Preparation method of urushiol-loading pH responsive amphiphilic copolymer micelle

An amphiphilic copolymer, responsive technology, used in the field of biomedicine to achieve the effects of good stability, simple operation and improved water solubility

Active Publication Date: 2019-02-05
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no relevant research reports on the application of urushiol-loaded copolymer micelles at home and abroad. In addition, there are no reports on the preparation and application of urushiol-loaded pH-responsive amphiphilic block copolymer micelles at home and abroad.

Method used

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  • Preparation method of urushiol-loading pH responsive amphiphilic copolymer micelle
  • Preparation method of urushiol-loading pH responsive amphiphilic copolymer micelle
  • Preparation method of urushiol-loading pH responsive amphiphilic copolymer micelle

Examples

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Embodiment 1

[0034] Synthesis of Amphiphilic Copolymer Polyethylene Glycol-Poly β-Amino Ester (mPEG-PBAE)

[0035] Take a certain amount of methoxypolyethylene glycol with amino groups at the end, hydrophobic amine monomer, 5-amino-1-pentanol and 1,4-butanediol diacrylate and dissolve them in dimethyl sulfoxide to form a concentration It is a 0.2mg / mL reaction solution, put it in a polymerization tube and stir at 60°C for 20-48 hours, then add a certain amount of 1,3-pentanediamine, and continue the reaction for 24 hours. Dilute, wash with deionized water three times, separate the organic phase, dry over anhydrous magnesium sulfate, filter the organic phase, remove the solvent by rotary evaporation of the filtrate, and dry in vacuum at 40°C for 20-48 hours to obtain the target amphiphilic copolymer.

[0036] The number-average molecular weight Mn of the methoxypolyethylene glycol with amino groups at the end is 2000 or 5000.

[0037] The molar ratio of methoxypolyethylene glycol with amin...

Embodiment 2

[0044] Preparation of pH-responsive amphiphilic copolymer micelles loaded with urushiol

[0045] Accurately weigh 40-100 mg of polyethylene glycol-poly-β-amino ester amphiphilic copolymer and urushiol each, dissolve them in 4-10 mL of N, N'-dimethylformamide, mix them uniformly by ultrasonic and pour into In a dialysis bag with a molecular weight of 3000, dialyze with 1.0-2.0L deionized water for 20-30 hours, and change the water every 1-2 hours; The supernatant was filtered through a water membrane with a pore size of 0.45 μm to remove unencapsulated urushiol; finally, the filtrate was freeze-dried at -40°C to -45°C for 24h to 36h to obtain pH-responsive amphiphilic copolymers loaded with urushiol micelles.

[0046] The present invention has studied urushiol and copolymer charging amount (A), N, N'-dimethylformamide solvent consumption (B) in the preparation technology of the copolymer micelle of loaded urushiol by adopting star point design-response surface optimization met...

Embodiment 3

[0051] Determination of Morphology, Particle Size and Zeta Potential of Urushiol-loaded Copolymer Micelles

[0052] The present invention adopts transmission electron microscope (TEM) to characterize the morphology of loaded urushiol copolymer micelle; Adopt dynamic light scattering method (DLS) to measure particle diameter and Zeta potential of loaded urushiol copolymer micelle, transmission electron microscope result The results showed that the appearance of drug-loaded micelles was relatively round, with regular spherical structure, uniform size and good dispersion. DLS measurement results showed that the average particle size of urushiol-loaded copolymer micelles was 140-160nm, which could penetrate tumor tissue more effectively, improve penetration ability and achieve targeted aggregation at tumor sites through the EPR effect. The zeta potential value is 32-35mV, which shows that it has good stability. The positive charge it carries helps it bind to the negatively charged...

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Abstract

The invention relates to a preparation method of urushiol-loading pH responsive amphiphilic copolymer micelle. The preparation method comprises the following steps: firstly, dissolving a certain amount of mPEG, hydrophobic amine monomer, 5-amino-1-pentanol and 1,4-butanediol diacrylate in DMSO to prepare a reaction solution with a certain concentration, performing polyreaction for 20-48h, then adding a certain amount of 1,3-pentanediamine, and continuing the reaction for 24h to synthesize polyethylene glycol-poly-beta-amino ester amphiphilic copolymer (mPEG-PBAE); and then taking and dissolving a certain amount of mPEG-PBAE and urushiol in DMF, performing uniform ultrasonic mixing, and performing dialyzing, centrifuging and filtering to obtain the urushiol-loading pH responsive amphiphiliccopolymer micelle. The drug-loading micelle has an average particle diameter of 140-160nm, good stability, obvious pH responsive drug-release property, good biocompatibility, and good targeting anti-tumor activity, can be applied to clinical targeting anti-tumor drugs, has very high added value, and can become a new technique for clinically developing urushiol targeting anti-tumor drugs.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and relates to a method for preparing pH-responsive amphiphilic block copolymer polyethylene glycol-poly-β-amino ester (mPEG-PBAE) micelles loaded with urushiol medicine. Background technique [0002] Urushiol is a natural active ingredient in the secretion of lacquer (Toxicodendron verniciflum (Stokes) F.A.Barkl.), and it is an important forest special product in China. 85% of the lacquer in the world is produced in China. Urushiol is an alkylphenol compound with a catechol structure, and its side chains are C with different degrees of saturation. 15 of alkanes. Urushiol has good anti-tumor biological activity, and it has inhibitory effects on 29 types of tumor cells in 9 organs of the human body. The mechanism of action includes inducing tumor cell apoptosis, inhibiting tumor cell proliferation, inhibiting tumor angiogenesis, inhibiting nuclear transcription factors, Toxicize tumor cells,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/107A61K31/05A61K47/34A61P35/00C08G81/00
CPCA61K9/1075A61K31/05A61K47/34A61P35/00C08G81/00
Inventor 王成章周昊
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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