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Further Dimensions for Sensing in Biofluids: Distinguishing Bioorganic Analytes by the Salt-Induced Adaptation of a Cucurbit[7]uril-Based Chemosensor

Hu, Changming ORCID iD icon 1; Jochmann, Thomas; Chakraborty, Papri 1,2; Neumaier, Marco ORCID iD icon 1; Levkin, Pavel A. ORCID iD icon 3; Kappes, Manfred M. 1,2; Biedermann, Frank 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)


Insufficient binding selectivity of chemosensors often renders biorelevant metabolites indistinguishable by the widely used indicator displacement assay. Array-based chemosensing methods are a common workaround but require additional effort for synthesizing a chemosensor library and setting up a sensing array. Moreover, it can be very challenging to tune the inherent binding preference of macrocyclic systems such as cucurbit[n]urils (CBn) by synthetic means. Using a novel cucurbit[7]uril-dye conjugate that undergoes salt-induced adaptation, we now succeeded in distinguishing 14 bioorganic analytes from each other through the facile stepwise addition of salts. The salt-specific concentration-resolved emission provides additional information about the system at a low synthetic effort. We present a data-driven approach to translate the human-visible curve differences into intuitive pairwise difference measures. Ion mobility experiments combined with density functional theory calculations gave further insights into the binding mechanism and uncovered an unprecedented ternary complex geometry for CB7. TThis work introduces the non-selectively binding, salt-adaptive cucurbit[n]uril system for sensing applications in biofluids such as urine, saliva, and blood serum.

Verlagsausgabe §
DOI: 10.5445/IR/1000150028
Veröffentlicht am 22.08.2022
DOI: 10.1021/jacs.2c01520
Zitationen: 30
Web of Science
Zitationen: 27
Zitationen: 33
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 27.07.2022
Sprache Englisch
Identifikator ISSN: 1520-5126, 0002-7863, 1943-2984
KITopen-ID: 1000150028
HGF-Programm 43.31.02 (POF IV, LK 01) Devices and Applications
Erschienen in Journal of the American Chemical Society
Verlag American Chemical Society (ACS)
Band 144
Heft 29
Seiten 13084–13095
Vorab online veröffentlicht am 18.07.2022
Nachgewiesen in Web of Science
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