title: An N-halamine-based rechargeable antimicrobial and biofilm controlling polyurethane.
abstract: An N-halamine precursor, 5,5-dimethylhydantoin (DMH), was covalently linked to the surface of polyurethane (PU) with 1,6-hexamethylene diisocyanate (HDI) as the coupling agent. The reaction pathways were investigated using propyl isocyanate (PI) as a model compound. The results suggested that the imide and amide groups of DMH have very similar reactivities toward the isocyanate groups on PU surfaces activated with HDI. After bleach treatment the covalently bound DMH moieties were transformed into N-halamines. The new N-halamine-based PU provided potent antimicrobial effects against Staphylococcus aureus (Gram-positive bacterium), Escherichia coli (Gram-negative bacterium), methicillin-resistant Staphylococcus aureus (MRSA, drug-resistant Gram-positive bacterium), vancomycin-resistant Enterococcus faecium (VRE, drug-resistant Gram-positive bacterium), and Candida albicans (fungus), and successfully prevented bacterial and fungal biofilm formation. The antimicrobial and biofilm controlling effects were stable for longer than 6 months under normal storage in open air. Furthermore, if the functions were lost due to prolonged use they could be recharged by another chlorination treatment. The recharging could be repeated as needed to achieve long-term protection against microbial contamination and biofilm formation.
authors.affiliation: Biomedical Engineering Program, The University of South Dakota, 4800 North Career Avenue, Sioux Falls, SD 57107, USA.
authors.forename: Xinbo
authors.initials: X
authors.lastname: Sun
authors.forename: Zhengbing
authors.initials: Z
authors.lastname: Cao
authors.forename: Nuala
authors.initials: N
authors.lastname: Porteous
authors.forename: Yuyu
authors.initials: Y
authors.lastname: Sun
mesh_terms: D000588:Amines / Q000737:chemistry*; D000890:Anti-Infective Agents / Q000494:pharmacology*; D000935:Antifungal Agents / Q000494:pharmacology; D018441:Biofilms / Q000187:drug effects*; D002176:Candida albicans / Q000187:drug effects / Q000502:physiology / Q000648:ultrastructure; D002713:Chlorine / Q000737:chemistry; D003485:Cyanates / Q000737:chemistry / Q000494:pharmacology; D004926:Escherichia coli / Q000187:drug effects / Q000502:physiology / Q000648:ultrastructure; D054879:Halogenation / Q000187:drug effects; D006827:Hydantoins / Q000737:chemistry / Q000494:pharmacology; D017953:Isocyanates; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D050296:Microbial Viability / Q000187:drug effects; D011140:Polyurethanes / Q000737:chemistry / Q000494:pharmacology*; D017550:Spectroscopy, Fourier Transform Infrared; D013211:Staphylococcus aureus / Q000187:drug effects / Q000502:physiology / Q000648:ultrastructure; D013499:Surface Properties / Q000187:drug effects
chemical_list: D000588:Amines; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D003485:Cyanates; D006827:Hydantoins; D017953:Isocyanates; D011140:Polyurethanes; C015262:1,6-hexamethylene diisocyanate; C030615:5,5-dimethylhydantoin; D002713:Chlorine