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Surface functionalization by covalent immobilization of an innovative carvacrol derivative to avoid fungal biofilm formation.

Gharbi A, Legigan T, Humblot V, Papot S, Berjeaud JM - AMB Express (2015)

Bottom Line: On the contrary, when a phenyl group replaced the terpenic moiety, the yeast culturability increased by about 30%, highlighting the specific activity of carvacrol grafted on the surfaces.Confocal microscopy analyses showed that the mode of action of the functionalized surfaces with the ester or the ether of carvacrol was, in both cases, fungicidal and not anti-adhesive.Finally, this study shows that covalently immobilization of terpenic compounds can be used to design promising antimicrobial surfaces.

View Article: PubMed Central - PubMed

Affiliation: Ecologie & Biologie des Interactions - UMR CNRS 7267, Microbiologie de l'eau, Université de Poitiers, 1 Rue Georges Bonnet, TSA 51106, 86073 Poitiers Cedex 9, France.

ABSTRACT
Carvacrol, an aromatic terpenic compound, known to be antimicrobial was grafted onto gold surfaces via two strategies based on newly-synthesized cross-linkers involving either an ester bond which can be cleaved by microbial esterases, or a covalent ether link. Surface functionalizations were characterized at each step by reflection absorption infrared spectroscopy (RAIRS). The two functionalized gold samples both led to a loss of culturability of the yeast Candida albicans, higher than 65%, indicating that the activity of the freshly-designed surfaces was probably due to still covalently immobilized carvacrol. On the contrary, when a phenyl group replaced the terpenic moiety, the yeast culturability increased by about 30%, highlighting the specific activity of carvacrol grafted on the surfaces. Confocal microscopy analyses showed that the mode of action of the functionalized surfaces with the ester or the ether of carvacrol was, in both cases, fungicidal and not anti-adhesive. Finally, this study shows that covalently immobilization of terpenic compounds can be used to design promising antimicrobial surfaces.

No MeSH data available.


XPS general spectra of gold surfaces.A: XPS general spectra of gold surfaces functionalized (a) only with MUA (control) or (b) with the EstC-NH2 molecule. B: XPS high-resolution spectra of gold EstC-NH2 functionalized-surfaces for Carbon (a), for Oxygen (b) and for Nitrogen (c).
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Fig3: XPS general spectra of gold surfaces.A: XPS general spectra of gold surfaces functionalized (a) only with MUA (control) or (b) with the EstC-NH2 molecule. B: XPS high-resolution spectra of gold EstC-NH2 functionalized-surfaces for Carbon (a), for Oxygen (b) and for Nitrogen (c).

Mentions: The general spectrum obtained by XPS spectroscopy as shown on Figure 3A for the gold surface functionalized with the EstC-NH2, reveals a signal at ~400 eV corresponding to nitrogen (indicated on the figure as N1s) that is not present on the Au-MUA control (spectrum a), clearly suggesting the presence of the EstC-NH2 molecules at the surface.Figure 3


Surface functionalization by covalent immobilization of an innovative carvacrol derivative to avoid fungal biofilm formation.

Gharbi A, Legigan T, Humblot V, Papot S, Berjeaud JM - AMB Express (2015)

XPS general spectra of gold surfaces.A: XPS general spectra of gold surfaces functionalized (a) only with MUA (control) or (b) with the EstC-NH2 molecule. B: XPS high-resolution spectra of gold EstC-NH2 functionalized-surfaces for Carbon (a), for Oxygen (b) and for Nitrogen (c).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4384722&req=5

Fig3: XPS general spectra of gold surfaces.A: XPS general spectra of gold surfaces functionalized (a) only with MUA (control) or (b) with the EstC-NH2 molecule. B: XPS high-resolution spectra of gold EstC-NH2 functionalized-surfaces for Carbon (a), for Oxygen (b) and for Nitrogen (c).
Mentions: The general spectrum obtained by XPS spectroscopy as shown on Figure 3A for the gold surface functionalized with the EstC-NH2, reveals a signal at ~400 eV corresponding to nitrogen (indicated on the figure as N1s) that is not present on the Au-MUA control (spectrum a), clearly suggesting the presence of the EstC-NH2 molecules at the surface.Figure 3

Bottom Line: On the contrary, when a phenyl group replaced the terpenic moiety, the yeast culturability increased by about 30%, highlighting the specific activity of carvacrol grafted on the surfaces.Confocal microscopy analyses showed that the mode of action of the functionalized surfaces with the ester or the ether of carvacrol was, in both cases, fungicidal and not anti-adhesive.Finally, this study shows that covalently immobilization of terpenic compounds can be used to design promising antimicrobial surfaces.

View Article: PubMed Central - PubMed

Affiliation: Ecologie & Biologie des Interactions - UMR CNRS 7267, Microbiologie de l'eau, Université de Poitiers, 1 Rue Georges Bonnet, TSA 51106, 86073 Poitiers Cedex 9, France.

ABSTRACT
Carvacrol, an aromatic terpenic compound, known to be antimicrobial was grafted onto gold surfaces via two strategies based on newly-synthesized cross-linkers involving either an ester bond which can be cleaved by microbial esterases, or a covalent ether link. Surface functionalizations were characterized at each step by reflection absorption infrared spectroscopy (RAIRS). The two functionalized gold samples both led to a loss of culturability of the yeast Candida albicans, higher than 65%, indicating that the activity of the freshly-designed surfaces was probably due to still covalently immobilized carvacrol. On the contrary, when a phenyl group replaced the terpenic moiety, the yeast culturability increased by about 30%, highlighting the specific activity of carvacrol grafted on the surfaces. Confocal microscopy analyses showed that the mode of action of the functionalized surfaces with the ester or the ether of carvacrol was, in both cases, fungicidal and not anti-adhesive. Finally, this study shows that covalently immobilization of terpenic compounds can be used to design promising antimicrobial surfaces.

No MeSH data available.