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Active oxygen-responsive polymer support and preparation method thereof

A polymer carrier and responsive technology, applied in the direction of organic active ingredients, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc., can solve problems such as poor stability, failure to meet application needs, and unsatisfactory effects, etc. problem, to achieve the effect of simple preparation method, improvement of water solubility and stability

Active Publication Date: 2017-08-22
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation and comprehensive performance of the existing oxidation-responsive systems still need to be optimized and improved, which cannot meet the actual application needs.
[0003] Quercetin and other polyphenolic compounds containing ortho-diphenol structure have various biological activities such as anti-oxidation, anti-tumor, anti-inflammation, etc., but most of them have disadvantages such as poor water solubility, poor stability, and lack of in vivo targeting
Although it can be improved to a certain extent by preparing water-soluble derivatives and physical encapsulation and other preparation technologies, the effect is not very satisfactory

Method used

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  • Active oxygen-responsive polymer support and preparation method thereof
  • Active oxygen-responsive polymer support and preparation method thereof
  • Active oxygen-responsive polymer support and preparation method thereof

Examples

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Effect test

Embodiment 1

[0041] The preparation of 4-nitrophenyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzyl ester (NBC) comprises the following steps:

[0042] Measure 20mL of anhydrous 1,4-dioxane, dissolve 0.234g (1.0mmol) of 4-hydroxymethylphenyl borate in a 100mL round bottom flask, stir in an oil bath at 40°C, add 0.30mL of dioxane Methylguanidine, after 30 minutes, add 0.222g (1.1mmol) of p-nitrophenyl chloroformate, react for 4h, and thin layer chromatography (TLC) detects that the reaction is complete. Add 20mL of ethyl acetate to stop the reaction, stir for 10 minutes, then wash with saturated NaHCO 3 Wash with water, followed by 0.5M hydrochloric acid to remove excess NaHCO in the system 3 . Anhydrous MgSO was added to the organic phase 4 Drying, spin-drying, column chromatography, get pure product, its 1 H-NMR spectrum as figure 1 shown.

Embodiment 2

[0044] The preparation of aryl boronic acid modified hydroxyethyl chitosan (GC-NBC) comprises the following steps:

[0045] Weigh 0.205g (about 1mmol) of hydroxyethyl chitosan (Gly-Cs), weigh 0.21g (about 2mmol) of Na 2 CO 3 In a 100mL round bottom flask, add 15mL of deionized water, stir evenly, then add 3mL of DMSO as solution A; weigh 0.200g (about 0.50mmol) of compound NBC raw material, add 15mL of DMSO solution as a solution b.

[0046]Add solution B dropwise to solution A, stir at room temperature, monitor the reaction by TLC, react overnight (time 10h), after the reaction, the system is alkaline, adjust pH=6.5 with 0.5M hydrochloric acid solution, stir at room temperature for 30 minutes, deionized water Dialyzed for 3 days, freeze-dried to obtain the product (GC-NBC), which 1 H-NMR spectrum as figure 2 shown.

Embodiment 3

[0048] Arylboronic acid modified PEG-NH 2 The preparation comprises the following steps:

[0049] Weigh 0.176g (about 1mmol) of O, O-bis(3-aminopropyl) polyethylene glycol (PEG-NH 2 ), weighed 0.21g (about 2mmol) of Na 2 CO 3 In a 100mL round bottom flask, add 15mL of deionized water, stir evenly, then add 3mL of THF, as solution A; weigh 0.6g (about 1.0mmol) of compound NBC raw material, add 15mL of THF solution, as a solution b.

[0050] Add solution B dropwise to solution A, stir at room temperature, monitor the reaction by TLC, react overnight (time 10h), after the reaction, the system is alkaline, adjust pH=6.5 with 0.5M hydrochloric acid solution, stir at room temperature for 30 minutes, deionized water Dialyzed for 3 days, freeze-dried to obtain the product PEG-NBC.

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Abstract

The invention discloses an active oxygen-responsive polymer support and a preparation method thereof. The preparation method comprises the following steps: mixing 4-(hydroxymethyl) phenylboronic acid pinacol ester with organic alkali and nitrophenyl chloroformate, and stirring to react to obtain NBC; dissolving a water-soluble polymer containing amino into water, adding an organic solvent, so as to form a solution A; dissolving NBC into the organic solvent, so as to obtain a solution B; adding alkali and the solution A into the solution B; stirring to react, and adjusting the pH value of the reaction system to 6.5-7.0, so as to obtain a modified polymer crude product; and purifying crude product, and carrying out freeze-drying, so as to obtain an active oxygen-responsive polymer support pure product. The preparation method of the active oxygen-responsive polymer support is simple, and the prepared arylboronic acid modified polymer support is easy to be chemically coupled with polyphenol active substances containing a catechol structure, so that the water solubility and stability of the support are improved, and the oxygen-responsive release of the support can be realized; and the support has important application prospects in the fields of anti-inflammation, anti-cancer treatment and the like.

Description

technical field [0001] The invention belongs to the field of medical polymer materials, in particular to an active oxygen responsive polymer carrier and a preparation method thereof. Background technique [0002] Diseases such as inflammation, fibrosis, tumors and aging are often accompanied by oxidative stress, manifested as local reactive oxygen species (ROS), mainly including OH , H 2 o 2 The concentration of etc. was increased. Smart polymer carrier systems with reactive oxygen species are expected to be used to carry therapeutic or imaging substances to achieve targeted and controlled release of disease lesions, thus attracting widespread attention. The developing oxidation-responsive carriers mainly include polypropylene sulfide (PPS), thioketal polymers, selenium-containing polymers, and aryl boronic acid or borate-containing polymers. However, the preparation and comprehensive performance of the existing oxidation-responsive systems still need to be optimized and ...

Claims

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Application Information

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IPC IPC(8): C08B37/08C08G65/48A61K47/60A61K47/61A61K47/54A61K31/352A61K31/7048A61P35/00A61P29/00A61P39/06
Inventor 曾戎乔仁忠杨锋
Owner JINAN UNIVERSITY
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