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Ph-responsive polyaspartic acid grafted with hydrophobic amino acid and preparation method thereof

A technology of hydrophobic amino acid and polyaspartic acid is applied in the field of biomedical drug carrier materials, which can solve the problems of unseen continuous grafting of two hydrophobic amino acids, and achieves good cell compatibility, easy availability of experimental materials, The effect of mild reaction conditions

Active Publication Date: 2021-09-14
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the anionic polyamino acids currently reported are side chains grafted with a single hydrophobic amino acid ester, and there are no reports of consecutive grafting of two hydrophobic amino acids.

Method used

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  • Ph-responsive polyaspartic acid grafted with hydrophobic amino acid and preparation method thereof
  • Ph-responsive polyaspartic acid grafted with hydrophobic amino acid and preparation method thereof
  • Ph-responsive polyaspartic acid grafted with hydrophobic amino acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Preparation of polyaspartic acid-graft-phenylalanine-graft-benzyloxycarbonyl lysine

[0031] 1) polyaspartic acid (molecular weight M w =4500) (3.00g, the amount of carboxyl substance is 0.026mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide 4.98g, 0.026mol) is dissolved in 150mL mass concentration is 0.63 In wt% aqueous sodium bicarbonate solution, a solution having a polyaspartic acid concentration of 2.0 wt% was obtained and stirred for 30 min;

[0032] 2) According to the molar ratio of polyaspartic acid carboxyl group and L-phenylalanine methyl ester hydrochloride 1:1.2, add L-phenylalanine methyl ester hydrochloride (6.69g, 0.031mol) aqueous solution and react at room temperature 72h;

[0033] 3) Add 75 mL of 5.0 wt% sodium hydroxide ethanol solution for alkali washing, and stir overnight at room temperature;

[0034] 4) The solution is packed into a dialysis bag with a molecular weight cut-off of 0.5kDa, dialyzed with deionized water for 3 days, purif...

Embodiment 2

[0069] (1) Preparation of polyaspartic acid-graft-phenylalanine-graft-benzyloxycarbonyl lysine

[0070] 1) polyaspartic acid (molecular weight M w =46100) (1.50g, the amount of carboxyl substance is 0.013mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide 4.98g, 0.026mol) dissolved in 150mL mass concentration is 0.21 wt% aqueous sodium bicarbonate solution to obtain a solution with a polyaspartic acid concentration of 1.0 wt%, and stir for 60 min;

[0071] 2) According to the molar ratio of polyaspartic acid carboxyl group and L-phenylalanine methyl ester hydrochloride 1:0.6, add L-phenylalanine methyl ester hydrochloride (1.68g, 0.0078mol) aqueous solution and react at room temperature 72h;

[0072] 3) Add 80 mL of 2.0 wt% sodium hydroxide ethanol solution for alkali washing, and stir overnight at room temperature;

[0073] 4) Put the solution into a dialysis bag with a molecular weight cut-off of 1 kDa, dialyze with deionized water for 3 days, purify, and freeze-dry fo...

Embodiment 3

[0108] (1) Preparation of polyaspartic acid-graft-phenylalanine-graft-benzyloxycarbonyl lysine

[0109] 1) polyaspartic acid (molecular weight M w =16800) (2.0g, the amount of carboxyl substance is 0.017mol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide 2.3g, 0.012mol) are dissolved in 100mL mass concentration is 0.54 wt% aqueous sodium bicarbonate solution to obtain a solution with a polyaspartic acid concentration of 2.0 wt%, and stir for 50 min;

[0110] 2) According to the molar ratio of polyaspartic acid carboxyl group and L-phenylalanine methyl ester hydrochloride 1:0.9, add L-phenylalanine methyl ester hydrochloride (3.33g, 0.015mol) aqueous solution and react at room temperature 72h;

[0111] 3) Add 50 mL of 4.0 wt% sodium hydroxide ethanol solution for alkali washing, and stir overnight at room temperature;

[0112] 4) Put the solution into a dialysis bag with a molecular weight cut-off of 1 kDa, perform dialysis for 3 days, purify, freeze-dry for 24 hours to o...

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Abstract

The invention relates to a pH-responsive polyaspartic acid grafted with hydrophobic amino acids and a preparation method thereof, using polyaspartic acid and L-phenylalanine methyl ester hydrochloride as raw materials, through 1-(3- Dimethylaminopropyl)-3-ethyl carbodiimide coupling reaction and alkali washing, obtain polyaspartic acid-grafting-phenylalanine; use polyaspartic acid-grafting-phenylalanine Amino acid and hydrophobic amino acid hydrochloride are used as raw materials, and the product is obtained through coupling reaction and alkali washing. Hydrophobic amino acid hydrochloride including N ε ‑Benzyloxycarbonyllysine benzyl ester hydrochloride, tryptophan methyl ester hydrochloride, valine methyl ester hydrochloride and isoleucine methyl ester hydrochloride; The amino acid contains a pH-responsive anionic carboxyl group and has good biocompatibility. When the polymer concentration is less than 0.1 mg / mL, the survival rate of smooth muscle cells is above 80%. The operation is simple and the cost is low. It is suitable for the field of biomedical drug carrier materials.

Description

technical field [0001] The invention relates to a pH-responsive polyaspartic acid grafted with hydrophobic amino acids and a preparation method thereof, in particular to the preparation and application of pH-responsive polyaspartic acid grafted with hydrophobic amino acids, belonging to biomedical The field of drug carrier materials. Background technique [0002] As the pH of the solution changes, the conformation of the pH-responsive polymer will change accordingly. At present, there have been a lot of reports on the research on pH-responsive polymers (Kanamala M, Wilson WR, Yang M, Palmer BD, WuZ. Mechanisms and biomaterials in pH-responsive tumor targeted drug delivery:A Review.Biomaterials,2016,85,152 167). pH-responsive polymers can be divided into anionic polymers and cationic polymers according to the ionic properties in their structures. Among them, pH-responsive anionic polymers include polyaspartic acid, polyacrylic acid, polyethylacrylic acid, polymethacrylic a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/10A61K47/34
CPCA61K47/34C08G73/1092
Inventor 袁晓燕刘波张启发任丽霞赵蕴慧
Owner TIANJIN UNIV
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