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A kind of synthetic method of bioadhesive thiol chitosan

A technology of thiolated chitosan and a synthesis method, which is applied in the field of biomedical materials, can solve the problems of reducing the catalytic activity of P-gp, and achieve the effects of ensuring performance, controllable reaction, and simple preparation process

Active Publication Date: 2019-07-16
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

③ P-gp inhibition: TCS can form a covalent bond with the cysteine ​​residues located on the Walker A consensus sequence of the two ATP-binding domains of P-gp, although the changes in the structure of the cysteine ​​residues do not Affects the function of P-gp, but the steric hindrance generated by the covalent combination with TCS will reduce the catalytic activity of P-gp, thereby inhibiting its function

Method used

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  • A kind of synthetic method of bioadhesive thiol chitosan
  • A kind of synthetic method of bioadhesive thiol chitosan
  • A kind of synthetic method of bioadhesive thiol chitosan

Examples

Experimental program
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Effect test

Embodiment 1

[0031] (1) Dissolve N-acetyl-L-cysteine ​​(NAC), EDC·HCl, HOBT (molar ratio 4:1:1) with a total mass of 2g in 10mL N,N-dimethylformamide (DMF), continuous stirring at room temperature for 3-6 hours to activate NAC.

[0032] (2) Dissolve CS in a 20% hydrochloric acid solution to prepare a polymer solution with a concentration of 1.25% (w / v).

[0033] (3) Add activated NAC to the CS solution (the molar ratio of NAC to CS is 4:1), adjust the pH to 5 with NaOH, and react for 3-6 hours in the dark at room temperature.

[0034] (4) To purify the product, remove the unreacted NAC. The reaction solution was dialyzed once with 5mmol / L hydrochloric acid solution, twice with 1% NaCl-containing hydrochloric acid (5mmol / L), and then with 5mmol / L The hydrochloric acid solution was dialyzed twice, each time was 12 hours, and all the dialysis processes were performed at 4°C and protected from light. Take out the solution after dialysis, pass through a 0.8μm filter membrane to remove impurities, an...

Embodiment 2

[0037] (1) Dissolve cysteine, EDC·HCl, HOBT (molar ratio 10:9:1) with a total mass of 2g in 10mL N,N-dimethylformamide (DMF), and stir continuously at room temperature 3-6 hours to activate cysteine.

[0038] (2) Dissolve CS in a 10% hydrochloric acid solution to prepare a polymer solution with a concentration of 0.8% (w / v).

[0039] (3) Add activated cysteine ​​to the CS solution (the molar ratio of cysteine ​​to CS is 20:1), adjust the pH to 4 with NaOH, and react for 3-6 hours in the dark at room temperature.

[0040] (4) To purify the product, to remove unreacted NAC, the reaction solution was dialyzed once with 1mmol / L hydrochloric acid solution, twice with 0.5% NaCl-containing hydrochloric acid (1mmol / L), and then with 1mmol / L The hydrochloric acid solution was dialyzed twice, each time was 12 hours, and all the dialysis processes were performed at 4°C and protected from light. Take out the solution after dialysis, pass through a 0.8μm filter membrane to remove impurities, an...

Embodiment 3

[0043] (1) Dissolve thioglycolic acid (TGA), EDC·HCl, HOBT (molar ratio 10:0.5:8) with a total mass of 2g in 10mL N,N-dimethylformamide (DMF), continuous at room temperature Stir for 3-6 hours to activate TGA.

[0044] (2) Dissolve CS in a 20% hydrochloric acid solution to prepare a polymer solution with a concentration of 1% (w / v).

[0045] (3) Add the activated TGA to the CS solution (the molar ratio of TGA to CS is 10:1), adjust the pH to 5 with NaOH, and react for 3-6 hours in the dark at room temperature.

[0046] (4) To purify the product, remove the unreacted TGA. The reaction solution was dialyzed once with hydrochloric acid solution containing 3mmol / L, twice with hydrochloric acid containing 1% NaCl (3mmol / L), and then with 3mmol / L The hydrochloric acid solution was dialyzed twice, each time was 12 hours, and all the dialysis processes were performed at 4°C and protected from light. Take out the solution after dialysis, pass through a 0.8μm filter membrane to remove impuri...

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Abstract

The invention relates to a novel bioadhesive thiolated chitosan synthesis method.By taking a sulfydryl donor and chitosan as initial materials, taking 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1-hydroxybenzotriazole as condensing agents and selecting a proper organic solvent as an inert solvent for NAC activation, free amino groups of the sulfydryl donor and the chitosan are connected to obtain thiolated chitosan.Compared with the chitosan, the thiolated chitosan has the advantages of excellent water solubility, high electropositivity, remarkably improved bioadhesiveness and biocompatibility and wide applicability to fields of biomedicine, food, chemical engineering and the like.In a sulfydryl donor activation process, a reaction solvent is changed into the inert organic solvent from deionized water, and accordingly hydrolysis of the activated sulfydryl donor is effectively avoided, the free sulfydryl content of products is increased, and biopotency is guaranteed.The novel bioadhesive thiolated chitosan synthesis method is mild in preparation condition, controllable in reaction, simple in preparation process and suitable for large-scale continuous production.

Description

[0001] Technical field: [0002] The invention relates to a method for synthesizing bioadhesive sulfhydryl chitosan, and belongs to the technical field of biomedical materials. [0003] Background technique: [0004] Chitosan (Chitosan, CS) is the only alkaline polysaccharide that exists in nature. It has a positive charge on the surface. It has good water solubility, biocompatibility, biodegradability and bioadhesion, and is an excellent function Sexual biological materials. However, due to the strong hydrogen bonding in the CS molecule, it cannot be directly dissolved in water and general organic solvents, but can only be dissolved in acidic solutions, which greatly limits the application of CS. [0005] Thiolated chitosan (Thiolated chitosan, TCS) is a polymer with free sulfhydryl groups and better water solubility prepared by reacting the amino groups on chitosan with sulfhydryl-containing compounds. The introduction of sulfhydryl groups gives CS more excellent biological propert...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08
CPCC08B37/003
Inventor 潘卫三刘丹丹李金宇
Owner SHENYANG PHARMA UNIVERSITY
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