Highly water-soluble, fluorescent, conjugated fluorene-based glycopolymers with poly(ethylene glycol)-tethered spacers for sensitive detection of escherichia coli

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Department of Chemistry; Department of Biological Sciences


Two bromide-bearing, fluorene-based, conjugated polymers with oligo(ethylene glycol)- and polyethylene glycol)-tethered spacers have been prepared by the Suzuki coupling polymerization of bromide-bearing, fluorene monomers. β-Glucose and α-mannose residues have been covalently attached to the conjugated polymers by post-polymerization functionalization of the precursor polymers with thiolfunctionalized carbohydrates under basic conditions through thioether link-age. 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 α-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.

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Chemistry - A European Journal