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Synthesis and micellization application of amphiphilic beta-cyclodextrin star polymer

An amphiphilic polymer, star polymer technology, applied in the fields of polymer chemistry and pharmaceutical preparations, can solve the problems of affecting the efficacy of drugs, only absolute bioavailability, etc.

Active Publication Date: 2013-11-20
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Vinpocetine is almost insoluble in water, and its absolute bioavailability is only 7%, which affects the efficacy of the drug

Method used

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  • Synthesis and micellization application of amphiphilic beta-cyclodextrin star polymer
  • Synthesis and micellization application of amphiphilic beta-cyclodextrin star polymer
  • Synthesis and micellization application of amphiphilic beta-cyclodextrin star polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment example 1

[0069] Material β-CD-[P(AA-co-MMA)-b-PNVP] 6 (PAA:PMMA:PNVP=10:1:12) specific synthesis steps

[0070] Dissolve 5.675 g β-CD, 4.566 g MBA, 0.421 g KOH, and 6.668 g P in 80 mL of 1,4-dioxane 2 S 5 , and then reflux at 120°C for 30h. After the reaction, let cool and filter, the obtained solid was washed with acetone-water (1:1, v / v) and filtered three times, and vacuum-dried at 50°C to obtain hexa-substituted dithiobenzoate β-CD (CTA4) .

[0071] Add 0.4g of CTA4 reagent to the dry reaction eggplant bottle that has been deaired by argon, add 25mL of ethanol-water (1.5:1) mixed solvent to dissolve; then add 10.38mL of AA, 1.07mL of MMA, 0.016g of AIBN and then carry out circulation pumping Exhaust - fill in argon to remove oxygen, then seal the reaction at 70°C for 18 hours; after the reaction, take out the reaction bottle and cool it, the reaction mixture is precipitated with ethyl acetate, and the resulting precipitate is vacuum-dried at 45°C to obtain β-CD- [P(AA-co...

Embodiment example 2

[0076] Material β-CD-[P(AA-co-MMA)-b-PNVP] 4 (PAA:PMMA:PNVP=7:1:8) specific synthesis steps

[0077] Dissolve 5.675 g β-CD, 2.283 g MBA, 0.421 g KOH, and 3.334 g P in 80 mL of 1,4-dioxane 2 S 5 , and then reflux at 120°C for 30h. After the reaction, let cool and filter, the obtained solid was washed with acetone-water (1:1, v / v) and filtered three times, and vacuum-dried at 50°C to obtain tetrasubstituted dithiobenzoate β-CD (CTA2) .

[0078] Add 0.4g of CTA2 reagent to the dry reaction eggplant bottle that has been deaired by argon, add 25mL of ethanol-water (1.5:1) mixed solvent to dissolve; then add 8.10mL of AA, 1.14mL of MMA, 0.016g of AIBN and then carry out circulation pumping Exhaust - fill in argon to remove oxygen, then seal the reaction at 70°C for 18 hours; after the reaction, take out the reaction bottle and cool it, the reaction mixture is precipitated with ethyl acetate, and the resulting precipitate is vacuum-dried at 45°C to obtain β-CD- [P(AA-co-MM...

Embodiment example 3

[0081] Implementation Case 3 The process of preparing micelles by thin film hydration method

[0082] Accurately weigh 40 mg of the product prepared in Example 2 (β-CD-[P(AA-co-MMA)-b-PNVP] 4(PAA:PMMA:PNVP=7:1:8)) and 20mg of vinpocetine were placed in a 250mL dry round bottom flask with magnetic stirring; add 50mL of methanol and stir to dissolve the polymer and the drug and disperse evenly in the organic solvent ;Place the flask in a 40°C water bath, remove methanol by rotary evaporation under reduced pressure, so that the solute forms a film and adheres to the wall of the flask; transfer to a 60°C water bath and keep warm for 5min to melt the solid skeleton film; add 10mL of 60°C deionized water , stirred for 2h (1500r / min) to hydrate into micelles; quenched to room temperature, and filtered out the uncoated drug with a 0.22μm syringe filter to obtain a drug-loaded micellar solution with a drug loading of 3.52%.

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PUM

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Abstract

The invention belongs to the technical field of high polymer chemistry and pharmaceutical preparations, relates to a synthesis and a micellization application of an amphiphilic beta-cyclodextrin (beta-CD) star polymer, and provides an amphiphilic beta-cyclodextrin (beta-CD) star polymer taking beta-cyclodextrin (beta-CD) as a core, acrylic acid and a methyl methacrylate copolymer as a lipotropy block and poly (N-vinyl pyrrolidone) as a hydrophilic block, and a synthesizing method of the amphiphilic beta-cyclodextrin (beta-CD) star polymer. The amphiphilic beta-cyclodextrin (beta-CD) star polymer is formed by connecting amphiphilic block polymers to 3-6 hydroxide radicals of the beta-cyclodextrin (beta-CD). The molar mass ratio of the acrylic acid and the methyl methacrylate in the lipotropy block and the poly (N-vinyl pyrrolidone) in the hydrophilic block in the amphiphilic polymer is 4:1:(1-15):1:16. The invention further relates to a vinpocetine micelle taking the amphiphilic beta-cyclodextrin (beta-CD) star polymer as a carrier material and a preparation method of the vinpocetine micelle. The medicine carrying micelle of the amphiphilic beta-cyclodextrin (beta-CD) star polymer provided by the invention has the characteristics of slow-release effect, pH sensitivity and lung targeting.

Description

[0001] technical field [0002] The invention belongs to the technical field of macromolecular chemistry and pharmaceutical preparations, and in particular relates to a new type of drug carrier material amphiphilic β-CD star polymer and its synthesis method, amphiphilic β-CD star polymer drug-loaded micelles and the Preparation method of micelles. Background technique [0003] Amphiphilic copolymer means that the same copolymer has both hydrophilicity and lipophilicity. In a selected solvent, the parts with the same affinity in the macromolecular chain are easy to aggregate with each other to form micelles. The micelles formed by the self-assembly of amphiphilic copolymers have a unique core-shell structure, which can solubilize insoluble drugs and improve the bioavailability of drugs. Through the EPR effect of tumor tissue, the passive targeting can be enhanced, and the toxic and side effects of drugs can be reduced. [0004] β-CD is a cyclic oligosaccharide compound form...

Claims

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Application Information

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IPC IPC(8): C08F293/00C08F220/06C08F220/14C08F226/10C08B37/16A61K47/40A61K9/51A61K31/4375A61P9/10A61P7/04
Inventor 杨帆刘意黄淑玲梁润成
Owner GUANGDONG PHARMA UNIV
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