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首页> 外文期刊>Chemistry: A European journal >Trianguleniums as Optical Probes for G-Quadruplexes: APhotophysical, Electrochemical, and Computational Study
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Trianguleniums as Optical Probes for G-Quadruplexes: APhotophysical, Electrochemical, and Computational Study

机译：Triangulenium作为G-四链体的光学探针：光物理，电化学和计算研究

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摘要

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.
机译：核酸可以采用非双链体拓扑，例如体外的G-四链体。然而，由于缺乏合适的工具，在体内建立它们的存在和功能一直是一个挑战。最近，我们确定了三角菊化合物DAOTA-M2作为此类研究的独特荧光探针。该探针的发射寿命在很大程度上取决于与它相互作用的DNA的拓扑结构，从而开启了进行活细胞成像研究的可能性。在本文中，我们描述了其对G-四链体的荧光选择性的起源。循环伏安法预测，附加的吗啉代基团可以充当分子内光致电子转移（PET）猝灭剂。光物理研究表明，这种作用与分子间PET与核碱基之间的微妙平衡是观察到核酸结合后整体荧光增强的关键。我们利用计算模型来证明分子内PET的构象依赖性。最后，我们对其中去除了吗啉代基团的三角化合物进行了正交研究，并证明了这种变化将三角荧光的选择性从G-四链体转变为双链体DNA，从而强调了微调分子结构的重要性不仅限于靶标亲和力，还用于荧光反应。

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