Okamoto Akimitsu, Tainaka Kazuki, Fujiwara Yoshimasa
Department of Synthetic Chemistry and Biological Chemistry, Faculty of Engineering, Kyoto University, Kyoto 615-8510, Japan.
J Org Chem. 2006 Apr 28;71(9):3592-8. doi: 10.1021/jo060168o.
The fluorophore, Nile Red, effectively works as a polarity-sensitive fluorescence probe. We have designed a new nucleoside modified by Nile Red for examining the change in the polarity of the microenvironment surrounding DNA. We synthesized a Nile Red nucleoside (1), formed by replacing nucleobases with Nile Red, through the coupling of a 2-hydroxylated Nile Red derivative and 1,2-dideoxyglycan. This nucleoside showed a high solvatofluorochromicity. The fluorescence of 1 incorporated into DNA was greatly shifted to shorter wavelength by the addition of beta-cyclodextrin. The photophysical function of the Nile Red nucleoside will be a good optical indicator for monitoring the change in the micropolarity properties at a specific site on target sequences with interaction between DNA and DNA-binding molecules.
荧光团尼罗红可有效用作极性敏感荧光探针。我们设计了一种由尼罗红修饰的新型核苷，用于检测DNA周围微环境极性的变化。我们通过2-羟基化尼罗红衍生物与1,2-二脱氧糖苷的偶联，合成了一种用尼罗红取代核苷酸碱基形成的尼罗红核苷（1）。该核苷表现出高溶剂化荧光变色性。通过添加β-环糊精，掺入DNA中的1的荧光大大移向较短波长。尼罗红核苷的光物理功能将是一种很好的光学指示剂，用于监测目标序列上特定位点的微极性性质变化以及DNA与DNA结合分子之间的相互作用。
