Extracting functional groups of ALLINI to design derivatives of FDA-approved drugs: Inhibition of HIV-1 integrase

Biotechnol Appl Biochem. 2018 Jul;65(4):594-607. doi: 10.1002/bab.1646. Epub 2018 Feb 21.

Abstract

HIV-1 integrase (IN) is crucial for integration of viral DNA into the host genome and a promising target in development of antiretroviral inhibitors. In this work, six new compounds were designed by linking the structures of two different class of HIV-1 IN inhibitors (active site binders and allosteric IN inhibitors (ALLINIs)). Among newly designed compounds, INRAT10b was found most potent HIV-1 IN inhibitor considering different docking results. To further validate protein-ligand interactions obtained from dockings, molecular dynamics simulations were performed for inhibitor raltegravir and INRAT10b placed either at active site or allosteric site of HIV-1 IN (monomer or dimer). Results suggest that both raltegravir and INRAT10b were interacting with residue Gln62, Gly140, Ile141, and Ser147. However, INRAT10b interacts better with high H-bond occupancy, which can explain the strong binding affinity of INRAT10b than raltegravir with the HIV-1 IN protein. Subdomains rearrangements in HIV-1 IN suggest that the C-terminal and catalytic core domains develop their closeness in the presence of ligand. More significantly, the newly designed derivatives represent novel compounds targeting catalytic site and C-terminal (protein-protein interaction) domains simultaneously. And we also propose INRAT10b as a promising lead compound for the development of potent HIV-1 IN inhibitors.

Keywords: HIV-1 integrase; active site; allosteric site; docking; inhibitors; molecular dynamics.

MeSH terms

  • Catalytic Domain / drug effects
  • Drug Design*
  • HIV Integrase / metabolism*
  • HIV Integrase Inhibitors / chemical synthesis
  • HIV Integrase Inhibitors / chemistry
  • HIV Integrase Inhibitors / pharmacology*
  • Humans
  • Intestinal Absorption
  • Intestinal Mucosa / metabolism
  • Intestines / chemistry
  • Molecular Docking Simulation
  • Molecular Dynamics Simulation
  • Molecular Structure
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacology*
  • Pyrimidinones / chemical synthesis
  • Pyrimidinones / chemistry
  • Pyrimidinones / pharmacology*
  • United States
  • United States Food and Drug Administration

Substances

  • HIV Integrase Inhibitors
  • INRAT10b
  • Oxadiazoles
  • Pyrimidinones
  • HIV Integrase