Developing novel indoles as antitubercular agents and simulated annealing-based analysis of their binding with MmpL3

Future Med Chem. 2025 Jan;17(1):19-34. doi: 10.1080/17568919.2024.2444872. Epub 2024 Dec 25.

Abstract

Aim: This research aimed to develop novel indole-2-carboxamides as potential antitubercular agents using rational drug design. It also focused on identifying the critical interactions required for these compounds to exhibit effective antitubercular activity.

Materials and methods: Novel indole-2-carboxamides targeting MmpL3 were designed based on SAR, synthesized, and tested for their antitubercular and iniBAC induction properties. Classical docking and simulated annealing were utilized to understand protein-ligand binding affinity.

Results: Compounds 5c, 5f, and 5i, were active against H37Rv and different MDR and XDR strains of M. tuberculosis. iniBAC promoter induction study indicated that those were inhibitors of MmpL3. Through the docking and simulated annealing studies, we identified key protein-ligand interactions at the MmpL3 binding site.

Conclusion: We have identified three potent antitubercular molecules that supposedly act via inhibiting MmpL3. Results from the molecular modeling studies can be used in future drug designing.

Keywords: MmpL3; indole-2-carboxamides; molecular docking; simulated annealing; tuberculosis.

MeSH terms

  • Antitubercular Agents* / chemical synthesis
  • Antitubercular Agents* / chemistry
  • Antitubercular Agents* / pharmacology
  • Bacterial Proteins* / antagonists & inhibitors
  • Bacterial Proteins* / chemistry
  • Bacterial Proteins* / metabolism
  • Binding Sites
  • Drug Design
  • Indoles* / chemical synthesis
  • Indoles* / chemistry
  • Indoles* / pharmacology
  • Membrane Transport Proteins
  • Microbial Sensitivity Tests*
  • Molecular Docking Simulation*
  • Molecular Structure
  • Mycobacterium tuberculosis* / drug effects
  • Structure-Activity Relationship

Substances

  • Antitubercular Agents
  • Indoles
  • Bacterial Proteins
  • MmpL3 protein, Mycobacterium tuberculosis
  • Membrane Transport Proteins

Grants and funding

The work was supported by the All India Council for Technical Education [((RPS File No: 8–77/FDC/RPS) (POLICY-I)|2O19-2O)]; Division of Intramural Research, National Institute of Allergy and Infectious Diseases, National Institutes of Health.