Branched antibacterial polyamino acid, and preparation method and application thereof

A polyamino acid and polylysine technology, applied in the field of medicine, can solve the problems of increasing charge density, hindering the development and limitation of antimicrobial peptides or polymers, etc.

Active Publication Date: 2020-10-23
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, traditional linear antimicrobial peptides are limited by their structure, and their charge density is difficult to increase significant

Method used

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  • Branched antibacterial polyamino acid, and preparation method and application thereof
  • Branched antibacterial polyamino acid, and preparation method and application thereof
  • Branched antibacterial polyamino acid, and preparation method and application thereof

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preparation example Construction

[0037] The invention also provides a preparation method of the branched antibacterial polyamino acid, including a liquid phase synthesis method (amino acid N-carboxy-anhydride (NCA) ring-opening polymerization method) and a solid phase synthesis method. The branched antibacterial polyamino acid synthesized by the liquid phase synthesis method (amino acid N-carboxyl-anhydride ring-opening polymerization method) has the advantages of simple operation, high yield, low production cost, no racemization, and easy access to high molecular polyamino acid And many other advantages, but the molecular weight distribution of the synthesized polymer is relatively wide. The sequence and molecular weight of the polypeptide can be precisely controlled by solid-phase synthesis, but the synthesis time is long, the cost is high, and the sequence directly synthesized is relatively short. Therefore, although the antibacterial polyamino acids synthesized by the two methods have the characteristics ...

Embodiment 1

[0057] The liquid phase synthesis method of embodiment 1 star-shaped PLL antibacterial polyamino acid (PEI-g-PLL) (amino acid N-carboxyl-ring-opening polymerization method of acid anhydride in the ring)

[0058] 1. Synthesis of star-shaped poly-L-lysine (PLL)

[0059] (1) Synthesis of amino acid N-carboxy-anhydride (NCA)

[0060] Weigh an appropriate amount of ε-benzyloxycarbonyl-L-lysine, activated carbon and triphosgene (BTC) into anhydrous ethyl acetate (EA) and heat to reflux, and filter with suction to obtain the filtrate containing the crude NCA product. The reaction scheme is as follows:

[0061]

[0062] Freeze the filtrate to below -18°C, wash with 4°C saturated sodium bicarbonate solution and saturated sodium chloride solution respectively to remove residual hydrochloric acid and triphosgene in the system. Finally, the product passes through the process of crystallization and recrystallization in ethyl acetate-petroleum ether mixed solvent to obtain high-purity N...

Embodiment 2

[0072] The solid-phase synthesis method of embodiment 2 star-shaped PLL antibacterial polyamino acids

[0073] 1. Synthesis of star PLL

[0074] (1) Synthesis of dendritic PLL core

[0075]Remove the Fmoc protecting group of Rink Amide-MBHA Resin resin with 20% piperidine in DMF solution, and add N,N'-bisfluorenylmethoxycarbonyl-L-lysine (Fmoc-Lys(Fmoc)-OH) , using DMF as a solvent, 1-hydroxybenzotriazole (HOBt) and N, N'-diisopropylcarbodiimide (DIC) as a condensing agent for coupling reaction, and then using DMF containing 20% ​​piperidine The solution removes the Fmoc protecting group to obtain a generation of dendritic poly-L-lysine. Then, through repeated coupling and deprotection processes, the second-generation dendritic PLL with 4 amino groups and the third-generation dendritic poly-PLL with 8 amino groups are obtained as the core of the star-shaped PLL. The synthetic route is as follows:

[0076]

[0077] (2) Synthesis and characterization of star PLL

[0078] ...

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Abstract

The invention provides branched antibacterial polyamino acid. The branched antibacterial polyamino acid is a star-shaped branched polymer or a brush-shaped branched polymer, and consists of an inner core and a branched chain, wherein the inner core is a branched polymer containing 4-15 amino groups, and the branched chain is coupled with the inner core through a peptide bond; the branched chain isa hydrophilic polymer block with a polymerization degree of 5-20; and monomers of the pure hydrophilic polymer block do not comprise hydrophobic monomers. The branched antibacterial polyamino acid has good antibacterial activity, is not prone to hemolysis and shows good biological safety.

Description

technical field [0001] The invention belongs to the field of medicine, in particular to a branched antibacterial polyamino acid and its preparation method and application. Background technique [0002] The emergence of antibiotics can be regarded as one of the greatest discoveries in the history of human medicine. Since its discovery, countless lives have been saved. However, the abuse of antibiotics in recent years has led to the emergence of a large number of drug-resistant and even fatal pathogens, such as methicillin-resistant Staphylococcus aureus and antibiotic-resistant Pseudomonas aeruginosa. These antibiotic-resistant "super bacteria" have spread widely around the world. In the face of this huge health crisis, antimicrobial peptides (such as: defensin, human antimicrobial peptide LL-37 and bombesin, etc.) have brought hope for killing these drug-resistant pathogens. Antimicrobial peptides, also known as antimicrobial peptides or host defense peptides, are a class...

Claims

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Application Information

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IPC IPC(8): C08G69/10C09D177/04C09D187/00C09D5/14A61K31/785A61P31/04
CPCC08G69/10C09D177/04C09D187/005C09D5/14A61K31/785A61P31/04
Inventor 陆超吴传斌
Owner SUN YAT SEN UNIV
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