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Full Paper
Highly Water-Soluble, Fluorescent, Conjugated Fluorene-Based Glycopolymers with Poly(ethylene glycol)-Tethered Spacers for Sensitive Detection of Escherichia coli
Article first published online: 13 JAN 2009
DOI: 10.1002/chem.200801875
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Xue, C., Velayudham, S., Johnson, S., Saha, R., Smith, A., Brewer, W., Murthy, P., Bagley, Susan T. and Liu, H. (2009), Highly Water-Soluble, Fluorescent, Conjugated Fluorene-Based Glycopolymers with Poly(ethylene glycol)-Tethered Spacers for Sensitive Detection of Escherichia coli. Chem. Eur. J., 15: 2289–2295. doi: 10.1002/chem.200801875
Publication History
- Issue published online: 12 FEB 2009
- Article first published online: 13 JAN 2009
- Manuscript Received: 11 SEP 2008
Funded by
- Research Excellence Fund of Michigan Technological University
- 21st Century Jobs Fund of Michigan. Grant Number: 06-1-P1-0283
- National Research Initiative. Grant Number: 2007-35603-17740
- Abstract
- Article
- References
- Cited By
Keywords:
- bacterial detection;
- bioimaging;
- biosensors;
- conjugation;
- fluorescence;
- glycopolymers
Abstract
Know your bacteria! Two fluorene-based, conjugated polymers with oligo(ethylene glycol)- and poly(ethylene glycol)-tethered spacers have been prepared by the Suzuki coupling polymerization reactions. β-Glucose and α-mannose residues were covalently attached to the conjugated polymers by post-polymerization functionalization with thiol-functionalized carbohydrates under basic conditions. Investigations on their use as biosensing materials for the detection of Escherichia coli are reported (see figure).
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. β-Glucose and α-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 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.