Highly water-soluble, fluorescent, conjugated fluorene-based glycopolymers with poly(ethylene glycol)-tethered spacers for sensitive detection of Escherichia coli.
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.
Xue
Cuihua
C
Department of Chemistry, Michigan Technological University, 1400 Townsend Drive, Houghton, MI 49931, USA.
Velayudham
Singaravelu
S
Johnson
Steve
S
Saha
Ratul
R
Smith
Adrian
A
Brewer
Wilbel
W
Murthy
Pushpalatha
P
Bagley
Susan T
ST
Liu
Haiying
H
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
D005449:Fluorenes; D005456:Fluorescent Dyes; D011108:Polymers; D011092:Polyethylene Glycols; D019855:Ethylene Glycol; D005947:Glucose; D008358:Mannose