title: Antimicrobial N-brominated hydantoin and uracil grafted polystyrene beads.
abstract: Hydantoin-N-halamine derivatives conjugated on polystyrene beads are promising disinfectants with broad antimicrobial activity affected by the gradual release of oxidizing halogen in water. The objective of this work was to identify and test of hydantoin-like molecules possessing urea moiety, which may provide N-haloamines releasing oxidizing halogens when exposed to water at different rates and release profiles for tailored antimicrobial agents. In this work, several hydantoin (five member ring) and for the first time reported, uracil (six member ring) derivatives have been conjugated to polystyrene beads and tested for their lasting antimicrobial activity. Four molecules of each series were conjugated onto polystyrene beads from the reaction of the N-potassium hydantoin or uracil derivatives onto chloromethylated polystyrene beads. A distinct difference in bromine loading capacity and release profiles was found for the different conjugated derivatives. All tested materials exhibit strong antimicrobial activity against Escherichia coli and bacteriophages MS2 of 7 and ~4 log reduction, respectively. These results highlight the antimicrobial potential of halogenated cyclic molecules containing urea groups as water disinfection agents.
authors.affiliation: Institute of Drug Research, School of Pharmacy-Faculty of Medicine, Center for Nanoscience & Nanotechnology and The Alex Grass Center for Drug Design and Synthesis, The Hebrew University of Jerusalem, 91120, Jerusalem, Israel.
authors.forename: Shady
authors.initials: S
authors.lastname: Farah
authors.affiliation: Institute of Drug Research, School of Pharmacy-Faculty of Medicine, Center for Nanoscience & Nanotechnology and The Alex Grass Center for Drug Design and Synthesis, The Hebrew University of Jerusalem, 91120, Jerusalem, Israel.
authors.forename: Oren
authors.initials: O
authors.lastname: Aviv
authors.affiliation: Institute of Drug Research, School of Pharmacy-Faculty of Medicine, Center for Nanoscience & Nanotechnology and The Alex Grass Center for Drug Design and Synthesis, The Hebrew University of Jerusalem, 91120, Jerusalem, Israel.
authors.forename: Natalia
authors.initials: N
authors.lastname: Laout
authors.affiliation: Institute of Drug Research, School of Pharmacy-Faculty of Medicine, Center for Nanoscience & Nanotechnology and The Alex Grass Center for Drug Design and Synthesis, The Hebrew University of Jerusalem, 91120, Jerusalem, Israel.
authors.forename: Stanislav
authors.initials: S
authors.lastname: Ratner
authors.affiliation: Institute of Drug Research, School of Pharmacy-Faculty of Medicine, Center for Nanoscience & Nanotechnology and The Alex Grass Center for Drug Design and Synthesis, The Hebrew University of Jerusalem, 91120, Jerusalem, Israel; Jerusalem College of Engineering (JCE), Jerusalem, Israel. Electronic address: avid@ekmd.huji.ac.il.
authors.forename: Abraham J
authors.initials: AJ
authors.lastname: Domb
mesh_terms: D000588:Amines / Q000737:chemistry; D000890:Anti-Infective Agents / Q000737:chemistry* / Q000494:pharmacology*; D003692:Delayed-Action Preparations; D004926:Escherichia coli / Q000187:drug effects; D054879:Halogenation; D006827:Hydantoins / Q000737:chemistry* / Q000494:pharmacology*; D007455:Iodine / Q000737:chemistry; D017909:Levivirus / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D009555:Ninhydrin / Q000032:analysis; D010084:Oxidation-Reduction; D011137:Polystyrenes / Q000737:chemistry*; D014498:Uracil / Q000737:chemistry*; D014508:Urea / Q000737:chemistry
chemical_list: D000588:Amines; D000890:Anti-Infective Agents; D003692:Delayed-Action Preparations; D006827:Hydantoins; D011137:Polystyrenes; D014498:Uracil; D014508:Urea; D007455:Iodine; D009555:Ninhydrin
keywords: Hydantoin; N-bromoamine; N-halamine disinfectant; Polystyrene beads; Uracil; Water disinfection