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Polyamino acid, preparation method thereof and drug loaded micelle

A polyamino acid and citrulline technology, applied in the field of polymers, can solve the problem of less research on polymer micelles, and achieve the effects of good biocompatibility, biodegradability, and good enzyme responsiveness

Active Publication Date: 2015-11-18
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

People are paying more attention to the study of nano-sized drug delivery systems. Among them, the research on the way of physical packaging of drugs is more extensive. Polymers can self-assemble into nanocarriers in water, such as micelles, vesicles and liposomes. Polymer nano Micelles have the advantages of controllable particle size, long circulation time in vivo, and targeted modification, but there are few studies on environment-responsive polymer micelles that respond to external environmental stimuli.

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  • Polyamino acid, preparation method thereof and drug loaded micelle
  • Polyamino acid, preparation method thereof and drug loaded micelle
  • Polyamino acid, preparation method thereof and drug loaded micelle

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preparation example Construction

[0059] The present invention provides a method for preparing the polyamino acid described in the above technical solution, comprising:

[0060] In an organic solvent, react amino-terminated polyethylene glycol monomethyl ether, citrulline-N-internal carboxylic acid anhydride and valine-N-internal carboxylic anhydride to obtain polyamino acids; the amino-terminated polyethylene glycol Monomethyl ether has the structure shown in formula II:

[0061]

[0062] In formula II, 50≤n≤200;

[0063] The citrulline-N-internal carboxylic acid anhydride has a structure shown in formula III:

[0064]

[0065] The valine-N-internal carboxylic acid anhydride has a structure shown in formula IV:

[0066]

[0067] The invention reacts amino-terminated polyethylene glycol monomethyl ether, citrulline-N-internal carboxylic acid anhydride and valine-N-internal carboxylic acid anhydride in an organic solvent to obtain polyamino acid. In the embodiments of the present invention, the temp...

Embodiment 1

[0113] Put 20g of polyethylene glycol monomethyl ether with a number average molecular weight of 2000 into a dry reaction bottle, then vacuumize it at 120°C for 2 hours while stirring, put the reaction bottle in an oil bath, and when the temperature is 60°C 10g of anhydrous magnesium sulfate and 200mL of dichloromethane were added to the reaction flask respectively, and 5mL of triethylamine and 30mL of methanesulfonyl chloride were added to the reaction flask in an ice-water bath. React for 72 hours under the condition of agitator stirring. After the reaction, the obtained reaction product was washed five times with saturated sodium chloride solution, and then dried overnight by adding anhydrous magnesium sulfate; After drying under vacuum for 24h, an intermediate product was obtained;

[0114] Dissolve the intermediate product and ammonium chloride with the same quality as the intermediate product in ammonia water, the volume of ammonia water is 10 times the mass of the inter...

Embodiment 2

[0122] Put 20g of polyethylene glycol monomethyl ether with a number-average molecular weight of 4000 into a dry reaction bottle, then vacuumize it at 120°C for 2 hours while stirring, put the reaction bottle in an oil bath, and when the temperature is 60°C , add 10g of anhydrous magnesium sulfate, 200mL of dichloromethane dehydrated into the reaction flask respectively, add 2.5mL of triethylamine and 15mL of methanesulfonyl chloride into the reaction flask under the condition of ice-water bath, at 25°C 1. Reaction 72h under stirring bar stirring condition, after the reaction finishes, the reaction product obtained is washed five times with saturated sodium chloride solution and then dried overnight by adding anhydrous magnesium sulfate; the product after drying is settled with anhydrous ether, and the After vacuum drying at ℃ for 24h, an intermediate product was obtained;

[0123] Dissolve the intermediate product and ammonium chloride with the same quality as the intermediat...

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Abstract

The invention provides polyamino acid. The polyamino acid is of a structure shown in the formula I (please see in the specification), wherein n is larger than or equal to 50 and smaller than or equal to 200, i is larger than or equal to 1 and smaller than or equal to 10, and j is larger than or equal to 3 and smaller than or equal to 30. One end of the polyamino acid is provided with hydrophilic methoxypolyethylene glycols, the other end of the polyamino acid is provided with a hydrophobic citrulline and valine copolymer, the amphiphilic polyamino acid with the hydrophilic chain section and the hydrophobic chain section can autonomously form micelle which is of a kernel-shell structure and has a nanometer size in water; chemical bonds between citrulline and valine of the polyamino acid can crack under the effect of cathepsin B, and therefore the polyamino acid can be degraded by enzymes, and the drug loaded micelle has high cathepsin B responsiveness. In addition, the drug loaded micelle has high biocompatibility and biodegradability.

Description

technical field [0001] The invention relates to the technical field of polymers, in particular to a polyamino acid and its preparation method and drug-loaded micelles. Background technique [0002] Malignant tumors have become one of the most serious diseases threatening human beings. In recent years, there have been new anti-tumor drugs, and the treatment plan has been continuously improved. However, there are many problems in the application of small-molecule anti-tumor drugs used in clinical practice, such as poor water solubility, fast metabolism, and drug utilization. Low, the toxicity to normal tissue cells is relatively large, and some tumors are prone to drug resistance during chemotherapy, so the dose of chemotherapy drugs must be increased to achieve the purpose of treatment. [0003] In order to solve the above problems, researchers have been working on a new drug delivery system for anti-tumor drugs. People are paying more attention to the study of nano-sized d...

Claims

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Application Information

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IPC IPC(8): C08G69/40C08G69/16A61K9/107A61K47/34A61P35/00
Inventor 丁建勋何陶媛庄秀丽陈学思
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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