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

Agafontsev AM, Shumilova TA, Oshchepkov AS, Hampel F, Kataev E (2020)

Publication Type: Journal article

Publication year: 2020

Journal

Chemistry - A European Journal Wiley

DOI: 10.1002/chem.202001523

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.

Authors with CRIS profile

Frank Hampel Lehrstuhl für Organische Chemie I Evgeny Kataev Lehrstuhl für Organische Chemie I

Involved external institutions

N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry (NIOCH SB RAS) / Новосибирский институт органической химии им. Н.Н. Ворожцова RU Russian Federation (RU) Technische Universität Chemnitz DE Germany (DE)

How to cite

APA:

Agafontsev, A.M., Shumilova, T.A., Oshchepkov, A.S., Hampel, F., & Kataev, E. (2020). Ratiometric Detection of ATP by Fluorescent Cyclophanes with Bellows-Type Sensing Mechanism. Chemistry - A European Journal. https://doi.org/10.1002/chem.202001523

MLA:

Agafontsev, Aleksandr M., et al. "Ratiometric Detection of ATP by Fluorescent Cyclophanes with Bellows-Type Sensing Mechanism." Chemistry - A European Journal (2020).

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