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Issue 27, 2019
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Rational design and implementation of a cucurbit[8]uril-based indicator-displacement assay for application in blood serum

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Abstract

In this study, we report the first supramolecular indicator-displacement assay (IDA) based on cucurbit[n]uril (CBn) hosts that is operational in blood serum. Rational design principles for host–guest chemosensing in competitively binding media were derived through detailed mathematical simulations. It was shown that currently known CBn-based chemosensing ensembles are not suited for use in highly competitive matrices such as blood serum. Conversely, the simulations indicated that a combination of cucurbit[8]uril (CB8) and an ultra-high affinity dye would be a promising IDA reporter pair for the detection of Alzheimer's drug memantine in blood serum. Therefore, a novel class of [2.2]paracyclophane-derived indicator dyes for the host CB8 was developed that possesses one of the highest host–guest affinities (Ka > 1012 M−1 in water) known in supramolecular host–guest chemistry, and which provides a large Stokes shift (up to 200 nm). The novel IDA was then tested for the detection of memantine in blood serum in a physiologically relevant sub- to low micromolar concentration range.

Graphical abstract: Rational design and implementation of a cucurbit[8]uril-based indicator-displacement assay for application in blood serum

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Publication details

The article was received on 09 Feb 2019, accepted on 31 May 2019 and first published on 04 Jun 2019


Article type: Edge Article
DOI: 10.1039/C9SC00705A
Chem. Sci., 2019,10, 6584-6593
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Rational design and implementation of a cucurbit[8]uril-based indicator-displacement assay for application in blood serum

    S. Sinn, E. Spuling, S. Bräse and F. Biedermann, Chem. Sci., 2019, 10, 6584
    DOI: 10.1039/C9SC00705A

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