Oxazoline-Based Antimicrobial Oligomers: Synthesis by CROP Using Supercritical CO2

A method using supercritical CO2 to obtain biocompatible 2‐oxazoline‐based oligomers quaternized with different amines is described. The synthesized oligo(2‐oxazoline)s display partial carbamic‐acid insertion at one end. The syntheses of quaternary oligo(2‐bisoxazoline)s and linear oligoethylenimine...

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Veröffentlicht in:Macromolecular bioscience 2011-08, Vol.11 (8), p.1128-1137
Hauptverfasser: Correia, Vanessa G., Bonifácio, Vasco D.B., Raje, Vivek P., Casimiro, Teresa, Moutinho, Guilhermina, da Silva, Cláudia Lobato, Pinho, Mariana G., Aguiar-Ricardo, Ana
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container_end_page 1137
container_issue 8
container_start_page 1128
container_title Macromolecular bioscience
container_volume 11
creator Correia, Vanessa G.
Bonifácio, Vasco D.B.
Raje, Vivek P.
Casimiro, Teresa
Moutinho, Guilhermina
da Silva, Cláudia Lobato
Pinho, Mariana G.
Aguiar-Ricardo, Ana
description A method using supercritical CO2 to obtain biocompatible 2‐oxazoline‐based oligomers quaternized with different amines is described. The synthesized oligo(2‐oxazoline)s display partial carbamic‐acid insertion at one end. The syntheses of quaternary oligo(2‐bisoxazoline)s and linear oligoethylenimine hydrochlorides are reported. Oligo(2‐methyl‐2‐oxazoline) and oligo(2‐bisoxazoline) quaternized with N,N‐dimethyldodecylamine are the most efficient biocidal agents showing fast killing rates against Staphylococcus aureus and Escherichia coli. Linear oligoethylenimine hydrochloride shows the lowest MIC values but higher killing times against both bacteria. Based on the antimicrobial activity studies, a cooperative action of carbamic acid with the ammonium end group is proposed. Biocompatible and antimicrobial quaternary‐ammonium oligo(2‐oxazoline)s, oligo(2‐bisoxazoline) and linear oligo(ethylenimine) hydrochloride are synthesized using a supercritical‐fluid‐assisted strategy. Detailed descriptions and evaluations of their antimicrobial properties, comprising MIC and killing time determination, and cytotoxic behavior against pathogenic bacteria and a fungus strains are reported.
doi_str_mv 10.1002/mabi.201100126
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Biosci</addtitle><description>A method using supercritical CO2 to obtain biocompatible 2‐oxazoline‐based oligomers quaternized with different amines is described. The synthesized oligo(2‐oxazoline)s display partial carbamic‐acid insertion at one end. The syntheses of quaternary oligo(2‐bisoxazoline)s and linear oligoethylenimine hydrochlorides are reported. Oligo(2‐methyl‐2‐oxazoline) and oligo(2‐bisoxazoline) quaternized with N,N‐dimethyldodecylamine are the most efficient biocidal agents showing fast killing rates against Staphylococcus aureus and Escherichia coli. Linear oligoethylenimine hydrochloride shows the lowest MIC values but higher killing times against both bacteria. Based on the antimicrobial activity studies, a cooperative action of carbamic acid with the ammonium end group is proposed. Biocompatible and antimicrobial quaternary‐ammonium oligo(2‐oxazoline)s, oligo(2‐bisoxazoline) and linear oligo(ethylenimine) hydrochloride are synthesized using a supercritical‐fluid‐assisted strategy. Detailed descriptions and evaluations of their antimicrobial properties, comprising MIC and killing time determination, and cytotoxic behavior against pathogenic bacteria and a fungus strains are reported.</description><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. 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Biosci</addtitle><date>2011-08-11</date><risdate>2011</risdate><volume>11</volume><issue>8</issue><spage>1128</spage><epage>1137</epage><pages>1128-1137</pages><issn>1616-5187</issn><issn>1616-5195</issn><eissn>1616-5195</eissn><abstract>A method using supercritical CO2 to obtain biocompatible 2‐oxazoline‐based oligomers quaternized with different amines is described. The synthesized oligo(2‐oxazoline)s display partial carbamic‐acid insertion at one end. The syntheses of quaternary oligo(2‐bisoxazoline)s and linear oligoethylenimine hydrochlorides are reported. Oligo(2‐methyl‐2‐oxazoline) and oligo(2‐bisoxazoline) quaternized with N,N‐dimethyldodecylamine are the most efficient biocidal agents showing fast killing rates against Staphylococcus aureus and Escherichia coli. Linear oligoethylenimine hydrochloride shows the lowest MIC values but higher killing times against both bacteria. Based on the antimicrobial activity studies, a cooperative action of carbamic acid with the ammonium end group is proposed. Biocompatible and antimicrobial quaternary‐ammonium oligo(2‐oxazoline)s, oligo(2‐bisoxazoline) and linear oligo(ethylenimine) hydrochloride are synthesized using a supercritical‐fluid‐assisted strategy. Detailed descriptions and evaluations of their antimicrobial properties, comprising MIC and killing time determination, and cytotoxic behavior against pathogenic bacteria and a fungus strains are reported.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>21674806</pmid><doi>10.1002/mabi.201100126</doi><tpages>10</tpages></addata></record>
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ispartof Macromolecular bioscience, 2011-08, Vol.11 (8), p.1128-1137
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source Wiley Online Library - AutoHoldings Journals; MEDLINE
subjects Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - pharmacology
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
antimicrobial activity
Applied sciences
Aziridines - chemistry
Bacteria
biocompatibility
Biological and medical sciences
Carbamates - chemistry
Carbon dioxide
Carbon Dioxide - chemistry
Escherichia coli
Escherichia coli - drug effects
Escherichia coli - growth & development
Escherichia coli Infections - drug therapy
Escherichia coli Infections - microbiology
Exact sciences and technology
Humans
Hydrochlorides
Insertion
Killing
Magnetic Resonance Spectroscopy
Medical sciences
Microbial Sensitivity Tests
oligo(2-oxazoline)s
Oligomers
Organic polymers
Oxazoles - chemical synthesis
Oxazoles - pharmacology
Pharmacology. Drug treatments
Physicochemistry of polymers
Polymers - chemical synthesis
Polymers - pharmacology
Polymers with particular properties
Preparation, kinetics, thermodynamics, mechanism and catalysts
Quaternary Ammonium Compounds - chemistry
Spectroscopy, Fourier Transform Infrared
Staphylococcal Infections - drug therapy
Staphylococcal Infections - microbiology
Staphylococcus aureus
Staphylococcus aureus - drug effects
Staphylococcus aureus - growth & development
supercritical carbon dioxide
water-soluble polymers
title Oxazoline-Based Antimicrobial Oligomers: Synthesis by CROP Using Supercritical CO2
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