Binding and Sensing Properties of a Hybrid Naphthalimide-Pyrene Aza-Cyclophane towards Nucleotides in an Aqueous Solution

Binding and Sensing Properties of a Hybrid Naphthalimide-Pyrene Aza-Cyclophane towards Nucleotides in an Aqueous Solution Full article

Journal

Molecules
, E-ISSN: 1420-3049

Output data

Year: 2021, Volume: 26, Number: 4, Article number : 980, Pages count : DOI: 10.3390/molecules26040980

Tags

cyclophane; nucleotide recognition; supramolecular recognition; host– guest chemistry; fluorescent probe

Authors

Agafontsev Aleksandr M. ¹ , Oshchepkov Aleksandr S. ^2,3 , Shumilova Tatiana A. ² , Kataev Evgeny A. ³

Affiliations

1	(Данные Web of science) RAS, SB, NN Vorozhtsov Inst Organ Chem, 9th Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Tech Univ Chemnitz, Inst Chem, D-09107 Chemnitz, Germany
3	(Данные Web of science) Univ Erlangen Nurnberg, Dept Chem & Pharm, Nikolaus Fiebiger Str 10, D-91058 Erlangen, Germany

Selective recognition of nucleotides with synthetic receptors is an emerging direction to solve a series of nucleic acid-related challenges in biochemistry. Towards this goal, a new aza-cyclophane with two different dyes, naphthalimide and pyrene, connected through a triamine linker has been synthesized and studied for the ability to bind and detect nucleoside triphosphates in an aqueous solution. The receptor shows Foerster resonance energy transfer (FRET) in fluorescence spectra upon excitation in DMSO, which is diminished dramatically in the presence of water. According to binding studies, the receptor has a preference to bind ATP (adenosine triphosphate) and CTP (cytidine triphosphate) with a "turn-on" fluorescence response. Two separate emission bands of dyes allow one to detect nucleotides in a ratiometric manner in a broad concentration range of 10(-5)-10(-3) M. Spectroscopic measurements and quantum chemical calculations suggest the formation of receptor-nucleotide complexes, which are stabilized by dispersion interactions between a nucleobase and dyes, while hydrogen bonding interactions of nucleobases with the amine linkers are responsible for selectivity.

Agafontsev A.M. , Oshchepkov A.S. , Shumilova T.A. , Kataev E.A.
Binding and Sensing Properties of a Hybrid Naphthalimide-Pyrene Aza-Cyclophane towards Nucleotides in an Aqueous Solution

Molecules. 2021. V.26. N4. 980 . DOI: 10.3390/molecules26040980 WOS Scopus

Full text from publisher

Published online:

Feb 12, 2021

Web of science	WOS:000624165500001
Scopus	2-s2.0-85102697964
OpenAlex	W3131096876