title: Biocidal Properties of a Glycosylated Surface: Sophorolipids on Au(111).
abstract: 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.
authors.affiliation: †Sorbonne Universités, UPMC Univ Paris 06, CNRS, Collège de France, Laboratoire de Chimie de la Matière Condensée de Paris, UMR 7574, 11 Place Marcelin Berthelot, 75005 Paris, France.|‡Sorbonne Universités, UPMC Univ Paris 06, CNRS, Laboratoire de Réactivité de Surface, UMR 7197, 4 Place Jussieu, 75005 Paris, France.
authors.forename: Claire
authors.initials: C
authors.lastname: Valotteau
authors.affiliation: ‡Sorbonne Universités, UPMC Univ Paris 06, CNRS, Laboratoire de Réactivité de Surface, UMR 7197, 4 Place Jussieu, 75005 Paris, France.
authors.forename: Christophe
authors.initials: C
authors.lastname: Calers
authors.affiliation: ‡Sorbonne Universités, UPMC Univ Paris 06, CNRS, Laboratoire de Réactivité de Surface, UMR 7197, 4 Place Jussieu, 75005 Paris, France.
authors.forename: Sandra
authors.initials: S
authors.lastname: Casale
authors.affiliation: §SynBioC Research Group, Departement of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Gent, Belgium.
authors.forename: Jan
authors.initials: J
authors.lastname: Berton
authors.affiliation: §SynBioC Research Group, Departement of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Gent, Belgium.
authors.forename: Christian V
authors.initials: CV
authors.lastname: Stevens
authors.affiliation: †Sorbonne Universités, UPMC Univ Paris 06, CNRS, Collège de France, Laboratoire de Chimie de la Matière Condensée de Paris, UMR 7574, 11 Place Marcelin Berthelot, 75005 Paris, France.
authors.forename: Florence
authors.initials: F
authors.lastname: Babonneau
authors.affiliation: ‡Sorbonne Universités, UPMC Univ Paris 06, CNRS, Laboratoire de Réactivité de Surface, UMR 7197, 4 Place Jussieu, 75005 Paris, France.
authors.forename: Claire-Marie
authors.initials: CM
authors.lastname: Pradier
authors.affiliation: ‡Sorbonne Universités, UPMC Univ Paris 06, CNRS, Laboratoire de Réactivité de Surface, UMR 7197, 4 Place Jussieu, 75005 Paris, France.
authors.forename: Vincent
authors.initials: V
authors.lastname: Humblot
authors.affiliation: †Sorbonne Universités, UPMC Univ Paris 06, CNRS, Collège de France, Laboratoire de Chimie de la Matière Condensée de Paris, UMR 7574, 11 Place Marcelin Berthelot, 75005 Paris, France.
authors.forename: Niki
authors.initials: N
authors.lastname: Baccile
mesh_terms: D039903:Actinobacteria / Q000187:drug effects; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001422:Bacterial Adhesion / Q000187:drug effects; D006031:Glycosylation; D006046:Gold / Q000737:chemistry*; D006801:Humans; D008087:Listeria; D008826:Microbial Sensitivity Tests; D018625:Microscopy, Atomic Force; D019301:Oleic Acid / Q000737:chemistry; D013055:Spectrophotometry, Infrared; D013438:Sulfhydryl Compounds / Q000737:chemistry; D013499:Surface Properties
chemical_list: D000900:Anti-Bacterial Agents; D013438:Sulfhydryl Compounds; D019301:Oleic Acid; D006046:Gold
keywords: antibacterial coating; biocidal mechanism; glycolipid; killing-by-contact; self-assembled monolayer; sophorolipid; surface functionalization