Biocidal Properties of a Glycosylated Surface: Sophorolipids on Au(111)
Classical antibacterial surfaces usually involve antiadhesive and/or biocidal strategies. Glycosylated surfaces are usually used to prevent biofilm formation via antiadhesive mechanisms. We report here the first example of a glycosylated surface with biocidal properties created by the covalent graft...
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| Veröffentlicht in: | ACS applied materials & interfaces 2015-08, Vol.7 (32), p.18086-18095 |
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| creator | Valotteau, Claire Calers, Christophe Casale, Sandra Berton, Jan Stevens, Christian V Babonneau, Florence Pradier, Claire-Marie Humblot, Vincent Baccile, Niki |
| description | Classical antibacterial surfaces usually involve antiadhesive and/or biocidal strategies. Glycosylated surfaces are usually used to prevent biofilm formation via antiadhesive mechanisms. We report here the first example of a glycosylated surface with biocidal properties created by the covalent grafting of sophorolipids (a sophorose unit linked by a glycosidic bond to an oleic acid) through a self-assembled monolayer (SAM) of short aminothiols on gold (111) surfaces. The biocidal effect of such surfaces on Gram+ bacteria was assessed by a wide combination of techniques including microscopy observations, fluorescent staining, and bacterial growth tests. About 50% of the bacteria are killed via alteration of the cell envelope. In addition, the roles of the sophorose unit and aliphatic chain configuration are highlighted by the lack of activity of substrates modified, respectively, with sophorose-free oleic acid and sophorolipid-derivative having a saturated aliphatic chain. This system demonstrates thus the direct implication of a carbohydrate in the destabilization and disruption of the bacterial cell envelope. |
| doi_str_mv | 10.1021/acsami.5b05090 |
| format | Article |
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Glycosylated surfaces are usually used to prevent biofilm formation via antiadhesive mechanisms. We report here the first example of a glycosylated surface with biocidal properties created by the covalent grafting of sophorolipids (a sophorose unit linked by a glycosidic bond to an oleic acid) through a self-assembled monolayer (SAM) of short aminothiols on gold (111) surfaces. The biocidal effect of such surfaces on Gram+ bacteria was assessed by a wide combination of techniques including microscopy observations, fluorescent staining, and bacterial growth tests. About 50% of the bacteria are killed via alteration of the cell envelope. In addition, the roles of the sophorose unit and aliphatic chain configuration are highlighted by the lack of activity of substrates modified, respectively, with sophorose-free oleic acid and sophorolipid-derivative having a saturated aliphatic chain. 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Mater. Interfaces</addtitle><description>Classical antibacterial surfaces usually involve antiadhesive and/or biocidal strategies. Glycosylated surfaces are usually used to prevent biofilm formation via antiadhesive mechanisms. We report here the first example of a glycosylated surface with biocidal properties created by the covalent grafting of sophorolipids (a sophorose unit linked by a glycosidic bond to an oleic acid) through a self-assembled monolayer (SAM) of short aminothiols on gold (111) surfaces. The biocidal effect of such surfaces on Gram+ bacteria was assessed by a wide combination of techniques including microscopy observations, fluorescent staining, and bacterial growth tests. About 50% of the bacteria are killed via alteration of the cell envelope. In addition, the roles of the sophorose unit and aliphatic chain configuration are highlighted by the lack of activity of substrates modified, respectively, with sophorose-free oleic acid and sophorolipid-derivative having a saturated aliphatic chain. This system demonstrates thus the direct implication of a carbohydrate in the destabilization and disruption of the bacterial cell envelope.</description><subject>Actinobacteria - drug effects</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Bacterial Adhesion - drug effects</subject><subject>Chemical Sciences</subject><subject>Glycosylation</subject><subject>Gold - chemistry</subject><subject>Humans</subject><subject>Listeria</subject><subject>Material chemistry</subject><subject>Microbial Sensitivity Tests</subject><subject>Microscopy, Atomic Force</subject><subject>Oleic Acid - chemistry</subject><subject>Spectrophotometry, Infrared</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Surface Properties</subject><issn>1944-8244</issn><issn>1944-8252</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kE1PAjEQhhujEUSvHs0exQRsu_1gvSFRMCHRBD03s91uKFno2u6a8O8tWeTmaSYzz_seHoRuCR4TTMkj6ABbO-Y55jjDZ6hPMsZGE8rp-WlnrIeuQthgLFKK-SXqUUGZFJj30fzZOm0LqJIP72rjG2tC4soEknm11y7sK2hMkaxaX4I2T8nK1WvnXWVrW0Rwl0zbe0LI8BpdlFAFc3OcA_T1-vI5W4yW7_O32XQ5AoZZM8ohwwUA0xRSUYIoJONCC4Nl_OgMWEYNw0KnTKQggIqCycxIoIakIpvk6QANu941VKr2dgt-rxxYtZgu1eGGCZU8yvghkb3v2Nq779aERm1t0KaqYGdcGxSRmMuUcplFdNyh2rsQvClP3QSrg2jViVZH0TFwd-xu860pTvif2Qg8dEAMqo1r_S5q-a_tFxcOha4</recordid><startdate>20150819</startdate><enddate>20150819</enddate><creator>Valotteau, Claire</creator><creator>Calers, Christophe</creator><creator>Casale, Sandra</creator><creator>Berton, Jan</creator><creator>Stevens, Christian V</creator><creator>Babonneau, Florence</creator><creator>Pradier, Claire-Marie</creator><creator>Humblot, Vincent</creator><creator>Baccile, Niki</creator><general>American Chemical Society</general><general>Washington, D.C. : American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0003-0342-5779</orcidid><orcidid>https://orcid.org/0000-0002-6266-3956</orcidid><orcidid>https://orcid.org/0000-0002-6961-1331</orcidid><orcidid>https://orcid.org/0000-0002-1436-8506</orcidid><orcidid>https://orcid.org/0000-0003-3142-3228</orcidid></search><sort><creationdate>20150819</creationdate><title>Biocidal Properties of a Glycosylated Surface: Sophorolipids on Au(111)</title><author>Valotteau, Claire ; 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| subjects | Actinobacteria - drug effects Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Bacterial Adhesion - drug effects Chemical Sciences Glycosylation Gold - chemistry Humans Listeria Material chemistry Microbial Sensitivity Tests Microscopy, Atomic Force Oleic Acid - chemistry Spectrophotometry, Infrared Sulfhydryl Compounds - chemistry Surface Properties |
| title | Biocidal Properties of a Glycosylated Surface: Sophorolipids on Au(111) |
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