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

Hu, C. ORCID iD icon 1; Grimm, L. 1; Prabodh, A. ORCID iD icon 1; Baksi, A. 2; Siennicka, A. 1; Levkin, P. A. ORCID iD icon 3; Kappes, M. M. 2; Biedermann, F. 1
1 Institut für Nanotechnologie (INT), Karlsruher Institut für Technologie (KIT)
2 Institut für Physikalische Chemie (IPC), Karlsruher Institut für Technologie (KIT)
3 Institut für Biologische und Chemische Systeme (IBCS), Karlsruher Institut für Technologie (KIT)


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 S$_{N}$2-type guest–dye exchange mechanism, which shortens assay times and opens new avenues for tailoring analyte-selectivity.

Verlagsausgabe §
DOI: 10.5445/IR/1000126491
Veröffentlicht am 22.11.2020
DOI: 10.1039/d0sc03079a
Zitationen: 28
Web of Science
Zitationen: 29
Zitationen: 31
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Nanotechnologie (INT)
Institut für Physikalische Chemie (IPC)
Publikationstyp Zeitschriftenaufsatz
Publikationsdatum 07.11.2020
Sprache Englisch
Identifikator ISSN: 2041-6520, 2041-6539
KITopen-ID: 1000126491
HGF-Programm 43.21.04 (POF III, LK 01) Molecular Engineering
Weitere HGF-Programme 47.01.01 (POF III, LK 01) Biol.Netzwerke u.Synth.Regulat. ITG+ITC
Erschienen in Chemical science
Verlag Royal Society of Chemistry (RSC)
Band 11
Heft 41
Seiten 11142-11153
Vorab online veröffentlicht am 22.09.2020
Nachgewiesen in Dimensions
Web of Science
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