Journal article

An optimised Cu(0)-RDRP approach for the synthesis of lipidated oligomeric vinyl azlactone: toward a versatile antimicrobial materials screening platform

James L Grace, Maite Amado, Janet C Reid, Alysha G Elliott, Cornelia B Landersdorfer, Nghia P Truong, Kristian Kempe, Matthew A Cooper, Thomas P Davis, Veronique Montembault, Sagrario Pascual, Laurent Fontaine, Tony Velkov, John F Quinn, Michael R Whittaker

Journal of Materials Chemistry B | ROYAL SOC CHEMISTRY | Published : 2019

Abstract

This report details the synthesis of lipidated 2-vinyl-4,4-dimethyl-5-oxazolone (VDM) oligomers via an optimised Cu(0)-mediated reversible-deactivation radical polymerisation approach, and the use of these oligomers as a versatile functional platform for the rapid generation of antimicrobial materials. The relative amounts of CuBr2 and Me6TREN were optimised to allow the fast and controlled polymerisation of VDM. These conditions were then used with the initiators ethyl 2-bromoisobutyrate, dodecyl 2-bromoisobutyrate, and (R)-3-((2-bromo-2-methylpropanoyl)oxy)propane-1,2-diyl didodecanoate to synthesise a library of oligo(VDM) (degree of polymerisation = 10) with ethyl, dodecyl or diglyceride..

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University of Melbourne Researchers

Grants

Awarded by Australian Research Council (ARC) Centre of Excellence in Convergent Bio-Nano Science and Technology


Awarded by ARC


Awarded by Wellcome Trust


Funding Acknowledgements

This collaborative research was conducted by the Australian Research Council (ARC) Centre of Excellence in Convergent Bio-Nano Science and Technology (project number CE140100036). J. L. G. wishes to acknowledge receiving an RTP scholarship. T. P. D. wishes to acknowledge the award of an Australian Laureate Fellowship and J. F. Q. a Future Fellowship from the ARC (FT170100144). M. A., J. C. R., and A. G. E are supported in apart by Wellcome Trust Strategic grant WT141107. M. A. C. is a NHMRC professorial research fellow (APP1059354). Microbes and HEK293 cells were sourced from ATCC (American Type Culture Collection). We thank Gabrielle Lowe for performing antifungal assays.