Highly Water-Soluble, Fluorescent, Conjugated Fluorene-Based Glycopolymers with Poly(ethylene glycol)-Tethered Spacers for Sensitive Detection of Escherichia coli

被引：62

作者：

Xue, Cuihua ^{[1
]}

Velayudham, Singaravelu ^{[1
]}

Johnson, Steve ^{[1
]}

Saha, Ratul ^{[2
]}

Smith, Adrian ^{[1
]}

Brewer, Wilbel ^{[1
]}

Murthy, Pushpalatha ^{[1
]}

Bagley, Susan T. ^{[2
]}

Liu, Haiying ^{[1
]}

机构：

[1] Michigan Technol Univ, Dept Chem, Houghton, MI 49931 USA

[2] Michigan Technol Univ, Dept Biol Sci, Houghton, MI 49931 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2009年 / 15卷 / 10期

关键词：

bacterial detection; bioimaging; biosensors; conjugation; fluorescence; glycopolymers; CHEMICAL SENSORS; POLYMERS; PROTEINS; LECTINS;

D O I：

10.1002/chem.200801875

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two bromide-hearing, fluorene-based, conjugated polymers with oligo(ethylene glycol)- and poly(ethylene glycol)-tethered spacers have been prepared by the Suzuki coupling poly-merization 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 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 clue to their long, flexible, hydrophilic spacers. Incubation of the ORN178 strain of Escherichia coli (E. coli) with (x-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.

引用

页码：2289 / 2295

页数：7

共 28 条

[1]

AFRICA GB, 2001, SYNTHESIS-STUTTGART, P1057

[2] Design and synthesis of novel glycopolythiophene assemblies for colorimetric detection of influenza virus and E-coli [J].

Baek, MG ;

Stevens, RC ;

Charych, DH .

BIOCONJUGATE CHEMISTRY, 2000, 11 (06) :777-788

[3] The affinity of the FimH fimbrial adhesin is receptor-driven and quasi-independent of Escherichia coli pathotypes [J].

Bouckaert, Julie ;

Mackenzie, Jenny ;

de Paz, Jose L. ;

Chipwaza, Beatrice ;

Choudhury, Devapriya ;

Zavialov, Anton ;

Mannerstedt, Karin ;

Anderson, Jennifer ;

Pierard, Denis ;

Wyns, Lode ;

Seeberger, Peter H. ;

Oscarson, Stefan ;

De Greve, Henri ;

Knight, Stefan D. .

MOLECULAR MICROBIOLOGY, 2006, 61 (06) :1556-1568

[4] Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications [J].

Bunz, UHF .

CHEMICAL REVIEWS, 2000, 100 (04) :1605-1644

[5] Type 1 fimbrial expression enhances Escherichia coli virulence for the urinary tract [J].

Connell, H ;

Agace, W ;

Klemm, P ;

Schembri, M ;

Marild, S ;

Svanborg, C .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (18) :9827-9832

[6]

DEMAS JN, 1971, J PHYS CHEM-US, V75, P991, DOI 10.1021/j100678a001

[7] Detection of bacteria with carbohydrate-functionalized fluorescent polymers [J].

Disney, MD ;

Zheng, J ;

Swager, TM ;

Seeberger, PH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (41) :13343-13346

[8] Convergent synthesis of fluorescein-labelled lysine-based cluster glycosides [J].

Grandjean, C ;

Rommens, C ;

Gras-Masse, H ;

Melnyk, O .

TETRAHEDRON LETTERS, 1999, 40 (40) :7235-7238

[9] Carbohydrate biosensors [J].

Jelinek, R ;

Kolusheva, S .

CHEMICAL REVIEWS, 2004, 104 (12) :5987-6015

[10] Poly(arylene ethynylene)s in chemosensing and biosensing [J].

Juan, Z ;

Swager, TM .

POLY(ARYLENE ETYNYLENE)S: FROM SYNTHESIS TO APPLICATION, 2005, 177 :151-179

← 1 2 3 →