Amphiphilic derivative of oil acylated chitosan oligosaccharide guanidine grafted polyethyleneimine and preparation method thereof

A technology of oleoylated chitosan and polyethylenimine, which is applied in the field of biomedical materials, can solve the problems of non-degradability, poor solubility of chitosan, and inability to fully utilize the advantages of chitosan, and achieve low cytotoxicity, Effect of High Transfection Efficiency

Inactive Publication Date: 2019-03-29
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chinese patent document CN103030813A discloses a preparation method of chitosan-grafted polyethylenimine non-viral transgene carrier, which combines the biocompatibility of chitosan and the transfection efficiency of polyethylenimine to show good biological Compatibility and high transfection efficiency, but the poor solubility of chitosan still limits its further application
The chemical link used for construction is a non-degradable link, and the respective advantages of chitosan and polyethyleneimine cannot be fully utilized

Method used

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  • Amphiphilic derivative of oil acylated chitosan oligosaccharide guanidine grafted polyethyleneimine and preparation method thereof
  • Amphiphilic derivative of oil acylated chitosan oligosaccharide guanidine grafted polyethyleneimine and preparation method thereof
  • Amphiphilic derivative of oil acylated chitosan oligosaccharide guanidine grafted polyethyleneimine and preparation method thereof

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Experimental program
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Effect test

Embodiment 1

[0035] 1) Dissolve (MW=1.5kDa) chitosan oligosaccharide in (0.02wt%, pH4.5) sodium acetate buffer, add 70wt% potassium periodate aqueous solution, and react at 4°C for 48h. After dialysis and lyophilization, oxidized chitosan (OXCOS) was obtained.

[0036] 2) Add 5 times the number of moles of chitosan oligosaccharide structural units (MW=0.8kDa) polyethyleneimine to the above aqueous solution, and react for 48 hours at -10 degrees Celsius in the dark, and add sodium tetrahydroborate to continue the reaction for 24 hours. The product is purified and lyophilized to obtain polyethyleneimine grafted chitosan (COS-PEI).

[0037] 3) Add CS-PEI to 1H-pyrazole-1-carboxamidine hydrochloride 1.5 times the moles of polyethyleneimine and N, N'1.5 times the moles of polyethyleneimine at 25°C -Reaction in diisopropylethylamine aqueous solution for 24h. The product was purified by dialysis and lyophilized to obtain COSG-PEI white solid.

[0038] 4) Add COSG-PEI and methanesulfonic acid into the...

Embodiment 2

[0040] 1) Dissolve (MW=3.0kDa) chitooligosaccharides in (0.05%, pH 5) sodium acetate buffer, add 80wt% potassium periodate, and react at 10°C for 60 hours. After dialysis and lyophilization, oxidized chitosan (OXCOS) was obtained.

[0041] 2) Add 6 times the moles of chitosan oligosaccharide structural unit (2.0kDa) polyethyleneimine to the above aqueous solution, react at -10 degrees Celsius and avoid light for 60 hours, add sodium tetrahydroborate and continue the reaction for 48 hours, and the product is purified After freeze-drying, polyethylenimine grafted chitosan oligosaccharide (COS-PEI) was obtained.

[0042] 3) At 35℃, add CS-PEI to 1H-pyrazole-1-carboxamidine hydrochloride 2 times the moles of polyethyleneimine and N, N'2 times the moles of polyethyleneimine -Reaction in diisopropylethylamine aqueous solution for 48h. The product was purified by dialysis and lyophilized to obtain COSG-PEI white solid.

[0043] 4) Add COSG-PEI and methanesulfonic acid to the four-neck fl...

Embodiment 3

[0045] 1) Dissolve ((MW=2.0kDa) chitosan oligosaccharides in (0.08wt%, pH 3.5) sodium acetate buffer, add 50wt% potassium periodate aqueous solution, and react at 15°C for 36 hours. Lyophilized by dialysis Then get oxidized chitosan (OXCOS).

[0046] 2) Add 3 times the mole number of chitosan oligosaccharide structural unit (1.5kDa) polyethyleneimine to the above aqueous solution, react for 36h at -10 degrees Celsius and avoid light, add sodium tetrahydroborate to continue the reaction for 36h, and the product is purified After lyophilization, polyethylenimine grafted chitosan oligosaccharide (COS-PEI) was obtained.

[0047] 3) Add CS-PEI to 1H-pyrazole-1-carboxamidine hydrochloride 3 times the moles of polyethyleneimine and N, N'3 times the moles of polyethyleneimine at 20°C -React 36h in diisopropylethylamine aqueous solution. The product was purified by dialysis and lyophilized to obtain COSG-PEI white solid.

[0048] (4) Add COSG-PEI and methanesulfonic acid to the four-neck f...

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Abstract

The invention discloses an amphiphilic derivative of oil acylated chitosan oligosaccharide guanidine grafted polyethyleneimine and a preparation method thereof. The amphiphilic derivative takes low molecular weight polyethyleneimine and chitosan oligosaccharide as a low cytotoxicity template, and then introduces guanidyl and lipophilic segment-oleoyl. The derivative takes the chitosan oligosaccharide as a base, so that non-toxicity and high bioactivity can be endowed to the derivative; nuclear localization ability, high transfection efficiency and lower cytotoxicity can be endowed to the derivative by introducing the guanidyl; and through the introduction of the lipophilic segment, the derivative can have amphipathy, so that the derivative is easier to take in by cells.

Description

Technical field [0001] The invention belongs to the field of biomedical materials, and more specifically relates to an amphiphilic derivative of oleoacylated chitooligosaccharide guanidine grafted with polyethyleneimine and a preparation method thereof. Background technique [0002] Gene therapy refers to the continuous expression of therapeutic proteins by carrying target genes to target cells, so as to achieve therapeutic effects. Gene vectors mainly include viral vectors and non-viral vectors. In recent years, non-viral vectors have developed rapidly due to their advantages such as simple preparation, no immune response and large nucleic acid carrying capacity. Non-viral vectors mainly include chitosan, polyethyleneimine, liposomes, dendrimers and so on. Polyethyleneimine (PEI) is the most widely used carrier material in polycationic composites. Compared with other vectors, the transfection efficiency is high and the price is low, but its cytotoxicity also limits its furthe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08B37/08
CPCC08B37/003C08G81/00
Inventor 刘晓非王园园邹雅露柳小宝张圣圣张海
Owner TIANJIN UNIV
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