Issue 6, 2015

Preparation of luminescent chemosensors by post-functionalization of vesicle surfaces

Abstract

Surface-reactive luminescent vesicles were prepared by self-assembly of phospholipids, amphiphilic maleimides and fluorophors in aqueous solution. Those preformed liposomes were functionalized with various thiolated receptor units using a thiol-click reaction. As recognition elements, a bis-Zn2+-cyclen derivative for the detection of phosphate moieties or a DNA aptamer for the specific binding of the antibiotic ampicillin were utilized. A FRET-based assay revealed the close spatial proximity of the membrane-embedded dansyl molecules with the subsequently immobilized thiols, which is the origin for the signaling mechanism of the obtained vesicular sensors. Those receptor-functionalized liposomes indicate the binding of the targets to their surface by changes of the fluorescence emission properties of the membrane co-embedded carboxyfluorescein dyes. The post-functionalization concept can also be used for molecular imprinting on vesicle surfaces. The template-guided patterning of receptors based on bis-Zn2+-cyclen resulted in fluorescent sensors suitable for the specific recognition of a bivalent peptide.

Graphical abstract: Preparation of luminescent chemosensors by post-functionalization of vesicle surfaces

Supplementary files

Article information

Article type
Paper
Submitted
01 nov. 2014
Accepted
26 nov. 2014
First published
27 nov. 2014
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 1690-1699

Author version available

Preparation of luminescent chemosensors by post-functionalization of vesicle surfaces

A. Müller and B. König, Org. Biomol. Chem., 2015, 13, 1690 DOI: 10.1039/C4OB02327G

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