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Preparation, raw material, product and application of photo-coupling co-crosslinking hydrogel material

A technology of photo-trigger and halogen atoms, which is applied in the field of preparation of photocoupling synergistically crosslinked hydrogel materials, can solve the problems of unfavorable clinical operation, limiting the clinical transformation of non-free radical photocoupling crosslinking technology, slowing down of crosslinking speed, etc.

Active Publication Date: 2019-05-21
ZHONGSHAN GUANGHE MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, compared with the free radical crosslinking mode, the crosslinking speed of aldehyde groups and amine groups is greatly slowed down (the initial gelation time is about 30s, and the complete gelation time is about 2min), which is not conducive to clinical operation, thus limiting this type of Clinical translation of non-radical photocoupling cross-linking technology

Method used

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  • Preparation, raw material, product and application of photo-coupling co-crosslinking hydrogel material
  • Preparation, raw material, product and application of photo-coupling co-crosslinking hydrogel material
  • Preparation, raw material, product and application of photo-coupling co-crosslinking hydrogel material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0245] Embodiment one: the synthesis of component A-1

[0246]

[0247] (1) Synthesis of compound 1: synthesized according to the method disclosed in references Kunihiko Morihiro.; Tetsuya Kodama.; Shohei Mori.; Satoshi Obika.Org.Biomol.Chem.2014,12,2468. 1 H NMR (400MHz, CDCl 3 ):δ=7.71(s,1H),7.22(s,1H),4.03(s,2H),4.13(t,J=6.1Hz,2H),3.99(s,3H),3.32(dd,J= 11.6,5.7Hz,2H),2.82(t,J=5.9Hz,2H),2.44(t,J=7.2Hz,2H),2.26-2.17(m,2H). MS(ESI):[M+H ] 344.1207.

[0248] (2) Synthesis of component A-1: ​​dissolve hyaluronic acid (2g, 340kDa) in 100mL of 0.01mol / L 2-(N-morpholine)ethanesulfonic acid MES buffer solution (pH=5.2), stir Until it is completely dissolved, weigh compound 1 (69mg, 0.2mmol) and dissolve it in 10mL dimethyl sulfoxide DMSO, add the above reaction solution, weigh 4-(4,6-dimethoxytriazin-2-yl)- 4-Methylmorpholine hydrochloride DMTMM (0.4g, 1.5mmol) was dissolved in 3mL MES buffer solution, added to the above reaction solution three times (every 1h), and reacted a...

Embodiment 2

[0249] Embodiment two: the synthesis of component A-2

[0250]

[0251] (1) Synthesis of compound 2: according to the method disclosed in the references Yunlong Yang; Jieyuan Zhang; Zhenzhen Liu; Qiuning Lin; Xiaolin Liu; Chunyan Bao; Yang Wang; Linyong Zhu.Adv.Mater.2016,28,2724. .

[0252] (2) Synthesis of compound 3: Dissolve compound 2 (1g, 3.0mmol) in 50mL tetrahydrofuran, add carbon tetrabromide CBr 4 (2g, 6.0mmol), and triphenylphosphine PPh 3 (1.6g, 6.0mmol), under the protection of argon, stirred at room temperature for 2h, after the reaction, 5mL of water was added to quench the reaction, the solvent was spin-dried, extracted with ethyl acetate, and separated by column chromatography (PE:DCM=4:1) , to obtain compound 3 (1.0 g, yield 84%). 1 H NMR (400MHz, CDCl 3 ): δ=7.71(s,1H),7.22(s,1H),4.56(s,2H),4.13(t,J=6.1Hz,2H),3.99(s,3H),3.32(dd,J= 11.6,5.7Hz,2H),2.82(t,J=5.9Hz,2H),2.44(t,J=7.2Hz,2H),2.26-2.17(m,2H).MS (ESI):[M+H ] 390.0623.

[0253] (3) Synthesis o...

Embodiment 3

[0255] Embodiment three: the synthesis of component A-3

[0256]

[0257] (1) Synthesis of compound 5: synthesized according to the method disclosed in references James F.Cameron.; JeanM.J.Frechet.J.Am.Chem.Soc.1991,113,4303.

[0258] (2) Synthesis of Compound 6: According to the method of Example 2, Compound 6 was prepared from Compound 5 (yield 73%). 1 H NMR (400MHz, CDCl 3 ):δ=7.71(s,1H),7.22(s,1H),4.66(m,1H),4.13(t,J=6.1Hz,2H),3.99(s,3H),3.32(dd,J= 11.6,5.7Hz,2H),2.82(t,J=5.9Hz,2H),2.44(t,J=7.2Hz,2H),2.26-2.17(m,2H),1.33(d,J=6.9Hz, 3H).MS(ESI):[M+H]404.0863.

[0259] (3) Synthesis of Compound 7: According to the method of Example 2, Compound 7 was prepared from Compound 6 (yield 70%). 1 H NMR (400MHz, CDCl 3 ):δ=7.71(s,1H),7.22(s,1H),4.86(m,1H),4.42(m,1H),4.13(t,J=6.1Hz,2H),3.99(s,3H) ,3.95(s,3H),3.43(d,J=5.6,2H),3.32(dd,J=11.6,5.7 Hz,2H),2.82(t,J=5.9Hz,2H),2.44(t,J =7.2Hz,2H),2.26-2.17(m,2H),1.42(s,9H), 1.33(d,J=6.9Hz,3H).MS(ESI):[M+H]559.2402.

[0260] (4) Syn...

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Abstract

The invention provides a preparation method, a raw material, a product and an application of a photo-coupling co-crosslinking hydrogel material. The preparation method comprises the steps of dissolving a component A, namely an o-nitrobenzyl photo-trigger modified high polymer derivative in a biocompatible medium to obtain a solution A, dissolving a component B, namely an amidogen-containing high polymer derivative or a double bond containing high polymer derivative or a sulfydryl containing high polymer derivative in the biocompatible medium to obtain a solution B, uniformly mixing the solution A (or adding the solution B) to obtain a hydrogel precursor solution, illuminating the hydrogel precursor solution under a light source, and allowing o-nitrobenzyl groups in the component A to generate aldehyde groups / ketonic groups or nitroso-groups by optical excitation for double crosslinking to exert a co-crosslinking effect. The invention further provides a reagent kit for preparing hydrogel, and the application of the hydrogel material in tissue engineering, regeneration medicine and 3D (three dimensional) printing and as a cell, protein or drug carrier.

Description

technical field [0001] The invention belongs to the field of biological materials, and specifically relates to the preparation, raw materials, products and applications of photocoupling synergistically crosslinked hydrogel materials. Background technique [0002] Hydrogel is a kind of highly water-containing polymer material with a three-dimensional network cross-linked structure. Due to its excellent biocompatibility and certain mechanical strength, it can highly fit the microenvironment of biological tissues, so it is widely used in tissue engineering and regenerative medicine. In clinical applications, in situ curable hydrogels have excellent tissue shaping capabilities. Currently, in situ curable hydrogels mainly include temperature-sensitive types, two-component injection types, and photosensitive types according to different gelation mechanisms. wait. The temperature-sensitive type is mainly through the gel precursor that is liquid phase at low temperature, and after...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D291/08C08B11/12C08B37/08C08G65/334C08G69/48C08H1/00C08B37/02C08B37/04C08B37/10
CPCC08B37/0072C08B37/0084C08B37/0069C08B11/12C08G69/48C08G65/3348C08B37/003C08H1/00C08B37/0075C07D291/08C09D11/14C09D11/102A61L27/60A61L27/52A61L27/20A61L27/222A61L27/18A61L27/54A61L27/50A61L26/008A61L26/0038A61L26/0019A61L26/0023A61L26/0061A61L26/0066A61L31/145A61L31/045A61L31/06A61L31/042A61L31/14A61L31/16A61L17/005A61L17/00A61K47/42A61K47/34A61K47/36A61K47/38B33Y70/10A61L2430/02A61L2430/06A61L2400/04A61K31/727A61K31/785C07D273/01A61K31/77A61K31/722A61K31/728A61K31/738A61K31/737C08J3/075C08J3/246C08J2371/02C08J2471/02C08J2401/00C08J2301/00C08J2489/00C08J2389/00C08J2305/00C08J2405/00A61L24/0031A61L24/046A61L24/08B33Y70/00C08J2301/28C08J2305/08C08J2305/10C08J2377/04
Inventor 朱麟勇华宇杰林秋宁张依晴包春燕钟学鹏
Owner ZHONGSHAN GUANGHE MEDICAL TECH CO LTD
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