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Issue 41, 2020
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Covalent cucurbit[7]uril–dye conjugates for sensing in aqueous saline media and biofluids

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Abstract

Non-covalent chemosensing ensembles of cucurbit[n]urils (CBn) have been widely used in proof-of-concept sensing applications, but they are prone to disintegrate in saline media, e.g. biological fluids. We show here that covalent cucurbit[7]uril–indicator dye conjugates are buffer- (10× PBS buffer) and saline-stable (up to 1.4 M NaCl) and allow for selective sensing of Parkinson's drug amantadine in human urine and saliva, where the analogous non-covalent CB7⊃dye complex is dysfunctional. The in-depth analysis of the covalent host–dye conjugates in the gas-phase, and deionized versus saline aqueous media revealed interesting structural, thermodynamic and kinetic effects that are of general interest for the design of CBn-based supramolecular chemosensors and systems. This work also introduces a novel high-affinity indicator dye for CB7 through which fundamental limitations of indicator displacement assays (IDA) were exposed, namely an impractical slow equilibration time. Unlike non-covalent CBn⊃dye reporter pairs, the conjugate chemosensors can also operate through a SN2-type guest–dye exchange mechanism, which shortens assay times and opens new avenues for tailoring analyte-selectivity.

Graphical abstract: Covalent cucurbit[7]uril–dye conjugates for sensing in aqueous saline media and biofluids

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Supplementary files

Article information


Submitted
01 Jun 2020
Accepted
16 Sep 2020
First published
22 Sep 2020

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2020,11, 11142-11153
Article type
Edge Article

Covalent cucurbit[7]uril–dye conjugates for sensing in aqueous saline media and biofluids

C. Hu, L. Grimm, A. Prabodh, A. Baksi, A. Siennicka, P. A. Levkin, M. M. Kappes and F. Biedermann, Chem. Sci., 2020, 11, 11142
DOI: 10.1039/D0SC03079A

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