Acridone-tagged DNA as a new probe for DNA detection by fluorescence resonance energy transfer and for mismatch DNA recognition

Bioorg Med Chem. 2008 Jul 15;16(14):7013-20. doi: 10.1016/j.bmc.2008.05.050. Epub 2008 May 29.

Abstract

Acridone is highly fluorescent and stable against photodegradation, oxidation, and heat. It is also a small molecule with no charge, making it a promising fluorescent agent for use in a DNA probe. Thus, we have prepared 5'-terminal acridone-labeled DNAs by post-modification, and have examined their photophysical properties and their use as donors for a fluorescence resonance energy transfer (FRET) system in combination with a 3'-terminal dabcyl-tagged DNA as an acceptor, which can detect the target DNA by emission-quenching caused by FRET. The FRET with an acridone and dabcyl pair has been found to complement that with fluorescence and dabcyl and other fluorescence-quencher pairs. Significant amounts of quenching of the acridone emissions by guanine in the DNA were observed when guanine was close to acridone, which can be applied as a quencher-free probe for the detection of special sequence of DNA. The DNA bearing acridone at the C5 position of inner thymidine could discriminate the opposite T-T base mismatch, although enhancement of discrimination ability is needed for the practical use of SNP typing.

MeSH terms

  • Acridines*
  • Acridones
  • Base Pair Mismatch*
  • DNA / genetics*
  • DNA Mutational Analysis / methods
  • DNA Probes / chemistry*
  • Fluorescence Resonance Energy Transfer*
  • Fluorescent Dyes
  • Guanine

Substances

  • Acridines
  • Acridones
  • DNA Probes
  • Fluorescent Dyes
  • Guanine
  • acridone
  • DNA