Dopamine functionalized poly(beta-amino ester) as well as preparation method and application thereof

A dopamine and functionalized technology, applied in the biological field, can solve the problems of insufficient intracellular release and increased cytotoxicity, and achieve the effects of improving stability, low cytotoxicity and high transfection efficiency.

Active Publication Date: 2021-06-01
ZHEJIANG UNIV HANGZHOU GLOBAL SCI & TECH INNOVATION CENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In the prior art, the main focus of improving the transfection efficiency is to increase the molecular weight, positive charge and branching degree of the polymer, but too high a positive charge will cause the nanoparticles formed after wrapping siRNA to be too compact and endocytosis. After that, it cannot be fully released in the cell, and the large molecular weight will also lead to an increase in cytotoxicity

Method used

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  • Dopamine functionalized poly(beta-amino ester) as well as preparation method and application thereof
  • Dopamine functionalized poly(beta-amino ester) as well as preparation method and application thereof
  • Dopamine functionalized poly(beta-amino ester) as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) Hydroxyl protection of dopamine phenol: dissolve dopamine hydrochloride (2mmol) and imidazole (2.4mmol) in dichloromethane solution (10mL), add dimethyl tert-butylchlorosilane (4mmol) dropwise in ice bath , The reaction was stirred at 25°C for 12h. After the reaction, the mixed solution is rotary evaporated to obtain a crude product, and the dopamine monomer whose phenolic hydroxyl group is protected is obtained by solution washing, liquid separation, rotary evaporation, and drying;

[0041] (2) After mixing the dopamine monomer (0.5mmol) prepared in step (1) with 5-amino-1-pentanol (2mmol), together with 1,4-butanediol diacrylate (2.75mmol) in di Stirring and reacting in methyl sulfoxide at 90°C for 24 hours to obtain a polymer;

[0042] (3) Dissolving the polymer (1 mmol) prepared in step (2) in tetrahydrofuran solution (4 mL), adding 2 mmol N-aminopropylmorpholine to the reaction system, and stirring at room temperature for 4 h to obtain a capped polymer;

[00...

Embodiment 2～3

[0045] According to the preparation process of Example 1, the amounts of dopamine monomer and 5-amino-1-pentanol in step (2) were replaced by 1mmol and 1.5mmol, 1.25mmol and 1.25mmol respectively, and the remaining steps were unchanged to obtain dopamine respectively. Functionalized poly(β-amino ester) PBAE2 and PBAE3.

Embodiment 4～5

[0047] According to the preparation process of Example 1, the 5-amino-1-pentanol in step (1) is replaced by N,N-dimethylethylenediamine and N,N-diethylethylenediamine respectively, and the remaining steps are not Changes to obtain dopamine-functionalized poly(β-amino ester) PBAE4 and PBAE5, respectively.

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Abstract

The invention relates to the technical field of biology, and discloses dopamine functionalized poly(beta-amino ester) as well as a preparation method and application thereof. The structural formula of the poly(beta-amino ester) is shown in the specification, and the preparation method of the poly(beta-amino ester) comprises the steps: carrying out a polymerization reaction on 1,4-butanediol diacrylate and an amino-containing monomer; carrying out end capping on the polymer by adopting small molecular amine; and finally, carrying out deprotection on the phenolic hydroxyl group of dopamine to obtain the dopamine functionalized poly(beta-amino ester). Dopamine is introduced into PBAE, and ferric ions are complexed with the PBAE to form an encapsulated nanoparticle structure, so that the stability of a compound is improved, and a gene transfection vector with high transfection efficiency and low cytotoxicity is obtained, so that the gene transfection vector has potential clinical application value in the aspect of non-viral gene vectors.

Description

technical field [0001] The invention relates to the field of biotechnology, in particular to a dopamine functionalized poly(β-amino ester) and its preparation method and application. Background technique [0002] Interfering RNA (RNAi) is a naturally occurring cellular mechanism that culminates in the knockdown of specific genes. Targeted gene knockdown delivered by siRNA has potential clinical utility in treating diseases caused by abnormal gene expression. However, safe and efficient intracellular siRNA delivery remains challenging. Current studies have used the carrier materials (liposomes, inorganic materials and polymers) that can deliver DNA to deliver siRNA. Two major delivery hurdles unique to siRNA are: nanoparticle stability and cytoplasmic targeting. Since siRNA is approximately 200 times smaller than DNA plasmids and relatively rigid, it has low electrostatic interactions with cationic polymers, hindering the self-assembly of the two to form stable and small-s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02C12N15/87
CPCC08G73/02C12N15/87
Inventor 申有青刘衍朋周珠贤
Owner ZHEJIANG UNIV HANGZHOU GLOBAL SCI & TECH INNOVATION CENT
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