Rudman, JM; (2017) Novel light-activated antibacterial surfaces. Doctoral thesis , UCL (University College London).

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Abstract

The aim of this project was to covalently link chemically modified organic dyes, such as methylene blue, toluidine blue O, or crystal violet, to the surface of a polymer, via a 1,3-dipolar cycloaddition reaction. The synthesis of variants of methylene blue and toluidine blue O was attempted; unfortunately, we were unable to synthesise any analogues from phenothiazine or from the dyes themselves. The synthesis of a crystal violet analogue via a double Grignard reaction was investigated. We were unable to isolate the desired product in the final step. Instead, two leucocrystal violet analogues were prepared by reacting appropriately functionalised tertiary anilines with Michler’s hydrol. Another leucocrystal violet analogue was prepared by reacting 4-(prop-2-yn-1-yloxy)benzaldehyde with two equivalents of N,N-dimethylaniline. The leucocrystal violet analogues were oxidised to give the corresponding crystal violet analogues, which were incorporated into polyurethane by a dip-coating process. The antibacterial activities of the resultant polymer films were assessed: each displayed differing antibacterial properties when illuminated (no activity was observed in the dark). We were unable to covalently attach any crystal violet analogues to the surface of pre-functionalised silicone, polyurethane, or poly(vinyl chloride) (PVC). Considering the differences that were observed between the antibacterial activities of the crystal violet analogues, the antibacterial activity of silicone incorporated with commercially available ethyl violet was compared with that of the same material containing crystal violet. The superiority of crystal violet over ethyl violet as a photobactericidal agent was demonstrated. Several porphyrins and metalloporphyrins were synthesised and incorporated into silicone. The resultant films were characterised by measuring their UV-Vis, IR, and fluorescence spectra. Unfortunately, due to time constraints, the antibacterial properties of these polymers were not assessed. Finally, we were unable to synthesise polyurethane with covalently attached crystal violet moieties via a polymerisation reaction.

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