Design and Synthesis of Novel Glycopolythiophene Assemblies for Colorimetric Detection of Influenza Virus and E. coli

Abstract

A novel family of glycopolythiophenes containing sialic acid or mannose ligands were prepared and evaluated for their ability to bind lectins, virus, and bacteria. For the set of glycopolythiophenes studied, the spacer-length between the polymer backbone and the ligand was varied to optimize binding interactions. The glycopolymers were blue-shifted (absorbance of ca. 400 nm) relative to the corresponding homo-polythiophenes (absorbance ca. 440 nm), suggesting a twisted conformation for the glycopolymers. The altered conformation is likely due to electrostatic or H-bonding interactions between the polymer chains, arising from the carbohydrate ligand. Further conformational changes in the polythiophene backbone were detected by the binding of specific receptors; lectins (wheat germ agglutinin, concanavalin A), Influenza virus, and Escherichia coli. The binding interactions result in an unusual red-shift in the visible absorption of the polymer backbone, suggesting a lengthening of the effective conjugated length upon interaction of the ligand with its congnate receptor. These conjugated glycopolymeric systems offer a potentially new platform for the detection of molecular binding interactions.

Asymmetric Oligothiophenes : Chemical Evolution of Multimodal Amyloid Ligands

“…Many groups have used the FeCl 3 route discussed above to generate conjugated polymers in many different biosensing applications, e.g. virus detection [21],DNA hybridization [22,23] and protein misfolding studies [24,25]. One of the first groups to use conjugated polymers as conformational dependent bioimaging-agents was Charych et al Their application was to covalently bind a polymer to influenza virus and use the conformational color change of the polymer as detection signal [26].…”

Macromolecules with Сarbohydrate Residues and Their Application in Glycobiology, Biotechnology and Material Science

“…[23][24][25] As these compounds incorporate a fluorescent marker and a glycoside component, they display an interesting combination of properties: fluorescence and high sensitivity to the external signal.…”

Triphenylamine-based fluorescent conjugated glycopolymers: Synthesis, characterization and interactions with lectins

“…As multivalent model systems and artificial glycoconjugates, synthetic glycopolymers have demonstrated to be important well-defined tools for investigating carbohydrate-based biological events [6][7][8]. In particular, fluorescent conjugated glycopolymers that possess both fluorescent scaffolding and reporting carbohydrate ligands are attractively used in carbohydrate-protein interaction studies and biosensor applications because of their intrinsic optical properties, high sensitivities to minor stimuli, and good biocompatibilities [9][10][11][12][13]. A few conjugated polymers, such as polythiophene [10,11], polyfluorene [12], poly(p-phenylene-ethynylene) [13][14][15][16][17], poly(phenylene-vinylene) [18], and poly(p-phenylene) [19], have been chosen to design this type of multivalent glycoconjugates.…”

“…In particular, fluorescent conjugated glycopolymers that possess both fluorescent scaffolding and reporting carbohydrate ligands are attractively used in carbohydrate-protein interaction studies and biosensor applications because of their intrinsic optical properties, high sensitivities to minor stimuli, and good biocompatibilities [9][10][11][12][13]. A few conjugated polymers, such as polythiophene [10,11], polyfluorene [12], poly(p-phenylene-ethynylene) [13][14][15][16][17], poly(phenylene-vinylene) [18], and poly(p-phenylene) [19], have been chosen to design this type of multivalent glycoconjugates. One approach to such a system is represented by the polymerization or copolymerization of well-defined carbohydrate-carrying monomers through classical C-C coupling reactions [10,13,[15][16][17][18].…”

“…A few conjugated polymers, such as polythiophene [10,11], polyfluorene [12], poly(p-phenylene-ethynylene) [13][14][15][16][17], poly(phenylene-vinylene) [18], and poly(p-phenylene) [19], have been chosen to design this type of multivalent glycoconjugates. One approach to such a system is represented by the polymerization or copolymerization of well-defined carbohydrate-carrying monomers through classical C-C coupling reactions [10,13,[15][16][17][18]. Another synthetic approach is the so-called postpolymerization functionalization, in which sugar moieties are grafted to the backbones after the formation of conjugated polymers [11,12,14,19].…”