Epoxy–amine oligomers from terpenes with applications in synergistic antifungal treatments. Issue 34 (1st August 2019)

• Record Type: Journal Article
• Authors: O'Brien, Dara M.; Vallieres, Cindy; Alexander, Cameron; Howdle, Steven M.; Stockman, Robert A.; Avery, Simon V.
• Is Part Of: Journal of materials chemistry. Volume 7:Issue 34(2019)
• Page Start: 5222
• Page End: 5229
• Publication Date: 2019-08-01
• Subjects: Materials -- Periodicals; Chemistry, Analytic -- Periodicals; Biomedical materials -- Research -- Periodicals; 543.0284
• DOI: 10.1039/c9tb00878k
• Languages: English
• ISSNs: 2050-750X

Abstract

Abstract : Epoxy–amine oligomers synthesised from a renewable terpenoid feedstock are found to act in synergy with known antifungal drug amphotericin B against Candida albicans, and fungicide IPBC against Trichoderma virens . 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.