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A Selective Cucurbit[8]uril‐Peptide Beacon Ensemble for the Ratiometric Fluorescence Detection of Peptides
Author(s) -
Maity Debabrata,
Assaf Khaleel I.,
Sicking Wilhelm,
Hirschhäuser Christoph,
Nau Werner M.,
Schmuck Carsten
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901037
Subject(s) - pyrene , excimer , chemistry , fluorescence , supramolecular chemistry , monomer , peptide , amphiphile , host–guest chemistry , combinatorial chemistry , cucurbituril , photochemistry , biophysics , organic chemistry , biochemistry , copolymer , molecule , polymer , physics , quantum mechanics , biology
A convenient supramolecular strategy for constructing a ratiometric fluorescent chemosensing ensemble, consisting of a macrocyclic host (cucurbit[8]uril CB[8]), and a pyrene‐tagged amphiphilic peptide beacon (AP 1), is reported. AP 1 unfolds upon encapsulation of the pyrene termini into the hydrophobic CB[8] cavity. This changes pyrene excimer to monomer emission. Substrates with higher affinity for the CB[8] cavity can displace AP 1 from the ensemble. The released AP 1 folds again to form a pyrene excimer, which allows for the ratiometric fluorescence monitoring of the substrate. In this report, the ensemble capacity for ratiometric fluorescence monitoring of biological substrates, such as amino acid derivatives, specific peptides, and proteins, in aqueous media is demonstrated.