Exploring eukaryotic versus prokaryotic ribosomal RNA recognition with aminoglycoside derivatives

Medchemcomm. 2018 Feb 2;9(3):503-508. doi: 10.1039/c8md00001h. eCollection 2018 Mar 1.

Abstract

New derivatives of aminoglycosides containing 6'-carboxylic acid or 6'-amide on their ring I were designed, synthesized and their ability to readthrough nonsense mutations was examined in vitro, along with the protein translation inhibition in prokaryotic and eukaryotic systems. The observed structure-activity relationships, along with the comparative molecular dynamics simulations within the eukaryotic rRNA decoding site, showed high sensitivity of 6'-position to substitution, indicating that the rational design of potent stop-codon read-through inducers requires consideration of not only the structure and energetics of the drug-RNA interaction but also the dynamics associated with that interaction.