Design, Synthesis, and Proof-of-Concept of Triple-Site Inhibitors against Aminoacyl-tRNA Synthetases

Journal of Medicinal Chemistry
2022.0

Abstract

Aminoacyl-tRNA synthetases (aaRSs) are promising drug targets due to their essential roles in protein translation. Although current inhibitors primarily occupy one or two of the three substrate binding sites on aaRSs, we report here the structure-based design of the first class of triple-site aaRS inhibitors by targeting <i>Salmonella enterica</i> threonyl-tRNA synthetase (<i>Se</i>ThrRS). Competition of our compounds with all three substrates on <i>Se</i>ThrRS binding was confirmed <i>via</i> isothermal titration calorimetry assays. Cocrystal structures of three compounds bound to <i>Se</i>ThrRS unambiguously confirmed their substrate-mimicking triple-site binding mode. Compound <b>36j</b> exhibited the best enzyme activity against <i>Se</i>ThrRS with IC<sub>50</sub> = 19 nM and <i>K</i><sub>d</sub> = 35.4 nM. Compounds <b>36b</b>, <b>36k</b>, and <b>36l</b> exhibited antibacterial activities with minimum inhibitory concentration values of 2-8 μg/mL against the tested bacteria, which are superior to those of the reported dual-site ThrRS inhibitors. Our study provides the first proof-of-concept for developing triple-site inhibitors against aaRSs, inspiring future aaRS-based drug discoveries.

Knowledge Graph

Similar Paper

Design, Synthesis, and Proof-of-Concept of Triple-Site Inhibitors against Aminoacyl-tRNA Synthetases
Journal of Medicinal Chemistry 2022.0
Structure-guided optimization and mechanistic study of a class of quinazolinone-threonine hybrids as antibacterial ThrRS inhibitors
European Journal of Medicinal Chemistry 2020.0
Discovery of novel tRNA-amino acid dual-site inhibitors against threonyl-tRNA synthetase by fragment-based target hopping
European Journal of Medicinal Chemistry 2020.0
Synthesis and evaluation of adenosine containing 3-arylfuran-2(5 H )-ones as tyrosyl-tRNA synthetase inhibitors
European Journal of Medicinal Chemistry 2017.0
Structure-Guided Design of Halofuginone Derivatives as ATP-Aided Inhibitors Against Bacterial Prolyl-tRNA Synthetase
Journal of Medicinal Chemistry 2022.0
Dual-target inhibitors of mycobacterial aminoacyl-tRNA synthetases among N-benzylidene-N′-thiazol-2-yl-hydrazines
MedChemComm 2019.0
Synthesis and structure-activity studies of novel anhydrohexitol-based Leucyl-tRNA synthetase inhibitors
European Journal of Medicinal Chemistry 2021.0
Adenosine analogs as inhibitors of tyrosyl-tRNA synthetase: Design, synthesis and antibacterial evaluation
Bioorganic &amp; Medicinal Chemistry 2015.0
Natural products and their derivatives as tRNA synthetase inhibitors and antimicrobial agents
MedChemComm 2016.0
Tyrosyl-tRNA synthetase inhibitors as antibacterial agents: Synthesis, molecular docking and structure–activity relationship analysis of 3-aryl-4-arylaminofuran-2(5H)-ones
European Journal of Medicinal Chemistry 2011.0