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Non-radical photochemical crosslinked hydrogel material preparation method, product and application

A hydrogel and free radical technology, applied in biochemical equipment and methods, cosmetic preparations, medical preparations of non-active ingredients, etc., can solve problems such as toxic side effects, sensitivity, and difficulty in in-situ gelation

Active Publication Date: 2015-12-09
上海戴云化工科技有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in this system, small molecule photoinitiators must participate, and the free radicals produced by photoinitiators have great toxic side effects on cells or biological tissues
In addition, this photoinitiator is also extremely sensitive to oxygen, making it difficult to prepare relatively thin-layer hydrogels
In tissue repair and isolation of wounds, thin-layer coating is often required. Therefore, it is difficult for the above-mentioned traditional light-induced gelation materials to achieve the purpose of in-situ gelation on the wound.

Method used

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  • Non-radical photochemical crosslinked hydrogel material preparation method, product and application
  • Non-radical photochemical crosslinked hydrogel material preparation method, product and application
  • Non-radical photochemical crosslinked hydrogel material preparation method, product and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Example 1: Synthesis of o-nitrobenzyl-modified hyaluronic acid derivatives (HA-NB)

[0065]

[0066] (1) Synthesis of Compound 1: According to references Pauloehrl, T.; Delaittre, G.; Bruns, M.; Meiβler, M.; H.G.; Bastmeyer, M.; Barner-Kowollik, C.Angew.Chem.Int.Ed.

[0067] (2) Synthesis of compound 2: Dissolve compound 1 (1g, 3.3mmol) and ethylenediamine (1.1mL) in methanol (50mL), reflux for overnight reaction, rotary evaporation under reduced pressure, and dissolve the crude product in methanol , and reprecipitated from ethyl acetate. After several times of dissolution-reprecipitation, filtration and vacuum drying, the pure compound 2 (0.93 g, yield 85%) was obtained.

[0068] (3) Synthesis of HA-NB: Dissolve hyaluronic acid HA (400mg) in 50mL distilled water until completely dissolved, add hydroxybenzotriazole (HOBt, 153mg), and then dissolve compound 2 (224mg, 0.69mmol) and 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC-HCl, 200mg) were add...

Embodiment 2

[0069] Example 2: Synthesis of dextran derivatives (dextran-NB) modified by o-nitrobenzyl groups

[0070]

[0071] (1) Synthesis of compound 3: according to references Pauloehrl, T.; Delaittre, G.; Bruns, M.; Meiβler, M.; H.G.; Bastmeyer, M.; Barner-Kowollik, C.Angew.Chem.Int.Ed.

[0072] (2) Synthesis of dextran-NB: Weigh 1g of dry Dextran and dissolve it in dry DMSO solution, compound 3 (0.23g, 0.62mmol), EDC-HCl (0.76g, 3.96mmol) and DPTS (0.12g ) were sequentially added to the above-mentioned dextran solution, and stirred and reacted for 48h at room temperature. After the reaction, pour the solution into cold ethanol for re-precipitation, purify through three dissolution-re-precipitation processes, and obtain pure dextran-NB (0.8g) after vacuum drying. According to its H NMR spectrum picture , it can be calculated that the degree of modification of the o-nitrobenzyl group is about 10%.

Embodiment 3

[0073] Embodiment three: the synthesis of the chitosan derivative (chitosan-NB) of o-nitrobenzyl modification

[0074]

[0075] (1) Synthesis of small bromo-o-nitrobenzyl molecules:

[0076]

[0077] (2) Synthesis of Compound 4: Weigh vanillin 3-methoxy 4-hydroxybenzaldehyde (0.76g, 4.9mmol), K 2 CO 3 (1.37g, 9.9mmol) and dibromoethane (1.28g, 6.9mmol) were co-dissolved in a dry DMF solution and reacted at 80°C for about 1h. After the reaction was completed, the reaction solution was poured into ice water to precipitate, filtered and washed. The crude product was purified by column chromatography (petroleum ether:ethyl acetate=8:2) to obtain pure compound 4 (1.1 g, 80%).

[0078] (3) Synthesis of Compound 5: Compound 4 (2.00 g, 7.32 mmol) was dissolved in 15 mL of ice-cold concentrated H 2 SO 4 Medium to completely dissolved. Guanidine nitrate (0.9 g, 7.37 mmol) was slowly added to the above solution, and reacted at room temperature for about 30 min. After the rea...

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Abstract

The present invention provides a non-radical photo-crosslinked hydrogel preparation method, comprising the following steps: a component A is dissolved in a biocompatible medium to obtain a solution A, component B-hydrazide, hydroxylamine or primary amine high molecular derivative is dissolved in a biocompatible medium to obtain a solution B; the solution A and the solution B are evenly mixed to obtain a hydrogel precursor solution; under illumination, aldehyde group produced by light excitation of o-nitrobenzyl in the component A of the hydrogel precursor solution is crosslinked with hydrazone, hydroxylamine or primary amine group in the component B in the form of respective formation of oxime and Schiff base to produce the hydrogel. The present invention also provides a kit for the hydrogel preparation, and application of the hydrogel in tissue repair, beauty and as a cell, protein or drug carrier. The tissue surface light-situ gel can be achieved by the hydrogel, in particular, wound surface in-situ thin glue formation can be achieved, and the hydrogel is especially suitable for clinical wound surface tissue repair and isolation.

Description

technical field [0001] The invention belongs to the field of biological materials, and in particular relates to a method for preparing a hydrogel material through non-radical photochemical crosslinking and an application thereof. 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. Among them, tissue repair and isolation of clinical wounds is an important category of tissue engineering and regenerative medicine. The materials currently applied to wound tissue repair and isolation mainly include solid membrane materials (RoyceJohnsonet.al.U.S.Pat.No.US7070584B2, issuedJuly4, 2006), formed colloid materials (YeongHuaHuanget.al.U.S.Pat.No.6238691B1, issuedMay29, 2001) and wound in ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/28C08J3/24C08J3/075C08L5/08C08L5/02C08L51/08C08L71/08C08B37/08C08B37/02C08F220/36C08F283/06C08G65/48A61L27/26A61L27/52A61L27/60A61L31/04A61L31/06A61L31/14A61K47/36A61K47/34
CPCA61K8/042A61K8/45A61K8/73A61K8/735A61K8/736A61K8/8152A61K9/0024A61K9/06A61K31/728A61K47/34A61K47/36A61K2800/882A61K2800/95A61L27/28A61L27/52A61L2430/34A61Q19/00A61Q19/02A61Q19/08C08J3/075C08J3/28C08J2305/02C08J2305/08C08J2371/02C08J2389/00C08L5/08A61K8/0212A61K8/65A61L31/042A61L31/145C08J3/246C08J2333/14C12N5/0012C12N5/0018C12N2500/60
Inventor 朱麟勇刘珍珍汪泱包春燕林秋宁方伟
Owner 上海戴云化工科技有限公司
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