Neamine dimers targeting the HIV-1 TAR RNA

Bioorg Med Chem Lett. 2005 Nov 1;15(21):4651-5. doi: 10.1016/j.bmcl.2005.07.082.

Abstract

Natural aminoglycoside antibiotics, such as neomycin, target bacterial ribosomal RNA. Neomycin also binds strongly to HIV TAR and RRE RNA through the predominant interactions of its neamine core. In the search for antiviral agents targeting multiple binding sites for aminoglycosides in RNA, we report here the synthesis of new neamine dimers and a trimer in which the neamine cores are connected by different linking chains attached at the 4'- and/or 5-positions. Inhibition of TAR-Tat complexation by these oligomers was studied via fluorimetric binding assays performed under two ionic strengths. All dimers strongly inhibit TAR-Tat association, with IC50 values 17-85 times better than the value obtained with neomycin. These results demonstrate that modifying neamine at the 4'- or the 5-position is a promising strategy in the search for antiviral agents.

MeSH terms

  • Aminoglycosides / chemical synthesis*
  • Aminoglycosides / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Dimerization
  • Drug Delivery Systems
  • Framycetin / chemical synthesis*
  • Framycetin / pharmacology
  • Gene Products, tat / metabolism
  • HIV Long Terminal Repeat / drug effects*
  • Inhibitory Concentration 50
  • Protein Binding / drug effects
  • Structure-Activity Relationship

Substances

  • Aminoglycosides
  • Antiviral Agents
  • Gene Products, tat
  • Framycetin
  • neamine