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Hypoxia-sensitive drug carrier polymer as well as preparation method and application thereof

A technology of polymers and compounds, which is applied in the field of hypoxia-sensitive polymers and their preparation, can solve the problems of affecting the recognition of DNA transcription points, increasing non-specific adsorption, and reducing transfection efficiency, so as to enhance joint killing ability and enhance hypoxia Oxygen, improve the effect of degradation

Active Publication Date: 2021-12-21
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The cationic carrier and the gene drug are combined through electrostatic interaction, which can better protect the nucleic acid drug from being degraded by nucleases, but after entering the cell, it usually needs to compete with intracellular proteins to release the negatively charged siRNA, which reduces the transfection efficiency
At the same time, the presence of cations may affect the recognition of DNA transcription points and even interact with translation-related proteins, further reducing the transfection efficiency
The charge density of cations may be inextricably linked to their toxicity, leading to increased nonspecific adsorption leading to normal cytotoxicity

Method used

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  • Hypoxia-sensitive drug carrier polymer as well as preparation method and application thereof
  • Hypoxia-sensitive drug carrier polymer as well as preparation method and application thereof
  • Hypoxia-sensitive drug carrier polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Embodiment 1: the preparation of compound 4-((4-nitrobenzyloxy)phenyl)methanol

[0084]

[0085] Prepare a 100mL round-bottomed flask with branched mouth, add 3.0g (0.024mol) of solid p-hydroxybenzyl alcohol, 5.52g (0.04mol) of anhydrous potassium carbonate, add 30mL of N,N-dimethylformamide, and stir to make it Hydroxybenzyl alcohol dissolved. Bubble argon and allow to stir under argon for 10 minutes. Dissolve p-nitrobenzyl bromide in 20 mL of N,N-dimethylformamide, and add the solution dropwise into a round-bottomed flask through an atmospheric pressure dropping funnel under argon purging. After the dropwise addition, the solution was light yellow, and after overnight reaction, the solution was dark green. After reacting for 24 hours, remove solid insolubles by filtration, wash the reaction solution with saturated sodium chloride aqueous solution and ethyl acetate successively, and finally collect the organic phase with anhydrous magnesium sulfate to remove water...

Embodiment 2

[0086] Embodiment 2: Preparation of 4-((4-nitrobenzyl)oxy)benzyl acrylate

[0087]

[0088] First, weigh 2.6g (0.01mol) of 4-((4-nitrobenzyloxy)phenylcarbinol prepared in Example 1 and dissolve it in 30mL of dichloromethane and add it to a 100mL round-bottomed flask. Add 1mL (1.1mol ) triethylamine as an acid-binding agent, the reaction solution was placed in an ice bath and stirred for 10 minutes so that the temperature of the reaction solution dropped to a lower temperature, and 0.83 mL of acryloyl chloride (0.012 mol) was slowly added dropwise under ice bath conditions, and after overnight reaction Wash with saturated NaCl aqueous solution three times, collect the organic phase, remove water through anhydrous magnesium sulfate, filter to remove the solid, and then evaporate the solvent by rotary evaporation, and separate the product by column chromatography with ethyl acetate:n-hexane volume ratio 1:4, the first point is is the product point. 1 HNMR (CDCl 3 ppm):8.27(m...

Embodiment 3

[0089] Example 3: Preparation of Hypoxia Responsive Gene Carrier Polymer A

[0090]

[0091] Accurately weigh 0.1 g of branched polyethyleneimine with a molecular weight of 10K (0.01 mM, containing about 2.3 mM NH for subsequent reaction) into a 5 mL round bottom flask, add 1 mL of anhydrous N, N-dimethylformazine Stir the amide until the polyethyleneimine is completely dissolved. After the dissolution is complete (no obvious viscous liquid), add 1g (3.4mM) of 4-((4-nitrobenzyl)oxy)benzyl acrylate prepared in Example 2 , stirred and reacted at room temperature for 48 hours, and then transferred to a water bath at 45° C. for 24 hours. Add 0.44 mL (7 mM) of iodomethane into the reaction system, and react overnight in the dark. After completion of the reaction, precipitate with ether three times to remove unreacted methyl iodide. After that, dichloromethane was used to precipitate three times to remove unreacted monomers, and the precipitated solid was placed in a vacuum ove...

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Abstract

The invention relates to a hypoxia-sensitive gene vector as well as a preparation method and application thereof. According to the invention, polyethyleneimine is grafted with a nitro compound, and then the hypoxia-sensitive gene vector is formed through a nano precipitation method. The polyethyleneimine grafted nitro compound provided by the invention can generate charge reversal under the combined action of nitroreductase and NADH in cells, so that gene drug release is realized, and the transfection efficiency is improved. Various negatively charged medicine molecules can be loaded, and the invention has a wide application prospect and a huge research value.

Description

technical field [0001] The invention belongs to the field of nanometer and biomedicine, and in particular relates to a hypoxia-sensitive polymer and its preparation method and application. Background technique [0002] Due to the aging of the population, changes in lifestyles brought about by economic development, such as smoking, overweight, lack of physical exercise, and environmental pollution caused by economic development, etc., the risk of cancer is increasing. It is an urgent public health problem and seriously endangers human health. Currently, cancer treatment methods are mainly based on various forms of chemotherapy and radiotherapy, with surgical resection as an auxiliary means. Most chemotherapeutic drugs are small molecule drugs, and their low water solubility, low bioavailability, and multidrug resistance limit their application. Radiation therapy is not specific, and it can damage normal cells while killing tumor cells, which brings serious toxic and side ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02A61K47/34A61K45/00A61P35/00
CPCC08G73/0226C08G73/0206C08G73/0213A61K47/34A61K45/00A61P35/00Y02A50/30
Inventor 喻青松甘志华周敏
Owner BEIJING UNIV OF CHEM TECH
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