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

• Published in: Biomacromolecules 2012-10, Vol.13 (10), p.3138-3150
• Main Authors: Gule, Nonjabulo P, Bshena, Osama, de Kwaadsteniet, Michèle, Cloete, Thomas E, Klumperman, Bert
• Format: Article
• Language: English
• Subjects: Applied sciences; Bacterial Adhesion - drug effects; Cell Adhesion - drug effects; Chemical modifications; Chemical reactions and properties; Escherichia coli; Escherichia coli - cytology; Escherichia coli - drug effects; Exact sciences and technology; Fibers and threads; Forms of application and semi-finished materials; Furans - chemical synthesis; Furans - chemistry; Furans - pharmacology; Klebsiella pneumoniae; Klebsiella pneumoniae - cytology; Klebsiella pneumoniae - drug effects; Maleates - chemistry; Microbial Sensitivity Tests; Microscopy, Fluorescence; Molecular Structure; Organic polymers; Physicochemistry of polymers; Polymer industry, paints, wood; Polystyrenes - chemistry; Pseudomonas aeruginosa; Pseudomonas aeruginosa - cytology; Pseudomonas aeruginosa - drug effects; Salmonella; Salmonella - cytology; Salmonella - drug effects; Staphylococcus aureus; Staphylococcus aureus - cytology; Staphylococcus aureus - drug effects; Surface Properties; Technology of polymers
• ISSN: 1525-7797; 1526-4602
• DOI: 10.1021/bm300932u

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 (1H 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).