New Dual Inhibitors of Bacterial Topoisomerases with Broad-Spectrum Antibacterial Activity and In Vivo Efficacy against Vancomycin-Intermediate Staphylococcus aureus

Journal of Medicinal Chemistry
2023.0

Abstract

A new series of dual low nanomolar benzothiazole inhibitors of bacterial DNA gyrase and topoisomerase IV were developed. The resulting compounds show excellent broad-spectrum antibacterial activities against Gram-positive <i>Enterococcus faecalis</i>, <i>Enterococcus faecium</i> and multidrug resistant (MDR) <i>Staphylococcus aureus</i> strains [best compound minimal inhibitory concentrations (MICs): range, <0.03125-0.25 μg/mL] and against the Gram-negatives <i>Acinetobacter baumannii</i> and <i>Klebsiella pneumoniae</i> (best compound MICs: range, 1-4 μg/mL). Lead compound <b>7a</b> was identified with favorable solubility and plasma protein binding, good metabolic stability, selectivity for bacterial topoisomerases, and no toxicity issues. The crystal structure of <b>7a</b> in complex with <i>Pseudomonas aeruginosa</i> GyrB24 revealed its binding mode at the ATP-binding site. Expanded profiling of <b>7a</b> and <b>7h</b> showed potent antibacterial activity against over 100 MDR and non-MDR strains of <i>A. baumannii</i> and several other Gram-positive and Gram-negative strains. Ultimately, in vivo efficacy of <b>7a</b> in a mouse model of vancomycin-intermediate <i>S. aureus</i> thigh infection was also demonstrated.

Knowledge Graph

Similar Paper

New Dual Inhibitors of Bacterial Topoisomerases with Broad-Spectrum Antibacterial Activity and In Vivo Efficacy against Vancomycin-Intermediate Staphylococcus aureus
Journal of Medicinal Chemistry 2023.0
Discovery of Benzothiazole Scaffold-Based DNA Gyrase B Inhibitors
Journal of Medicinal Chemistry 2016.0
Novel Dual-Targeting Benzimidazole Urea Inhibitors of DNA Gyrase and Topoisomerase IV Possessing Potent Antibacterial Activity: Intelligent Design and Evolution through the Judicious Use of Structure-Guided Design and Stucture−Activity Relationships
Journal of Medicinal Chemistry 2008.0
New dual ATP-competitive inhibitors of bacterial DNA gyrase and topoisomerase IV active against ESKAPE pathogens
European Journal of Medicinal Chemistry 2021.0
Quercetin Diacylglycoside Analogues Showing Dual Inhibition of DNA Gyrase and Topoisomerase IV as Novel Antibacterial Agents
Journal of Medicinal Chemistry 2011.0
Discovery of substituted oxadiazoles as a novel scaffold for DNA gyrase inhibitors
European Journal of Medicinal Chemistry 2017.0
Discovery of a novel azaindole class of antibacterial agents targeting the ATPase domains of DNA gyrase and Topoisomerase IV
Bioorganic &amp; Medicinal Chemistry Letters 2012.0
Discovery of 4,5,6,7-Tetrahydrobenzo[1,2-d]thiazoles as Novel DNA Gyrase Inhibitors Targeting the ATP-Binding Site
Journal of Medicinal Chemistry 2015.0
An optimised series of substituted N-phenylpyrrolamides as DNA gyrase B inhibitors
European Journal of Medicinal Chemistry 2019.0
Dual inhibition of Staphylococcus aureus DNA gyrase and topoisomerase IV activity by phenylalanine-derived (Z)-5-arylmethylidene rhodanines
Bioorganic &amp; Medicinal Chemistry 2015.0