Journal
CHEMICAL SCIENCE
Volume 11, Issue 41, Pages 11142-11153Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0sc03079a
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Funding
- China Scholarship Council [201806920036]
- Deutsche Forschungsgemeinscha [SPP 1807, BI-1805/2-1]
- German Academic Exchange Service (DAAD)
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Non-covalent chemosensing ensembles of cucurbit[n]urils (CBn) have been widely used in proof-ofconcept 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- (10x PBS buffer) and salinestable (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 superset of 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 CBnIdye reporter pairs, the conjugate chemosensors can also operate through a S(N)2-type guest-dye exchange mechanism, which shortens assay times and opens new avenues for tailoring analyte-selectivity.
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