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Controllable modified amphipathic block copolymerization peptide, preparation method and application thereof

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

Active Publication Date: 2015-09-23
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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  • Controllable modified amphipathic block copolymerization peptide, preparation method and application thereof
  • Controllable modified amphipathic block copolymerization peptide, preparation method and application thereof
  • Controllable modified amphipathic block copolymerization peptide, preparation method and application thereof

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) show that the block copolymers can form aggregates with a certain particle size in aqueous solution and THF, and have a narrow distribution range. This is t...

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Abstract

The invention discloses controllable modified amphipathic block copolymerization peptide and a preparation method thereof. The polyethylene glycol-b-poly(gamma-propargyl-L-glutamic acid) two-block copolymer (PEG-b-PPLG) containing alkynyl on the side chain is synthesized by taking monomethoxypolyethylene glycol primary amine as a macroinitiator and by a method for initiating gamma-propargyl-L-glutamic acid-N-carboxy-anhydride (NCA) for ring opening polymerization; polyamino acid PPLG blocks in the two-block copolymer are respectively modified with saturated alkane with common hydrophobicity and full hydrofluoroalkane with super-hydrophobicity by further adopting a click chemical method for sulfydryl-alkynyl addition, so that the amphipathic block copolymerization peptide in water or an organic solvent can be conveniently and efficiently obtained. The controllable modified amphipathic block copolymerization peptide is high in yield, high in purity, easy to operate and universal, and the preparation method is suitable for conveniently and quickly preparing the amphipathic block copolymerization peptide by 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 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 diverse sid...

Claims

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Application Information

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