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PH-sensitive quaternary ammonium salt amphiphilic block copolymer and application thereof

A technology of amphiphilic block and block copolymer, applied in the field of functional polymers and nano-gene delivery technology, amphiphilic pH-sensitive tri-block quaternary ammonium cationic copolymer, which can solve the problem of no proton buffering ability and other problems, to achieve the effect of high gene loading capacity and high transfection efficiency

Inactive Publication Date: 2019-11-12
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, compared with amino groups (primary amines, secondary amines, tertiary amines), quaternary ammonium is a stable organic cation without proton buffering capacity

Method used

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  • PH-sensitive quaternary ammonium salt amphiphilic block copolymer and application thereof
  • PH-sensitive quaternary ammonium salt amphiphilic block copolymer and application thereof
  • PH-sensitive quaternary ammonium salt amphiphilic block copolymer and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Take a 25ml schlink tube and add 0.4g (0.2mmol) PEG to the tube 2k -CTAm (Theranostics, 2017, 7, 3432-3445), 5ml dry dimethylformamide (DMF), then add 18.0mmol DMA and 2.0mmol DPA to the tube, add 6.56mg under argon protection after vacuuming (0.04mmol) AIBN, then continue to vacuumize and fill with argon, after circulating three times, place it in an oil bath at 70°C for 24h, and the product is determined by nuclear magnetic resonance in DDE (deuterium band chloroform), as figure 1 ). After the reaction is finished, add 3600mg (12mmol) TMA I, 5ml dry DMF to each tube, add 6.56mg (0.04mmol) AIBN under argon protection after vacuumizing, continue to vacuumize and fill with argon, after circulating three times, place The reaction was continued in a 70°C oil bath for 24h. After the reaction, dialyze with distilled water to remove DMF, freeze-dry, and obtain the final product as an A-C-T triblock copolymer, marked as TDDE (T represents T segment, DD represents DPA / DMA cop...

Embodiment 2

[0037] Take a 25ml schlink tube, add 0.4g (0.2mmol) PEG2k-CTAm (Theranostics, 2017, 7, 3432-3445) and 5ml dry DMF to the tube, then add 16.0mmol DMA and 4.5mmol DPA to the tube, After vacuuming, add 6.56mg (0.04mmol) AIBN under the protection of argon, then continue to vacuumize and fill with argon, after three cycles, put it in an oil bath at 70°C for 24h. After the reaction is over, add 12.0mmolTMA·I and 5ml dry DMF to each tube, add 6.56mg (0.04mmol) AIBN under the protection of argon after vacuuming, continue to vacuumize and fill with argon, after three cycles, place at 70°C The reaction was continued in the oil bath for 24h. After the reaction, dialyze with distilled water to remove DMF, and freeze-dry to obtain A-C-T type block copolymer TDDE-2. The NMR characterization is shown in Table 1.

Embodiment 3-15

[0039] Press the synthetic method of embodiment 2, change the molecular weight of PEG or use RGD-PEG-CTAm, change the charging capacity of DPA, DMA, TMA I, prepare the series pH sensitive three-block quaternary ammonium salt cationic copolymers of different compositions, as Table 1 and figure 1 .

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Abstract

The invention relates to a pH-sensitive quaternary ammonium salt amphiphilic block copolymer and application thereof. The macromolecular chain at least contains a polymer of a C block and a T block, the C block is a copolymer of methacrylic-N,N-diisopropylaminoethyl ester and methacrylic-N,N-dimethylaminoethyl ester or methacrylic acid aminoethyl ester, and the T block is a quaternary ammonium salt cationic polymer. The invention also discloses an A-C-T or A-T-C block copolymer, which is formed by bonding a water-soluble polymer A with a polymer containing C and T blocks, and the A segment isselected from betaine polycarboxylate, betaine polyphosphate, polyethylene glycol, or target molecule or cell-penetrating peptide modified betaine polycarboxylate, betaine polyphosphate and polyethylene glycol. The copolymer self-assembles or participates in assembly in an aqueous solution with a pH greater than 7 to form nanoparticles with a particle size of 40-300 nm, which can be used for DNA,siRNA delivery and transfection reagents, or detection or immune preparations, or as an antibacterial agent.

Description

technical field [0001] The invention relates to a pH-sensitive quaternary ammonium salt amphiphilic block copolymer and its application, in particular to an amphiphilic pH-sensitive tri-block quaternary ammonium salt cationic copolymer, which belongs to functional polymers and nano-gene delivery technology . Background technique [0002] Cationic polymers are an important class of functional polymers. Because of its special structure, it has important application value in petrochemical industry, water treatment agent, antibacterial agent, gene delivery and other fields, and has attracted people's attention. At present, the cationic polymers that have been studied more include primary amine polycations, tertiary amine polycations, quaternary ammonium salt polymers, quaternary phosphorus salt polymers and quaternary sulfur salt polymers. Among them, quaternary ammonium salt polymers are the most widely used products. In order to adapt to new requirements and improve the per...

Claims

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Application Information

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IPC IPC(8): C08F293/00C08F220/34C12N15/87A01P1/00A61P31/00
CPCA61P31/00C08F220/34C08F293/005C12N15/87
Inventor 董岸杰周俊辉邓联东张建华
Owner TIANJIN UNIV
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