Department of Chemistry, BK School of Molecular Science, Pohang University of Science and Technology, Pohang 790-784, South Korea.
Org Biomol Chem. 2013 Sep 14;11(34):5605-14. doi: 10.1039/c3ob41222a.
With the goal of developing a fluorescent nucleoside sensitive to its environment, in this study we synthesized (DNS)C, a novel modified 2'-deoxycytidine bearing a 5-(dimethylamino)naphthalene-1-sulfonyl (dansyl) moiety at the N4 position, and tested its properties in monomeric and oligomeric states. (DNS)C undergoes intramolecular photoinduced electron transfer between its dansyl and cytosine units, resulting in remarkable changes in fluorescence that depend on the choice of solvent. In addition, the fluorescence behavior and thermal stability of oligonucleotides containing (DNS)C are dependent on the nature of the flanking and neighboring bases. Notably, (DNS)C exhibits fluorescence enhancement only in fully matched duplex DNA containing a GGG triad sequence. The environmental sensitivity of (DNS)C can be exploited as a fluorescence tool for monitoring the interactions of DNA with other biomolecules, including DNA, RNA, and proteins.
为了开发一种对环境敏感的荧光核苷，本研究合成了（DNS）C，这是一种新型的修饰 2'-脱氧胞苷，在 N4 位带有 5-(二甲氨基)萘-1-磺酰基（丹磺酰基）部分。并在单体和寡聚体状态下测试了其性质。（DNS）C 在其丹磺酰基和胞嘧啶单元之间发生分子内光诱导电子转移，导致荧光发生显著变化，这取决于溶剂的选择。此外，含有（DNS）C 的寡核苷酸的荧光行为和热稳定性取决于侧翼和相邻碱基的性质。值得注意的是，（DNS）C 仅在含有 GGG 三核苷酸序列的完全匹配的双链 DNA 中表现出荧光增强。（DNS）C 的环境敏感性可被用作荧光工具，用于监测 DNA 与其他生物分子（包括 DNA、RNA 和蛋白质）的相互作用。
