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Reduction-sensitive amphiphilic block copolymer and micelle thereof

An amphiphilic block and sensitive technology, which is applied in the direction of drug combination, organic active ingredients, medical preparations of non-active ingredients, etc., to achieve the effect of high encapsulation efficiency and simple method

Inactive Publication Date: 2010-06-16
常熟紫金知识产权服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Japan Kataoka et al recently reviewed the research progress of using polymer micelles to load anticancer drugs for pre-clinical and clinical research [Yasuhiro Matsumura, and Kazunori Kataoka, Preclinical and clinical studies of anticancer agent-incorporating polymer micelles, Cancer Sci, 2009, 100( 4), 572-579], but did not involve the introduction of polymer micellar drug carriers linked by disulfide bonds

Method used

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  • Reduction-sensitive amphiphilic block copolymer and micelle thereof
  • Reduction-sensitive amphiphilic block copolymer and micelle thereof
  • Reduction-sensitive amphiphilic block copolymer and micelle thereof

Examples

Experimental program
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Embodiment

[0023] Synthetic Copolymer Example 1: First, 4,4'-Azobis (4-cyanovaleric acid) (4,4'-Azobis (4-cyanovaleric acid)) and polyethylene glycol 5000 with a methoxy group at one end ( mPEG5000) reaction to prepare 4,4'-azobis (4-cyanovaleric acid) methoxypolyethylene glycol ester macromolecular free radical initiator (PEG 2 -ABCPA) [Neradovic D, vanNostrum CF, Hennink WE. Thermoresponsive polymeric micelles with controlled instability based on hydrolytically sensitive N-isopropylacrylamide copolymers, MACROMOLECULES, 2001, 34(22), 7589-7591]. Polyethylene glycol methacrylate (PEG-MEMA, Mn~300, CAS number: 26915-72-0) hydrophilic monomer 0.40g, tert-butoxycarbonyl cystamine methacrylamide (Boc-Cyst- MAAm) hydrophobic monomer 0.64g and macromolecular initiator PEG 2 - ABCPA 0.25g were dissolved together in 6mL DMF. After vacuuming and nitrogen protection, after repeated three times, radical polymerization was initiated in an oil bath at 70°C for 7 hours, and precipitated with ether,...

preparation example 7

[0029] Micelle Preparation Example 7: Add 10.0 mg of low-temperature water-soluble copolymer PEG-P1 to a sample bottle containing 5.0 mL of sodium phosphate (PBS, 0.15M) buffer solution with pH=7.4, and place in a refrigerator (4°C) Allow it to fully dissolve overnight (2.0mg / mL), then take out the sample bottle from the refrigerator and place it in a water bath at 55°C for one minute, then take it out and cool it to room temperature naturally to obtain stable micellar nanoparticles, which are analyzed by dynamic light scattering (DLS ) The measured average particle diameter is 63nm, and the dispersion index PDI is 0.06. The stability of the micelles was continuously tested by DLS for the particle size and particle size distribution and the change of light scattering intensity at 37°C, see Figure 1a and 1c . At the same time, as a comparison, to 1.0 mL of the same polymer micelles, 20 μL of dithiothreitol (DTT, 0.5 M) was added so that the final concentration of DTT was 10 ...

preparation example 8

[0030] Micelle Preparation Example 8: Dissolve the low-temperature water-insoluble polymer PEG-P2 in ethanol (20 mg / mL), take out 250 μL of the dissolved polymer ethanol solution, add it to 2.25 mL of PBS buffer solution with pH=7.4, and shake well to prepare The stable polymer micellar nanoparticles containing 10% ethanol were obtained, and the polymer concentration was 2.0 mg / mL. The average particle diameter measured by dynamic light scattering (DLS) is 70nm, and the dispersion index PDI is 0.02.

[0031] Micellar drug loading example 9: For the micelle drug loading process of soluble copolymer PEG-P1 in low temperature water, first dissolve paclitaxel in ethanol to make 20 mg / mL paclitaxel ethanol mother solution, and then take a certain amount (for sample A , 20 μL, for sample B, 30 μL, for sample C, 40 μL; for sample D, 70 μL) was diluted to 0.20 mL with ethanol; polymer PEG-P1 was dissolved in PBS buffer solution (2.2 mg / mL) at pH=7.4 , placed overnight in the refriger...

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Abstract

The invention discloses a reduction-sensitive amphiphilic block copolymer, which contains polyethylene glycol serving as a hydrophilic fragment component and a hydrophobic fragment component, wherein the hydrophobic fragment component contains a monomer unit of a reduction degradable disulfide bond connected hydrophobic group side chain and a methylacrylic acid polyethylene glycol ester or acrylic acid polyethylene glycol ester monomer unit; and the hydrophobic fragment component is converted to be hydrophilic under the reducing condition because the connection breakage of the disulfide bond loses a hydrophobic group. The copolymer can be dissolved in an ethanol solvent with lower toxicity or in low-temperature water. By directly adding ethanol solution of the copolymer into the water or through simple heating, a heat-sensitive polymer dissolved in the low-temperature water quickly forms micelle nano particles and a loaded medicament; and the loaded medicament has higher encapsulation rate and does not need to use a toxic organic solvent. The medicament loaded micelle particles stably wrap the medicament during storage, transportation and circulation of body fluid, and quickly degrade and release the loaded toxic medicament after entering cells through tumor targeting.

Description

technical field [0001] The invention relates to a reduction-sensitive amphiphilic block copolymer, a preparation method thereof, micelles formed by the copolymers and drugs loaded in the micelles. Background technique [0002] Polymer micelles are nanoparticles formed by the self-assembly of amphiphilic polymer copolymers in aqueous solution. Due to their wide range of drug loading and long circulation in the body, they have been used in the past ten years as insoluble drugs such as Anticancer drug carriers have been extensively studied. At present, the methods for effectively loading insoluble antineoplastic drugs into polymer micelles mainly use dialysis or solvent evaporation [Rapoport N, Physical stimuli-responsive polymeric micelles for anti-cancer drug delivery, PROGRESS IN POLYMER SCIENCE, 2007, 32(8-9), 962-990]. Dialysis is a classic method for preparing polymer micelles in the laboratory, but the general dialysis drug loading and encapsulation efficiency is not h...

Claims

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Application Information

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IPC IPC(8): C08F283/06C08F220/28C08F220/60C08J3/12A61K47/32A61K31/337A61K31/4745A61K31/704A61P35/00
Inventor 蒋序林李丽花卓仁禧
Owner 常熟紫金知识产权服务有限公司
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