Predictive Molecular Design and Structure–Property Validation of Novel Terpene-Based, Sustainably Sourced Bacterial Biofilm-Resistant Materials

Cuzzucoli Crucitti, Valentina; Ilchev, Aleksandar; Moore, Jonathan C.; Fowler, Harriet R.; Dubern, Jean-Frédéric; Sanni, Olutoba; Xue, Xuan; Husband, Bethany K.; Dundas, Adam A.; Smith, Sean; Wildman, Joni L.; Taresco, Vincenzo; Williams, Paul; Alexander, Morgan R.; Howdle, Steven M.; Wildman, Ricky D.; Stockman, Robert A.; Irvine, Derek J.

Abstract

Presented in this work is the use of a molecular descriptor, termed the α parameter, to aid in the design of a series of novel, terpene-based, and sustainable polymers that were resistant to biofilm formation by the model bacterial pathogen Pseudomonas aeruginosa. To achieve this, the potential of a range of recently reported, terpene-derived monomers to deliver biofilm resistance when polymerized was both predicted and ranked by the application of the α parameter to key features in their molecular structures. These monomers were derived from commercially available terpenes (i.e., α-pinene, β-pinene, and carvone), and the prediction of the biofilm resistance properties of the resultant novel (meth)acrylate polymers was confirmed using a combination of high-throughput polymerization screening (in a microarray format) and in vitro testing. Furthermore, monomers, which both exhibited the highest predicted biofilm anti-biofilm behavior and required less than two synthetic stages to be generated, were scaled-up and successfully printed using an inkjet “valve-based” 3D printer. Also, these materials were used to produce polymeric surfactants that were successfully used in microfluidic processing to create microparticles that possessed bio-instructive surfaces. As part of the up-scaling process, a novel rearrangement was observed in a proposed single-step synthesis of α-terpinyl methacrylate via methacryloxylation, which resulted in isolation of an isobornyl–bornyl methacrylate monomer mixture, and the resultant copolymer was also shown to be bacterial attachment-resistant. As there has been great interest in the current literature upon the adoption of these novel terpene-based polymers as green replacements for petrochemical-derived plastics, these observations have significant potential to produce new bio-resistant coatings, packaging materials, fibers, medical devices, etc.

Citation

Cuzzucoli Crucitti, V., Ilchev, A., Moore, J. C., Fowler, H. R., Dubern, J., Sanni, O., …Irvine, D. J. (2023). Predictive Molecular Design and Structure–Property Validation of Novel Terpene-Based, Sustainably Sourced Bacterial Biofilm-Resistant Materials. Biomacromolecules, https://doi.org/10.1021/acs.biomac.2c00721

• Journal Article Type: Article
• Acceptance Date: Dec 19, 2022
• Online Publication Date: Jan 4, 2023
• Publication Date: Jan 4, 2023
• Deposit Date: Jan 24, 2023
• Publicly Available Date: Jan 5, 2024
• Journal: Biomacromolecules
• Print ISSN: 1525-7797
• Electronic ISSN: 1526-4602
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• DOI: https://doi.org/10.1021/acs.biomac.2c00721
• Keywords: Materials Chemistry; Polymers and Plastics; Biomaterials; Bioengineering
• Public URL: https://nottingham-repository.worktribe.com/output/15718369
• Publisher URL: https://pubs.acs.org/doi/10.1021/acs.biomac.2c00721#