Immobilized Furanone Derivatives as Inhibitors for Adhesion of Bacteria on Modified Poly(styrene-co-maleic anhydride)

Abstract

The ability of brominated furanones and other furanone compounds with 2(3H) and 2(5H) cores to inhibit bacterial adhesion of surfaces as well deactivate (destroy) them has been previously reported. The furanone derivatives 4-(2-(2-aminoethoxy)-2,5-dimethyl-3(2H)-furanone and 5-(2-(2-aminoethoxy)-ethoxy)methyl)-2(5H)-furanone were synthesized in our laboratory. These furanone derivatives were then covalently immobilized onto poly(styrene-co-maleic anhydride) (SMA) and electrospun to fabricate nonwoven nanofibrous mats with antimicrobial and cell-adhesion inhibition properties. The electrospun nanofibrous mats were tested for their ability to inhibit cell attachment by strains of bacteria commonly found in water ( Klebsiella pneumoniae Xen 39, Staphylococcus aureus Xen 36, Escherichia coli Xen 14, Pseudomonas aeruginosa Xen 5, and Salmonella tymphimurium Xen 26). Proton nuclear magnetic resonance spectroscopy ((1)H NMR), electrospray mass spectroscopy (ES-MS), and attenuated total reflectance Fourier transform infrared spectroscopy (ATR-FTIR) were used to confirm the structures of the synthesized furanones as well as their successful immobilization on SMA. To ascertain that the immobilized furanone compounds do not leach into filtered water, samples of water, filtered through the nanofibrous mats were analyzed using gas chromatography coupled with mass spectroscopy (GC-MS). The morphology of the electrospun nanofibers was characterized using scanning electron microscopy (SEM).

Synthesis and Characterization of Fluorescent Brightening Agents with Chiral 2(5H)-Furanone and Bis-1,2,3-triazole Structure

“…Many molecules possessing 2(5 H )-furanone moiety, which is a type of α,β-unsaturated lactone substructure frequently found in natural products, have received considerable interest, because of the significant biological activities, such as antifungal, antibacterial, anti-inflammatory, and anticancer. − On the other hand, because of the biological activities and unique structure of bis-1,2,3-triazoles, increasing amounts of importance has been attached to their application in different aspects, such as pesticides, pharmaceuticals, materials, artificial receptors, and biomimetic self-assembly, etc. − Therefore, more and more attention has been paid to the syntheses of compounds containing 2(5 H )-furanone and bis-1,2,3-triazole structures. − …”

Wettability of Amino Acid-Functionalized PSMA Electrospun Fibers for the Modulated Release of Active Agents and Its Effect on Their Bioactivity

“…[ 36 , 37 , 38 ]. In contrast, the use of copolymers such as poly(methyl vinyl ether- alt -maleic anhydride) [ 39 ], poly(methyl methacrylate- b -methacrylic acid) (PMMA- b -MA) [ 40 ], and poly(styrene- co -maleic anhydride) [ 41 ], have been less explored for the elaboration of wound dressings. Bearing in mind that the wettability property of polymeric fibers is important in the performance of a polymeric dressing, there are particular advantages for fibers elaborated from copolymers, for instance, their chemical versatility associated with greater availability of functional groups or their facility to anchor molecules of different polarities, which will allow for obtaining fibers with variable wettability.…”

Dental Composites: Bioactive Polymeric Amorphous Calcium Phosphate-Based

“…To eliminate some of the drawbacks of the QAs, we intend to incorporate furanone derivatives into ACP matrices. Furanones have been indicated as the potent inhibitors of biofilm formation [43]. Their inhibitory effects appear to be mediated through the interference with the microbial communication (quorum sensing; QS) rather than the microbial growth [44].…”