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.-F., Sanni, O., Xue, X., Husband, B. K., Dundas, A. A., Smith, S., Wildman, J. L., Taresco, V., Williams, P., Alexander, M. R., Howdle, S. M., Wildman, R. D., Stockman, R. A., & 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#