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Polymer, pH-sensitive nano vesicle, and preparation method and application thereof

A nanovesicle and polymer technology, applied in the fields of polymer chemistry and biomedical engineering, can solve the problems of insufficient pH sensitivity of the medium, difficult to control the mutation range, wide mutation range, etc. The effect of accelerated rate and fast response rate

Active Publication Date: 2019-11-22
无锡享源信息科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the inventors of the present disclosure found that its hydrophobic segment is polymerized by carbon-carbon double bonds, and it is difficult to degrade in vivo after releasing the drug
[0008] In general, the inventors of the present disclosure found that the existing pH-sensitive nanovesicles have the disadvantages of wide mutation range, insufficient sensitivity to medium pH, and difficult control of the mutation range

Method used

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  • Polymer, pH-sensitive nano vesicle, and preparation method and application thereof
  • Polymer, pH-sensitive nano vesicle, and preparation method and application thereof
  • Polymer, pH-sensitive nano vesicle, and preparation method and application thereof

Examples

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preparation example Construction

[0095] Preparation of PyDH:

[0096] Under dry argon, dissolve 21.03g 4-vinylpyridine and 21.63g 3-mercapto-1,2-propanediol in 100mL DMF, add 0.65g N,N-diisopropylethylamine, stir at room temperature for 24h, and then Diethyl ether (~5°C) was settled, filtered with suction, and vacuum-dried at room temperature to constant weight to obtain the single-ended dihydroxypyridine compound PyDH (41.35 g, yield 96.9%). 1 H NMR as figure 1 shown.

Embodiment 1

[0098] (1) Preparation of Polymer A1

[0099] 10.4 g of compound PyDH, 25.59 g of hexamethylene diisocyanate-1,4-butanediol-hexamethylene diisocyanate and 0.2 g of dibutyltin dilaurate were dissolved in 50 mL of N,N'-dimethylformamide ( DMF), the oil bath was heated to 80°C for a constant temperature reaction for 3.5h. Then cool to 22°C, add chitosan oligosaccharide (number average molecular weight 1610, degree of deacetylation: 90%) in DMF solution (80.5g chitosan oligosaccharide+100mL DMF), maintain the temperature and continue the reaction for 2.5h. After the reaction, add DMF solution to the reaction flask to dilute to 0.25g / mL, then settle with eight times the volume of deionized water, repeat twice, filter with suction, and vacuum dry at 50°C to constant weight to obtain polymer A1. 1 H NMR as figure 2 shown.

[0100] (2) Preparation of Polymer B1

[0101] Dissolve 6.82g of polymer A1 in 50mL of anhydrous chloroform, add 3.6g of acetaldehyde phosphorylcholine, and r...

Embodiment 2

[0107] (1) Preparation of Polymer A2

[0108] 10.4 g of compound PyDH, 22.5 g of tetramethylene diisocyanate-1,4-butanediol-hexamethylene diisocyanate and 0.18 g of dibutyltin dilaurate were dissolved in 50 mL of N,N'-dimethylformamide ( DMF), the oil bath was heated to 75°C for constant temperature reaction for 3h. Then cool to 25° C., add a DMF solution (80.5 g chitooligosaccharide + 100 mL DMF) of chitosan oligosaccharide (number average molecular weight 1610, deacetylation degree: 90%), and maintain the temperature to continue the reaction for 2.5 h. After the reaction, add DMF solution to the reaction bottle to dilute to 0.25g / mL, then settle with eight times the volume of deionized water, repeat twice, filter with suction, and vacuum dry at 50°C to constant weight to obtain polymer A2.

[0109] (2) Preparation of Polymer B2

[0110] Dissolve 6.51g of polymer A2 in 50mL of anhydrous chloroform, add 3.6g of acetaldehyde phosphorylcholine, and react at a constant temperat...

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Abstract

The invention provides a polymer, a pH-sensitive nano-vesicle, a preparation method and an application. The structural formula of the polymer is shown in the specification, wherein m1 + n1 is equal to9 to 19, m2 + n2 = 9-19; p = 5-10, R1 and R2 are selected from the vesicles formed by the polymer, and the particle size of the vesicles is 100-160nm. According to the present invention, with the method, the weak acid medium with the pH value of 4.5-6.8 is substantially expanded, the particle size is increased to 1.4-1.8 times, the particle size increase multiple in the neutral medium and the alkaline medium is less than 1.1 times, the mutation interval is less than 0.25 pH value, and the adjustment can be performed by adjusting the number of the pyridine groups in a side chain. The vesicle provided by the invention can realize the directional administration to the pathological cells with weak acidity.

Description

technical field [0001] The disclosure belongs to the technical field of polymer chemistry and biomedical engineering, and relates to a polymer, a pH-sensitive nanovesicle, a preparation method and an application. Background technique [0002] The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art. [0003] Polymer vesicles are a special self-assembled body with a water-containing cavity formed by self-assembly of amphiphilic polymers in a certain way. It has high stability, adjustable membrane properties, and can simultaneously encapsulate hydrophilic and Hydrophobic component capacity. It is precisely because of these properties that polymersomes have broad application prospects in drug delivery, gene therapy and tissue engineering. With the development of nano-delivery systems, stimuli-responsive nanocarriers are becoming more and more popular for the treatment of cancer because they can ...

Claims

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Application Information

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IPC IPC(8): C08G18/84C08G18/65C08G18/64C08G18/32C08J3/00A61K9/127A61K47/34A61K45/00C08L75/04
CPCA61K9/1273A61K45/00A61K47/34C08G18/3844C08G18/6484C08G18/65C08G18/84C08J3/00C08J2375/04
Inventor 侯昭升滕金伟徐钧王雪洁
Owner 无锡享源信息科技有限公司
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