Molecular Umbrellas Modulate the Selective Toxicity of Polyene Macrolide Antifungals

Bioconjug Chem. 2018 Apr 18;29(4):1454-1465. doi: 10.1021/acs.bioconjchem.8b00136. Epub 2018 Mar 5.

Abstract

Antifungal polyene macrolide antibiotics Amphotericin B (AmB) and Nystatin (NYS) were conjugated through the ω-amino acid linkers with diwalled "molecular umbrellas" composed of spermidine-linked deoxycholic or cholic acids. The presence of "umbrella" substituents modulated biological properties of the antibiotics, especially their selective toxicity. Some of the AmB-umbrella conjugates demonstrated antifungal in vitro activity comparable to that of the mother antibiotic but diminished mammalian toxicity, especially the hemolytic activity. In contrast, antifungal in vitro activity of NYS-umbrella conjugates was strongly reduced and all these conjugates demonstrated poorer than NYS selective toxicity. No correlation between the aggregation state and hemolytic activity of the novel conjugates was found.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amphotericin B / analogs & derivatives*
  • Amphotericin B / pharmacology*
  • Amphotericin B / toxicity
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology*
  • Antifungal Agents / toxicity
  • Fungi / drug effects
  • HEK293 Cells
  • Hemolysis / drug effects
  • Hep G2 Cells
  • Humans
  • Mycoses / drug therapy
  • Nystatin / analogs & derivatives*
  • Nystatin / pharmacology*
  • Nystatin / toxicity
  • Polyenes / chemistry
  • Polyenes / pharmacology
  • Polyenes / toxicity

Substances

  • Antifungal Agents
  • Polyenes
  • Nystatin
  • Amphotericin B