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

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.Electronic supplementary materialThe online version of this article (doi:10.1186/s13568-014-0091-2) contains supplementary material, which is available to authorized users.

Magnetic Nanoparticles Conjugated with Peptides Derived from Monocyte Chemoattractant Protein-1 as a Tool for Targeting Atherosclerosis

“…The O1s peaking at 532.0 and 533.3 eV could be assigned to oxygen in the form of O=C bonds and C-O bonds. In addition, the binding energies at 529.7 eV and 535.3 eV represented Fe 3 O 4 and H 2 O, respectively [ 43 , 44 ].…”

Tailored Functionalization of Natural Phenols to Improve Biological Activity

“…A more advanced approach was related to the carvacrol anchoring on a gold surface, to develop antimicrobial coats [ 104 ]. Indeed, carvacrol functionalization at the phenolic group was performed to obtain a carvacrol ester and an ether, with a -NH 2 terminal group ( Scheme 5 ).…”

“… Synthesis of carvacrol ester and ether with a -NH 2 terminal group [ 104 ]. Abbreviations: NHS = N -hydroxysuccinimide; EDAC = N -(3-dimethylaminopropyl)- N ′-ethylcarbodiimide hydrochloride; Azido-PEG-amine = O -(2-aminoethyl)- O ′-(2-azidoethyl)triethylene glycol.…”

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

“…The original version of this article (Gharbi et al 2015 ) unfortunately contained a mistake. Dr. Christine Imbert and associated affiliation was missing from the author list in the HTML and PDF versions of this article.…”