Institut de Chimie de Nice, CNRS UMR 7272, Université Côte d'Azur, Parc Valrose, CEDEX 2, 06108 Nice, France.
Molecules. 2022 Mar 31;27(7):2267. doi: 10.3390/molecules27072267.
The intensive research for hybridization probes based on organic molecules with fluorogenic properties is currently attracting particular attention due to their potential to efficiently recognize different DNA conformations and the local environment. However, most established organic chromophores do not meet the requirements of this task, as they do not exhibit good brightness in aqueous buffer media, develop aggregation and/or are not easily conjugated to oligodeoxynucleotides (ODNs) while keeping their photophysics intact. Herein, an important modification strategy was employed for a well-known fluorophore, 2-(4-(diethylamino)phenyl)-3-hydroxychromone (). Although this push-pull dye absorbs intensively in the visible range and shows emission with large Stokes shifts in all organic solvents, it is strongly quenched in water. This Achilles' heel prompted us to implement a new strategy to obtain a series of dyes that retain all the photophysical features of in water, conjugate readily with oligonucleotides, and furthermore demonstrate sensitivity to hydration, thus paving the way for a high-performance fluorogenic DNA hybridization probe.
目前，基于具有荧光性质的有机分子的杂交探针的深入研究引起了人们的特别关注，因为它们有可能有效地识别不同的 DNA 构象和局部环境。然而，大多数已建立的有机生色团不符合这一任务的要求，因为它们在水性缓冲介质中不具有良好的亮度，会发生聚集和/或不易与寡脱氧核苷酸 (ODN) 缀合，同时保持其光物理性质完整。在这里，采用了一种重要的修饰策略来修饰一种著名的荧光团，2-(4-(二乙氨基)苯基)-3-羟基色酮()。尽管这种推拉染料在可见光范围内强烈吸收，并在所有有机溶剂中显示出大斯托克斯位移的发射，但它在水中强烈猝灭。这个致命弱点促使我们实施了一项新策略，以获得一系列保留在水中的所有光物理特征的染料，易于与寡核苷酸缀合，并且对水合作用具有敏感性，从而为高性能荧光 DNA 杂交探针铺平了道路。
