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Photo-induced nitroso-crosslinked hydrogel material and its preparation method and application

An alkylene and o-nitrobenzyl technology is applied in the field of photoinduced nitroso cross-linked hydrogel materials and their preparation, which can solve unfavorable clinical operations, limit the clinical transformation of non-radical photo-coupling cross-linking technology, Problems such as slowing down of cross-linking speed

Active Publication Date: 2020-09-25
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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  • Photo-induced nitroso-crosslinked hydrogel material and its preparation method and application
  • Photo-induced nitroso-crosslinked hydrogel material and its preparation method and application
  • Photo-induced nitroso-crosslinked hydrogel material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0180] Example 1: Synthesis of component A-1

[0181]

[0182] (1) Synthesis of compound 1: According to the referenced literature Yunlong Yang; Jieyuan Zhang; Zhenzhen Liu; Qiuning Lin; Xiaolin Liu; Chunyan Bao; Yang Wang; Linyong Zhu. Adv. Mater. 2016, 28, 2724. . 1 H NMR(400MHz, CDCl 3 ): δ=7.71(s,1H),7.22(s,1H), 4.96(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 ]328.1507.

[0183] (2) Synthesis of component A-1: ​​Dissolve Hyaluronic acid (2g, 340kDa) in 100mL0.01mol / L 2-(N-morpholine)ethanesulfonic acid MES buffer solution (pH=5.2), stir To completely dissolve, weigh compound 1 (65 mg, 0.2 mmol), dissolve in 10 mL 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 and added to the above reaction solution three times (every 1h) and reacted at 35°C fo...

Embodiment 2

[0184] Example 2: Synthesis of component A-2

[0185]

[0186] (1) Synthesis of compound 2: According to the method disclosed in reference James F. Cameron.; Jean M.J. Frechet. J. Am. Chem. Soc. 1991, 113, 4303.

[0187] (2) Synthesis of compound 3: Dissolve compound 2 (1g, 3.2mmol) and ethylenediamine (1.1mL) in methanol (50mL), reflux for overnight reaction, and rotatory evaporation under reduced pressure, and dissolve the crude product in methanol , Reprecipitated in ethyl acetate. After multiple dissolution-reprecipitation, filtration and vacuum drying, compound 3 (0.89 g, yield 82%) can be obtained. 1 H NMR (400MHz, CDCl 3 ): δ=7.71(s,1H),7.22(s,1H), 4.96(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]342.1624.

[0188] (3) Synthesis of component A-2: Dissolve Hyaluronic acid (2g, 340kDa) in 100mL0.01mol / L 2-(N-morpholine)ethanesulfonic acid MES buffer solution (pH=5.2...

Embodiment 3

[0189] Example 3: Synthesis of component A-3

[0190]

[0191] (1) Synthesis of compound 4: According to the published method of Michael C. Pirrung.; Yong Rok Lee.; Kaapjoo.; James B. Springer. J. Org. Chem. 1999, 64, 5042.

[0192] (2) Synthesis of compound 5: Dissolve compound 4 (1g, 2.7mmol) and ethylenediamine (1.1mL) in methanol (50mL), reflux for overnight reaction, and rotatory evaporation under reduced pressure, and dissolve the crude product in methanol , Reprecipitated in ethyl acetate. After multiple dissolution-reprecipitation, filtration and vacuum drying, compound 5 (0.80 g, yield 74%) can be obtained. 1 H NMR (400MHz, CDCl 3 ): δ = 7.71 (s, 1H), 7.22 (s, 1H), 6.35 (dd, J = 10.0, 15.0 Hz, 1H), 6.04 (m, 1H), 5.8 (m, 1H), 5.4 (m, 1H), 4.96 (m, 1H), 4.13 (t, J = 6.1Hz, 2H), 3.99 (s, 3H), 3.32 (dd, J = 11.6, 5.7 Hz, 2H), 2.82 (t, J = 5.9 Hz,2H),2.44(t,J=7.2Hz,2H),2.26-2.17(m,2H),1.75(d, J=6.5Hz,3H).MS(ESI):[M+H]394.1908.

[0193] (3) Synthesis of component A-3: Dissolve ...

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Abstract

The invention relates to a photoinduced nitroso crosslinked hydrogel material and a preparation method and application thereof. The preparation method comprises the following steps of dissolving a macromolecular derivative which is modified by an o-nitrobenzyl photo trigger in a component A into a biocompatible medium, so as to obtain a solution A; uniformly mixing the solution A, or adding a solution B containing a component B, so as to obtain a hydrogel precursor solution; under the condition of using light source to radiate the hydrogel precursor solution, enabling the o-nitrobenzyl photo trigger in the component A to produce nitroso groups through photo-inducing, and enabling the nitroso group to generate dimerization crosslinking by self to form the hydrogel, or generate addition crosslinking with nucleophile or electrophile in the component B to form the hydrogel. The invention also provides a kit for preparing the hydrogel, and application of the hydrogel in tissue engineering,regeneration medicines, 3D (three-dimensional) printing or cell, protein or drug carriers. The photoinduced nitroso crosslinked hydrogel material has the advantages that the hydrogel precursor solution can be sprayed or smeared onto the surface of the tissue, so as to realize the in-situ gelling under the condition of light radiation; the photoinduced nitroso crosslinked hydrogel material is especially suitable for the post-operation wound sealing and the tissue liquid leakage blockage.

Description

Technical field [0001] The invention belongs to the technical field of biological materials, and specifically relates to a photo-nitroso cross-linked hydrogel material and a preparation method and application thereof. Background technique [0002] Hydrogel is a kind of highly water-containing polymer material with a three-dimensional network cross-linked structure. Because of its excellent biocompatibility and certain mechanical strength, it can highly fit the microenvironment of biological tissues, so it is widely used in tissues. Engineering and regenerative medicine fields. The hydrogel cured in situ has excellent tissue shaping properties in clinical applications. At present, the hydrogels that can be cured in situ are mainly temperature-sensitive (such as LeGoo, hydroxybutyl chitosan, etc.), two-component injection type (such as Fibrin Glue, Adherus AutoSpray, etc.), and photosensitive Type (such as FocalSeal, ChonDux, etc.) etc. [0003] Among them, the photosensitive hydr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08J3/075C08J3/24C08B37/08C08B37/04C08B37/02C08H1/00C08G69/48C08G65/333C08B11/12A61L24/04A61L26/00A61L27/18A61K47/34C09D11/14C09D11/102C09D11/04B33Y70/00C08L5/08C08L5/04C08L77/04C08L77/02C08L71/02C08L89/00C08L1/28
CPCA61K47/34A61L24/046A61L26/0019A61L27/18A61L2430/02A61L2430/06B33Y70/00C08B11/12C08B37/0009C08B37/003C08B37/0069C08B37/0072C08B37/0084C08G65/33396C08G69/48C08H1/00C08J3/075C08J3/246C08J2301/28C08J2305/04C08J2305/08C08J2371/02C08J2377/02C08J2377/04C08J2389/00C09D11/04C09D11/102C09D11/14
Inventor 林秋宁朱麟勇华宇杰张依晴包春燕钟学鹏
Owner ZHONGSHAN GUANGHE MEDICAL TECH CO LTD
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