Discovery of 2-Aminothiazole-4-carboxylic Acids as Broad-Spectrum Metallo-β-lactamase Inhibitors by Mimicking Carbapenem Hydrolysate Binding

J Med Chem. 2023 Oct 12;66(19):13746-13767. doi: 10.1021/acs.jmedchem.3c01189. Epub 2023 Oct 4.

Abstract

Metallo-β-lactamases (MBLs) are zinc-dependent enzymes capable of hydrolyzing all bicyclic β-lactam antibiotics, posing a great threat to public health. However, there are currently no clinically approved MBL inhibitors. Despite variations in their active sites, MBLs share a common catalytic mechanism with carbapenems, forming similar reaction species and hydrolysates. We here report the development of 2-aminothiazole-4-carboxylic acids (AtCs) as broad-spectrum MBL inhibitors by mimicking the anchor pharmacophore features of carbapenem hydrolysate binding. Several AtCs manifested potent activity against B1, B2, and B3 MBLs. Crystallographic analyses revealed a common binding mode of AtCs with B1, B2, and B3 MBLs, resembling binding observed in the MBL-carbapenem product complexes. AtCs restored Meropenem activity against MBL-producing isolates. In the murine sepsis model, AtCs exhibited favorable synergistic efficacy with Meropenem, along with acceptable pharmacokinetics and safety profiles. This work offers promising lead compounds and a structural basis for the development of potential drug candidates to combat MBL-mediated antimicrobial resistance.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Carbapenems* / pharmacology
  • Carboxylic Acids
  • Meropenem / pharmacology
  • Mice
  • beta-Lactamase Inhibitors* / chemistry
  • beta-Lactamase Inhibitors* / pharmacology
  • beta-Lactamases / metabolism

Substances

  • beta-Lactamase Inhibitors
  • Carbapenems
  • Meropenem
  • 2-aminothiazole
  • Carboxylic Acids
  • beta-Lactamases
  • Anti-Bacterial Agents