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 |
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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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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><identifier>ISSN: 1616-5187</identifier><identifier>ISSN: 1616-5195</identifier><identifier>EISSN: 1616-5195</identifier><identifier>DOI: 10.1002/mabi.201100126</identifier><identifier>PMID: 21674806</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>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</subject><ispartof>Macromolecular bioscience, 2011-08, Vol.11 (8), p.1128-1137</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fmabi.201100126$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fmabi.201100126$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24412318$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/21674806$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Correia, Vanessa G.</creatorcontrib><creatorcontrib>Bonifácio, Vasco D.B.</creatorcontrib><creatorcontrib>Raje, Vivek P.</creatorcontrib><creatorcontrib>Casimiro, Teresa</creatorcontrib><creatorcontrib>Moutinho, Guilhermina</creatorcontrib><creatorcontrib>da Silva, Cláudia Lobato</creatorcontrib><creatorcontrib>Pinho, Mariana G.</creatorcontrib><creatorcontrib>Aguiar-Ricardo, Ana</creatorcontrib><title>Oxazoline-Based Antimicrobial Oligomers: Synthesis by CROP Using Supercritical CO2</title><title>Macromolecular bioscience</title><addtitle>Macromol. 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. Antiparasitic agents</subject><subject>antimicrobial activity</subject><subject>Applied sciences</subject><subject>Aziridines - chemistry</subject><subject>Bacteria</subject><subject>biocompatibility</subject><subject>Biological and medical sciences</subject><subject>Carbamates - chemistry</subject><subject>Carbon dioxide</subject><subject>Carbon Dioxide - chemistry</subject><subject>Escherichia coli</subject><subject>Escherichia coli - drug effects</subject><subject>Escherichia coli - growth & development</subject><subject>Escherichia coli Infections - drug therapy</subject><subject>Escherichia coli Infections - microbiology</subject><subject>Exact sciences and technology</subject><subject>Humans</subject><subject>Hydrochlorides</subject><subject>Insertion</subject><subject>Killing</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>oligo(2-oxazoline)s</subject><subject>Oligomers</subject><subject>Organic polymers</subject><subject>Oxazoles - chemical synthesis</subject><subject>Oxazoles - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Physicochemistry of polymers</subject><subject>Polymers - chemical synthesis</subject><subject>Polymers - pharmacology</subject><subject>Polymers with particular properties</subject><subject>Preparation, kinetics, thermodynamics, mechanism and catalysts</subject><subject>Quaternary Ammonium Compounds - chemistry</subject><subject>Spectroscopy, Fourier Transform Infrared</subject><subject>Staphylococcal Infections - drug therapy</subject><subject>Staphylococcal Infections - microbiology</subject><subject>Staphylococcus aureus</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Staphylococcus aureus - growth & development</subject><subject>supercritical carbon dioxide</subject><subject>water-soluble polymers</subject><issn>1616-5187</issn><issn>1616-5195</issn><issn>1616-5195</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUtvEzEUha0K1PeWZTUbVDZT_H6wSyJaKkIGmlZIbCx74mlN55HaE9H019clYdh1ZV_d7_ie6wPAOwTPEIT4Y2OsP8MQpQJhvgP2EUc8Z0ixN8Ndij1wEOPvhAip8C7Yw4gLKiHfB1fFo3nqat-6fGyiW2SjtveNL0Nnvamzova3XeNC_JTN121_56KPmV1nk6vie3YTfXubzVdLF8rge18mwaTAR-BtZerojrfnIbg5_3w9-ZJPi4vLyWiae6ySL4UEYxBbSsyCVIJXDHOiKqtEyRVxFlvGJUEWCe5gVcmKcpH2oQtRQoYRJofgdPPuMnQPKxd73fhYuro2retWUUuJqMASyUR-eJVEkCCsKKUsoSdbdGUbt9DL4BsT1vrfjyXg_RYwMS1cBdOWPv7nKE3W_s5UG-6Pr9166COoX3LTL7npITf9bTS-HKqkzTdaH3v3OGhNuNdcEMH0z9mF_jH-Nfs6nc31jDwDmLKX8g</recordid><startdate>20110811</startdate><enddate>20110811</enddate><creator>Correia, Vanessa G.</creator><creator>Bonifácio, Vasco D.B.</creator><creator>Raje, Vivek P.</creator><creator>Casimiro, Teresa</creator><creator>Moutinho, Guilhermina</creator><creator>da Silva, Cláudia Lobato</creator><creator>Pinho, Mariana G.</creator><creator>Aguiar-Ricardo, Ana</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7SR</scope><scope>7U5</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>20110811</creationdate><title>Oxazoline-Based Antimicrobial Oligomers: Synthesis by CROP Using Supercritical CO2</title><author>Correia, Vanessa G. ; Bonifácio, Vasco D.B. ; Raje, Vivek P. ; Casimiro, Teresa ; Moutinho, Guilhermina ; da Silva, Cláudia Lobato ; Pinho, Mariana G. ; Aguiar-Ricardo, Ana</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i2916-9175502b43ad3f76f52639fb97c693eb2b56831b176e0ff8f4676164d7c052123</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>antimicrobial activity</topic><topic>Applied sciences</topic><topic>Aziridines - chemistry</topic><topic>Bacteria</topic><topic>biocompatibility</topic><topic>Biological and medical sciences</topic><topic>Carbamates - chemistry</topic><topic>Carbon dioxide</topic><topic>Carbon Dioxide - chemistry</topic><topic>Escherichia coli</topic><topic>Escherichia coli - drug effects</topic><topic>Escherichia coli - growth & development</topic><topic>Escherichia coli Infections - drug therapy</topic><topic>Escherichia coli Infections - microbiology</topic><topic>Exact sciences and technology</topic><topic>Humans</topic><topic>Hydrochlorides</topic><topic>Insertion</topic><topic>Killing</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>oligo(2-oxazoline)s</topic><topic>Oligomers</topic><topic>Organic polymers</topic><topic>Oxazoles - chemical synthesis</topic><topic>Oxazoles - pharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Physicochemistry of polymers</topic><topic>Polymers - chemical synthesis</topic><topic>Polymers - pharmacology</topic><topic>Polymers with particular properties</topic><topic>Preparation, kinetics, thermodynamics, mechanism and catalysts</topic><topic>Quaternary Ammonium Compounds - chemistry</topic><topic>Spectroscopy, Fourier Transform Infrared</topic><topic>Staphylococcal Infections - drug therapy</topic><topic>Staphylococcal Infections - microbiology</topic><topic>Staphylococcus aureus</topic><topic>Staphylococcus aureus - drug effects</topic><topic>Staphylococcus aureus - growth & development</topic><topic>supercritical carbon dioxide</topic><topic>water-soluble polymers</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Correia, Vanessa G.</creatorcontrib><creatorcontrib>Bonifácio, Vasco D.B.</creatorcontrib><creatorcontrib>Raje, Vivek P.</creatorcontrib><creatorcontrib>Casimiro, Teresa</creatorcontrib><creatorcontrib>Moutinho, Guilhermina</creatorcontrib><creatorcontrib>da Silva, Cláudia Lobato</creatorcontrib><creatorcontrib>Pinho, Mariana G.</creatorcontrib><creatorcontrib>Aguiar-Ricardo, Ana</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Macromolecular bioscience</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Correia, Vanessa G.</au><au>Bonifácio, Vasco D.B.</au><au>Raje, Vivek P.</au><au>Casimiro, Teresa</au><au>Moutinho, Guilhermina</au><au>da Silva, Cláudia Lobato</au><au>Pinho, Mariana G.</au><au>Aguiar-Ricardo, Ana</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxazoline-Based Antimicrobial Oligomers: Synthesis by CROP Using Supercritical CO2</atitle><jtitle>Macromolecular bioscience</jtitle><addtitle>Macromol. 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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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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