Chemical synthesis and biological activities of analogues of 2',5'-oligoadenylates containing 8-substituted adenosine derivatives

Nucleic Acids Res. 1990 Aug 11;18(15):4439-46. doi: 10.1093/nar/18.15.4439.

Abstract

The synthesis of sequence-specific 2'-5'-oligonucleotides and analogues of 2'-5' linked oligoadenylates containing 8-substituted adenosine derivatives [8-hydroxypropyladenosine (AHPr) and 8-hydroxyadenosine (AOH)] is reported. The reaction of 5'-phosphoroimidazolidate of 8-substituted adenosines under conditions of lead ion catalyst did not give the corresponding 2'-5' oligoadenylates containing pAHPr and pAOH. When these reactions were carried out in the presence of uranyl ion (UO2(2+] in place of lead ion as a catalyst, the desired 2'-5' oligoadenylates were obtained. The p5'AHPr2'p5'AHPr2'p5'AHPr and p5'AOH2'p5'AOH2'p5'AOH, p5'A2'p5'A2'pAOH were slightly resistant to snake venom phosphodiesterase. The both circular dichroism and 1H-NMR spectra studies were used to characterize the modified 2'-5' oligoadenylates. Further, the biological activity evaluations of 8-substituted analogues of 2-5A are also described.

MeSH terms

  • Adenine Nucleotides* / pharmacology
  • Adenosine* / analogs & derivatives*
  • Chemical Phenomena
  • Chemistry
  • Circular Dichroism
  • Endoribonucleases / metabolism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oligoribonucleotides* / pharmacology
  • Phosphodiesterase I
  • Phosphoric Diester Hydrolases
  • RNA, Ribosomal / metabolism
  • Uranium

Substances

  • Adenine Nucleotides
  • Oligoribonucleotides
  • RNA, Ribosomal
  • Uranium
  • 2',5'-oligoadenylate
  • Endoribonucleases
  • 2-5A-dependent ribonuclease
  • Phosphoric Diester Hydrolases
  • Phosphodiesterase I
  • phosphodiesterase I, snake venom
  • Adenosine