Trianguleniums as Optical Probes for G-Quadruplexes: A Photophysical, Electrochemical, and Computational Study

Chemistry : a European Journal
Arun ShivalingamRamon Vilar

Abstract

Nucleic acids can adopt non-duplex topologies, such as G-quadruplexes in vitro. Yet it has been challenging to establish their existence and function in vivo due to a lack of suitable tools. Recently, we identified the triangulenium compound DAOTA-M2 as a unique fluorescence probe for such studies. This probe's emission lifetime is highly dependent on the topology of the DNA it interacts with opening up the possibility of carrying out live-cell imaging studies. Herein, we describe the origin of its fluorescence selectivity for G-quadruplexes. Cyclic voltammetry predicts that the appended morpholino groups can act as intra- molecular photo-induced electron transfer (PET) quenchers. Photophysical studies show that a delicate balance between this effect and inter-molecular PET with nucleobases is key to the overall fluorescence enhancement observed upon nucleic acid binding. We utilised computational modelling to demonstrate a conformational dependence of intra-molecular PET. Finally, we performed orthogonal studies with a triangulenium compound, in which the morpholino groups were removed, and demonstrated that this change inverts triangulenium fluorescence selectivity from G-quadruplex to duplex DNA, thus highlighting the import...Continue Reading

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Citations

Apr 27, 2018·Chemistry : a European Journal·Irene Hernández DelgadoJérôme Lacour
Jan 27, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Delphine Naud-MartinMarie-Paule Teulade-Fichou
Sep 2, 2017·Current Protocols in Cell Biology·Souheila AmorDavid Monchaud
Sep 9, 2020·Physical Chemistry Chemical Physics : PCCP·Irina BarsukÉric Brémond
Sep 22, 2020·MedChemComm·Euphemia LeungJóhannes Reynisson

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Methods Mentioned

BETA
fluorescence spectroscopy
fluorescence lifetime imaging
Fluorescence
light scattering

Software Mentioned

MatLab
IEFPCM
ADOTA
TOTA

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