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A triblock amphiphilic copolymer and its preparation method, drug-protein co-delivery carrier and its preparation method

A tri-block and copolymer technology, applied in the field of polymers, to achieve the effect of inhibiting tumor cell proliferation

Active Publication Date: 2021-07-02
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 physical and chemical properties of chemotherapeutic drugs and protein molecules are very different, such as stability, molecular weight, hydrophilicity and hydrophobicity, and surface charge, etc., making the development of co-delivery nanocarriers face great challenges.

Method used

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  • A triblock amphiphilic copolymer and its preparation method, drug-protein co-delivery carrier and its preparation method
  • A triblock amphiphilic copolymer and its preparation method, drug-protein co-delivery carrier and its preparation method
  • A triblock amphiphilic copolymer and its preparation method, drug-protein co-delivery carrier and its preparation method

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Experimental program
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preparation example Construction

[0051] The present invention provides a method for preparing the triblock amphiphilic copolymer described in the above technical scheme, comprising the following steps:

[0052] In the presence of a solvent and a catalyst, polyethylene glycol monomethyl ether-b-poly(L-glutamic acid)-b-poly(γ- 1 N-(N,N-diisopropylethylamine)-1,2,3-triazole-4-methyl-L-glutamate) block copolymer and dopamine with the structure of formula III pass Amidation reaction, obtains the triblock amphiphilic copolymer with formula I structure;

[0053] Formula II, 10≤x≤500; 5≤y≤100; 5≤z≤100;

[0054]

[0055] In the present invention, in order to distinguish it from the catalyst in the following technical scheme, polyethylene glycol monomethyl ether-b-poly( L -glutamate)-b-poly(γ- 1 N-(N,N-diisopropylethylamine)-1,2,3-triazole-4-methyl- L -glutamic acid ester) block copolymer and the dopamine that has formula III structure carry out amidation reaction and adopt the catalyst name as the first catal...

Embodiment 1

[0098] Weigh 20 g of diisopropylaminoethyl chloride hydrochloride and 19.48 g of sodium azide, and add 60 mL of water into the reaction flask. The reaction was stirred at 80°C overnight, and the resulting mixture was adjusted to pH 10 with potassium hydroxide, and then extracted three times with 50 ml of ether. The organic phase was collected and dried with anhydrous magnesium sulfate, and the diethyl ether was removed by rotary evaporation to obtain 2-ethylazido-N,N-diisopropylamine as a light yellow oily product.

[0099] The 2-ethylazido-N,N-diisopropylamine obtained above is detected, figure 1 The proton nuclear magnetic resonance spectrum of 2-ethylazido-N,N-diisopropylamine prepared for Example 1 of the present invention shows that the 2-ethylazido-N,N-diisopropylamine has the formula V structure.

Embodiment 2

[0101] Weigh 1.6 g of terminally aminated polyethylene glycol monomethyl ether (molecular weight: 2000) synthesized in reference 2, use toluene-azeotropic water removal treatment, and add 70 ml of anhydrous DMF to dissolve. Then weigh 5.3 g of the γ-benzyl-glutamate-N-carboxyl internal anhydride synthesized in reference 1, and add it to the above-mentioned terminally aminated polyethylene glycol monomethyl ether solution at one time, at 25°C After stirring and reacting for 72 hours, weigh 3.4 g of γ-propargyl-glutamate-N-carboxyl internal anhydride synthesized in Reference 1, dissolve it in 30 ml of anhydrous DMF, and then add it to the above mixed solution at one time After stirring and reacting at 25°C for 72h, weigh 117.3mg of DMAP and add it to the above mixed solution, then add 5mL of acetic anhydride to the above mixed solution, stir and react at 25°C for 24h, dialyze and freeze-dry to obtain a white powder product with Polyethylene glycol monomethyl ether-b-poly(γ-benzy...

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Abstract

The invention provides a block amphiphilic copolymer, which comprises polyethylene glycol monomethyl ether segment, catechol side group-containing polyglutamic acid segment and tertiary amine side group-containing polyglutamic acid segment in sequence Acid segment, the copolymer has the structure of formula I. The triblock copolymer provided by the present invention supports hydrophobic chemotherapeutic drugs through hydrophobic interaction, and simultaneously supports phenylboronic acid-modified protein drugs through reversible covalent bonding of catechol and phenylboronic acid, thereby obtaining a drug / protein co-delivery carrier system. The drug / protein co-delivery carrier can transduce chemotherapeutic drugs and proteins into tumor cells, and release drugs and proteins in the acidic environment of tumor cells, and mediate the proton sponge effect generated by the protonation of tertiary amino acids under acidic conditions. The endosome / lysosome escape of the molecule realizes the synergistic anti-tumor effect of chemotherapy drugs and proteins. The invention also provides a preparation method of a triblock amphiphilic copolymer and a drug / protein co-delivery carrier.

Description

technical field [0001] The invention belongs to the technical field of polymers, and in particular relates to a three-block amphiphilic copolymer and a preparation method thereof, a drug-protein co-delivery carrier and a preparation method thereof. Background technique [0002] Cancer has become a major public health problem that seriously threatens the life and health of our people and social and economic development. Currently, cancer treatments mainly include surgery, radiation therapy, and chemotherapy. Among them, chemotherapy is a very important means in cancer treatment. Studies have found that the use of a single chemotherapy drug can easily induce drug resistance in tumor cells, and has the disadvantages of large toxic and side effects and limited treatment options, which greatly reduces the therapeutic effect; combined drug use, that is, the simultaneous use of two or more drugs with different Drugs with anti-cancer mechanisms can effectively overcome the shortco...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/48C08G69/10A61K47/34A61K31/704A61K38/46A61P35/00
CPCA61K31/704A61K38/465A61K47/34A61P35/00C08G69/10C08G69/48C12Y301/27005A61K2300/00
Inventor 肖春生张鹏陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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