Synthesis and properties of triplex-forming oligonucleotides containing 2'-O-(2-methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine

Bioorg Med Chem. 2010 Sep 1;18(17):6389-97. doi: 10.1016/j.bmc.2010.07.005. Epub 2010 Jul 30.

Abstract

2'-O-(2-Methoxyethyl)-5-(3-aminoprop-1-ynyl)-uridine phosphoramidite (MEPU) has been synthesized from d-ribose and 5-iodouracil and incorporated into triplex-forming oligonucleotides (TFOs) by automated solid-phase oligonucleotide synthesis. The TFOs gave very high triplex stability with their target duplexes as measured by ultraviolet/fluorescence melting and DNase I footprinting. The incorporation of MEPU into TFOs renders them resistant to degradation by serum nucleases.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • DNA Footprinting
  • Humans
  • Nucleic Acid Conformation
  • Oligodeoxyribonucleotides / chemical synthesis
  • Oligodeoxyribonucleotides / chemistry*
  • Structure-Activity Relationship
  • Uridine / analogs & derivatives*
  • Uridine / chemistry*

Substances

  • Oligodeoxyribonucleotides
  • Uridine