Aqueous Molecular Dynamics Simulations of the M. tuberculosis Enoyl-ACP Reductase-NADH System and Its Complex with a Substrate Mimic or Diphenyl Ethers Inhibitors

Int J Mol Sci. 2015 Oct 7;16(10):23695-722. doi: 10.3390/ijms161023695.

Abstract

Molecular dynamics (MD) simulations of 12 aqueous systems of the NADH-dependent enoyl-ACP reductase from Mycobacterium tuberculosis (InhA) were carried out for up to 20-40 ns using the GROMACS 4.5 package. Simulations of the holoenzyme, holoenzyme-substrate, and 10 holoenzyme-inhibitor complexes were conducted in order to gain more insight about the secondary structure motifs of the InhA substrate-binding pocket. We monitored the lifetime of the main intermolecular interactions: hydrogen bonds and hydrophobic contacts. Our MD simulations demonstrate the importance of evaluating the conformational changes that occur close to the active site of the enzyme-cofactor complex before and after binding of the ligand and the influence of the water molecules. Moreover, the protein-inhibitor total steric (ELJ) and electrostatic (EC) interaction energies, related to Gly96 and Tyr158, are able to explain 80% of the biological response variance according to the best linear equation, pKi=7.772-0.1885×Gly96+0.0517×Tyr158 (R²=0.80; n=10), where interactions with Gly96, mainly electrostatic, increase the biological response, while those with Tyr158 decrease. These results will help to understand the structure-activity relationships and to design new and more potent anti-TB drugs.

Keywords: Mycobacterium tuberculosis; diphenyl ethers inhibitors; enoyl-ACP reductase (InhA); molecular dynamics simulation; triclosan derivatives; water-bridge hydrogen bond.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Motifs
  • Bacterial Proteins / antagonists & inhibitors
  • Bacterial Proteins / metabolism*
  • Enoyl-(Acyl-Carrier-Protein) Reductase (NADH) / antagonists & inhibitors
  • Enoyl-(Acyl-Carrier-Protein) Reductase (NADH) / metabolism*
  • Hydrogen Bonding
  • Hydrophobic and Hydrophilic Interactions
  • Molecular Dynamics Simulation*
  • Mycobacterium tuberculosis / drug effects
  • Mycobacterium tuberculosis / enzymology*
  • Phenyl Ethers / pharmacology*
  • Protein Structure, Tertiary
  • Structure-Activity Relationship
  • Thermodynamics

Substances

  • Bacterial Proteins
  • Phenyl Ethers
  • Enoyl-(Acyl-Carrier-Protein) Reductase (NADH)