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Double-responsiveness glucan-polyamino acid block copolymer, preparation method of copolymer and drug-loaded micelle

A technology of block copolymers and polyamino acids, which is applied in capsule delivery, antineoplastic drugs, microcapsules, etc., can solve the problems of lack of intelligence in drug release, achieve good reduction responsiveness, enhance drug efficacy, and reduce toxicity.

Active Publication Date: 2015-07-22
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned drug-loaded micelles have the problem of lack of intelligence in drug release because the chemical bonds between polymer compounds are too stable.

Method used

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  • Double-responsiveness glucan-polyamino acid block copolymer, preparation method of copolymer and drug-loaded micelle
  • Double-responsiveness glucan-polyamino acid block copolymer, preparation method of copolymer and drug-loaded micelle
  • Double-responsiveness glucan-polyamino acid block copolymer, preparation method of copolymer and drug-loaded micelle

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preparation example Construction

[0040] The present invention also provides a method for preparing a double-responsive dextran-polyamino acid block copolymer having a structure of formula (I), comprising the following steps:

[0041] A1) mix dextran, cystamine dihydrochloride and buffer solution, and react to obtain the compound shown in formula (II);

[0042]

[0043] B1) mixing the compound represented by formula (II), amino acid-N-internal carboxylic acid anhydride and an organic solvent, and reacting to obtain a double-responsive dextran-polyamino acid block copolymer;

[0044] The double-responsive dextran-polyamino acid block copolymer has a structure shown in formula (I):

[0045]

[0046] Among them, 10≤n≤3125; 10≤m≤200;

[0047] -R selected from -H, -CH 3 、-CH(CH 3 )CH 3 、-CH 2 CH(CH 3 )CH 3 、-CH(CH 3 )CH 2 CH 3 , -CH 2 Oh, -CH 2 SH, -CH(OH)CH 3 ,

[0048] In the present invention, dextran, cystamine dihydrochloride and buffer solution are mixed and reacted to obtain t...

Embodiment 1～4

[0077] Prepare an acetate buffer solution with pH=5, measure 50 mL of the configured buffer solution and place them in 4 round-bottomed flasks respectively, add 0.225 g of cystamine dihydrochloride to each flask, stir to dissolve, and then Add 5g glucan in each flask, the number average molecular weight of described dextran is 5000g / mol, then seal each reaction bottle, according to the reaction temperature condition of table 1, react 52h, after reaction finishes, with sodium bicarbonate The solution adjusted the pH of each reaction solution to 7.4, and then dialyzed with a dialysis bag with a molecular weight cut-off of 3500 Dalton for 48 hours, filtered and freeze-dried to obtain compounds represented by formula (II). The experimental results are shown in Table 1, and Table 1 shows the reaction conditions of Examples 1-4 of the present invention and the yields of the obtained products.

[0078] The reaction conditions of table 1 embodiment of the present invention 1~4 and the...

Embodiment 5～8

[0081] Prepare acetate buffer solution respectively according to the pH value condition of table 2, and respectively measure the buffer solution of 50mL configuration and place in 4 round bottom flasks respectively, add 0.225g cystamine dihydrochloride respectively in each flask, After stirring and dissolving, add 5g of dextran to each flask, the number-average molecular weight of the glucan is 5000g / mol, then seal each reaction bottle, and react for 52h at a reaction temperature of 40°C. After completion, the pH of each reaction solution was adjusted to 7.4 with sodium bicarbonate solution, and then dialyzed with a dialysis bag with a molecular weight cut-off of 3500 Dalton for 48 hours, filtered and freeze-dried to obtain compounds represented by formula (II). The experimental results are shown in Table 2, and Table 2 shows the reaction conditions of Examples 5-8 of the present invention and the yields of the obtained products.

[0082] The reaction conditions of table 2 emb...

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Abstract

The invention provides a double-responsiveness glucan-polyamino acid block copolymer which adopts the structure shown in formula (I), can be self-assembled into a micelle in a water environment and is used for loading a hydrophobic antitumor drug. Compared with the prior art, the double-responsiveness glucan-polyamino acid block copolymer has the advantages that hydrophilic-chain glucan and hydrophobic-chain polyamino acid are connected through an oxime bond and a disulfide bond, so that the double-responsiveness glucan-polyamino acid block copolymer has the good pH responsiveness as well as the good reduction responsiveness, the prepared drug-loaded micelle can quickly release the drug in tumor tissue or cells, under low-pH-value environments or high-GSH (glutathione)-concentration environments, the efficacy is enhanced, and the toxicity is reduced.

Description

technical field [0001] The invention relates to the technical field of biomedical polymer materials, and more specifically relates to a double-responsive dextran-polyamino acid block copolymer, a preparation method thereof, and drug-loaded micelles. Background technique [0002] Tumor has become one of the most serious diseases threatening human health. At present, the commonly used clinical cancer treatment methods include chemotherapy, radiotherapy and surgery. Among them, chemotherapy is the most commonly used and important treatment. However, the clinically used antineoplastic drugs have many defects in their application, such as: poor water solubility and stability, and large toxic and side effects of drugs. In order to solve these problems, drugs can be combined with drug carriers to improve the water solubility and stability of drugs, and achieve controlled release of drugs, thereby reducing the side effects of drugs on normal tissues and giving full play to the eff...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/10C08B37/02A61K9/51A61K47/36A61K31/4745A61K31/704A61K31/337A61P35/00
Inventor 丁建勋卢升帆庄秀丽陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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