Synthesis and evaluation of novel neamine derivatives effectively targeting to RNA

Bioorg Med Chem Lett. 2009 Apr 15;19(8):2103-6. doi: 10.1016/j.bmcl.2009.03.021. Epub 2009 Mar 13.

Abstract

Three new derivatives of neamine, 3 (NE), 6 (NEA) and 9 (NEL), were synthesized by connecting arginine or lysine to 5-hydroxyl group of neamine using ethylenediamine as a linker. The binding affinities of these derivatives to A site of 16S RNA and TAR RNA indicate that the modification on 5-hydroxyl of neamine by amino acid can enhance the binding affinity of neamine. Compound 9 (NEL) shows some antibacterial activities. These results demonstrate that modification on 5-hydroxyl group of neamine may provide a promising way for the development of potential candidates effectively targeting to RNAs.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / pharmacology
  • Base Sequence
  • Binding Sites / drug effects
  • Drug Delivery Systems / methods*
  • Drug Evaluation, Preclinical / methods
  • Framycetin / chemical synthesis*
  • Framycetin / pharmacology*
  • Microbial Sensitivity Tests / methods
  • Models, Molecular
  • Molecular Sequence Data
  • RNA, Viral / chemistry
  • RNA, Viral / metabolism*

Substances

  • Anti-HIV Agents
  • RNA, Viral
  • Framycetin
  • neamine