期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 22, 期 12, 页码 4129-4139出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201504099
关键词
DNA; optical probes; nucleic acids; quadruplexes; triangulenium
资金
- UK's Engineering and Physical Sciences Research Council (EPSRC) [EP/I003983/1, EP/H005285/1]
- Engineering and Physical Sciences Research Council [EP/I003983/1, EP/K039946/1, EP/H005285/1, 1231179] Funding Source: researchfish
- EPSRC [EP/H005285/1, EP/K039946/1, EP/I003983/1] Funding Source: UKRI
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 importance of fine tuning the molecular structure not only for target affinity, but also for fluorescence response.
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