Synthesis of a cosalane analog with an extended polyanionic pharmacophore conferring enhanced potency as an anti-HIV agent

Bioorg Med Chem Lett. 1998 Apr 7;8(7):833-6. doi: 10.1016/s0960-894x(98)00121-8.

Abstract

A novel cosalane analog having an extended polyanionic pharmacophore was synthesized in order to target specific cationic residues on the surface of CD4. The design rationale is based on a hypothetical binding model of cosalane to the surface of the protein. The new analog displayed an EC50 of 0.55 microM as an inhibitor of the cytopathic effect of HIV-1RF in CEM-SS cells, which represents a significant increase in potency over cosalane itself (EC50 5.1 microM). Both cosalane and the new analog are inhibitors of viral entry into target cells.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology
  • Aurintricarboxylic Acid / analogs & derivatives*
  • Aurintricarboxylic Acid / chemical synthesis*
  • Aurintricarboxylic Acid / chemistry
  • Aurintricarboxylic Acid / pharmacology
  • CD4 Antigens / chemistry
  • CD4 Antigens / drug effects
  • Drug Design
  • HIV-1 / drug effects*
  • HIV-1 / growth & development
  • Humans
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Protein Conformation
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Anti-HIV Agents
  • CD4 Antigens
  • cosalane
  • Aurintricarboxylic Acid