Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Korea.
Org Biomol Chem. 2011 Dec 21;9(24):8340-5. doi: 10.1039/c1ob06344h. Epub 2011 Nov 3.
Naphthoimidazolium groups can form unique ionic hydrogen bonds with anions as imidazolium moieties, and in addition, they are fluorescent, so no further elaborative synthesis is needed to introduce a fluorescent group. In this paper, three naphthoimidazolium derivatives were synthesized and studied for the recognition of nucleotides. Compound 1 composed of a single naphthoimidazolium group and quaternary ammonium group did not show any significant fluorescent changes with various anions and nucleotides, such as ATP, GTP, CTP, TTP, UTP, ADP and AMP. A tripodal compound 3 bearing three naphthoimidazolium groups and three quaternary ammonium groups, respectively, showed large fluorescence enhancements with UTP, CTP and TTP and moderate fluorescence enhancements with ATP and pyrophosphate and a fluorescence quenching effect with GTP. On the other hand, compound 2 bearing two naphthoimidazolium groups and two quaternary ammonium groups displayed a selective fluorescence enhancement with ATP and a selective fluorescence quenching effect with GTP in 100% aqueous solution.
萘并咪唑基团可以与阴离子形成独特的离子氢键，就像咪唑部分一样，此外，它们还具有荧光性，因此无需进一步的精细合成来引入荧光团。在本文中，我们合成了三种萘并咪唑衍生物，并研究了它们对核苷酸的识别性能。由单个萘并咪唑基团和季铵基团组成的化合物 1 与各种阴离子和核苷酸（如 ATP、GTP、CTP、TTP、UTP、ADP 和 AMP）没有表现出任何明显的荧光变化。分别带有三个萘并咪唑基团和三个季铵基团的三足化合物 3 与 UTP、CTP 和 TTP 有较大的荧光增强，与 ATP 和焦磷酸有中等的荧光增强，与 GTP 有荧光猝灭效应。另一方面，带有两个萘并咪唑基团和两个季铵基团的化合物 2 在 100%水溶液中对 ATP 表现出选择性的荧光增强，对 GTP 则表现出选择性的荧光猝灭效应。
