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Cation-type chitosan bionic derivative and application thereof

A cationic, chitosan technology, applied in non-active ingredients medical preparations, medical preparations containing active ingredients, peptide/protein ingredients, etc., can solve the problem of low cell entry efficiency, high toxicity and affecting protein activity and other problems, to achieve the effect of improving intracellular transport efficiency, promoting escape, and helping to maintain

Active Publication Date: 2016-01-20
浙江梅迪维斯生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, cationic polymer carriers are beneficial to realize the delivery of protein drugs into cells, but there are still various deficiencies, such as high toxicity, low efficiency of cell entry, and affecting protein activity.

Method used

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  • Cation-type chitosan bionic derivative and application thereof
  • Cation-type chitosan bionic derivative and application thereof
  • Cation-type chitosan bionic derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthesis of embodiment 1 acetylhistidine-phosphate dicholine chitosan hydrochloride

[0034] 1. Dissolve 200 mg of 6-O-triphenylmethyl etherified chitosan (CsTr) modified by chitosan (x / n=0) in 10 mL of anhydrous dimethylacetamide, and add 0.42 mL of triethylamine and 0.19 mL of carbon tetrachloride; slowly add 0.76 g of disubstituted choline phosphonate, wherein the molar ratio of the amino group in CsTr to phosphonate is 1:4, and stir for 10 hours; spin to dry the solvent , add formic acid, stir at room temperature for 2 hours; spin dry formic acid, dialyze with physiological saline and deionized water, and freeze-dry to obtain phosphoric acid dicholine chitosan hydrochloride.

[0035] 2. Dissolve 520mg (2.6mmol) of acetyl histidine in 20mL of anhydrous DMSO, remove a small amount of water by rotary evaporation, add 1.62g (10mmol) of N,N-carbonyldiimidazole (CDI), stir at room temperature for 4 hours, and rotate to evaporate Remove DMSO, then add 100 mg phosphor...

Embodiment 2

[0036] The synthesis of embodiment 2 acetylhistidine-phosphate dicholine chitosan hydrochloride

[0037] 1. Dissolve 500mg of 6-O-triphenylmethyl etherified chitosan (CsTr) modified by chitosan (x / n=0.2) in 40mL of anhydrous dimethylacetamide, and add 1.05mL of triethylamine and 0.49mL of carbon tetrachloride; slowly add 2.3g of disubstituted choline phosphonate, wherein the molar ratio of the amino group in CsTr to phosphonate is 1:6, and stir for 12 hours; spin to dry the solvent , add formic acid, stir at room temperature for 3 hours; spin dry formic acid, dialyze with normal saline and deionized water for 3 days, and freeze-dry to obtain phosphoric acid dicholine chitosan hydrochloride.

[0038] 2. Dissolve 260mg (1.3mmol) of acetyl histidine in 15mL of anhydrous DMSO, remove a small amount of water by rotary evaporation, add 1.62g (10mmol) of N,N-carbonyldiimidazole (CDI), stir at room temperature for 12 hours, and rotate to evaporate Remove DMSO, then add 100 mg phospho...

Embodiment 3

[0039] The synthesis of embodiment 3 acetylhistidine-phosphate dicholine chitosan hydrochloride

[0040] 1. Dissolve 300mg of 6-O-triphenylmethyl etherified chitosan (CsTr) modified by chitosan (x / n=0.1) into 30mL of anhydrous dimethylacetamide, and add 0.63mL triethylamine and 0.29 mL of carbon tetrachloride; slowly add 1.84 g of disubstituted choline phosphonate, wherein the molar ratio of the amino group in CsTr to phosphonate is 1:8, and stir for 12 hours; spin to dry the solvent , add formic acid, stir at room temperature for 6 hours; spin dry formic acid, dialyze with normal saline and deionized water for 3 days, and freeze-dry to obtain phosphoric acid dicholine chitosan hydrochloride.

[0041] 2. Dissolve 520mg (2.6mmol) of acetyl histidine in 20mL of anhydrous DMSO, remove a small amount of water by rotary evaporation, add 0.81g (5mmol) N,N-carbonyldiimidazole (CDI), stir at room temperature for 6h, and rotate to evaporate Remove DMSO, then add 100 mg phosphoric acid d...

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Abstract

The invention discloses a cation-type chitosan bionic derivative and application thereof and belongs to the technical field of biomedical polymer materials. The cation-type chitosan bionic derivative contains citicoline groups (PdC) provided with a locally branched dual positive charge structure, and acetyl histidine groups with pH sensitivity, wherein water solubility, cell toxicity and blood compatibility are also taken into consideration, and protein conformation is kept easily; endosomal escape in carrier system cells can be promoted, and the acetyl histidine groups and PdC cooperate with each other to improve intracellular transmission efficiency of protein medicine. The derivative and the protein medicine can be automatically assembled through a simple technology under moderate conditions to form a nano composite system, good biocompatibility and endocytosis efficiency are presented, activity of protein can be maintained, and the derivative is used for protein medicine conveying.

Description

technical field [0001] The invention belongs to the technical field of biomedical polymer materials, and in particular relates to a cationic chitosan biomimetic derivative and an application thereof. Background technique [0002] With the development of genes and proteomics, through recombinant DNA technology, proteins such as peptides, proteins, vaccines and monoclonal antibodies can be developed for cancer, diabetes, AIDS, multiple sclerosis, anemia, heart failure and some rare diseases Drugs for prevention and treatment. On the one hand, macromolecular protein drugs have the outstanding characteristics of being close to normal physiological substances in the body, good compliance, easy to be absorbed by the body, high pharmacological activity, strong pertinence, low toxicity, and no accumulation of poisoning, etc., making protein drugs a cure for many human diseases. the most indispensable part of it. On the other hand, protein drugs also have disadvantages such as poor...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K47/36A61K38/00
Inventor 曾戎吴铭敏屠美赵剑豪
Owner 浙江梅迪维斯生物技术有限公司
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