Dara M. O�Brien
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.
Authors
Cindy Vallieres
Professor CAMERON ALEXANDER CAMERON.ALEXANDER@NOTTINGHAM.AC.UK
Professor of Polymer Therapeutics
Prof. STEVE HOWDLE STEVE.HOWDLE@NOTTINGHAM.AC.UK
Professor of Chemistry
ROBERT STOCKMAN robert.stockman@nottingham.ac.uk
Professor of Organic Chemistry
SIMON AVERY SIMON.AVERY@NOTTINGHAM.AC.UK
Professor of Eukaryotic Microbiology
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 ?-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-(?-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-(?-aminoalcohol)s. These data suggest potential future use of these renewable feedstock derived oligomers in antifungal material and related biomedical applications.
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 |
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