Potent triple helix stabilization by 5',3'-modified triplex-forming oligonucleotides

Chembiochem. 2009 Jul 20;10(11):1839-51. doi: 10.1002/cbic.200900232.

Abstract

Anthraquinone and pyrene analogues attached to the 3' and/or 5' termini of triplex-forming oligonucleotides (TFOs) by various linkers increased the stability of parallel triple helices. The modifications are simple to synthesize and can be introduced during standard solid-phase oligonucleotide synthesis. Potent triplex stability was achieved by using doubly modified TFOs, which in the most favourable cases gave an increase in melting temperature of 30 degrees C over the unmodified counterparts and maintained their selectivity for the correct target duplex. Such TFOs can produce triplexes with melting temperatures of 40 degrees C at pH 7 even though they do not contain any triplex-stabilizing base analogues. These studies have implications for the design of triplex-forming oligonucleotides for use in biology and nanotechnology.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemical synthesis
  • Amines / chemistry
  • Anthraquinones / chemical synthesis
  • Anthraquinones / chemistry*
  • Base Sequence
  • DNA / chemistry*
  • Nucleic Acid Conformation
  • Oligonucleotides / chemistry*
  • Pyrenes / chemical synthesis
  • Pyrenes / chemistry*
  • Transition Temperature
  • Ultraviolet Rays

Substances

  • Amines
  • Anthraquinones
  • Oligonucleotides
  • Pyrenes
  • triplex DNA
  • DNA