Antiretroviral activity of semisynthetic derivatives of glycopeptide antibiotics

J Med Chem. 2003 Jun 19;46(13):2755-64. doi: 10.1021/jm0300882.

Abstract

A variety of semisynthetic derivatives of natural antibacterial glycopeptide antibiotics such as vancomycin, eremomycin, ristocetin A, teicoplanin A(2)-2, DA-40926, their aglycons, and also the products of their partial degradation with a destroyed or modified peptide core show marked anti-retroviral activity in cell culture. In particular, aglycon antibiotic derivatives containing various substituents of a preferably hydrophobic nature displayed activity against human immunodeficiency virus type 1 (HIV-1), HIV-2, and Moloney murine sarcoma virus at a 50% inhibitory concentration in the lower micromolar (1-5 microM) concentration range while not being cytostatic against human lymphocytic cells at 250 microM or higher. The mode of anti-HIV action of the antibiotic aglycon derivatives could be ascribed to inhibition of the viral entry process.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Cell Line
  • Cytopathogenic Effect, Viral / drug effects
  • Fibroblasts / drug effects
  • Fibroblasts / virology
  • Glycopeptides*
  • HIV-1 / drug effects*
  • HIV-2 / drug effects*
  • Humans
  • Mice
  • Moloney murine sarcoma virus / drug effects*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Anti-HIV Agents
  • Antiviral Agents
  • Glycopeptides