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Antimicrobial polymers and antimicrobial hydrogels

A hydrogel, polymer technology, used in antibacterial drugs, topical antibacterial agents, botanical devices and methods, etc.

Active Publication Date: 2019-12-13
NANYANG TECH UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are no reports on hydrogels using PEI as an antimicrobial coating

Method used

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  • Antimicrobial polymers and antimicrobial hydrogels
  • Antimicrobial polymers and antimicrobial hydrogels
  • Antimicrobial polymers and antimicrobial hydrogels

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0151] In this example, a method with Durable antimicrobial hydrogel coatings for contact lenses. The thus developed PEI-decane-PEGMA hydrogel coating exhibited excellent broad-spectrum antibacterial activity against both Gram-negative and Gram-positive bacteria and fungi. The % kill and log reduction of the coating were above 99.99% and 4.0, respectively.

[0152] Materials and methods

[0153] Material

[0154] Branched polyethyleneimine (PEI, Sigma-Aldrich, M n=10 4 , M w / M n =2.5) freeze-dried to dryness. Chlorine-functionalized polyethylene glycol methacrylate (Cl-PEGMA) was synthesized as briefly described below. First, 11.8 mL (35.3 mmol) of PEGMA was dissolved in 100 mL of toluene, 11.25 mL (141.2 mmol) of chloroacetyl chloride was added to the solution, and then stirred and refluxed at 120° C. for 24 hours. After the reaction, the solution was subjected to solvent evaporation, followed by adding dichloromethane (100 mL) to the concentrate for dissolution. P...

Embodiment 2

[0210] In this example, polyethyleneimine-grafted-polyethylene glycol methacrylate (PEI-PEGMA) and its alkylated form with the addition of decane groups (PEI-decane- PEGMA) in combination with UV photopolymerization to develop a durable antimicrobial hydrogel coating for biomedical devices. These PEI-PEGMA and PEI-decane-PEGMA coatings showed excellent broad-spectrum antibacterial activity against both Gram-negative and Gram-positive bacteria and fungi. The % kill and log reduction of the hydrogel were higher than 99.99% and 7.0, respectively. The hydrogel is biocompatible with human cells as it was shown to have over 95% cell viability when tested in vitro against human dermal fibroblast (HDF) cells.

[0211] Materials and methods

[0212] Material

[0213] Branched polyethyleneimine (PEI, Sigma-Aldrich, M n =10 4 , M w / M n =2.5) freeze-dried to dryness. 1-bromodecane, sodium hydroxide, potassium carbonate, isopropanol, polyethylene glycol methacrylate (PEGMA, M n =...

Embodiment 3

[0323] In this example, a polymer was developed by UV photopolymerization of polyethyleneimine-graft-polyethylene glycol methacrylate (PEI-PEGMA) followed by sonication in ethanol and water for 2 h to remove residual monomers. Non-leachable cationic polymer-based hydrogels for wound infection control. The UV-visible absorbance test supported the conclusion of non-leaching, as no signal was detected in the solution (100 mg of hydrogel in 5 mL of water) where the hydrogel was soaked for 24 h, while even at a low concentration of 1 μg / mL of hydrogel polymer A peak can also be observed at 200 nm in .

[0324] In a biofilm infection model comparing the efficacy of hydrogels with commercially available antimicrobial wound dressings (Allevyn Ag and AlgisiteAg, Smith & Nephew), PEI hydrogels performed better, killing 4 logs (over 99.99%) of resistant Staphylococcus aureus (MRSA USA300), while commercial antimicrobial dressings only reduced bacterial counts by one log (over 90%). Fur...

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Abstract

An antimicrobial polymer or hydrogel and a method of forming thereof comprising a branched polyethylenimine (PEI) grafted with poly(ethylene glycol) methacrylate (PEGMA) of formula (I); a branched polyethylenimine (PEI) grafted with poly(ethylene glycol) methacrylate (PEGMA) and decane of formula (II), or a branched polyethylenimine (PEI) grafted with polyethylene glycol) methacrylate (PEGMA) andalkyl (R) of formula (III), wherein: m is an integer ranging from 1 to 20; n is an integer ranging from 1 to 20; in formula (I), the grafting ratio of PEI-PEGMA ranges from 1 :1 to 1 :20; in formula (II), the grafting ratio of PEI-decane-PEGMA ranges from 1 :1 :1 to 1 :20:20; in formula (I II), R is a linear or branched, substituted or unsubstituted C5-C15 alkyl; and the grafting ratio of PEI-alkyl-PEGMA ranges from 1 :1 :1 to 1 :20:20. Provided is also a device having a surface coated with said antimicrobial hydrogel of formulae (I), (II) or (III).

Description

[0001] Cross References to Related Applications [0002] This application claims priority to Singapore Patent Application No. 10201702149V filed on 16 March 2017, the contents of which are hereby incorporated by reference in their entirety for all purposes. technical field [0003] The various embodiments relate generally to antimicrobial polymers and antimicrobial hydrogels, and in particular to polymers and hydrogels composed of branched polyethyleneimine, and more specifically, to polymers and hydrogels composed of polyethyleneimine-graft-polymer Polymers composed of ethylene glycol methacrylate (PEI-PEGMA) or polyethyleneimine-graft-decane-graft-polyethylene glycol methacrylate (PEI-decane-PEGMA) and hydraulic glue. Background technique [0004] Hydrogels may be suitable materials for generating antimicrobial coatings, as their properties can be tuned to suit the intended application. Antibacterial hydrogels that kill bacteria on contact can be synthesized from cationi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00A61K31/785A61P31/04A61P31/02A61P17/02A61Q17/00
CPCA61Q17/005A61K8/84A61K8/91A61K8/042A61K31/47A61K31/49C08G81/00A61K2800/81A61P31/04A61P17/02A61P31/02C08G81/025C08G73/0213C08L87/005C08J3/075C08J3/24C08J3/28C09D187/005A01N37/44C08F283/04C09D5/14C09D151/08
Inventor 陈美英杨俊杰陈源顺李鹏郭赞如米娅·米娅·钦
Owner NANYANG TECH UNIV