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A controllable modified amphiphilic block copolypeptide, its preparation method and its application

An amphiphilic block and copolymerization technology, applied in the field of polymer materials

Active Publication Date: 2017-10-27
HUAIYIN TEACHERS COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the smooth progress of the azide-alkynyl cycloaddition reaction requires a valent copper ion as a catalyst, which also limits the application of this type of reaction.

Method used

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  • A controllable modified amphiphilic block copolypeptide, its preparation method and its application
  • A controllable modified amphiphilic block copolypeptide, its preparation method and its application
  • A controllable modified amphiphilic block copolypeptide, its preparation method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The synthesis of polyethylene glycol-b-poly(γ-propargyl-L-glutamic acid) (PEG-b-PPLG) comprises the following steps:

[0048] Monomethoxypolyethylene glycol primary amine (mPEG-NH 2 , 0.50g, 0.139mmol) dried in vacuum at 50°C for about six hours, and then cooled to room temperature. γ-propargyl-L-glutamic acid-N-carboxy-cyclic anhydride (PLG-NCA) (0.634 g, 3.00 mmol) was dissolved in 12.7 mL of dry DMF in the glove box, and then transferred with a syringe into the reaction system (monomer / initiator=22:1). After four days of reaction at room temperature under the protection of nitrogen, it was precipitated with ether and dried in vacuo overnight to obtain the product polyethylene glycol-b-poly(γ-propargyl-L-glutamic acid) (PEG-b-PPLG) (0.70 g, harvested rate: 85%).

[0049] attached figure 1 The copolypeptide synthesized in Example 1 was characterized by SEC / LLS using 0.02M LiBr DMF solution as the mobile phase, and its molecular weight was about 6500g / mol, and its m...

Embodiment 2

[0051] PEG-b-PPLG is modified by mercapto-alkyne photochemical reaction, which includes the following steps:

[0052] A typical mercapto-yne chemical modification process is described as follows: Diblock copolymer PEG-b-PPLG, excess mercapto compound 1-mercaptooctane or 1-mercapto-1H, 1H, 2H, 2H-perfluorooctane, After dissolving in an appropriate amount of THF, the photoinitiator 2,2-dimethoxy-2-phenylacetophenone (DMPA) was added and reacted at room temperature for about four hours under 365 nm ultraviolet light. After the reaction, the reaction solution was precipitated in excess n-hexane, and the precipitate was further washed with n-hexane several times to remove excess unreacted raw mercapto compounds. Finally, after drying the solid product in vacuum, the two-block copolymer PEG-b-(PPLG-g-R) modified by octyl group and the two-block copolymer PEG-b-(PPLG-g-R modified by perfluorooctane) were respectively obtained. f ).

[0053] by attaching figure 2 b. figure 2 c's...

Embodiment 3

[0057] The solution self-assembly of diblock copolymer, it comprises the following steps:

[0058] The self-assembled structure of the synthesized diblock copolymer in the organic solvent THF was obtained by directly dissolving it in THF (the concentration of the polymer was 1 mg / mL) and stirring overnight at room temperature. The nano-aggregated structure of the copolymer in aqueous solution is obtained by dialysis. Specifically, 5 mg of the copolymer PEG-b-PPLG or PEG-b-(PPLG-g-R) were respectively dissolved in 1 mL of THF, and then 4 mL of deionized water was slowly added dropwise under stirring. After stirring overnight, THF was completely removed by dialysis in deionized water to obtain their self-assembled structures in aqueous solution.

[0059] by attaching Figure 4 The results of dynamic light dispersion (DLS) showed that block copolymers could form aggregates with a certain particle size in aqueous solution and THF, and had a narrow distribution range. This is th...

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Abstract

The invention discloses a controllable synthesis of amphiphilic block copolypeptide and its preparation method. Monomethoxypolyethylene glycol primary amine is used as a macromolecular initiator to trigger γ-propargyl-L-glutamic acid ‑N‑carboxyl‑in-ring acid anhydride (NCA) ring-opening polymerization method, synthetic polyethylene glycol‑b‑poly(γ‑propargyl‑L‑glutamic acid) two-block copolymerization containing alkyne groups on the side chain (PEG-b-PPLG); further through the "click" chemical method of mercapto-alkynyl addition, the polyamino acid PPLG blocks in the two-block copolymer were modified with ordinary hydrophobic saturated alkanes and superhydrophobic properties. perfluoroalkanes, can conveniently and efficiently obtain amphiphilic block copolymerized polypeptides in water or organic solvents. The invention has high yield, good purity, simple and universal operation, and is suitable for the convenient and rapid preparation of amphiphilic block copolymerized peptides by using a controllable modification method.

Description

technical field [0001] The invention relates to the field of polymer materials, in particular to a controllably modified amphiphilic block copolypeptide prepared by a mercapto-alkyne addition reaction. Background technique [0002] The amphiphilic block copolypeptide based on polyamino acid has good biocompatibility and biodegradability, and has always been a research hotspot in the field of polymer materials. Its assembly in solution has special functions and structural characteristics, and has also attracted extensive attention in drug storage and transportation, controlled release, and carrier catalysis. Among them, the two-block hybrid copolymer containing polyamino acid can use the macromolecule functionalized with terminal primary amine as a macroinitiator to initiate the ring-opening polymerization method of α-amino acid-N-carboxy-anhydride (NCA) Easily synthesized. At the same time, polyamino acids are conducive to various functional modifications due to their dive...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G69/48C08G69/40C08G65/337C08G65/334C08G65/333
Inventor 陈平
Owner HUAIYIN TEACHERS COLLEGE
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