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Preparation of redox-sensitive cross-linked nanomicelles

A nano-micelle and sensitive technology, which is applied in the field of chemically cross-linked micelles with redox-sensitive properties and its preparation, can solve the problems of low modification and cumbersome synthesis process, and achieve easy-to-product, mild reaction conditions, and high-quality products. The effect of purification

Inactive Publication Date: 2018-02-27
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned self-assembly is characterized by the introduction of disulfide bonds into the main chain or side chain of the polymer, but the further modification is low, the synthesis process is cumbersome, and multi-step purification is required

Method used

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  • Preparation of redox-sensitive cross-linked nanomicelles
  • Preparation of redox-sensitive cross-linked nanomicelles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Dissolve 13mg of cumyl dithiobenzoate, 1.06g of glycidyl methacrylate and 3mg of azobisisobutyronitrile in 1.5mL of tetrahydrofuran, degas three times through continuous freezing and thawing, and place in a 70°C refrigerator after being protected by argon. Polymerization in an oil bath for 8 hours. After the end, the reaction was quenched with liquid nitrogen to stop the reaction, and the method of dissolving tetrahydrofuran by precipitation with n-hexane was used to obtain poly(glycidyl methacrylate) macromolecular chain transfer agent after repeated purification 3 times;

[0022] Dissolve 0.24g of poly(glycidyl methacrylate) macromolecular chain transfer agent, 0.16g of polyethylene glycol methacrylate and 3mg of azobisisobutyronitrile in 1mL of tetrahydrofuran, and degas five times through continuous freezing and thawing. After being filled with argon for protection, it was placed in an oil bath at 65°C for a polymerization reaction for 12 hours. After the end, the ...

Embodiment 2

[0025] Dissolve 14mg of 4-cyano-4-(phenylthioformylthio)pentanoic acid, 1.42g of 4-(formyl)phenyl methacrylate and 3mg of azobisisobutyronitrile in 2.5mL of tetrahydrofuran, and After freeze-thawing and degassing for 4 times, it was protected by argon and placed in an oil bath at 80°C for 24 hours of polymerization reaction. After the end, the reaction was quenched with liquid nitrogen to stop the reaction, and the method for dissolving tetrahydrofuran by precipitation with n-hexane was used to obtain poly(4-(formyl)phenyl methacrylate) macromolecular chain transfer agent after repeated purification for 5 times;

[0026] Dissolve 0.48g of poly(4-(formyl)phenyl methacrylate) macromolecular chain transfer agent, 0.8g of polyethylene glycol methacrylate and 3mg of azobisisobutyronitrile in 1mL of tetrahydrofuran. Gas 3 times, filled with argon protection, and placed in an oil bath at 75°C for 36 hours of polymerization. After the end, the liquid nitrogen was quenched to stop the...

Embodiment 3

[0029] Dissolve 14mg of 4-cyano-4-(phenylthioformylthio)pentanoic acid, 0.95g of 4-(formyl)phenyl methacrylate and 3mg of azobisisobutyronitrile in 2mL of tetrahydrofuran, and freeze Melting and degassing for 5 times, filling with argon for protection, and placing in an oil bath at 65°C for 48 hours of polymerization. After the end, the reaction was quenched with liquid nitrogen to stop the reaction, and the method for dissolving tetrahydrofuran by precipitation with n-hexane was used to obtain poly(4-(formyl)phenyl methacrylate) macromolecular chain transfer agent after repeated purification for 5 times;

[0030] Dissolve 0.32g of poly(4-(formyl)phenyl methacrylate) macromolecular chain transfer agent, 0.15g of polyethylene glycol methacrylate and 3mg of azobisisobutyronitrile in 1.5mL of tetrahydrofuran, and freeze-thaw continuously After degassing for 3 times, protect it with argon and place it in an oil bath at 80°C for 24 hours of polymerization reaction. After the end, ...

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Abstract

The invention discloses a cross-linked nano-micelle with redox-sensitive properties and a preparation method thereof. A macromolecular chain transfer agent is synthesized first by adopting a reversible addition-fragmentation chain transfer polymerization method, and combined with polyethylene glycol methacrylic acid A block polymer that can be further modified is synthesized by ester polymerization. On the basis of its self-assembly, a cross-linking agent containing a disulfide bond that can be chemically linked is introduced to construct a stable cross-linking method by first assembling and then cross-linking. nanomicelles with redox-responsive properties. The method is easy to control, the reaction conditions are mild, there is no metal catalyst, and the product is easy to purify. The obtained cross-linked nanomicelles can not only encapsulate hydrophobic drugs, but also prevent their early release in blood circulation.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a chemically cross-linked and redox-sensitive micelle and a preparation method thereof. Background technique [0002] Polymer self-assembly has potential application value in various fields due to its tunable shape, size and function. In the field of drug release, in order to promote tumor-specific drug aggregation and release, multifunctional environment-responsive polymer self-assemblies have been extensively studied. Usually, the drug is chemically linked or physically encapsulated in an environment-responsive self-assembly. Under the stimulation of the external environment, the self-assembly realizes the controlled release of the drug by changing its own structure, shape, and performance. [0003] Currently reported redox reactions caused by covalent bond cleavage are limited to disulfide bonds. Disulfide bonds in organisms can generate two sulfhydryl groups through the act...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F293/00C08F4/40C08J3/24
Inventor 戴李宗常迎袁丛辉宋存峰许一婷曾碧榕
Owner XIAMEN UNIV
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