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Multifunctional degradable polyasparaginate modified polymer and preparation method thereof

A polyasparagine and multifunctional technology, which is applied in the field of preparation of micelles and drug-loaded micelles, can solve the problems of being insoluble in ethanol, difficult to recover drugs, and difficult to remove, and achieves high encapsulation efficiency and method. Simple, low toxicity effect

Active Publication Date: 2013-04-24
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Dialysis is a classic method for preparing polymer micelles in the laboratory, but the general dialysis drug loading and encapsulation efficiency is not high, and the recovery of unencapsulated drugs in water is difficult, so it is not very suitable for large-scale industrial production [Soga, O .Biodegradable thermosensitive polymers: synthesis, characterization and drug delivery applications, Ph.D Thesis, Utrech University, 2006]
Since most of the polymers used are water-insoluble and hardly soluble in ethanol, dialysis or solvent evaporation methods generally use toxic organic solvents to dissolve the polymers, so it will be difficult to completely remove the solvents

Method used

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  • Multifunctional degradable polyasparaginate modified polymer and preparation method thereof
  • Multifunctional degradable polyasparaginate modified polymer and preparation method thereof
  • Multifunctional degradable polyasparaginate modified polymer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] 1-1 Preparation of polysuccinimide PSI

[0034] Add 15.9 g of phosphoric acid to 30 g of aspartic acid, under the catalysis of phosphoric acid, dehydrate by rotary steaming under reduced pressure for 2 hours at 180 ° C, stop the rotary steaming, add 200 mL of N,N-dimethylformamide (DMF) while hot, The solid was fully dissolved, and the solution was added dropwise to 1000mL distilled water to obtain a white precipitate, filtered, washed with distilled water until neutral, dried, re-dissolved with DMF, and then precipitated with distilled water again, filtered, and vacuum-dried to obtain polyamber Imide (PSI) 20.0 g. PSI with different molecular weights were synthesized by a similar method, and the molecular weight and molecular weight distribution (MWD) were measured by gel permeation chromatography (GPC). The results are shown in Table 1:

[0035] Table 1. Molecular weight characterization results of polysuccinimide (PSI)

[0036]

[0037] 1-2 activation containing...

preparation example 2

[0046] Pentanolamine Ring Opening PSI

[0047] Weigh 2 grams of the obtained polysuccinimide (PSI-3, Synthesis Example 1-1), dissolve it in 20 mL of DMF, add 5-aminopentanolamine (3.90 grams in 5 mL of DMF) dropwise under ice-cooling, Stir at room temperature for half an hour, then place it in an oil bath at 60°C for 24 hours, precipitate with anhydrous ether, and dry in vacuo to obtain 3.5 g of polymer (PHPA). The H NMR spectrum shows that PSI is completely ring-opened (there is no peak in the chemical shift between 5-6ppm on the H NMR spectrum).

[0048] 0.20 g of PHPA, 0.24 g of mPEG5k-CI (Synthesis Example 1-2) and 0.12 g of catalyst (DMAP) were placed in a round bottom flask, dissolved in 2 mL of anhydrous DMF, then heated up and reacted with magnetic stirring in an oil bath at 70°C for 48 hours . After cooling to room temperature, add 95 mg Ph-CI (Synthesis Example 1-3), continue the reaction at 70°C for 24 hours to stop, add anhydrous ether to precipitate, and dry in ...

preparation example 4

[0054] Weigh 0.2 gram of the obtained PHPA (temperature-sensitive polymer preparation example 2), 0.26 gram of mPEG5k-CI (synthesis example 1-2) and an appropriate amount of catalyst (DMAP) in a round bottom flask, add 2 mL of anhydrous DMF to dissolve, Then raise the temperature and react with magnetic stirring in an oil bath at 70°C for 24 hours; after cooling to room temperature, add 135mg Ph-CI (Synthesis Example 1-3), and continue the reaction at 70°C for 24 hours; after cooling to room temperature, add 85mg of DEAE-CI (Synthesis Examples 1-4), the reaction was continued at 70°C for 24 hours to stop, added to anhydrous ether for precipitation, and vacuum-dried to obtain 0.48 g of a polymer, which was designated as P7. Using the same method, keep the same feeding ratio of mPEG5k-CI and DEAE-CI and PHPA, change the feeding ratio of Ph-CI, and make polymer P8; In the proton NMR spectrum, the peak with a chemical shift of 7.2-7.3ppm is the proton peak of the connected benzene...

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Abstract

The invention discloses a multifunctional degradable polyasparaginate modified polymer, and further discloses a preparation method of the modified polymer and a method for preparing micelle and micelle loaded medicines by using the material. The modified polymer has functions of temperature sensation, pH sensation, fluorescent tracking and targeting. The polymer can be processed so as to rapidly form micelle nano particles and medicine loads; the loaded medicine is high in encapsulation efficiency, and no toxic solvents are used. The main chain part of the polymer is biologically degradable polyasparaginate with low toxicity; a side group hydrophobic section component can be hydrolyzed by using a carbonic ester bond so as to lose hydrophobic groups convert into hydrophily; and a tumor targeting group can lead the medicine loading micelle to enter tumor cells in a targeting mode to degrade and release loaded toxic medicines, so that damage of chemotherapeutic medicines to normal human body tissue cells is avoided.

Description

technical field [0001] The invention relates to a multifunctional degradable polyasparagine modified polymer and a preparation method thereof, and also relates to a preparation method of the micelle and the drug-loaded micelle. Background technique [0002] Cancer has become one of the major diseases that threaten human health. According to the World Health Organization, by 2020, there will be more than 15 million new cases of cancer and more than 10 million people will die of cancer every year in the world. Cancer treatments mainly include surgery, radiotherapy and chemotherapy. Surgical treatment is very traumatic to the human body, especially for patients with tumor metastasis, surgical treatment and radiotherapy are difficult to be effective, and chemotherapy is very important at this time. Although many chemotherapeutic drugs have been found to have anti-tumor activity, and some of them have been widely used in clinical treatment, there is still a long way to go to dev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10A61K9/10A61K47/34A61K31/337A61K31/4745A61K31/704A61P35/00
Inventor 蒋序林马颖颖余欢卓仁禧
Owner WUHAN UNIV
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