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Preparation method of L-cation chiral amino acid methylacrylate copolymer

An amino acid methacrylate and cation technology, which is applied in the preparation of cationic chiral amino acid methacrylate polymer and its antibacterial application field, can solve the problems of poor biocompatibility, weak antibacterial activity and the like

Inactive Publication Date: 2019-05-10
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to prepare a cationic polymethacrylate polymer based on chiral amino acids, and to study its application in antibacterial aspects, so as to overcome the weak antibacterial activity and poor biocompatibility of existing antibacterial polymers Shortcomings

Method used

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  • Preparation method of L-cation chiral amino acid methylacrylate copolymer
  • Preparation method of L-cation chiral amino acid methylacrylate copolymer
  • Preparation method of L-cation chiral amino acid methylacrylate copolymer

Examples

Experimental program
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Effect test

Embodiment 1

[0088] Example 1—Preparation of monomers D-leucine hydroxyethyl methacrylate, L-leucine hydroxyethyl methacrylate, D-lysine hydroxyethyl methacrylate and L-lysine methyl Hydroxyethyl Acrylate

[0089] First, add 5 g of chiral amino acid monomers (D-leucine, L-leucine, D-lysine, and L-lysine) dissolved in 22 mL of dry dichloromethane into a dry double-neck round bottom flask. acid, in order to ensure the activity of the functional group in the reaction, select the above four amino acids protected by tert-butoxycarbonyl Boc, and use trifluoroacetic acid to remove the Boc protecting group after the reaction), purify with nitrogen gas under magnetic stirring, and then add soluble in 1.5 0.24g of catalyst DMAP in mL of dry dichloromethane, put the reaction flask in an ice-water bath, slowly add 4.53g of dehydration condensation agent DCC dissolved in 20mL of dry dichloromethane dropwise, and add 2.86g of it within 20min under the protection of nitrogen HEMA. The reaction was carr...

Embodiment 2

[0091] Example 2—Using the four monomers prepared in Example 1 as raw materials, four homopolymers were prepared using reversible addition-fragmentation chain transfer polymerization

[0092] Cationic chiral amino acid hydroxyethyl methacrylate homopolymer was prepared by RAFT polymerization method: In a 25mL Schlenk bottle with a magnetic stirrer, add 1.5g of the monomer prepared in Example 1, CPADB 24.4mg, AIBN2.86mg and 1.5 g of anhydrous DMF solvent, after three freeze-pump-thaw cycles to remove impurity gases in the reaction system, placed in an oil bath at 70° C., and reacted for 10 hours under nitrogen protection. After the reaction was completed, it was exposed to the air and placed in an ice-water bath for rapid cooling to terminate the reaction, and then the acetone / n-hexane precipitation was repeated 5 times. The obtained product was dried in a vacuum oven at 30° C. for 8 hours to obtain a sample of each homopolymer. Under the condition of ice-water bath, according...

Embodiment 3

[0094] Example 3—Preparation of D-cationic chiral amino acid hydroxyethyl methacrylate copolymer

[0095] (1) Adopt the method of embodiment 2 to prepare the homopolymer of D-leucine at first: in the 25mLSchlenk bottle with magnetic stirrer, add the monomer D-leucine methacrylic acid prepared by 1.5g embodiment 1 Hydroxyethyl ester, CPADB24.4mg, AIBN 2.86mg and 1.5g of anhydrous DMF solvent, after three freeze-pump-thaw cycles to remove impurity gases in the reaction system, placed in an oil bath at 70°C under nitrogen protection React for 10 hours, after the reaction is basically finished, do not carry out the termination reaction of exposing the air, but keep the active group (CPADB) at the end of the D-leucine homopolymer as a macromolecular chain transfer for adding the second monomer to react agent;

[0096] (2) In the reaction vessel, add 3g of the same configuration of lysine methacrylate monomer (i.e. D-lysine hydroxyethyl methacrylate), AIBN 2.15mg and 3g of anhydrou...

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Abstract

The invention discloses a preparation method of an L-cation chiral amino acid methylacrylate copolymer. Preparing is performed by subjecting monomers, L-lysine methylacrylate and L-leucine methylacrylate to blocking copolymerization. First, a first L-type amino acid monomer is subjected to homopolymerization; RAFT (reversible addition-fragmentation chain transfer) polymerization is performed by using 4-cyanopentanoic acid dithiobenzoate as a chain transfer agent and azodiisobutyronitrile as an initiator; with an L-configuration amino acid monomer polymer as a macromolecular chain transfer agent and azodiisobutyronitrile as an initiator, a second L-type amino acid monomer is added to perform RAFT polymerization to obtain an L-lysine methylacrylate and L-leucine methylacrylate block copolymer. The copolymer herein has excellent antibacterial property, and can evidently destroy bacterial membrane structure to cause death of bacteria; hemolytic test and in-vitro test of smooth muscle cellcompatibility show that the copolymer retains evident biocompatibility.

Description

[0001] The present invention is a divisional application of the parent application "L-cationic chiral amino acid methacrylate copolymer and its preparation and antibacterial application". The application number of the parent application is 2016110295713, and the filing date is November 14, 2016. technical field [0002] The invention belongs to the field of biomedical polymer materials, and relates to a method for designing and synthesizing a novel imitation antimicrobial peptide polymer, in particular to the preparation of a cationic chiral amino acid methacrylate polymer and its antibacterial application. Background technique [0003] At present, the emergence of antibiotic-resistant bacteria has posed a great threat to public health. Bacterial adhesion, proliferation, and biofilm formation can lead to infection in patients and lead to a series of complications and even endanger the lives of patients. Although some progress has been made in the research of alternative new a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00C08F2/38A01N37/44A01P1/00A61K31/785A61P31/04
CPCA01N37/44A61K31/785C08F2/38C08F8/44C08F293/005C08F2438/03C08F2800/20C08F122/1006Y02A50/30
Inventor 赵蕴慧胡素利胡文虹李珍光袁晓燕
Owner TIANJIN UNIV
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