Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA

Nucleic Acids Res. 2011 May;39(10):4513-24. doi: 10.1093/nar/gkr010. Epub 2011 Jan 29.

Abstract

To increase the diversity of fluorescent base analogues with improved properties, we here present the straightforward click-chemistry-based synthesis of a novel fluorescent adenine-analogue triazole adenine (A(T)) and its photophysical characterization inside DNA. A(T) shows promising properties compared to the widely used adenine analogue 2-aminopurine. Quantum yields reach >20% and >5% in single- and double-stranded DNA, respectively, and show dependence on neighbouring bases. Moreover, A(T) shows only a minor destabilization of DNA duplexes, comparable to 2-aminopurine, and circular dichroism investigations suggest that A(T) only causes minimal structural perturbations to normal B-DNA. Furthermore, we find that A(T) shows favourable base-pairing properties with thymine and more surprisingly also with normal adenine. In conclusion, A(T) shows strong potential as a new fluorescent adenine analogue for monitoring changes within its microenvironment in DNA.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Pairing
  • Circular Dichroism
  • DNA / chemistry*
  • DNA, Single-Stranded / chemistry
  • Deoxyadenosines / chemistry*
  • Fluorescence
  • Fluorescent Dyes / chemistry*
  • Nucleic Acid Denaturation
  • Organophosphorus Compounds / chemical synthesis
  • Spectrometry, Fluorescence
  • Triazoles / chemistry*

Substances

  • 8-(1-pentyl-1H-1,2,3-triazole-4-yl)-2'-deoxyadenosine
  • DNA, Single-Stranded
  • Deoxyadenosines
  • Fluorescent Dyes
  • Organophosphorus Compounds
  • Triazoles
  • phosphoramidite
  • DNA