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A kind of dimethoxycurcumin polymer micelle and its preparation method and medical application

A technology of dimethoxycurcumin and polymer glue, which is applied in the field of dimethoxycurcumin polymer micelles and its preparation, can solve the problem of low drug loading and encapsulation efficiency, far-flung requirements, and poor quality. Poor controllability and other problems, to achieve the effect of improving bioavailability, uniform distribution, and reducing leakage

Inactive Publication Date: 2018-10-16
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the methylation of the hydroxyl group, the physical and chemical properties of DMC, especially the solubility characteristics, have changed significantly compared with curcumin. Therefore, the research on drug delivery system has become a new challenge for the development of DMC.
At present, there are only literature reports on DMC-dendrimer PAMAM complexes and DMC liposomes [Markatou E, et al. Molecular interactions between endimethoxycurcumin and Pamam dendrimer carriers. Int J Pharm 339 (2007): 231; al. Incorporation of dimethoxycurcumin into charged liposomes and the formation kinetics of fractal aggregates of uncharged vectors. J Liposome Res 23 (2013): 94.], but both have the defects of low drug loading and encapsulation efficiency, thermodynamic instability, and the preparation process Complex, poor quality controllability, far from the requirements of clinical application

Method used

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  • A kind of dimethoxycurcumin polymer micelle and its preparation method and medical application
  • A kind of dimethoxycurcumin polymer micelle and its preparation method and medical application
  • A kind of dimethoxycurcumin polymer micelle and its preparation method and medical application

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Experimental program
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Effect test

Embodiment 1

[0041] The total synthesis preparation of embodiment 1 dimethoxycurcumin

[0042] Dimethoxyturmeric crude drug was prepared with reference to the total synthesis process route provided by the US patent (US005679864A). The preparation process is briefly described as follows. Methyl vanillin (23.3 g), boron oxide (4.66 g), anhydrous dimethylformamide (90 mL), pentanedione (7.2 mL) and dimethoxypropane (17.2 mL) were put into 250 mL three-neck flask, tightly stoppered, shake evenly and store in N 2Slowly raise the temperature to 70°C under protection, and when the solids are completely dissolved, start to slowly add n-butylamine (2.8 mL) dropwise, finish adding within about 120 minutes, continue to react for about 1 hour, and pour the reaction solution into a 400 mL boiling 5% acetic acid solution, stir evenly, after naturally cooling to room temperature, add 200 mL deionized water, shake well, let stand in 4°C refrigerator for 2 days, pour off the upper layer solution, add ace...

Embodiment 2

[0044] The semi-synthetic preparation of embodiment 2 dimethoxycurcumin

[0045] Take curcumin (10 g) and put it in a 250 mL three-necked bottle, add 1:1 ether-methanol mixed solution (v / v, 80 mL), shake well, add sodium hydroxide (3.2 g), heat to reflux under stirring, Iodomethane (15 g) was added dropwise within 30 min, and the reaction was monitored by TLC until the starting material was consumed. Remove the solvent under reduced pressure, add ammonia water (60 mL) to precipitate a large number of yellow crystals, filter, wash with water until neutral, dry and perform silica gel column chromatography, and use petroleum ether-ethyl acetate (8: 2, v / v ) mixed solvent system for elution, collected and combined the yellow fractions in the middle section, removed the solvent under reduced pressure, and dried in vacuo to obtain an orange-yellow powdery solid (3.5 g). The results of spectrum analysis were consistent with the product prepared by total synthesis, and it was iden...

Embodiment 3

[0046] Example 3 Preparation of dimethoxycurcumin polymer micelles and freeze-dried powder thereof

[0047] (1) BOC-phenylalanine end-capped polyethylene glycol monomethyl ether-polycaprolactone block copolymer (mPEG 2000 -PCL 1800 -BP) / DMC micelles and its lyophilized powder

[0048] Weigh 180 mg of the copolymer polymer and 20 mg of dimethoxycurcumin, put them in a 50 mL eggplant-shaped bottle, add 15 mL of absolute ethanol, and ultrasonically dissolve in a water bath at 50°C until the solution is clear and free of insoluble matter. Ethanol was removed by pressure distillation to form a uniform film on the bottom and inner wall of the bottle. Inject 10 mL of warm purified water, hydrate in a water bath at 50°C for 45 min, until the drug film is completely peeled off and dissolved, add 80 mg of mannitol, filter the resulting solution through a 0.22 μm filter membrane, and freeze-dry to obtain dimethoxyturmeric Freeze-dried powder of drug-loaded micelles. The theoretical d...

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Abstract

The invention relates to a dimethoxycurcumin polymer micelle and a preparation method, an injection or oral administration system for the polymer micelle, and medical application of the polymer micelle. The drug-loaded micelle employs an amphiphilic segmented copolymer as a carrier material and forms a typical core-shell structure in an aqueous solution through self-assembly; and the structure has uniform particle size distribution,solubility and thermodynamic stability of dimethoxycurcumin in an aqueous medium are substantially improved, leakage, degradation and metabolism of dimethoxycurcumin in the body are effectively reduced, and long circulation and tumor tissue passive targeting are realized, so drug effect and security are improved. According to specific needs of clinical indications, freeze-dried powder or preparations of other dosage forms can be prepared from the drug-loaded micelle provided by the invention for injection or oral administration of the micelle; and the micelle is used for resisting tumors, oxidation, inflammation, bacteria and aging, realizing immunoloregulation, reducing blood fat, resisting atherosclerosis and senile dementia, etc., and is especially applicable to combination with tumor radiotherapeutics and chemotherapeutics to exert sensitivity-enhancing, efficiency-improving and toxicity-attenuating effects.

Description

technical field [0001] The invention belongs to the technical field of nanomedicine, and relates to a dimethoxycurcumin polymer micelle, a preparation method and a medical application thereof. Background technique [0002] Natural products have always been an important source of drug discovery and development [Newman JD, Cragg MG. Natural products as sources of new drug over the last 25 years. J Nat Prod 70 (2007)461.]. Turmeric is a natural yellow pigment derived from the rhizomes of ginger plants such as turmeric, turmeric, and zedoary. It is widely used as a condiment in Southeast Asia such as India. It has a long history of application in traditional medicine. The efficacy is mainly attributed to curcuminoids [Sharma RA, et al . Curcumin: the story sofa. Eur J Cancer 41 (2005): 1955.]. [0003] [0004] In terms of chemical structure, curcuminoids are diferuloyl derivatives linked by β-diketones, in which the β-diketone structure has enol-keto tautomerism, and the m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K9/107A61K31/12A61K47/34A61K47/10A61P35/00A61P39/06A61P31/04A61P37/02A61P3/06A61P9/10A61P25/28
Inventor 许卉刘卉刘珂江云霞
Owner YANTAI UNIV
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