Second-Generation Fluorescent Quadracyclic Adenine Analogues: Environment-Responsive Probes with Enhanced Brightness
Second-Generation Fluorescent Quadracyclic Adenine Analogues: Environment-Responsive Probes with Enhanced Brightness
复制标题
DOI：
10.1002/chem.201405759
复制
发表时间：
2015-03-02
影响因子：
4.3
通讯作者：
Wilhelmsson, L. Marcus
中科院分区：
文献类型：
--
作者：
Dumat, Blaise;Bood, Mattias;Wilhelmsson, L. Marcus
荧光碱基类似物包括一组越来越重要的分子，用于研究核酸结构、动力学以及与其他分子的相互作用。在此，我们报告了四个新的推定的四环腺嘌呤类似物的量子化学计算辅助设计，合成和表征。以Suzuki-Miyaura偶联反应为关键步骤，从一个共同的中间体出发，通过两步反应合成了这些化合物。其中两种化合物，qAN 1和qAN 4，在水中分别显示1700和2300的亮度（λ Phi（F）），并在酸性条件下表现为波长比pH探针。另外两个，qAN 2和qAN 3，显示较低的亮度，但表现出极性敏感的双带发射，可以证明是有用的调查DNA-蛋白质或药物相互作用引起的DNA结构变化。四种qAN是非常有前途的微环境敏感性荧光腺嘌呤类似物，其对于此类化合物显示出相当大的亮度。
Fluorescent base analogues comprise a group of increasingly important molecules for the investigation of nucleic acid structure, dynamics, and interactions with other molecules. Herein, we report on the quantum chemical calculation aided design, synthesis, and characterization of four new putative quadracyclic adenine analogues. The compounds were efficiently synthesized from a common intermediate through a two-step pathway with the Suzuki-Miyaura coupling as the key step. Two of the compounds, qAN1 and qAN4, display brightnesses (epsilon Phi(F)) of 1700 and 2300, respectively, in water and behave as wavelength-ratiometric pH probes under acidic conditions. The other two, qAN2 and qAN3, display lower brightnesses but exhibit polarity-sensitive dual-band emissions that could prove useful to investigate DNA structural changes induced by DNA-protein or -drug interactions. The four qANs are very promising microenvironment- sensitive fluorescent adenine analogues that display considerable brightness for such compounds.