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Methacrylic acid orthoesters new monomer, as well as preparation method and application of amphiphilic block copolymer of methacrylic acid orthoesters new monomer

A methacrylic acid ortho-acid and amphiphilic block technology, which can be used in pharmaceutical formulations, medical preparations of non-active ingredients, organic chemistry, etc. It can solve the problems of difficult removal of metal compounds, inconvenient handling, wide distribution of polymers, etc. problems, to achieve good application prospects, good acid sensitivity effect

Inactive Publication Date: 2014-02-19
ANHUI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, in domestic and foreign research, polymers with orthoesters are mainly obtained by the method of ATRP. The main disadvantages are that the reaction conditions are harsh, the distribution of the obtained polymers is wide, and the metal compounds produced during the reaction process are not easy to remove. Subsequent treatment inconvenient

Method used

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  • Methacrylic acid orthoesters new monomer, as well as preparation method and application of amphiphilic block copolymer of methacrylic acid orthoesters new monomer
  • Methacrylic acid orthoesters new monomer, as well as preparation method and application of amphiphilic block copolymer of methacrylic acid orthoesters new monomer
  • Methacrylic acid orthoesters new monomer, as well as preparation method and application of amphiphilic block copolymer of methacrylic acid orthoesters new monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The synthetic method of 2-methoxy-5-ethyl-[1,3]-dioxane-5-acetoacetate methyl ester monomer is realized through the following steps:

[0036] 1) Preparation of ethyl 2,2-dimethylolbutyrate

[0037] Under nitrogen atmosphere, add 20.00g (135.41mmoL) 2,2-dihydroxybutyric acid, 120mL absolute ethanol, 2mL concentrated sulfuric acid (98%) into a 250ml three-neck flask, reflux at 130°C for 12 hours, cool at room temperature, add Excess sodium carbonate solid neutralizes the remaining sulfuric acid, the reaction mixture is centrifuged at 13000rmp for 10 minutes, the upper layer solution is filtered, the filtrate is evaporated to dryness under reduced pressure, the crude product is dissolved in chloroform, washed with 10% sodium carbonate solution and saturated brine, and dried over magnesium sulfate , the solvent was distilled off under reduced pressure to obtain 17.31 g of a colorless oily pure product, with a yield of 72.60%. 1 H NMR (400MHz, CDCl 3 ,δ,ppm):0.82–0.86(m,3H...

Embodiment 2

[0045] 1.00g (4.10mmoL) of 2-methoxy-5-ethyl-[1,3]-dioxane-5-acetoacetate methyl ester, 0.74g (0.137mmoL) of polyethylene glycol macroinitiator , 1.12mg (0.0274mmoL) of 2,2-azobisisobutylcyanide was accurately weighed and put into a dry and clean glass polymerization tube, then N,N-dimethylformamide (2.0mL) was added, and the polymerization system was ventilated with nitrogen Seal the tube after degassing for 30 minutes, put the polymerization reaction tube into an oil bath at 70°C to heat and polymerize, and after 24 hours of reaction, dissolve the reaction mixture in N,N-dimethylformamide, then add it dropwise into glacial ether, and collect Precipitate, then rinse with a small amount of glacial ether, the product is vacuum-dried to constant weight to obtain the target copolymer P1, the polymer properties see figure 2 .

Embodiment 3

[0047] Add 0.50g (2.05mmoL) of 2-methoxy-5-ethyl-[1,3]-dioxane-5-acetoacetate methyl ester, 0.18g (0.0341mmoL) of polyethylene glycol macroinitiator , 1.12mg of 2,2-azobisisobutylcyanide (6.80×10-4mmoL) was accurately weighed and put into a dry and clean glass polymerization tube, then N,N-dimethylformamide (1.5mL) was added to polymerize After degassing the system with nitrogen for 30 minutes, seal the tube, put the polymerization reaction tube into an oil bath at 70°C to heat and polymerize, and after 24 hours of reaction, dissolve the reaction mixture in N,N-dimethylformamide, and then add glacial ether dropwise In the process, the sediment was collected, rinsed with a small amount of glacial ether, and the product was vacuum-dried to constant weight to obtain the target copolymer P2. The properties of the polymer are shown in figure 2 .

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Abstract

The invention discloses a synthesis method for side-chain orthoester group (hexatomic-ring)-containing acid-sensitivity amphiphilic block copolymer, and application of a medicine-carrying system in the field of medicine delivery. The copolymer has good acid sensitivity, biocompatibility and biodegradability, can be self-assembled in an aqueous solution to form a medicine carrier with a putamen structure, and has good application prospects in the field of targeted treatment.

Description

technical field [0001] The invention relates to a synthesis method of a novel acid-sensitive amphiphilic block copolymer containing orthoester groups in the side chain and its drug delivery performance. The invention belongs to the technical field of polymer carriers and sustained-release materials. Background technique [0002] Overcoming multiple drug resistance in tumor cells is one of the challenges faced by cancer chemotherapy, and the use of environment-responsive smart polymer micelles to deliver anticancer drugs is an effective way to solve this problem. The slightly acidic environment of the tumor can be used to trigger the rapid drug release of nanocarriers, deliver drugs to cells or even specific organelles, greatly increase the drug concentration in drug action sites such as cytoplasm and nucleus, avoid multiple drug resistance mechanisms of cancer cells, and overcome Tumor drug resistance, reduce the toxic side effects of tumor chemotherapy. [0003] pH-respon...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06C08F293/00A61K47/32
CPCC07D319/06A61K9/1075A61K47/32C08F293/00C08F2800/10
Inventor 唐汝培罗师
Owner ANHUI UNIVERSITY
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