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Preparation, raw material, product and application of optical coupling synergistic cross-linked hydrogel material

A technology of optical trigger and halogen atom, applied in the field of preparation of photocoupling synergistic cross-linking hydrogel materials, can solve the problems of limiting the clinical transformation of non-radical photo-coupling cross-linking technology, unfavorable clinical operation, slowing down of cross-linking speed, etc.

Active Publication Date: 2020-12-29
ZHONGSHAN GUANGHE MEDICAL TECH CO LTD
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  • 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 optical coupling synergistic cross-linked hydrogel material
  • Preparation, raw material, product and application of optical coupling synergistic cross-linked hydrogel material
  • Preparation, raw material, product and application of optical coupling synergistic cross-linked hydrogel material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0247] Embodiment one: the synthesis of component A-1

[0248]

[0249] (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.

[0250] (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

[0251] Embodiment two: the synthesis of component A-2

[0252]

[0253] (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. .

[0254] (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.

[0255] (3) Synthesis o...

Embodiment 3

[0257] Embodiment three: the synthesis of component A-3

[0258]

[0259] (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.

[0260] (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.

[0261] (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.

[0262] (4) Syn...

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Abstract

The invention provides preparation, raw materials, a product and application of an optical coupling synergistic cross-linked hydrogel material. The preparation method comprises the following steps: dissolving a component A o-nitrobenzyl photo-trigger modified polymer derivative into a biocompatible medium to obtain a solution A, and dissolving a component B amino-containing polymer derivative or double bond-containing polymer derivative or sulfydryl-containing polymer derivative into a biocompatible medium to obtain a solution B; uniformly mixing the solution A or the solution B to obtain a hydrogel precursor solution; and under the irradiation of a light source, making the o-nitrobenzyl in the component A generate aldehyde groups / keto groups or nitroso groups at the same time under the optical excitation to perform double cross-linking, so that a synergistic cross-linking effect can be achieved. The invention also provides a kit for preparing a hydrogel, and application of the hydrogel material in tissue engineering and regenerative medicine, 3D printing and as a cell, protein or drug carrier.

Description

[0001] This application is a divisional application. The parent application date of this divisional application is 2017 / 11 / 15, the application number is 2017111324366, and the invention name is "Preparation, raw materials, products and applications of photocoupling synergistic crosslinking hydrogel materials" . technical field [0002] 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 [0003] 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 capa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08C08B11/12C08G65/334C08G69/48C08H1/00C08B37/02C08B37/04C08B37/10C07D291/08C09D11/14C09D11/102A61K47/34A61K47/36A61K47/38A61K47/42A61L17/00A61L26/00A61L27/18A61L27/20A61L27/22A61L27/50A61L27/52A61L27/54A61L27/60A61L31/04A61L31/06A61L31/14A61L31/16B33Y70/10
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 朱麟勇林秋宁张依晴
Owner ZHONGSHAN GUANGHE MEDICAL TECH CO LTD
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