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

O�Brien, Dara M.; Vallieres, Cindy; Alexander, Cameron; Howdle, Steven M.; Stockman, Robert A.; Avery, Simon V.

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.

Citation

O’Brien, D. M., Vallieres, C., Alexander, C., Howdle, S. M., Stockman, R. A., & Avery, S. V. (2019). Epoxy–amine oligomers from terpenes with applications in synergistic antifungal treatments. Journal of Materials Chemistry B, 7(34), 5222-5229. https://doi.org/10.1039/c9tb00878k

• Journal Article Type: Article
• Acceptance Date: Jul 16, 2019
• Online Publication Date: Jul 18, 2019
• Publication Date: Jul 18, 2019
• Deposit Date: Aug 8, 2019
• Publicly Available Date: Jul 19, 2020
• Journal: Journal of Materials Chemistry B
• Print ISSN: 2050-750X
• Electronic ISSN: 2050-7518
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 7
• Issue: 34
• Pages: 5222-5229
• DOI: https://doi.org/10.1039/c9tb00878k
• Keywords: General Materials Science; General Chemistry; Biomedical Engineering; General Medicine
• Public URL: https://nottingham-repository.worktribe.com/output/2407237
• Publisher URL: https://pubs.rsc.org/en/content/articlelanding/2019/TB/C9TB00878K#!divAbstract
• Contract Date: Aug 8, 2019