Simple Pyranoside- and Furanoside-Functionalized Glass Surfaces: An Attractive Anti-Bioadhesion Strategy against Pseudomonas Aeruginosa

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1st EuroCarb Young Researcher (ECYR) Workshop

CarboMet Workshop

Mini symposium: Glycobiology at the LUMC and beyond

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Simple Pyranoside- and Furanoside-Functionalized Glass Surfaces: An Attractive Anti-Bioadhesion Strategy against Pseudomonas Aeruginosa

Mathieu Scalabrini 1,2 , Karine Réhel 1 , Vincent Ferrières 2

1 Univ, Bretagne-Sud, EA 3884, LBCM, IUEM, F-56100, Lorient, France, 2 Univ Rennes, école Nationale Supérieure de Chimie de Rennes, CNRS, ISCR – UMR6226, F-35000, Rennes, France

All immersed materials are vulnerable to the bacterial colonization and their development in biofilm. The matrix of extracellular polymeric substances provides a strong resistance to environment, bactericidal agents and thermic treatments that leads to major health and environmental issues. One possible approach for producing surfaces preventing bacterial adhesion is the use of amphiphilic copolymers, especially PDMS-PEG ones [1,2]. However, PEG units are subject to oxidation phenomena. Therefore, the use of carbohydrates-coated surfaces appears as one of the best non-biocidal and non-toxic strategy (Figure 1). Indeed, sugars afford an extensively possibility of structural modulations with their numerous functional groups. Although pyranosides are largely described, the biological impacts of furanosides are still to be elucidated. Their absence in mammal species and their known bacteriostatic activities provide an interest as potential anti-bioadhesion agent [3].

In this work, we examined the anti-bioadhesion activities of glass surfaces presenting simple monosaccharides such as D-glucose, D-galactose and D-mannose in both pyranose and furanose configurations. The latter glycosyl residues were connected to surfaces through a small propargylic linker thanks to either standard O-glycosidic bonds or S-glycosidic linkages which are more resistant to chemical and enzymatic hydrolysis. To achieve this, it was needful to design a new synthetic pathway for accessing O/S-Propargyl D-Glycofuranoside. The click chemistry with alkyl azide-functionalized glass surfaces allowed covalent attachment of carbohydrate thanks to copper(I)-catalysed alkyne-azide cycloaddition. Hydrophobicity, surface free energy and atomistic composition were characterised with a combination of contact angle goniometry and X-ray photoelectron spectroscopy. The adhesion studies with Pseudomonas aeruginosa (MPAO1) showed promising anti-bioadhesion activities from glycosidic surfaces which appeared to depend of the configuration [4]. Then, an in-depth study of apolar and polar interactions between bacteria and surfaces were explored through a thermodynamic approach. And we finally investigated the molecular interactions and their potential roles for the bacterial adhesion.

Figure 1. Anti-Bioadhesion Activity of Glycofuranoside-functionalized surface.

Faÿ, F.; Hawkins, M. L.; Réhel, K.; Grunlan, M. A.; Linossier, I. Non-Toxic, Anti-Fouling Silicones with Variable PEO-Silane Amphiphile Content. Green Mater. 2016, 4 (2), 53–62.

Hawkins, M. L.; Faÿ, F.; Réhel, K.; Linossier, I.; Hawkins, M. L.; Faÿ, F.; Réhel, K.; Linossier, I. Bacteria and Diatom Resistance of Silicones Modified with PEO-Silane Amphiphiles. Biofouling. 2014, 7014.

Legentil, L.; Belaz, S.; Gangneux, J. P.; Robert-Gangneux, F.; Ferrières, V. Synthesis and Biological Properties of Galactofuranosyl-Containing Fluorescent Dyes. Bioorganic Med. Chem. Lett. 2017, 27 (2), 152–155.

Scalabrini M.; Hamon J.; Réhel K.; Ferrières V. Submitted.

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