Synthesis and structure-activity relationships of the halovirs, antiviral natural products from a marine-derived fungus

Bioorg Med Chem. 2004 Sep 15;12(18):4929-36. doi: 10.1016/j.bmc.2004.06.044.

Abstract

The halovirs are linear, lipophilic peptides produced by a marine-derived fungus of the genus Scytalidium. We recently reported that these molecules possess potent in vitro activity against the herpes simplex viruses 1 and 2. Here we present structure-activity relationships defining key structural elements for optimal viral inhibition. Results demonstrate that an N(alpha)-acyl chain of at least 14 carbons and an Aib-Pro dipeptide are critical for maintaining the antiviral activity.

Publication types

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

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Biological Products / chemical synthesis*
  • Biological Products / pharmacology
  • Chlorocebus aethiops
  • Fungal Proteins / chemical synthesis*
  • Fungal Proteins / pharmacology
  • Herpesvirus 1, Human / drug effects
  • Herpesvirus 1, Human / physiology
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / pharmacology
  • Structure-Activity Relationship
  • Vero Cells

Substances

  • Antiviral Agents
  • Biological Products
  • Fungal Proteins
  • Oligopeptides
  • halovir A