Epoxy-amine oligomers from terpenes with applications in synergistic antifungal treatments

J Mater Chem B. 2019 Sep 14;7(34):5222-5229. doi: 10.1039/c9tb00878k. Epub 2019 Aug 1.

Abstract

A bis-epoxide monomer was synthesised in two steps from (R)-carvone, a terpenoid renewable feedstock derived from spearmint oil, and used to prepare β-aminoalcohol oligomers in polyaddition reactions with bis-amines without requiring solvent or catalyst. A sub-set of the resultant materials were readily water soluble and were investigated for antifungal activity in combination with the fungicide iodopropynyl-butylcarbamate (IPBC) or the antifungal drug amphotericin B. The oligo-(β-aminoalcohol)s alone were inactive against Trichoderma virens and Candida albicans but in combination with IPBC and amphotericin B demonstrated synergistic growth-inhibition of both fungi. Quantitative analysis showed that the presence of the terpene-based oligomers decreased the minimum inhibitory concentration (MIC) of IPBC by up to 64-fold and of amphotericin B by 8-fold. The efficacy of the combined formulation was further demonstrated with agar disk diffusion assays, which revealed that IPBC and amphotericin B reduced the growth of the fungi, as shown by zones of inhibition, to a greater extent when in the presence of the oligo-(β-aminoalcohol)s. These data suggest potential future use of these renewable feedstock derived oligomers in antifungal material and related biomedical applications.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Amines / pharmacology*
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Candida albicans / drug effects*
  • Epoxy Resins / chemistry
  • Epoxy Resins / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Particle Size
  • Surface Properties
  • Terpenes / chemistry
  • Terpenes / pharmacology*
  • Trichoderma / drug effects*

Substances

  • Amines
  • Antifungal Agents
  • Epoxy Resins
  • Terpenes