A kind of esterase-responsive polycurcumin thiodipropionic acid copolymer prodrug nanomicelle and its preparation method and application

A technology of poly-curcumin thiodipropionic acid and nano-micelle, which is applied in the directions of pharmaceutical formulations, inactive medical preparations, anti-tumor drugs, etc., can solve the problems of poor water solubility, low bioavailability, and turmeric It can solve the problems of poor absorption and other problems, and achieve good long-term circulation, improve solubility, and increase the effect of accumulation.

Active Publication Date: 2020-03-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Experiments have shown that about 1g / kg curcumin is administered orally to rats, and about 75% is excreted through feces in the original form, while the excretion in urine is negligible. poor absorption
The results of this study show that curcumin is not easily absorbed by oral administration, and most curcumin is excreted in the feces in the original form, and the bioavailability in the body is low
Therefore, curcumin's poor water solubility and low bioavailability are another key problem to be solved in many studies.

Method used

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  • A kind of esterase-responsive polycurcumin thiodipropionic acid copolymer prodrug nanomicelle and its preparation method and application
  • A kind of esterase-responsive polycurcumin thiodipropionic acid copolymer prodrug nanomicelle and its preparation method and application
  • A kind of esterase-responsive polycurcumin thiodipropionic acid copolymer prodrug nanomicelle and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Preparation of Methoxypolyethylene Glycol-Curcumin Polyprodrug Block Copolymer

[0052] MPEG 5000 -CPRSC 2500 Synthesis

[0053] (1) Add 1.72g curcumin to 80ml dichloromethane, add 1.07g thiodipropionic acid, 0.1g4-dimethylaminopyridine, and 2.97g dicyclohexylcarbodiimide to react for 24h, the product obtained after the reaction Precipitate with a precipitating agent, filter and then dissolve in a solvent, reprecipitate with a precipitating agent, and repeat the operation three times to obtain curcumin prodrug polymer short chain (CPRSC). The molecular weight measured by GPC was 3200.

[0054] (2) Add 0.32g of curcumin prodrug polymer short chain into 50ml of dichloromethane, add 31mg of dicyclohexylcarbodiimide, 0.1g of 4-methylaminopyridine, and 0.1ml of triethylamine to dissolve; After the glycol monomethyl ether is dissolved, it is added into the curcumin prodrug polymer short-chain solution, reacted overnight, and is precipitated with ether to obtain curcumin p...

Embodiment 2

[0056] MPEG 5000 -CPRSC 3500 Synthesis

[0057] (1) 1.81g curcumin is added in 80ml dichloromethane, add 1.07g thiodipropionic acid successively, 0.1g4-dimethylaminopyridine, 2.97g dicyclohexylcarbodiimide reacts 24h, the polymer after reaction Precipitate with ether, and the product obtained after the reaction is precipitated with a precipitating agent, filtered and then dissolved in a solvent, and reprecipitated with a precipitating agent, and the operation is repeated three times to obtain a curcumin prodrug polymer short chain (CPRSC). The molecular weight measured by GPC was 4500. The H NMR spectra of short polyprodrug chains of curcumin are shown in figure 1 .

[0058] (2) 0.45g curcumin prodrug polymer short chain is added in 50ml methylene chloride, add dicyclohexylcarbodiimide 31mg successively, 4-methylaminopyridine 0.1g, triethylamine 0.1ml dissolve; Add curcumin prodrug polymer short-chain solution after dissolving ethylene glycol monomethyl ether, react overn...

Embodiment 3

[0060] MPEG 5000 -CPRSC 5000 Synthesis

[0061] (1) Add 1.9g curcumin to 80ml dichloromethane, add 1.07g thiodipropionic acid, 0.1g4-dimethylaminopyridine, and 2.97g dicyclohexylcarbodiimide for 24 hours, and the product obtained after the reaction Precipitate with a precipitating agent, filter and then dissolve in a solvent, reprecipitate with a precipitating agent, and repeat the operation three times to obtain curcumin prodrug polymer short chain (CPRSC). The molecular weight measured by GPC was 6300.

[0062] (2) Add 0.63g of curcumin prodrug polymer short chain into 50ml of dichloromethane, add 31mg of dicyclohexylcarbodiimide, 0.1g of 4-methylaminopyridine, and 0.1ml of triethylamine to dissolve; After the glycol monomethyl ether is dissolved, it is added into the curcumin prodrug polymer short-chain solution, reacted overnight, and is precipitated with ether to obtain curcumin polyprodrug amphiphile molecules.

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Abstract

The invention belongs to the field of novel nanometer drugs, and discloses an esterase-responsive polycurcumin thiodipropionic acid copolymer prodrug nano-micelle, a preparation method and applications thereof, wherein the esterase-responsive polycurcumin thiodipropionic acid copolymer prodrug nano-micelle comprises, by mass, 28-93.6% of a carrier auxiliary material and 6.4-72% of a curcumin drug,the nano-micelle monomer is an amphiphilic block and comprises a hydrophilic segment and a hydrophobic segment, the hydrophilic block is methoxy polyethylene glycol with a molecular weight of 1500-6000, the hydrophobic chain segment is a curcumin poly prodrug short chain co-polymerized from thiodipropionic acid and an anticancer drug curcumin and having a molecular weight of 800-12000, and a weight ratio of the hydrophilic segment methoxypolyethylene glycol to the curcumin poly prodrug short chain is 0.1-20:1. According to the present invention, the novel nano-micelle monomer can be degradedand reduced under the action of the esterase in the cancer cells to obtain the anticancer drug curcumin bulk drug so as to achieve the precise controlled-release effect.

Description

technical field [0001] The invention belongs to the field of novel nano-medicines, and in particular relates to an esterase-responsive polycurcumin thiodipropionic acid copolymer prodrug nano-micelle and a preparation method and application thereof. Background technique [0002] Curcumin is a polyphenolic extract from the traditional Chinese medicine turmeric, which is listed as a third-generation cancer chemoprevention drug by the United States Pharmacopoeia. Recent studies have shown that curcumin has a strong preventive effect on the three stages of tumor carcinogenesis. At the same time, curcumin also has definite multidrug resistance against cytotoxic drugs. It is a natural tumor chemical with multi-target characteristics. Preventive and therapeutic agents. Curcumin has become one of the most eye-catching natural products in the world because of its non-toxic and broad-spectrum characteristics. It is known as a miracle drug that may provide long-term solutions for tumo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K47/54A61K47/60A61K47/69A61K31/12A61P35/00
CPCA61K31/12
Inventor 杜昶徐东万宇欣
Owner SOUTH CHINA UNIV OF TECH
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