Discovery of novel oxoindolin derivatives as atypical dual inhibitors for DNA Gyrase and FabH

Bioorg Chem. 2019 Dec:93:103309. doi: 10.1016/j.bioorg.2019.103309. Epub 2019 Sep 21.

Abstract

The antibacterial agents and therapies today are facing serious problems such as drug resistance. Introducing dual inhibiting effect is a valid approach to solve this trouble and bring advantages including wide adaptability, favorable safety and superiority of combination. We started from potential DNA Gyrase inhibitory backbone isatin to develop oxoindolin derivatives as atypical dual Gyrase (major) and FabH (assistant) inhibitors via a two-round screening. Aiming at blocking both duplication (Gyrase) and survival (FabH), most of synthesized compounds indicated potency against Gyrase and some of them inferred favorable inhibitory effect on FabH. The top hit I18 suggested comparable Gyrase inhibitory activity (IC50 = 0.025 μM) and antibacterial effect with the positive control Novobiocin (IC50 = 0.040 μM). FabH inhibitory activity (IC50 = 5.20 μM) was also successfully introduced. Docking simulation hinted possible important interacted residues and binding patterns for both target proteins. Adequate Structure-Activity Relation discussions provide the future orientations of modification. With high potency, low initial toxicity and dual inhibiting strategy, advanced compounds with therapeutic methods will be developed for clinical application.

Keywords: 3D QSAR; Antimicrobial; Atypical dual inhibitor; DNA Gyrase; FabH; Molecular docking.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3-Oxoacyl-(Acyl-Carrier-Protein) Synthase
  • Acetyltransferases / antagonists & inhibitors*
  • Acetyltransferases / metabolism
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology
  • Binding Sites
  • DNA Gyrase / chemistry*
  • DNA Gyrase / metabolism
  • Drug Evaluation, Preclinical
  • Escherichia coli / enzymology
  • Escherichia coli Proteins / antagonists & inhibitors*
  • Escherichia coli Proteins / metabolism
  • Fatty Acid Synthase, Type II / antagonists & inhibitors
  • Fatty Acid Synthase, Type II / metabolism
  • Indoles / chemistry*
  • Indoles / metabolism
  • Indoles / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation
  • Protein Structure, Tertiary
  • Structure-Activity Relationship
  • Topoisomerase II Inhibitors / chemistry*
  • Topoisomerase II Inhibitors / metabolism
  • Topoisomerase II Inhibitors / pharmacology

Substances

  • Anti-Bacterial Agents
  • Escherichia coli Proteins
  • Indoles
  • Topoisomerase II Inhibitors
  • Acetyltransferases
  • fabH protein, E coli
  • 3-Oxoacyl-(Acyl-Carrier-Protein) Synthase
  • DNA Gyrase
  • Fatty Acid Synthase, Type II