Detection of dsDNA with [1,3]Dioxolo[4,5-f]benzodioxol (DBD) Dyes

Chemistry. 2018 Oct 26;24(60):16183-16190. doi: 10.1002/chem.201804057. Epub 2018 Oct 4.

Abstract

DBD fluorescent dyes have proven to be useful in numerous applications. To widen the range of biological applications, we propose three different types of DBD molecules that have been modified in such a way that DNA interaction becomes probable. After the successful synthesis of all three compounds, we tested their fluorescent properties and their DNA binding abilities. Two of the three probes exhibit an interaction with dsDNA with subsequent fluorescence enhancement. The determined binding constants of the two new DNA dyes are comparable to other minor-groove-binding dyes. Their large Stokes shifts and their long fluorescent lifetimes are outstanding features of these dyes.

Keywords: DNA recognition; dyes/pigments; fluorescent probes; heterocycles; scatchard plot.

MeSH terms

  • Benzodioxoles / chemistry*
  • Biosensing Techniques / methods
  • DNA / analysis*
  • Fluorescent Dyes / chemistry*
  • Intercalating Agents / chemistry
  • Molecular Structure
  • Spectrometry, Fluorescence

Substances

  • Benzodioxoles
  • Fluorescent Dyes
  • Intercalating Agents
  • DNA