Lipid‐Based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities
Twelve new quaternary ammonium sophorolipids with long alkyl chains on the nitrogen atom were synthesized starting from oleic and petroselinic acid‐based sophorolipids. These novel derivatives were evaluated for their antimicrobial activity against selected Gram‐negative and Gram‐positive bacteria a...
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| Veröffentlicht in: | ChemSusChem 2019-08, Vol.12 (15), p.3642-3653 |
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| creator | Delbeke, Elisabeth I. P. Everaert, Jonas Lozach, Olivier Le Gall, Tony Berchel, Mathieu Montier, Tristan Jaffrès, Paul‐Alain Rigole, Petra Coenye, Tom Brennich, Martha Baccile, Niki Roelants, Sophie L. K. W. Soetaert, Wim Van Bogaert, Inge N. A. Van Geem, Kevin M. Stevens, Christian V. |
| description | Twelve new quaternary ammonium sophorolipids with long alkyl chains on the nitrogen atom were synthesized starting from oleic and petroselinic acid‐based sophorolipids. These novel derivatives were evaluated for their antimicrobial activity against selected Gram‐negative and Gram‐positive bacteria and their transfection efficacies on three different eukaryotic cell lines in vitro as good activities were demonstrated for previously synthesized derivatives. Self‐assembly properties were also evaluated. All compounds proved to possess antimicrobial and transfection properties, and trends could be observed based on the length of the nitrogen substituent and the total length of the sophorolipid tail. Moreover, all long‐chain quaternary ammonium sophorolipids form micelles, which proved to be a prerequisite to induce antimicrobial activity and transfection capacity. These results are promising for future healthcare applications of long‐chained quaternary ammonium sophorolipids.
A short tale about long tails: Twelve new quaternary ammonium sophorolipids were synthesized and evaluated on their antimicrobial, transfection, and self‐assembly properties. Trends could be observed for these properties based on the length of the nitrogen substituent and the total length of the lipid tail. |
| doi_str_mv | 10.1002/cssc.201900721 |
| format | Article |
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A short tale about long tails: Twelve new quaternary ammonium sophorolipids were synthesized and evaluated on their antimicrobial, transfection, and self‐assembly properties. Trends could be observed for these properties based on the length of the nitrogen substituent and the total length of the lipid tail.</description><identifier>ISSN: 1864-5631</identifier><identifier>EISSN: 1864-564X</identifier><identifier>DOI: 10.1002/cssc.201900721</identifier><identifier>PMID: 31081279</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>amphiphiles ; Antiinfectives and antibacterials ; Antimicrobial agents ; biological activity ; Chains ; Derivatives ; drug delivery ; Lipids ; Micelles ; renewable resources ; self-assembly ; Synthesis</subject><ispartof>ChemSusChem, 2019-08, Vol.12 (15), p.3642-3653</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4501-81e6d79ce437ed59b43021f9c48ca4d4f7cb371682f440ca1b9263e0f8392e853</citedby><cites>FETCH-LOGICAL-c4501-81e6d79ce437ed59b43021f9c48ca4d4f7cb371682f440ca1b9263e0f8392e853</cites><orcidid>0000-0003-4393-5327</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcssc.201900721$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcssc.201900721$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31081279$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Delbeke, Elisabeth I. P.</creatorcontrib><creatorcontrib>Everaert, Jonas</creatorcontrib><creatorcontrib>Lozach, Olivier</creatorcontrib><creatorcontrib>Le Gall, Tony</creatorcontrib><creatorcontrib>Berchel, Mathieu</creatorcontrib><creatorcontrib>Montier, Tristan</creatorcontrib><creatorcontrib>Jaffrès, Paul‐Alain</creatorcontrib><creatorcontrib>Rigole, Petra</creatorcontrib><creatorcontrib>Coenye, Tom</creatorcontrib><creatorcontrib>Brennich, Martha</creatorcontrib><creatorcontrib>Baccile, Niki</creatorcontrib><creatorcontrib>Roelants, Sophie L. K. W.</creatorcontrib><creatorcontrib>Soetaert, Wim</creatorcontrib><creatorcontrib>Van Bogaert, Inge N. A.</creatorcontrib><creatorcontrib>Van Geem, Kevin M.</creatorcontrib><creatorcontrib>Stevens, Christian V.</creatorcontrib><title>Lipid‐Based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities</title><title>ChemSusChem</title><addtitle>ChemSusChem</addtitle><description>Twelve new quaternary ammonium sophorolipids with long alkyl chains on the nitrogen atom were synthesized starting from oleic and petroselinic acid‐based sophorolipids. These novel derivatives were evaluated for their antimicrobial activity against selected Gram‐negative and Gram‐positive bacteria and their transfection efficacies on three different eukaryotic cell lines in vitro as good activities were demonstrated for previously synthesized derivatives. Self‐assembly properties were also evaluated. All compounds proved to possess antimicrobial and transfection properties, and trends could be observed based on the length of the nitrogen substituent and the total length of the sophorolipid tail. Moreover, all long‐chain quaternary ammonium sophorolipids form micelles, which proved to be a prerequisite to induce antimicrobial activity and transfection capacity. These results are promising for future healthcare applications of long‐chained quaternary ammonium sophorolipids.
A short tale about long tails: Twelve new quaternary ammonium sophorolipids were synthesized and evaluated on their antimicrobial, transfection, and self‐assembly properties. Trends could be observed for these properties based on the length of the nitrogen substituent and the total length of the lipid tail.</description><subject>amphiphiles</subject><subject>Antiinfectives and antibacterials</subject><subject>Antimicrobial agents</subject><subject>biological activity</subject><subject>Chains</subject><subject>Derivatives</subject><subject>drug delivery</subject><subject>Lipids</subject><subject>Micelles</subject><subject>renewable resources</subject><subject>self-assembly</subject><subject>Synthesis</subject><issn>1864-5631</issn><issn>1864-564X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkc1Kw0AUhQdRbK1uXUrAjZvW-ctkZhmLf1AQaQV3YTKZ0ClJJmYSS3c-gs_okzihtYIb4cK9XL574J4DwDmCEwQhvlbOqQmGSEAYYXQAhogzOg4ZfT3czwQNwIlzKwgZFIwdgwFBkCMciSEwM1Ob7Ovj80Y6nQXPnWx1U8lmE8RlaSvTlcHc1kvb2KIH_bZeGl-FdsHatMsgrlpTGtXY1MgikFUWLBpZuVyr1tgqiH17N63R7hQc5bJw-mzXR-Dl7nYxfRjPnu4fp_FsrGgI0ZgjzbJIKE1JpLNQpJRAjHKhKFeSZjSPVEoixDjOKYVKolRgRjTMORFY85CMwNVWt27sW6ddm5TGKV0UstK2cwnGBImIUcY9evkHXdnOf1_0FBOEUMh7arKl_JPONTpP6saU3qIEwaQPIelDSPYh-IOLnWyXljrb4z-ue0BsgbX3cfOPXDKdz6e_4t8S7JU4</recordid><startdate>20190808</startdate><enddate>20190808</enddate><creator>Delbeke, Elisabeth I. P.</creator><creator>Everaert, Jonas</creator><creator>Lozach, Olivier</creator><creator>Le Gall, Tony</creator><creator>Berchel, Mathieu</creator><creator>Montier, Tristan</creator><creator>Jaffrès, Paul‐Alain</creator><creator>Rigole, Petra</creator><creator>Coenye, Tom</creator><creator>Brennich, Martha</creator><creator>Baccile, Niki</creator><creator>Roelants, Sophie L. K. W.</creator><creator>Soetaert, Wim</creator><creator>Van Bogaert, Inge N. A.</creator><creator>Van Geem, Kevin M.</creator><creator>Stevens, Christian V.</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-4393-5327</orcidid></search><sort><creationdate>20190808</creationdate><title>Lipid‐Based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities</title><author>Delbeke, Elisabeth I. P. ; Everaert, Jonas ; Lozach, Olivier ; Le Gall, Tony ; Berchel, Mathieu ; Montier, Tristan ; Jaffrès, Paul‐Alain ; Rigole, Petra ; Coenye, Tom ; Brennich, Martha ; Baccile, Niki ; Roelants, Sophie L. K. W. ; Soetaert, Wim ; Van Bogaert, Inge N. 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P.</creatorcontrib><creatorcontrib>Everaert, Jonas</creatorcontrib><creatorcontrib>Lozach, Olivier</creatorcontrib><creatorcontrib>Le Gall, Tony</creatorcontrib><creatorcontrib>Berchel, Mathieu</creatorcontrib><creatorcontrib>Montier, Tristan</creatorcontrib><creatorcontrib>Jaffrès, Paul‐Alain</creatorcontrib><creatorcontrib>Rigole, Petra</creatorcontrib><creatorcontrib>Coenye, Tom</creatorcontrib><creatorcontrib>Brennich, Martha</creatorcontrib><creatorcontrib>Baccile, Niki</creatorcontrib><creatorcontrib>Roelants, Sophie L. K. W.</creatorcontrib><creatorcontrib>Soetaert, Wim</creatorcontrib><creatorcontrib>Van Bogaert, Inge N. A.</creatorcontrib><creatorcontrib>Van Geem, Kevin M.</creatorcontrib><creatorcontrib>Stevens, Christian V.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>ChemSusChem</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Delbeke, Elisabeth I. P.</au><au>Everaert, Jonas</au><au>Lozach, Olivier</au><au>Le Gall, Tony</au><au>Berchel, Mathieu</au><au>Montier, Tristan</au><au>Jaffrès, Paul‐Alain</au><au>Rigole, Petra</au><au>Coenye, Tom</au><au>Brennich, Martha</au><au>Baccile, Niki</au><au>Roelants, Sophie L. K. W.</au><au>Soetaert, Wim</au><au>Van Bogaert, Inge N. A.</au><au>Van Geem, Kevin M.</au><au>Stevens, Christian V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Lipid‐Based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities</atitle><jtitle>ChemSusChem</jtitle><addtitle>ChemSusChem</addtitle><date>2019-08-08</date><risdate>2019</risdate><volume>12</volume><issue>15</issue><spage>3642</spage><epage>3653</epage><pages>3642-3653</pages><issn>1864-5631</issn><eissn>1864-564X</eissn><abstract>Twelve new quaternary ammonium sophorolipids with long alkyl chains on the nitrogen atom were synthesized starting from oleic and petroselinic acid‐based sophorolipids. These novel derivatives were evaluated for their antimicrobial activity against selected Gram‐negative and Gram‐positive bacteria and their transfection efficacies on three different eukaryotic cell lines in vitro as good activities were demonstrated for previously synthesized derivatives. Self‐assembly properties were also evaluated. All compounds proved to possess antimicrobial and transfection properties, and trends could be observed based on the length of the nitrogen substituent and the total length of the sophorolipid tail. Moreover, all long‐chain quaternary ammonium sophorolipids form micelles, which proved to be a prerequisite to induce antimicrobial activity and transfection capacity. These results are promising for future healthcare applications of long‐chained quaternary ammonium sophorolipids.
A short tale about long tails: Twelve new quaternary ammonium sophorolipids were synthesized and evaluated on their antimicrobial, transfection, and self‐assembly properties. Trends could be observed for these properties based on the length of the nitrogen substituent and the total length of the lipid tail.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>31081279</pmid><doi>10.1002/cssc.201900721</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0003-4393-5327</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | amphiphiles Antiinfectives and antibacterials Antimicrobial agents biological activity Chains Derivatives drug delivery Lipids Micelles renewable resources self-assembly Synthesis |
| title | Lipid‐Based Quaternary Ammonium Sophorolipid Amphiphiles with Antimicrobial and Transfection Activities |
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