Abstract: Pyrene-based cyclophanes have been synthesized with the aim to realize a bellows-type sensing mechanism for the ratiometric detection of nucleotide concentrations in a buffered aqueous solution. The sensing mechanism involves the encapsulation of a nucleobase between two pyrene rings, which affects the monomer-excimer equilibrium of the receptor in the excited state. The nature of the spacer and its connection pattern to pyrene rings have been varied to achieve high selectivity for ATP. The 1,8-substituted pyrene-based cyclophane with the 2,2’-diaminodiethylamine spacer demonstrates the best selectivity for ATP showing a 50-fold increase in the monomer-excimer emission ratio upon saturation with the nucleotide. The receptor can detect ATP within the biological concentrations range over a wide pH range. NMR and spectroscopic studies have revealed the importance of hydrogen bonding and stacking interactions for achieving a required receptor selectivity. The probe has been successfully applied for the real-time monitoring of creatine kinase activity. © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.

Cite: Agafontsev A.M. , Shumilova T.A. , Oshchepkov A.S. , Hampel F. , Kataev E.A.
Ratiometric Detection of ATP by Fluorescent Cyclophanes with Bellows-Type Sensing Mechanism
Chemistry - A European Journal. 2020. V.26. N44. P.9991-9997. DOI: 10.1002/chem.202001523 WOS Scopus РИНЦ OpenAlex

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Dates:

Published online:	Jul 16, 2020
Published print:	Aug 6, 2020

Identifiers:

Web of science:	WOS:000548592000001
Scopus:	2-s2.0-85088019316
Elibrary:	45459696
OpenAlex:	W3033070830

Citing:

DB	Citing
Scopus	28
Web of science	27
OpenAlex	34

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