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Preparation method of non-radical photochemical cross-linked hydrogel material, product and application thereof

A hydrogel and free radical technology, applied in the direction of biochemical equipment and methods, cosmetic preparations, medical preparations of non-active ingredients, etc., can solve the problems of difficult preparation of hydrogel, difficulty in in-situ gelation, toxic and side effects And other issues

Active Publication Date: 2017-08-29
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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  • Preparation method of non-radical photochemical cross-linked hydrogel material, product and application thereof
  • Preparation method of non-radical photochemical cross-linked hydrogel material, product and application thereof
  • Preparation method of non-radical photochemical cross-linked hydrogel material, product and application thereof

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 group

[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 , 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

A method for preparing non-free radical photo-crosslinked hydrogels includes: dissolving component A that is a polymer derivative modified with o-nitrobenzyl phototrigger in a biocompatible medium to obtain solution A; dissolving component B that is a polymer derivative containing hydrazide, hydroxylamine or primary amine in a biocompatible medium to obtain solution B; mixing solution A and solution B to obtain a precursor solution of hydrogel; under light irradiation, crosslinking aldehyde generated from the o-nitrobenzyl with the hydrazine, hydroxylamine or primary amine to obtain a hydrogel by forming hydrazone, oxime or schiff base, respectively. A kit for preparation and application of the hydrogel in tissue repair, beauty therapy, and cells, proteins or drugs carriers is also described. The method or kit can achieve in situ photo-gelling on tissue surface or in situ forming thin gel on wounds in clinical treatment of wounds.

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 (Royce Johnson et. .6238691B1,issued May 29,2001) and wound in situ gelling materials. [0003] Among them, the cost of solid film material is relatively high, i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08J3/28C08J3/24C08J3/075C08L5/08C08L5/02C08L51/08C08L71/02C08B37/08C08B37/02C08F220/36C08F283/06C08G65/48A61L27/26A61L27/52A61L27/60A61L31/04A61L31/06A61L31/14A61K47/36A61K47/10A61K47/32
CPCC08J3/075A61K8/0212A61K8/042A61K8/45A61K8/65A61K8/73A61K8/735A61K8/736A61K8/8152A61K9/0024A61K9/06A61K31/728A61K47/34A61K47/36A61K2800/882A61K2800/95A61L27/28A61L27/52A61L31/042A61L31/145A61L2430/34A61Q19/00A61Q19/02A61Q19/08C08J3/246C08J3/28C08J2305/02C08J2305/08C08J2333/14C08J2371/02C08J2389/00C12N5/0012C12N5/0018C12N2500/60C08L5/08
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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