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Novel bioadhesive thiolated chitosan synthesis method

A technology of thiolated chitosan and a synthesis method, which is applied in the synthesis field of novel bioadhesive thiolated chitosan, can solve the problems of reducing the catalytic activity of P-gp, etc., so as to ensure the exertion of efficiency, avoid hydrolysis and reaction controllable effect

Active Publication Date: 2016-07-13
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 WalkerA consensus sequence of the two ATP-binding domains of P-gp, although the changes in the structure of the cysteine ​​residues do not affect The function of P-gp is exerted, but the steric hindrance generated by covalent binding with TCS will reduce the catalytic activity of P-gp, thereby inhibiting its function.

Method used

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  • Novel bioadhesive thiolated chitosan synthesis method
  • Novel bioadhesive thiolated chitosan synthesis method
  • Novel bioadhesive thiolated chitosan synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Dissolve 2 g of N-acetyl-L-cysteine ​​(NAC), EDC·HCl, and HOBT (molar ratio 4:1:1) in 10 mL N,N-dimethylformamide ( DMF), stirring continuously at room temperature for 3-6 hours to activate NAC.

[0028] (2) Dissolve CS in 20% hydrochloric acid solution to prepare a polymer solution with a concentration of 1.25% (w / v).

[0029] (3) Add the 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 in the dark for 3-6 hours at room temperature.

[0030] (4) To purify the product, remove unreacted NAC, dialyze the reaction solution once with hydrochloric acid solution containing 5mmol / L, dialyze twice with hydrochloric acid (5mmol / L) containing 1% NaCl, and then dialyze the reaction solution with hydrochloric acid solution containing 5mmol / L The hydrochloric acid solution was dialyzed twice, and the time of each dialysis was 12 hours, and the whole dialysis process was carried out at 4°C in the dark. The dialyzed ...

Embodiment 2

[0033] (1) Dissolve 2 g of cysteine, EDC·HCl, and HOBT (molar ratio 10:9:1) in 10 mL N,N-dimethylformamide (DMF), and stir continuously at room temperature for 3 -6 hours to activate cysteine.

[0034] (2) Dissolve CS in 10% hydrochloric acid solution to prepare a polymer solution with a concentration of 0.8% (w / v).

[0035] (3) Add the 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 in the dark for 3-6 hours at room temperature.

[0036] (4) To purify the product, remove unreacted NAC, dialyze the reaction solution once with hydrochloric acid solution containing 1mmol / L, dialyze twice with hydrochloric acid (1mmol / L) containing 0.5% NaCl, and then dialyze the reaction solution with hydrochloric acid solution containing 1mmol / L The hydrochloric acid solution was dialyzed twice, and the time of each dialysis was 12 hours, and the whole dialysis process was carried out at 4°C in the dark. The dialyz...

Embodiment 3

[0039] (1) Dissolve 2 g of thioglycolic acid (TGA), EDC·HCl, HOBT (molar ratio 10:0.5:8) in 10 mL N,N-dimethylformamide (DMF), and stir continuously at room temperature 3-6 hours to activate TGA.

[0040] (2) Dissolving CS in 20% hydrochloric acid solution to prepare a polymer solution with a concentration of 1% (w / v).

[0041](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 in the dark for 3-6 hours at room temperature.

[0042] (4) To purify the product, remove unreacted TGA, dialyze the reaction solution once with hydrochloric acid solution containing 3mmol / L, dialyze twice with hydrochloric acid (3mmol / L) containing 1% NaCl, and then dialyze the reaction solution with hydrochloric acid solution containing 3mmol / L The hydrochloric acid solution was dialyzed twice, and the time of each dialysis was 12 hours, and the whole dialysis process was carried out at 4°C in the dark. The dialyzed solution is...

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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

Technical field: [0001] The invention relates to a method for synthesizing novel bioadhesive thiol chitosan, which belongs to the technical field of biomedical materials. Background technique: [0002] Chitosan (Chitosan, CS) is the only alkaline polysaccharide existing in nature, with a positive charge on the surface, good water solubility, biocompatibility, biodegradability and bioadhesion, and is an excellent functional biological material. 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. [0003] Thiolated chitosan (Thiolatedchitosan, TCS) is a polymer with free thiol groups and better water solubility prepared by reacting the amino groups on chitosan with thiol-containing compounds. The introduction of sulfhydryl groups endows CS with more excellent biological characteristics: ① Mucoadhesion is...

Claims

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Application Information

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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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