Department of Chemistry and Nano Science and Department of Bioinspired Science, Ewha Womans University, Seoul, 120-750, Korea.
J Am Chem Soc. 2009 Oct 28;131(42):15528-33. doi: 10.1021/ja906855a.
A pincer-like benzene-bridged sensor 1 with a pyrene excimer as a signal source and imidazolium as a phosphate anion receptor was synthesized and investigated for ATP sensing. A unique switch of excimer vs monomer pyrene fluorescence of 1 is observed in the presence of ATP due to the charcteristic sandwich pi-pi stacking of pyrene-adenine-pyrene. On the other hand, four other bases of nucleoside triphosphates such as GTP, CTP, UTP, and TTP can interact only from the outside with the already stabilized stacked pyrene-pyrene dimer of 1, resulting in excimer fluorescence quenching. The fluorescent intensity ratio of monomer-to-excimer for 1 upon binding with ATP (I(375)/I(487)) is much larger than that upon binding with ADP and AMP. This difference is large enough to discriminate ATP from ADP and AMP. As one of the biological applications, sensor 1 is successfully applied to the ATP staining experiments. Sensor 1 is also applied to monitor the hydrolysis of ATP and ADP by apyrase. The results indicate that 1 is a useful fluorescent sensor for investigations of ATP-relevant biological processes.
一种具有苯桥联的钳子状传感器 1，其信号源为芘二聚体，受体为咪唑鎓，用于检测磷酸根阴离子。由于腺嘌呤-芘-腺嘌呤的特征性夹心 π-π 堆积，在存在 ATP 的情况下，观察到 1 的芘单体与芘二聚体荧光的独特开关。另一方面，四种其他核苷三磷酸（如 GTP、CTP、UTP 和 TTP）只能从外部与 1 中已经稳定堆叠的芘-芘二聚体相互作用，导致芘二聚体荧光猝灭。1 与 ATP 结合时（I(375)/I(487)）的单体到二聚体的荧光强度比与 ADP 和 AMP 结合时大得多。这种差异足以区分 ATP 与 ADP 和 AMP。作为生物应用之一，传感器 1 成功地应用于 ATP 染色实验。传感器 1 还用于监测核酸外切酶对 ATP 和 ADP 的水解。结果表明，1 是一种用于研究与 ATP 相关的生物学过程的有用荧光传感器。
