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Folic acid molecule-containing reduction response type vitamin E polyethylene glycol succinate micelle as well as preparation method and application thereof

A polyethylene glycol succinate and polyethylene glycol technology, which is applied in the field of biomedical materials, can solve the problem that vitamin E polyethylene glycol succinate derivatives cannot have tumor targeting and tumor microenvironment response at the same time problem, to achieve good tumor imaging effect and drug treatment effect, excellent biocompatibility effect

Pending Publication Date: 2020-12-25
广州市第一人民医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Aiming at the deficiency that the existing vitamin E polyethylene glycol succinate derivatives cannot simultaneously have tumor targeting and tumor microenvironmental response, the present invention redesigns and prepares a compound that can simultaneously satisfy tumor targeting and tumor microenvironmental response. Environmentally Responsive Reduction-Responsive Vitamin E Polyethylene Glycol Succinate Containing Folate Molecules

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  • Folic acid molecule-containing reduction response type vitamin E polyethylene glycol succinate micelle as well as preparation method and application thereof
  • Folic acid molecule-containing reduction response type vitamin E polyethylene glycol succinate micelle as well as preparation method and application thereof
  • Folic acid molecule-containing reduction response type vitamin E polyethylene glycol succinate micelle as well as preparation method and application thereof

Examples

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Embodiment 1

[0045] A reduction-responsive vitamin E polyethylene glycol succinate micelle containing folic acid molecules, characterized in that the micelles include the following components in parts by weight: reduction-responsive vitamin E polyethylene glycol containing folic acid molecules 10 parts of succinate, 1 part of doxorubicin, and 1 part of superparamagnetic iron oxide nanoparticles. The structural formula of the reduction-responsive vitamin E polyethylene glycol succinate containing folic acid molecules is shown in the following formula:

[0046]

[0047] The preparation method of present embodiment micelle is:

[0048] (1) Preparation of allyl polyethylene glycol p-toluenesulfonate: 20 g of 500 g / mol allyl polyethylene glycol was dissolved in 200 mL of anhydrous dichloromethane, stirred in an ice-water bath, and then added to Toluenesulfonyl chloride 4g, triethylamine 6mL, continue to stir for 2h, react at room temperature for 24h, after the reaction is completed, wash 3 t...

Embodiment 2

[0060] A reduction-responsive vitamin E polyethylene glycol succinate micelle containing folic acid molecules, characterized in that the micelles include the following components in parts by weight: reduction-responsive vitamin E polyethylene glycol containing folic acid molecules 10 parts of succinate, 1.5 parts of doxorubicin, and 1.5 parts of superparamagnetic iron oxide nanoparticles. The structural formula of the reduction-responsive vitamin E polyethylene glycol succinate containing folic acid molecules is the same as that in Example 1.

[0061] The preparation method of present embodiment micelle is:

[0062] (1) Preparation of allyl polyethylene glycol p-toluenesulfonate: dissolve 20 g of 1000 g / mol allyl polyethylene glycol in 250 mL of anhydrous dichloromethane, stir in an ice-water bath, and then add p-toluenesulfonate Toluenesulfonyl chloride 2g, triethylamine 3mL, continue to stir for 2h, react at room temperature for 24h, after the reaction is completed, wash 3 t...

Embodiment 3

[0073] A reduction-responsive vitamin E polyethylene glycol succinate micelle containing folic acid molecules, characterized in that the micelles include the following components in parts by weight: reduction-responsive vitamin E polyethylene glycol containing folic acid molecules 10 parts of succinate, 2 parts of doxorubicin, and 2 parts of superparamagnetic iron oxide nanoparticles. The structural formula of the reduction-responsive vitamin E polyethylene glycol succinate containing folic acid molecules is the same as that in Example 1.

[0074] The preparation method of present embodiment micelle is:

[0075] (1) Preparation of allyl polyethylene glycol p-toluenesulfonate: dissolve 2000g / mol allyl polyethylene glycol 20g in 300mL anhydrous dichloromethane, stir under ice-water bath, then add p-toluenesulfonate Toluenesulfonyl chloride 2g, triethylamine 2mL, continue to stir for 2h, react at room temperature for 24h, after the reaction is completed, wash 3 times with saturat...

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Abstract

The invention relates to a folic acid molecule-containing reduction response type vitamin E polyethylene glycol succinate micelle. The micelle is characterized by comprising the following components in parts by weight: 10 parts of folic acid molecule-containing reduction response type vitamin E polyethylene glycol succinate, 1-2 parts of adriamycin and 1-2 parts of superparamagnetic iron oxide nanoparticles. According to the micelle disclosed by the invention, disulfide bonds with corresponding reduction characteristics are respectively connected with a hydrophilic polyethylene glycol chain segment and a hydrophobic vitamin E chain segment thereof, and folic acid molecules are introduced, so that the micelle has a tumor targeting characteristic, micelle nanoparticles obtained by self-assembly have excellent biocompatibility, and the micelle can respond to glutathione in a tumor reducing microenvironment, realizes rapid release of drugs, and has the advantages of tumor targeting and intelligent controlled release of the drugs.

Description

technical field [0001] The invention relates to a reduction-responsive vitamin E polyethylene glycol succinate micelle containing folic acid molecules and a preparation method and application thereof, belonging to the technical field of biomedical materials. Background technique [0002] Multidrug resistance (MDR) refers to that after tumor cells develop resistance to a certain chemotherapy drug, they also develop cross-resistance to other chemotherapy drugs that have not been exposed to each other, have different chemical structures, and have different targets and mechanisms. It is the main reason for the failure of clinical chemotherapy. The generation of multidrug resistance is closely related to the movement protein, because the overexpression of multidrug resistance-related proteins and P-glycoprotein on the tumor cell membrane will pump out the drug, resulting in anti-tumor drugs in the cell aggregation will decrease. [0003] Nanotechnology can more accurately deliv...

Claims

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Application Information

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IPC IPC(8): A61K9/107A61K31/704A61K47/22A61K47/54A61K49/12A61K49/18A61P35/00C08G65/325C08G65/333C08G65/334
CPCA61K9/1075A61K31/704A61K47/545A61K47/22A61K49/126A61K49/1809A61P35/00C08G65/3344C08G65/325C08G65/33306C08G65/33327C08G65/3348
Inventor 杨惠康杨蕊梦魏新华江新青
Owner 广州市第一人民医院
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