Dye-conjugated complementary lipophilic nucleosides as useful probes to study association processes by fluorescence resonance energy transfer,Organic & Biomolecular Chemistry

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Dye-conjugated complementary lipophilic nucleosides as useful probes to study association processes by fluorescence resonance energy transfer
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-08-31 00:00:00 , DOI: 10.1039/c7ob01930k
M. J. Mayoral _{1,

2,

3,

4,

5} , J. Camacho-García _{1,

2,

3,

4,

5} , E. Magdalena-Estirado _{1,

2,

3,

4,

5} , M. Blanco-Lomas _{1,

2,

3,

4,

5} , E. Fadaei _{1,

2,

3,

4,

5} , C. Montoro-García _{1,

2,

3,

4,

5} , D. Serrano-Molina _{1,

2,

3,

4,

5} , D. González-Rodríguez _{1,

2,

3,

4,

5}

Affiliation

Modern supramolecular chemistry relies on the combination of diverse analytical techniques that can provide complementary information on complex self-assembly landscapes. Among them, resonance energy transfer, monitored by fluorescence emission spectroscopy, arises as a sensitive and convenient phenomenon to report binding intermolecular interactions. The use of molecular probes labelled with suitable complementary energy-transfer pairs can provide valuable information about the thermodynamics, kinetics and self-sorting characteristics of a particular self-assembled system. The objective of this work is to generate a set of nucleoside FRET probes that can be reliably employed to prove and analyse quantitatively H-bonding interactions between complementary Watson–Crick pairs. We first describe the preparation of a set of lipophilic nucleosides that are linked to a π-conjugated functional fragment. The bases include guanosine and 2-aminoadenosine as purine heterocycles, and cytidine and uridine as complementary pyrimidine bases. The π-conjugated moiety comprises either a short phenylene-ethynylene oligomer, a bithiophene, or a BODIPY dye. We then demonstrate that the last two chromophores constitute an energy donor–acceptor couple and that donor emission quenching can be related to the ratio of molecules bound to the complementary acceptor pair. Hence, fluorescence spectroscopy in combination with resonance energy transfer, is shown here to be a useful tool to study and quantify the association and self-sorting events between complementary and non-complementary nucleosides in apolar aromatic solvents, where the binding strength is considerably high, and sensitive techniques that employ low concentrations are demanded.

中文翻译：

染料共轭互补亲脂核苷作为有用探针，可通过荧光共振能量转移研究缔合过程

现代超分子化学依赖于多种分析技术的结合，这些技术可以提供有关复杂自组装态势的补充信息。其中，通过荧光发射光谱法监测的共振能量转移作为报告结合分子间相互作用的敏感而方便的现象而出现。使用标记有合适的互补能量转移对的分子探针可以提供有关特定自组装系统的热力学，动力学和自分类特性的有价值的信息。这项工作的目的是生成一套核苷FRET探针，可以可靠地用于证明和定量分析互补的Watson-Crick对之间的H键相互作用。我们首先描述一组亲脂性核苷的制备，该亲脂性核苷与π-共轭的功能性片段相连。该碱基包括鸟嘌呤和2-氨基腺苷作为嘌呤杂环，以及胞苷和尿苷作为互补嘧啶碱基。π-共轭部分包含短亚苯基-亚乙炔基低聚物，联噻吩或BODIPY染料。然后，我们证明了最后两个生色团构成了一个能量供体-受体对，并且供体发射猝灭可能与结合到互补受体对上的分子的比例有关。因此，荧光光谱与共振能量转移相结合，是研究和量化非极性芳族溶剂中互补和非互补核苷之间缔合和自分选事件的有用工具，

更新日期：2017-09-20

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