Ratiometric Detection of ATP by Fluorescent Cyclophanes with Bellows-Type Sensing Mechanism

Ratiometric Detection of ATP by Fluorescent Cyclophanes with Bellows-Type Sensing Mechanism Full article

Journal

Chemistry - A European Journal
ISSN: 0947-6539 , E-ISSN: 1521-3765

Output data

Year: 2020, Volume: 26, Number: 44, Pages: 9991-9997 Pages count : 7 DOI: 10.1002/chem.202001523

Tags

cyclophane; fluorescence sensing; host-guest chemistry; macrocycle; nucleotide recognition

Authors

Agafontsev A.M. ^1,2 , Shumilova T.A. ² , Oshchepkov A.S. ² , Hampel F. ³ , Kataev E.A. ³

Affiliations

1	(Scopus) N. N. Vorozhtsov Institute of Organic Chemistry SB RAS, 9th Lavrentiev Avenue, Novosibirsk, 630090, Russian Federation
2	(Scopus) Institute of Chemistry, Technische Universit?t Chemnitz, Chemnitz, 09107, Germany
3	(Scopus) Department of Chemistry and Pharmacy, University of Erlangen-N?rnberg, Nikolaus-Fiebiger-Str. 10, Erlangen, 91058, Germany

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.

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

Full text from publisher

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

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