Synthesis and evaluation of thiophene based small molecules as potent inhibitors of Mycobacterium tuberculosis

Eur J Med Chem. 2020 Dec 15:208:112772. doi: 10.1016/j.ejmech.2020.112772. Epub 2020 Aug 23.

Abstract

Herein, we report the synthesis and anti-tubercular studies of novel molecules based on thiophene scaffold. We identified two novel small molecules 4a and 4b, which demonstrated 2-fold higher in vitro activity (MIC99: 0.195 μM) compared to first line TB drug, isoniazid (0.39 μM). The identified leads demonstrated additive effect with front line TB drugs (isoniazid, rifampicin and levofloxacin) and synergistic effect with a recently FDA-approved drug, bedaquiline. Mechanistic studies (i) negated the role of Pks13 and (ii) suggested the involvement of KatG in the anti-tubercular activity of these identified leads.

Keywords: KatG; Pks13; Synergy; Thiophene; Tuberculosis.

MeSH terms

  • Antitubercular Agents / chemical synthesis
  • Antitubercular Agents / metabolism
  • Antitubercular Agents / pharmacology*
  • Bacterial Proteins / metabolism
  • Catalase / metabolism
  • Drug Synergism
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects*
  • Protein Binding
  • Structure-Activity Relationship
  • THP-1 Cells
  • Thiophenes / chemical synthesis
  • Thiophenes / metabolism
  • Thiophenes / pharmacology*

Substances

  • Antitubercular Agents
  • Bacterial Proteins
  • Thiophenes
  • Catalase
  • katG protein, Mycobacterium tuberculosis