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Hydrogel, preparation method thereof and applications

A hydrogel and buffer technology, applied in medical science, prosthesis, etc., can solve the problems of many synthesis steps of ring tension alkynyl group, low storage modulus of hydrogel, long gel time, etc., and achieve excellent biological activity. , excellent fluorescence performance, simple preparation effect

Active Publication Date: 2015-04-29
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Anseth and Becker et al. reported that the click chemical reaction of alkynyl and azide without catalyst was used for the preparation of polyethylene glycol hydrogel, and the prepared hydrogel showed good cytocompatibility, but the ring strained alkynyl Many synthetic steps and low yields (see: Deforest CA, Polizzotti BD, Anseth KS. Nat. Mater. 2009, 8, 659-664; Zheng J, Callahan LAS, Hao J, et al. ACS Macro Lett. 2012, 1, 1071-1073); Shoichet and Marra et al prepared hyaluronic acid hydrogel by Diels-Alder click chemical reaction without catalyst. Proteins such as enzymes achieve controlled release up to 21 days, but hydrogels prepared by Diels-Alder click chemistry have long gel times and low storage modulus of hydrogels (see: Nimmo CM, Owen SC, Shoichet MS. Biomacromolecules 2011, 12, 824-830; Tan H, Rubin JP, Marra KG. Macromol. Rapid Commun. 2011, 32, 905-911)

Method used

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  • Hydrogel, preparation method thereof and applications
  • Hydrogel, preparation method thereof and applications

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Experimental program
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Effect test

Embodiment 1

[0049] Embodiment one: four-arm polyethylene glycol tetrazole derivatives (PEG-TET 4 )Synthesis

[0050] (1) In a 100mL two-necked bottle, under nitrogen protection, take 0.75 g (5 mmol) of p-formylbenzoic acid and dissolve it in 50 mL of ethanol, fully dissolve, add 0.86 g (5 mmol) of benzenesulfonyl hydrazide, dissolve , stirred for half an hour, precipitated with secondary water, and dried to obtain 1.2975 g of light yellow solid phenylhydrazone, with a yield of 85.4%. Aniline 0.23 mL (0.23 g) was dissolved in a mixed solution (2 mL water, 2 mL ethanol, 0.65 mL concentrated HCl), and NaNO 2 The solid (0.175 g) was dissolved in 1 ml of secondary water, and after dissolving, it was added dropwise to the above mixed solution and stirred for 15 min to form a light yellow diazobenzene solution. Dissolve phenylhydrazone (0.6 g) in 15 ml of pyridine, fully dissolve, add dropwise to the diazobenzene solution mentioned above, and control the reaction temperature at 0°C with an ice...

Embodiment 2

[0052] Embodiment two: chitosan tetrazole derivatives (Chit-TET n )Synthesis

[0053] Under the condition of nitrogen protection, tetrazole (0.216 g) was dissolved in DMSO (15 mL), then DCC (120 mg) was added to react for 30 min, and then added to chitosan aqueous solution (80K, 0.5 g), and At the same time, DMAP (10 mg) was added, and the mixture was stirred at room temperature for 24 hours. The polymer solution was purified by ultrafiltration and freeze-dried to obtain the product Chit-TET n (0.39 g, 78.0%). Chit-TET n NMR characterization, 1 H NMR (400 MHz, D 2 O): δ 8.15-8.21 (m, 4H, C 6 h 4 of TET); 7.47, 7.55 and 8.28 (m, 5H, C 6 h 5 of TET); 4.46 (s, 1H, the proton on the methine at the α-position of chitosan); 3.27-4.10 (m, 9H, the methylene and methine linked to the ether bond and hydroxyl group in chitosan protons on methyl groups); 2.97-3.16 (m, 1H, methine protons attached to amino groups on chitosan).

Embodiment 3

[0054] Embodiment three: four-arm polyethylene glycol methacrylate derivatives (PEG-MA 4 )Synthesis

[0055] Under nitrogen protection conditions, add eight-arm polyethylene glycol PEG ( M n =10 K, 0.25g), triethylamine (Et 3 N, 120 μL), methacrylic anhydride (240 μL), DMAP (4.9 mg), toluene 10 mL, seal the reactor well, put it in a 70°C oil bath for 24 hours, then precipitate with ice ether, filter, and store at room temperature Vacuum drying to obtain product 0.45 g, yield 60.5%; PEG-4-MA NMR characterization see attached figure 2 , 1 H NMR (400 MHz, CDCl 3 ): δ 5.54 and 6.10 (s, 2H, -COC(CH 3 )CH 2 ), 4.28 (t, 2H, -COOCH 2 -), 3.61 (m, methylene protons on the PEG backbone), 1.91 (s, 3H, -COC(CH 3 )CH 2 ).

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Abstract

The invention discloses a hydrogel, a preparation method thereof and application The hydrogel is prepared by a simple light-operated 'tetrazolium and an alkene' click chemistry method, wherein the method has advantages of high efficiency, speediness, strong specificity, no need of catalyst and space-time controllability. The hydrogel prepared by the method not only has good mechanical properties, controllable gel time and excellent cell compatibility, but also can implement nondestructive wrapping and completely controllable release of a medicament and a cell. Therefore the light-operated 'tetrazolium and an alkene' click chemistry hydrogel has good application prospect in medicament controllably- releasing carrier and tissue engineering support material fields.

Description

technical field [0001] The present invention relates to a hydrogel, its preparation method and application, in particular to a hydrogel based on polymer tetrazole derivatives and polymer methacrylate derivatives, its preparation method, and the hydrogel in Applications in the field of medicine. Background technique [0002] Hydrogels have been widely used in the fields of tissue engineering and drug sustained release due to their high water content, size-adjustable porous structure, and good biocompatibility. Hydrogels can be prepared by physical cross-linking and chemical cross-linking: physical cross-linking includes hydrophobic interaction, stereocomplexation of polylactic acid, electrostatic interaction, etc. Physical gel preparation usually does not require toxic reagents, and can achieve non-damaging encapsulation of protein drugs , but usually have poor stability, and the encapsulated protein drug releases faster; chemical cross-linking includes free radical polymeri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G81/00C08G65/48C08G63/91C08B37/08C08B37/02C08H1/00A61K47/34A61L27/18A61L27/52
Inventor 邓超范亚萍孟凤华程茹钟志远
Owner SUZHOU UNIV
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