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Amphiphilic graft copolymer with catechol ligand as well as synthesis method and application thereof

A technology of grafting polymer and synthesis method, applied in the field of intelligent nanomicelle carrier, can solve problems such as toxic and side effects, drug leakage, destruction of micellar structure, etc., and achieve the effect of killing effect and stable existence.

Inactive Publication Date: 2018-09-07
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] When the drug-loaded nanomicelles circulate in the blood for a long time, they are subjected to high shear force and dilution of the blood, which will destroy the structure of the micelles and cause the encapsulated drugs to leak out in advance, resulting in toxic side effects and reducing the therapeutic effect.

Method used

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  • Amphiphilic graft copolymer with catechol ligand as well as synthesis method and application thereof
  • Amphiphilic graft copolymer with catechol ligand as well as synthesis method and application thereof
  • Amphiphilic graft copolymer with catechol ligand as well as synthesis method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0052] Synthesis of mPEG-g-PCD-DA

[0053] Step 1: N-tert-butoxycarbonylethylenediamine (3.2g, 0.02mol) and N,N'-bis(acryloyl)cystamine (5.2g, 0.02mol) were dissolved in 20mL methanol / water (9 / 1 , v / v) in a mixed solvent. The reaction was protected from light and nitrogen, and reacted at 60° C. for 4 days. Subsequently, an excess of 10% N-tert-butoxycarbonylethylenediamine was added to continue the reaction for 1 day to consume unreacted carbon-carbon double bonds; after the reaction was completed, the solvent was removed under reduced pressure, and 16 mL of DCM / TFA (1 / 1, v / v ) mixed solution, stirred at room temperature for 2h to remove the protecting group. The reaction solution was added dropwise to excess diethyl ether, repeated 3 times. The solid obtained by filtration was dissolved in deionized water, dialyzed against deionized water for 24 hours (MWCO: 1000), and freeze-dried to obtain a white solid. The structural formula of the poly(N,N'-bis(acryloyl)cystamine-eth...

Embodiment 3

[0059] Synthesis of control polymer mPEG-g-PHD-DA

[0060] Except that 1,6-hexamethylenediamine is used as a raw material, other synthesis steps and reaction material ratios are the same as those of mPEG-g-PCD-DA.

[0061] The structural formula of the mPEG-g-PHD-DA is shown in formula (II);

[0062]

Embodiment 4

[0064] Assembly of CCLMs / SS micelles

[0065] Weigh 20 mg of mPEG-g-PCD-DA solid and dissolve it in 2 mL of DMSO, and slowly inject it into 20 mL of deionized water with a micro-injection pump under stirring. It was then dialyzed against deionized water to remove DMSO. Under stirring, FeCl was added at a ratio of 2:1 molar ratio of catechol groups to iron ions. 3 solution (40mM). After stirring for 1 h, the pH was adjusted to 7.4 with 0.25M NaOH solution. Then deionized water was dialyzed to remove uncomplexed iron ions to obtain CCLMs / SS solution. like image 3 As shown in A, the average particle diameter measured by DLS is about 121 nm. like image 3 As shown in B, it is spherical in shape observed by TEM.

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Abstract

The invention discloses an amphiphilic graft copolymer with a catechol ligand as well as a synthesis method and application thereof, and is a transmission system which is constructed by taking the amphiphilic graft copolymer with the catechol ligand as a carrier. The synthesis method comprises the following steps: grafting polyethylene glycol on poly(cystaminebisacrylamide-ethylenediamine); then modifying through 3,4-dihydroxyphenylacetic acid to synthesize polyethylene glycol-grafted-poly(cystaminebisacrylamide-ethylenediamine)-3,4-dihydroxyphenylacetic acid (mPEG-g-PCD-DA); then covering with doxorubicin to form a drug-loading nano-micelle; then adding iron ions to form a core-crosslinked doxorubicin-loaded nano-micelle (DOX-CCLMs / SS). According to the amphiphilic grafted copolymer disclosed by the invention, the transmission system can keep stable in a blood environment and can realize charge reversal for endocytosis enhancement under a tumor microenvironment, and reduction-sensitive and pH (Potential of Hydrogen)-sensitive drug release also can be realized in tumor cells.

Description

technical field [0001] The invention belongs to the fields of biomedical technology, nanomedicine and new materials, and specifically relates to the synthesis of amphiphilic graft polymers with catechol ligands and their application to control drug release and enhance cell uptake in tumor microenvironments smart nanomicelle carrier. Background technique [0002] In the chemotherapy of tumors, small molecule anticancer drugs have achieved great success, but they are also accompanied by some side effects, such as poor selectivity leading to systemic toxic side effects, which limits their further efficacy. The nano-drug delivery system provides an effective way to realize the targeted and controlled release of chemotherapy drugs in tumor tissues, thereby reducing the damage to normal tissues and organs. The intelligent nano-drug delivery system is mainly based on the microenvironmental differences between tumor tissue and normal human tissue, such as tumor tissue has hypoxia, ...

Claims

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Application Information

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IPC IPC(8): C08G81/00C08G73/02A61K31/704A61K9/107A61K47/34A61P35/00
CPCA61K9/1075A61K31/704A61K47/34A61P35/00C08G73/0253C08G81/00
Inventor 余家会陈天冬
Owner EAST CHINA NORMAL UNIVERSITY
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