Synthesis and properties of cationic 2'-O-[N-(4-aminobutyl)carbamoyl] modified oligonucleotides

Bioorg Med Chem Lett. 2012 Apr 1;22(7):2470-3. doi: 10.1016/j.bmcl.2012.02.012. Epub 2012 Feb 13.

Abstract

2'-O-[N-(4-Aminobutylcarbamoyl)]uridine (U(abcm)) was synthesized and incorporated into oligonucleotides. The oligonucleotides incorporating U(abcm) formed more stable duplexes with their complementary and mismatched RNAs than those containing 2'-O-carbamoyluridine (U(cm)). The stability of duplex with a U(abcm)-rG base pair showed higher thermostability than the duplex having unmodified U-rG base pair. The U(abcm) residue showed enhanced resistance to snake venome phosphodiesterase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Base Pairing
  • Cations
  • Chromatography, Reverse-Phase
  • Drug Stability
  • Humans
  • Nucleic Acid Conformation
  • Oligonucleotides / chemical synthesis*
  • Phosphoric Diester Hydrolases / metabolism
  • RNA / chemistry*
  • RNA Interference
  • Snake Venoms
  • Uridine / analogs & derivatives*
  • Uridine / chemical synthesis*

Substances

  • Cations
  • Oligonucleotides
  • Snake Venoms
  • RNA
  • Phosphoric Diester Hydrolases
  • Uridine