Binding and Sensing Properties of a Hybrid Naphthalimide-Pyrene Aza-Cyclophane towards Nucleotides in an Aqueous Solution
Agafontsev AM, Oshchepkov AS, Shumilova TA, Kataev E (2021)
Publication Type: Journal article
Publication year: 2021
Journal
Book Volume: 26
Journal Issue: 4
DOI: 10.3390/molecules26040980
Abstract
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.
Authors with CRIS profile
Involved external institutions
Technische Universität Chemnitz
Germany (DE)
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry (NIOCH SB RAS) / Новосибирский институт органической химии им. Н.Н. Ворожцова
Russian Federation (RU)
Germany (DE)
N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry (NIOCH SB RAS) / Новосибирский институт органической химии им. Н.Н. Ворожцова
Russian Federation (RU)
How to cite
APA:
Agafontsev, A.M., Oshchepkov, A.S., Shumilova, T.A., & Kataev, E. (2021). Binding and Sensing Properties of a Hybrid Naphthalimide-Pyrene Aza-Cyclophane towards Nucleotides in an Aqueous Solution. Molecules, 26(4). https://doi.org/10.3390/molecules26040980
MLA:
Agafontsev, Aleksandr M., et al. "Binding and Sensing Properties of a Hybrid Naphthalimide-Pyrene Aza-Cyclophane towards Nucleotides in an Aqueous Solution." Molecules 26.4 (2021).
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