Elimination of antibacterial activities of non-peptide luteinizing hormone-releasing hormone (LHRH) antagonists derived from erythromycin A

Bioorg Med Chem Lett. 2004 Mar 22;14(6):1599-602. doi: 10.1016/j.bmcl.2003.12.059.

Abstract

Antibacterial SAR for a series of macrolides derived from erythromycin A that are potent LHRH antagonists was developed in an attempt to eliminate the antibiotic activities of these compounds. Increasing the size of the alkyl substituents on the desosamine 3'-amine resulted in potent LHRH antagonists that were inactive against staphylococcal bacteria strains, and were significantly (>10-fold) less active against streptococcal bacteria strains. Complete elimination of antibacterial activities could be achieved by replacement of one or both methyl groups on the 3'-amine with a large alkyl substituent.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / metabolism*
  • CHO Cells
  • Cricetinae
  • Erythromycin / chemistry*
  • Erythromycin / metabolism*
  • Gonadotropin-Releasing Hormone / antagonists & inhibitors*
  • Gonadotropin-Releasing Hormone / metabolism*
  • Humans
  • Microbial Sensitivity Tests
  • Protein Binding / physiology
  • Staphylococcus / drug effects
  • Staphylococcus / growth & development
  • Streptococcus / drug effects
  • Streptococcus / growth & development
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Gonadotropin-Releasing Hormone
  • Erythromycin