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Preparation method, raw material, product and application of optical coupling crosslinking hydrogel material

An optical trigger and halogen atom technology is applied in the field of preparation of photocoupling and cross-linked hydrogel materials, which can solve the problems of limiting the clinical transformation of non-radical photo-coupling and cross-linking technology, short light curing wavelength, and complicated synthesis.

Active Publication Date: 2018-04-27
ZHONGSHAN GUANGHE MEDICAL TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this system still has some shortcomings, such as short photocuring wavelength (365nm), slow photocrosslinking speed (the initial gelation time is about 30s, and the complete gelation time is about 2min), and the synthesis is cumbersome, etc. The clinical transformation of this kind of non-free radical photocoupling cross-linking technology

Method used

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  • Preparation method, raw material, product and application of optical coupling crosslinking hydrogel material
  • Preparation method, raw material, product and application of optical coupling crosslinking hydrogel material
  • Preparation method, raw material, product and application of optical coupling crosslinking hydrogel material

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Experimental program
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Embodiment 1

[0142] Embodiment one: the synthesis of component A-1

[0143]

[0144] (1) Synthesis of compound 1: synthesized according to the method disclosed in references Sarit S. Agasti.; Apiwat Chompoosor.; Vincent M. Rotello. J. Am. Chem. Soc. 2009, 131, 5728.

[0145] (2) Synthesis of compound 2: Dissolve compound 1 (1g, 2.9mmol) 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. Compound 2 (0.92 g, yield 85%) was obtained after several times of dissolution-reprecipitation, filtration and vacuum drying. 1 H NMR (400MHz, CDCl 3 ):δ=7.91(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]373.1373.

[0146] (3) Synthesis of component A-1: ​​dissolve hyaluronic acid (2 g, 340 kDa) in 100 mL of 0.01 mol / L 2-(N-morpholine) ethanesulfonic acid...

Embodiment 2

[0147] Embodiment two: the synthesis of component A-2

[0148]

[0149] (1) Synthesis of compound 3: synthesized according to the method disclosed in references James F.Cameron.; JeanM.J.Frechet.J.Am.Chem.Soc.1991,113,4303.

[0150] (2) Synthesis of compound 4: Dissolve compound 3 (1g, 2.8mmol) 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 gave compound 4 (0.86 g, yield 80%). 1 H NMR (400MHz, CDCl 3 ):δ=7.91(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]387.1553.

[0151] (3) Synthesis of component A-2: dissolve hyaluronic acid (2 g, 340 kDa) in 100 mL of 0.01 mol / L 2-(N-morpholine) ethanesulfonic acid MES buffer solu...

Embodiment 3

[0152] Embodiment three: the synthesis of component A-3

[0153]

[0154] (1) Synthesis of compound 5: synthesized according to the method disclosed in references Michael C. Pirrung.; Yong Rok Lee.; Kaapjoo.; James B. Springer. J. Org. Chem. 1999, 64, 5042.

[0155] (2) Synthesis of compound 6: Dissolve compound 5 (1g, 2.4mmol) 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. Compound 6 (0.73 g, yield 68%) was obtained by filtration and vacuum drying after several times of dissolution-reprecipitation. 1 H NMR (400MHz, CDCl 3 ):δ=7.91(s,1H),6.35(dd,J=10.0,15.0Hz,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, 5.7Hz, 2H), 2.82(t, J=5.9Hz, 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]439.1828.

[0156] (3) Synthesis of component A-3: disso...

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Abstract

The invention relates to a preparation method, a raw material, a product and an application of an optical coupling crosslinking hydrogel material. Component A-nitrobenzyl phototrigger modified high-molecular derivatives are dissolved in a medium with biological compatibility in order to obtain a solution A; component B-primary amine, diamine, hydrazide, hydroxylamine high-molecular derivatives aredissolved in a medium with biological compatibility in order to obtain a solution B; the solution A and the solution B are uniformly mixed in order to obtain a hydrogel precursor solution; the hydrogel precursor solution is under light source irradiation, aldehyde group or ketone group generated by nitrobenzyl in the component A and primary amine, diamine, hydrazide, hydroxylamine groups in the component B are crosslinked in form of Schiff base in order to form a hydrogel. The invention also provides a kit for preparation of the hydrogel, and applications of the hydrogel to tissue engineering, regenerative medicine, 3D printing, and carriers of cells, proteins or drugs. The hydrogel precursor solution is sprayed or smeared on the surface of tissue in order to realize in situ gelation under light, and the product is especially suitable for postoperative wound enclosing and tissue fluid leakage sealing.

Description

technical field [0001] The invention belongs to the field of biological materials, and in particular relates to a preparation method, raw material, product and application of an optically coupled crosslinked hydrogel material. 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 fields of engineering and regenerative medicine. In situ cured hydrogels have excellent tissue shaping properties in clinical applications. Currently, in-situ curable hydrogels mainly include thermosensitive type (such as LeGoo, hydroxybutyl chitosan, etc.), two-component injection type (such as Fibrin Glue, Adherus AutoSpray, etc.), photosensitive Type (such as FocalSeal, ChonDux, etc.), etc. [0003] Among them, photosensitive hydrogel mat...

Claims

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Application Information

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IPC IPC(8): C08B37/08C08B15/06C08B37/04C08G69/48C08G65/333C08B37/02C08B37/10C08J3/075C09D11/14C09D11/102A61K9/06A61K47/34A61K47/36A61L24/00A61L24/04A61L24/08A61L26/00A61L27/18A61L27/20A61L27/52
CPCA61K9/06A61K47/34A61K47/36A61L24/0031A61L24/046A61L24/08A61L26/0019A61L26/0023A61L26/008A61L27/18A61L27/20A61L27/52A61L2400/04A61L2430/06C08B15/06C08B37/0009C08B37/003C08B37/0069C08B37/0072C08B37/0075C08B37/0084C08G65/33341C08G65/33389C08G65/33393C08G69/48C08J3/075C08J2305/02C08J2305/04C08J2305/08C08J2305/10C08J2371/10C08J2377/04C09D11/102C09D11/14C08L77/04C08L71/10C08L5/08
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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