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Branched polyetherimide material containing ketone thioacetal bond, as well as preparation method and application thereof

A technology of branched polyetherimide and thioketal, which is applied in the field of polyetherimide, can solve the problems of limited efficiency of siRNA on target gene downregulation, biodistribution and targeting, and endogenous RNA competition. Achieve improved anti-tumor effect, good biocompatibility and degradability, simple and controllable synthesis

Active Publication Date: 2019-03-26
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are many problems in the treatment process of siRNA, such as the limited downregulation efficiency of siRNA on target genes, endogenous RNA competition, biodistribution and targeting, etc.

Method used

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  • Branched polyetherimide material containing ketone thioacetal bond, as well as preparation method and application thereof
  • Branched polyetherimide material containing ketone thioacetal bond, as well as preparation method and application thereof
  • Branched polyetherimide material containing ketone thioacetal bond, as well as preparation method and application thereof

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Experimental program
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Embodiment 1

[0043] Embodiment 1, the synthesis and characterization of branched polyetherimide material

[0044] 1. Reactive oxygen sensitive branched polyetherimide TK Synthesis of PEI-Ce6

[0045]Reactive oxygen sensitive branched polyetherimides are derived from branched polyethyleneimine and 3,3'-(propane-2,2-dienyl(sulfonylamino))dipropionic acid containing thioketal linkages. The cross-linking reaction between them was synthesized, and then PEG and photosensitizer Ce6 were bonded by amidation reaction.

[0046] TK The synthetic route of PEI-Ce6 branched polyetherimide material is as follows figure 1 shown.

[0047] Preparation and pretreatment of required components.

[0048] 1. Synthesis of 3,3'-(propane-2,2-dienyl (sulfonyl)) dipropionic acid containing thioketal bond

[0049] Acetone and 3-mercaptopropionic acid were dried to remove water. Mix anhydrous acetone (5.8g, 98.2mmol) and anhydrous 3-mercaptopropionic acid (5.2g, 49.1mmol) uniformly, stir in dry hydrogen chloride...

Embodiment 2

[0054] Embodiment 2, nanoparticle formation and application of branched polyetherimide

[0055] 1. Preparation of branched nanoparticles

[0056] The use of reactive oxygen species-sensitive polymer materials for nanocarriers has been extensively studied. The synthesis method of thioketal bond is simple and controllable. Under the action of active oxygen, it breaks to generate sulfhydryl groups, disintegrates the nanocarrier and releases the drug quickly, so it is a safe and efficient drug delivery carrier.

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Abstract

The invention discloses a branched polyetherimide material containing a ketone thioacetal bond, as well as a preparation method and application thereof. The preparation method comprises the followingsteps: (1) stirring acetone and acid containing thiol to react at room temperature; (2) adding polyetherimide and an activator after the reaction is finished, dissolving in an organic reagent, stirring to react, bonding chlorin e6 and carboxyl polyethylene glycol through an amidation reaction to obtain the reactive oxygen sensitive branched polyetherimide material containing the ketone thioacetalbond. The branched polyetherimide material has excellent biocompatibility and degradability, is entrapped with siRNA, and forms nano-particles by self-assembly, can generate a great number of reactiveoxygen under excitation of a light source with specific wavelength to destroy the structure of endosome, the reactive oxygen sensitive ketone thioacetal bond is broken, particles are disintegrated, and endosome escape and release of intracellular siRNA can be accelerated. The branched polyetherimide material containing a ketone thioacetal bond has a huge clinical application potential in the field of tumor treatment.

Description

technical field [0001] The invention relates to the field of polyetherimide, in particular to a branched polyetherimide material containing thioketal bonds, a preparation method and application thereof. Background technique [0002] RNA interference (RNAi) is a post-transcriptional regulation method of genes. In cells, double-stranded RNA specifically recognizes and degrades homologous mRNAs, thereby down-regulating the expression of specific genes. Compared with conventional tumor treatment methods, RNA interference technology has the advantages of high specificity and high stability. At present, the main RNA interference technologies include miRNA and siRNA. miRNA is a small non-coding RNA that is transcribed from genomic DNA and cleaved by nucleases. siRNA is a synthetic double-stranded RNAi molecule with a length of about 21 to 23 bp. [0003] In recent years, RNA interference technology has made great progress in the field of tumor treatment, and nearly ten small int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10A61K9/51A61K47/34A61K41/00A61P35/00A61K31/7105
CPCA61K9/5146A61K31/7105A61K41/0071A61P35/00C08G73/1046C08G73/1064A61K2300/00
Inventor 杨显珠金靓洁曹紫洋
Owner SOUTH CHINA UNIV OF TECH
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