Fluorescent sensing of triphosphate nucleotides via anthracene derivatives

J Org Chem. 2011 May 20;76(10):3805-11. doi: 10.1021/jo2000836. Epub 2011 Apr 29.

Abstract

A nucleotide is composed of a nucleobase, a five-carbon sugar, and phosphate groups. Recognition of these three sites can provide useful information for the development of selective fluorescent receptors for a specific nucleotide. In this paper, anthracene derivatives with two imidazolium groups at the 1,8- and 9,10-positions, quaternary ammonium groups, or the boronic acid group were examined for the recognition of nucleotides, such as ATP, GTP, CTP, TTP, UTP, ADP, and AMP, via fluorescence changes. The anthracene group provides the interaction between the bases of the nucleotides. The imidazolium and quaternary ammonium groups induce hydrogen bonding interactions with the phosphate groups of the nucleotides. The boronic acid group can interact with the ribose of the nucleotides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthracenes / chemical synthesis
  • Anthracenes / chemistry*
  • Chemistry Techniques, Analytical / instrumentation*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Hydrogen Bonding
  • Imidazoles / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Nucleotides / analysis*
  • Nucleotides / chemistry*
  • Polyphosphates / chemistry*
  • Quaternary Ammonium Compounds / chemistry

Substances

  • Anthracenes
  • Fluorescent Dyes
  • Imidazoles
  • Nucleotides
  • Polyphosphates
  • Quaternary Ammonium Compounds
  • imidazole
  • anthracene
  • triphosphoric acid