Retroinverso analogue of the antiviral octapeptide C8 inhibits feline immunodeficiency virus in serum

J Med Chem. 2003 May 8;46(10):1807-10. doi: 10.1021/jm034012h.

Abstract

We described the antiviral activity of an octapeptide corresponding to a Trp-rich domain of feline immunodeficiency virus (FIV) transmembrane glycoprotein. To overcome the limited enzymatic stability of short peptides, the retroinverso analogue was prepared and tested for inhibitory activity of FIV in the presence or absence of normal cat serum. Differently from the unmodified peptide, the retroinverso analogue maintains strong inhibitory activity in serum. NMR studies showed that it displays crucial conformational features believed to be important for antiviral activity.

MeSH terms

  • Animals
  • Antiviral Agents / blood
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Cats
  • Drug Stability
  • Immunodeficiency Virus, Feline / chemistry
  • Immunodeficiency Virus, Feline / drug effects*
  • Magnetic Resonance Spectroscopy
  • Membrane Glycoproteins / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Oligopeptides / blood
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / pharmacology
  • Retroviridae Proteins / chemistry*
  • Tryptophan / chemistry
  • Virus Replication / drug effects

Substances

  • Antiviral Agents
  • Membrane Glycoproteins
  • Oligopeptides
  • Retroviridae Proteins
  • acetyl-tryptophyl-glutamyl-aspartyl-tryptophyl-valyl-glycyl-tryptophyl-isoleucinamide
  • Tryptophan