situ crosslinking is furtherconducted to prepare the injectable high-strength hydrogel. The hydrogel has high biocompatibility, pH sensitivity and biodegradability, and can be widely applied to the field of biological medicine.

Description

technical field [0001] The invention belongs to the field of biomedical materials and tissue engineering, and specifically relates to an injectable intelligent high-strength chitin-based hydrogel product and its preparation method and application. Background technique [0002] Polymer hydrogel is a cross-linked polymer with a three-dimensional network structure that absorbs a large amount of water and is insoluble in water. Because it is close to the extracellular matrix, it has good hydrophilicity, excellent swelling performance and biocompatibility etc., have broad application prospects in the fields of biomedicine and tissue engineering materials. For example, as a medical device, hydrogel can be used for wound dressing, adhesion, sealing and anti-leakage during surgery, hemostasis during surgery, tissue filling, anti-adhesion after surgery, or as a carrier and tissue for biologically active substances and cells Engineering materials and other biomedical fields. [0003...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08J3/075A61L24/00A61L24/04A61L26/00A61L27/52A61L27/58A61L27/18A61L31/14A61L31/06
Inventor 蒋序林黄佳昌
Owner WUHAN UNIV
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