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Andrew Boden Thesis Immobilisation strategies for the tethering of polymers and antimicrobial peptides to design multifunctional surface coatings Andrew Boden BSc(Hons) Submitted to the Faculty of Science, Engineering and Technology Swinburne University of Technology In partial fulfilment of the degree of Doctorate of Philosophy 2020 i ABSTRACT Unwanted accumulation of proteins and bacterial cells on a surface is a major concern in a number of areas including but certainly not limited to, healthcare, food preparation, and shipping industries. This type of ‘biofouling’ can significantly perturb the function of a particular device or result in material degradation. Particularly within the healthcare industry, development of non- fouling surfaces (i.e. surfaces that can resist protein and bacterial adhesion) is of great importance due to the high incidence of infection associated with the use of indwelling medical devices. Fabrication of such surfaces have generally been achieved through lithographic or anti-adhesive techniques in order to manipulate surface topography and chemistry, however there has been little or no use of combining both of these strategies for the development of a multifunctional surface coating. As such, the research presented here examines various immobilisation strategies for the tethering of anti-adhesive polymers and antimicrobial peptides (AMPs) to different types of surfaces. This included investigating surface activation methods to generate surface-bound functional groups, and also the use of microparticles and binary colloidal crystal (BCC) layers as a platform for the covalent immobilisation of selected polymers and AMPs. After demonstrating that puroindoline-based synthetic AMPs were active in solution against clinically relevant bacteria, subsequent experimental work provided a proof of concept that these types of AMPs can be tethered to binary colloidal crystal layers by zero-length immobilisation using EDC/NHS coupling chemistry, and still exhibit antibacterial activity with a decrease of >70% in the viability of E.coli cells when compared to control samples (Chapter 4). Confirmation of AMP immobilisation was achieved through a range of physio-chemical characterisation techniques including zeta potential, X-ray photoelectron spectroscopy (XPS) and matrix-assisted ii laser desorption ionisation time-of-flight mass spectrometry (MALDI-ToF MS). Interestingly, MALDI analysis showed the importance of proper characterisation of small-molecule grafting, as traces of physically adsorbed AMP was detected for covalently immobilised samples. Considering the success of zero-length immobilisation of PuroA, subsequent experimental work was focussed on the incorporation of flexible polymer linkers to not only add an additional barrier from proteins and bacteria, but also increase AMP mobility and penetration depth. In-situ investigations using surface plasmon resonance (SPR) demonstrated that poly(ethylene glycol) (PEG) can significantly reduce the adsorption of protein compared to unmodified surfaces with graft density and protein resistant properties being able to be controlled by variations in ionic strength and polymer molecular weight (Chapter 5). It was also found that the choice of grafting method is crucial to achieve dense polymer layers, as variations in temperature, ionic strength, and pH may have positive or negative effects depending of the type of grafting method chosen for both flat and spherical surfaces (Chapter 6). The choice of grafting method is also dependant on the availability of appropriate functional groups present, thus it was necessary to optimise various surface activation methods to generate sufficient reactive functional groups at a surface. A particular focus within this project was the generation of thiol functional groups through silanisation of inorganic surfaces with (3- mercaptopropyl)trimethoxysilane (MPTS), as thiol-based immobilisation strategies are quite versatile and show minimal interference from other functional groups (i.e. amines and carboxylic acids) (Chapter 7). Given a 2hr pre-hydrolysis period at pH 4 it was shown that relatively thick MPTS layers can be obtained that have a high proportion of thiol functional groups providing there are minimal post-deposition treatments such as rinsing and drying. Thorough characterisation of MPTS films was achieved using ellipsometry, water contact angle (WCA) analysis, XPS, and Fourier transform infrared (FTIR) spectroscopy, which helped provide an in-depth description of iii MPTS deposition methods to generate optimised thiol-containing silane layers. Such optimisation was necessary for future experiments where two immobilisation methods utilising surface-bound thiols were investigated to tether heterobifunctional PEG and AMPs to MPTS-functionalised silica colloids (Chapter 8). Both thiol-ene ‘photo-click’ and thiol-maleimide coupling methods were determined to be quite effective in PEG and AMP tethering with characterisation through zeta potential and XPS revealing that PEG and AMPs were both bound to the surface of the particles. The AMPs; P1 and W8 were also determined to retain activity after immobilisation, with a reduction of >75% in the viability of P.aeriginosa cells compared to control samples. This research project presents an investigation in to the various immobilisation strategies for the tethering of polymers and AMPs to design functional surface coatings for potential biomedical applications. Key findings within the project have helped contribute to the field of biomaterials demonstrating new and novel ways to generate patterned surfaces based on PEG and AMP immobilisation to colloidal crystal layers. Additionally, this research has provided valuable information regarding the success of certain grafting methods, showing that the conditions and chemistry chosen is of upmost importance to achieve successful tethering. iv ACKNOWLEDGEMENTS The researcher wishes to extend their deepest gratitude to all people who have given their assistance and valuable time throughout the course of this research project and contributed to the completion of this Thesis. Firstly I would like to acknowledge the Wurundjeri people who are the Traditional Custodians of the Land and pay my respects to Elders past and present. I would also like to thank the Australian Government and Swinburne University of Technology (SUT) for funding through an Australian Postgraduate Award (APA). To my supervisory team; Prof. Peter Kingshott and Prof. Mrinal Bhave, I am extremely grateful and appreciative for all your guidance and valuable insights throughout the project, and also for your support in times of distress. I would also like to acknowledge the co-operation and help provided by SUT staff members and laboratory staff for technical support and help in instrument training. Finally, I am extremely grateful to my family for their unwavering love and patience. I could not have done this without your encouragement and support. I thank you all, tremendously v DECLARATION I declare that the information within this thesis is my own work and does not contain any material that has previously been submitted elsewhere for educational purposes or publication without acknowledgement through proper referencing. Name: Andrew Boden Signed: Date: 10-8-20 vi TABLE OF CONTENTS ABSTRACT .............................................................................................................................. ii ACKNOWLEDGEMENTS.........................................................................................................v DECLARATION ...................................................................................................................... vi TABLE OF CONTENTS ......................................................................................................... vii List of Figures .......................................................................................................................... xii List of Tables ......................................................................................................................... xvii 1 INTRODUCTION ...........................................................................................................1 1.1 Scope & aims of the PhD project .............................................................................1 1.2 Thesis structure ........................................................................................................4 2 LITERATURE REVIEW ................................................................................................9 2.1 General introduction ................................................................................................9 2.2 Interactions at the biointerface ............................................................................... 12 2.2.1 Biomaterial associated infections ...................................................................... 13 2.2.2 Biofouling and biofilm formation ..................................................................... 14 2.3 Non-fouling polymers ............................................................................................ 17 2.3.1 Self-assembled monolayers .............................................................................. 17 2.3.2 Ethylene glycol based polymer brushes ............................................................ 19 2.3.3 Other non-fouling polymers .............................................................................. 21 2.3.4 Immobilisation
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