Revealing interaction mode between HIV-1 protease and mannitol analog inhibitor

Chem Biol Drug Des. 2012 Jun;79(6):916-25. doi: 10.1111/j.1747-0285.2012.01348.x. Epub 2012 Feb 20.

Abstract

HIV protease is a key enzyme to play a key role in the HIV-1 replication cycle and control the maturation from HIV viruses to an infectious virion. HIV-1 protease has become an important target for anti-HIV-1 drug development. Here, we used molecular dynamics simulation to study the binding mode between mannitol derivatives and HIV-1 protease. The results suggest that the most active compound (M35) has more stable hydrogen bonds and stable native contacts than the less active one (M17). These mannitol derivatives might have similar interaction mode with HIV-1 protease. Then, 3D-QSAR was used to construct quantitative structure-activity models. The cross-validated q(2) values are found as 0.728 and 0.611 for CoMFA and CoMSIA, respectively. And the non-cross-validated r(2) values are 0.973 and 0.950. Nine test set compounds validate the model. The results show that this model possesses better prediction ability than the previous work. This model can be used to design new chemical entities and make quantitative prediction of the bioactivities for HIV-1 protease inhibitors before resorting to in vitro and in vivo experiment.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • HIV Protease / chemistry*
  • HIV Protease / metabolism
  • HIV Protease Inhibitors / chemical synthesis
  • HIV Protease Inhibitors / chemistry*
  • HIV-1 / enzymology*
  • Humans
  • Hydrogen Bonding
  • Mannitol / analogs & derivatives*
  • Mannitol / chemical synthesis
  • Molecular Dynamics Simulation
  • Protein Binding
  • Protein Structure, Tertiary
  • Quantitative Structure-Activity Relationship

Substances

  • HIV Protease Inhibitors
  • Mannitol
  • HIV Protease
  • p16 protease, Human immunodeficiency virus 1