Journal
JOURNAL OF MATERIALS CHEMISTRY B
Volume 7, Issue 34, Pages 5222-5229Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9tb00878k
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Funding
- Engineering and Physical Sciences Research Council [EP/N006615/1]
- Biotechnology and Biological Sciences Research Council [BB/P02369X/1]
- BBSRC [BB/P02369X/1] Funding Source: UKRI
- EPSRC [EP/N006615/1] Funding Source: UKRI
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A bis-epoxide monomer was synthesised in two steps from (R)-carvone, a terpenoid renewable feedstock derived from spearmint oil, and used to prepare beta-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-(beta-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-(beta-aminoalcohol)s. These data suggest potential future use of these renewable feedstock derived oligomers in antifungal material and related biomedical applications.
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