Synthesis and characterization of NH2-(AEEA)n-amphotericin B derivatives

J Antibiot (Tokyo). 2019 Apr;72(4):210-217. doi: 10.1038/s41429-018-0138-8. Epub 2019 Jan 11.

Abstract

To find novel amphotericin B (AmB) derivatives with high therapeutic potential, low toxicity, and water solubility, a series of nine N-substituted AmB derivatives were evaluated for their antifungal activity using the broth dilution method and for their hemolytic toxicity with sterile defibrinated sheep blood. Qualitative screening of the effect of the derivatives on two reference Candida albicans strains and of their solubility was performed based on the value of n (n is a positive integer), resulting in the identification of an optimal compound, NH2-(AEEA)5-AmB (DMR005; AEEA is 8-amino-3,6- dioxaoctanoic acid). Preliminary safety assessments of DMR005 were carried out via the MTT cell viability assay in vitro and acute toxicity assay in vivo. In general, DMR005 not only has higher water solubility and less toxicity than the parent polyene but also retains antifungal potency.

MeSH terms

  • Amphotericin B / analogs & derivatives
  • Amphotericin B / chemical synthesis*
  • Amphotericin B / pharmacology*
  • Amphotericin B / toxicity
  • Animals
  • Antifungal Agents / chemical synthesis*
  • Antifungal Agents / pharmacology*
  • Antifungal Agents / toxicity
  • Candida albicans / drug effects*
  • Cell Survival
  • Cytological Techniques
  • Disease Models, Animal
  • Erythrocytes / drug effects
  • HEK293 Cells
  • Hemolysis / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Poisoning / pathology
  • Sheep
  • Solubility

Substances

  • Antifungal Agents
  • Amphotericin B