Spectroscopic studies of diketoacids-metal interactions. A probing tool for the pharmacophoric intermetallic distance in the HIV-1 integrase active site

J Med Chem. 2004 Oct 21;47(22):5583-6. doi: 10.1021/jm0408464.

Abstract

The interactions with divalent cations of 4-phenyl-4-oxo-2-hydroxybuten-2-oic acid (benzoylpyruvic acid (BPA)), the pharmacophore of HIV-1 integrase inhibitors, were investigated using spectroscopic tools. In the absence of the enzyme, a 2:2 metal-ligand complex was characterized with an intermetallic distance of 4-6 A. Molecular modeling allowed us to propose a compatible structure for the metal-ligand complex. BPA does not inhibit the reactions catalyzed by HIV-1 IN, emphasizing the importance of the aromatic ring substitution in the antiviral activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cations, Divalent / chemistry
  • Electron Spin Resonance Spectroscopy
  • HIV Integrase / chemistry*
  • Ligands
  • Magnesium / chemistry*
  • Manganese / chemistry*
  • Mass Spectrometry
  • Models, Molecular
  • Molecular Structure
  • Pyruvic Acid / analogs & derivatives*
  • Pyruvic Acid / chemistry*

Substances

  • 4-phenyl-4-oxo-2-hydroxybuten-2-oic acid
  • Cations, Divalent
  • Ligands
  • Manganese
  • Pyruvic Acid
  • HIV Integrase
  • Magnesium