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Cation polymer capable of removing positive charges through oxidative response, and preparation method and application thereof

A cationic polymer and positive charge technology, which is applied in the direction of medical preparations, drug combinations, and pharmaceutical formulations of non-active ingredients, can solve the problems of reporting, no preparation methods, and applications, and achieve easy synthesis, low cytotoxicity, and structure simple effect

Active Publication Date: 2015-12-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no report on this kind of cationic polymer at present, and there is no report on its preparation method and application

Method used

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  • Cation polymer capable of removing positive charges through oxidative response, and preparation method and application thereof
  • Cation polymer capable of removing positive charges through oxidative response, and preparation method and application thereof
  • Cation polymer capable of removing positive charges through oxidative response, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Synthesis of polymer (1)

[0061] Polymer (1) can be synthesized by two methods;

[0062] Synthesis method 1:

[0063] Monomer N,N-diethylaminoethyl acrylate (2-(N,N-diethylaminoethyl)acrylate, DEAEA) was purified by vacuum distillation before use, weighed 5g of DEAEA, AIBN (azobisisobutyronitrile) 0.05g was mixed with a molar ratio of 100:1, argon was bubbled for 30 minutes to remove oxygen, heated to 65°C under anaerobic conditions and stirred for bulk polymerization, reacted for 24 hours, and then separated and purified, and the polymer was dissolved in Dichloromethane was precipitated with ice n-hexane, repeated three times, and dried to obtain 4.5 g of polymer PDEAEA as light yellow viscous liquid with a yield of 90%.

[0064]

[0065] The PDEAEA obtained above is carried out molecular weight determination, and assay method is gel permeation chromatography, polyethylene glycol (PEG) standard substance and the PDEAEA prepared by embodiment are samples, dissolve...

Embodiment 2

[0092] Oxidative response of polymer (1)

[0093] A certain amount of polymer (1) was weighed and dissolved in ultrapure water at a concentration of 0.3 mg / mL, and aqueous hydrogen peroxide solution was added, and the final concentration of hydrogen peroxide was 1 mM (mM stands for millimole per liter). The quinone generated by polymer (1) under oxidative conditions becomes p-hydroxybenzyl alcohol (HMP) very quickly in water, with 10% methanol aqueous solution as mobile phase, flow rate is 1mL / min, with high performance liquid chromatography (HPLC) When analyzing HMP, the peak time is 3.5 minutes, and the release curve of HMP can be obtained by monitoring the amount of HMP released at different times. This experiment proves that under the condition of 1mM hydrogen peroxide, the polymer polymer (1) is oxidized rapidly within 30 minutes, and is almost completely oxidized within 2 hours. For the test results, see figure 1 .

Embodiment 3

[0095] Charge reversal of polymer (1) under oxidative conditions

[0096] The first group: Weigh a certain amount of polymer Polymer (1) is dissolved in HEPES buffer solution (pH value is 7.4, 10mM), the concentration is 3mg / mL, and the final concentration of adding hydrogen peroxide solution is 80mM. Always maintain the pH value of the solution at 7.4, incubate at 37°C, and measure the Zeta potential of the solution at different times.

[0097] The second group: take a certain amount of polymer (1) and dissolve it in HEPES buffer solution (pH value is 7.4, 10mM), the concentration is 3mg / mL, add hydrogen peroxide aqueous solution and the final concentration is 80mM, the solution pH value is adjusted to 5.0, after incubating at 37°C for 2 hours, adjust the pH value of the solution to 7.4, maintain the pH value of the solution at 7.4, incubate at 37°C, and measure the Zeta potential of the solution at different times.

[0098] Test results such as figure 2 As shown, the expe...

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Abstract

The invention discloses a cation polymer capable of removing positive charges through oxidative response, a preparation method and application. The cation polymer is a charge reversal type gene delivery carrier synthesized from 4-(bromomethyl)phenylboronic acid and ethyl (E)-3-diethylaminoprop-2-enoate through quaternary amination. Compared with the prior art, the cation polymer is different from the common quaternary amination carrier; the synthesized charge reversal type gene delivery carrier for oxidative response has a large quantity of positive charges and can well coat a DNA, but the positive charges can be removed under the condition of intracellular oxidation when the charge reversal type gene delivery carrier enters a cell, a charge reverse is triggered (the positive charges turn to negative charges), and the DNA is quickly released for transfection. The charge reversal type gene delivery carrier is efficient, low in toxicity, and good in application prospect.

Description

technical field [0001] The invention belongs to the field of macromolecule and biotechnology, and in particular relates to a cationic polymer that responds to oxidation and removes positive charges, a preparation method and an application as a gene delivery carrier. Background technique [0002] Gene therapy, which is to deliver nucleic acid drugs to target cells to achieve therapeutic purposes, has been proven to be an effective method for treating cancer with low side effects. Currently commonly used delivery vectors can be divided into viral vectors and non-viral vectors. Non-viral vectors include cationic liposomes, polymers, dendrimers, polypeptides, etc. Compared with viral vectors, they have the advantages of good safety, low immunogenicity, biocompatibility and easy mass production. However, compared with viral vectors, lower transfection efficiency has always been a bottleneck for its application, and chemical modification is needed to improve the transfection effi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F120/34C08F120/36C08F8/42C08F283/00A61K48/00A61K47/48A61P35/00A61K47/58
Inventor 申有青刘欣唐建斌刘祥瑞
Owner ZHEJIANG UNIV
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