title: Highly water-soluble, fluorescent, conjugated fluorene-based glycopolymers with poly(ethylene glycol)-tethered spacers for sensitive detection of Escherichia coli.
abstract: Two bromide-bearing, fluorene-based, conjugated polymers with oligo(ethylene glycol)- and poly(ethylene glycol)-tethered spacers have been prepared by the Suzuki coupling polymerization of bromide-bearing, fluorene monomers. beta-Glucose and alpha-mannose residues have been covalently attached to the conjugated polymers by post-polymerization functionalization of the precursor polymers with thiol-functionalized carbohydrates under basic conditions through thioether linkage. A glucose-bearing glycopolymer with oligo(ethylene glycol)-tethered spacers (polymer A) displays poor water solubility. However, glycopolymers with poly(ethylene glycol)-tethered spacers (polymers B and C) are highly water-soluble due to their long, flexible, hydrophilic spacers. Incubation of the ORN178 strain of Escherichia coli (E. coli) with alpha-mannose-bearing glycopolymer (polymer C) results in the formation of fluorescent cell clusters, causing significant red shifts in UV/Vis absorption and fluorescent spectra of the polymer through multivalent cooperative interactions of the polymeric carbohydrates with the bacterial pili. In contrast, polymer C displays no interactions with a mutant ORN208 strain of E. coli.
authors.affiliation: Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA.
authors.forename: Cuihua
authors.initials: C
authors.lastname: Xue
authors.forename: Singaravelu
authors.initials: S
authors.lastname: Velayudham
authors.forename: Steve
authors.initials: S
authors.lastname: Johnson
authors.forename: Ratul
authors.initials: R
authors.lastname: Saha
authors.forename: Adrian
authors.initials: A
authors.lastname: Smith
authors.forename: Wilbel
authors.initials: W
authors.lastname: Brewer
authors.forename: Pushpalatha
authors.initials: P
authors.lastname: Murthy
authors.forename: Susan T
authors.initials: ST
authors.lastname: Bagley
authors.forename: Haiying
authors.initials: H
authors.lastname: Liu
mesh_terms: D015374:Biosensing Techniques / Q000379:methods; D004926:Escherichia coli / Q000302:isolation & purification*; D019855:Ethylene Glycol / Q000737:chemistry; D005449:Fluorenes / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D008358:Mannose / Q000737:chemistry; D008856:Microscopy, Fluorescence / Q000379:methods; D019906:Nuclear Magnetic Resonance, Biomolecular; D011092:Polyethylene Glycols / Q000737:chemistry; D011108:Polymers / Q000138:chemical synthesis / Q000737:chemistry*; D013050:Spectrometry, Fluorescence / Q000379:methods
chemical_list: D005449:Fluorenes; D005456:Fluorescent Dyes; D011108:Polymers; D011092:Polyethylene Glycols; D019855:Ethylene Glycol; D005947:Glucose; D008358:Mannose