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Kent Academic Repository Full Text Document (Pdf) Kent Academic Repository Full text document (pdf) Citation for published version Ferris, Trevor John (2015) Zirconium-89 Complexes for Cell Tracking with Positron Emission Tomography. Doctor of Philosophy (PhD) thesis, University of Kent,. DOI Link to record in KAR https://kar.kent.ac.uk/48147/ Document Version UNSPECIFIED Copyright & reuse Content in the Kent Academic Repository is made available for research purposes. Unless otherwise stated all content is protected by copyright and in the absence of an open licence (eg Creative Commons), permissions for further reuse of content should be sought from the publisher, author or other copyright holder. Versions of research The version in the Kent Academic Repository may differ from the final published version. Users are advised to check http://kar.kent.ac.uk for the status of the paper. Users should always cite the published version of record. Enquiries For any further enquiries regarding the licence status of this document, please contact: [email protected] If you believe this document infringes copyright then please contact the KAR admin team with the take-down information provided at http://kar.kent.ac.uk/contact.html Zirconium-89 Complexes for Cell Tracking with Positron Emission Tomography Trevor John Ferris School of Physical Sciences, University of Kent at Canterbury A thesis is submitted to the University of Kent at Canterbury in partial fulfilment of the requirements for the degree of Doctor of Philosophy DECLARATION No part of this thesis has been submitted by me or anyone else in support of an application for any other degree or qualification at the University of Kent or at any other University. Signed: Trevor Ferris Date: 18/03/2015 i Abstract Tracking cell migration in vivo by scintigraphy using cells labelled with gamma- emitting radionuclides (especially indium-111) is a well-established clinical and research tool. Positron emission tomography offers improved sensitivity and resolution, but there are no established cell labelling methods using suitable long- lived isotopes. The long half-life positron emitter zirconium-89 (half-life 78.4 h) is a strong candidate for cell labelling and cell tracking, and is becoming increasingly available. It has no known biological role or transport mechanisms. The aim of this research was to produce a range of candidate neutral zirconium L4 lipophilic complexes that could be prepared under radiopharmaceutical conditions and used in cell labelling. This aim was achieved with the ligands; oxine, tropolone and ethyl maltol. The resulting complexes can be prepared in high yield from zirconium precursors in hydrochloric or oxalic acid solution. A deferiprone complex was prepared from deferiprone and zirconium tetrachloride, but was found to lack lipophilic properties and it was not possible to prepare the deferiprone complex under radiopharmaceutical conditions. Analytical techniques such as carbon, hydrogen and nitrogen elemental analysis, nuclear magnetic resonance spectroscopy, fourier transform infrared spectroscopy, and Raman spectroscopy have been used to characterise the complexes. The oxine and tropolone complexes were the most amenable to chromatographic characterisation and high performance liquid chromatography and instant thin layer chromatography protocols have been established to monitor radiochemical purity. Cell uptake and efflux of zirconium-89 tetrakisoxine, tropolone and ethyl maltol utilising the following cell lines was determined; HCT116: colon cancer, J774: mouse macrophage and MDA-MB-231: breast cancer. Zirconium-89 tetrakisoxine has emerged as a lead compound. Zirconium-89 tetrakisoxine labelled myeloma cells retained the radiotracer in vivo for up to 7 days. Zirconium-89 tetrakisoxine was found to be a promising cell tracking agent for long term cell tracking studies. ii Publications and Presentations Peer-Reviewed Journal Articles: Synthesis and Characterisation of Zirconium Complexes for Cell Tracking with Zr- 89 by Positron Emission Tomography. T. J. Ferris, P. Charoenphun, L. K. Meszaros, G. E. D. Mullen, P. J. Blower and M. J. Went, Dalton Trans, 2014, 43, 14851-14857. [89Zr]-Zr(oxinate)4 for long term in vivo cell tracking by positron emission tomography. P. Charoenphun, L.K. Meszaros, K. Chuamsaamarkkee1, E. Sharif- Paghaleh, J. R. Ballinger, T. J. Ferris, M. J. Went, G. E.D. Mullen, P. J. Blower, Eur J Nucl Med Mol Imaging, 2015, 42, 2, 278-287. Conference Abstracts: 89Zr-Oxine Complex: a Long-Lived Radiolabel for Cell Tracking Using PET. L. K. Meszaros, P. Charoenphun, K. Chuamsaamarkkee, J. R. Ballinger, G. E. D. Mullen, T. J. Ferris, M. J. Went and P. J. Blower, 2013 World Molecular Imaging Conference, http://www.wmis.org/abstracts/2013/data/index.htm, Accessed 26 June 2014. Medical Imaging utilising Zirconium Complexes. T. J. Ferris, P. Charoenphun, M. J. Went and P. J. Blower, Nucl Med Commun, 2013, 34, 362. Poster Presentations: Medical Imaging utilising Zirconium Complexes. T. J. Ferris, P. Charoenphun, M. J. Went and P. J. Blower, Nucl Med Commun, 2013, 34, 362. Zirconium-89 Complexes for Positron Emission Tomography. Metal ions in medical imaging optical, radiopharmaceutical and MRI contrast. Dalton Discussion 15 08-SEP-2014 to 10-SEP-2014 University of York, UK. iii Acknowledgements I’d like to say thank you to the following people for their help and support with my research and production of this thesis. My supervisor Professor Michael Went for his outstanding support over the years as a lecturer during my undergraduate time at Kent through to my postgraduate research. His knowledge of the chemical sciences has been invaluable in guiding my research. His support has kept me motivated and inspired me to produce this work to the best of my ability. Our collobrator Professor Phil Blower from Kings College London for helping to guide my research and introducing me to nuclear medicine, his field of expertise. Without his knowledge, support and genorousity this research project would not have been possible and I am very gratefull. Sarah for her unending patience, understanding and encouragement not just through the course of this PhD but over the last 10 years. Watkin, Kitten and Bill Jenner Ferris for their quiet understanding and constant companionship. Liv for her honesty and words of support. Aaron, Alex (Chief), Christina (Red Ross) Christine Rogers, Emma, Holly, Jon James, Kate, Nanami (Nana), Ollie and Simon (Sensei) for making my time at Kent an enjoyable chapter in my life. I would like to finish with one of my favourite quotes that I have found most illuminating and inspirational; “Everything is determined, the beginning as well as the end, by forces over which we have no control. It is determined for the insect, as well as for the star. Human beings, vegetables, or cosmic dust, we all dance to a mysterious tune, intoned in the distance by an invisible piper.” Albert Einstein iv To Sarah Jane Jenner v CONTENTS Page Declaration i Abstract ii Publications and Presentations iii Acknowledgments iv Dedication v Figure Index xx Abbreviations xxv CHAPTER 1 Introduction 1.1 Medical Imaging 1 1.1.1 X-ray Imaging (Radiography) 2 1.1.2 Contrast Radiography 2 1.1.3 Mammography 3 1.1.4 Computed Tomography 3 1.1.5 Angiography 4 1.1.6 Ultrasound Imaging 4 1.1.7 Fluoroscopy 5 1.1.8 MRI 5 1.2 Nuclear Medicine and Imaging 6 1.3 Basis of Nuclear Medicine 7 1.3.1 Atomic structure 7 1.3.2 Isotopes 7 1.3.3 Radioisotopes 7 1.4 Radiopharmaceuticals 8 1.5 Steps of Imaging Agent Development 8 1.5.1 Introduction 8 1.5.2 Discovery 9 1.5.3 Preclinical Testing 9 vi 1.5.4 Pharmacokinetics 10 1.5.6 Toxicological Analysis 10 1.5.7 Clinical Trials 11 1.5.8 Registration 11 1.5.9 Post Marketing 11 1.6 Therapeutic Nuclear Medicine 12 1.7 Diagnostic Nuclear Medicine 12 1.8 Scintigraphy 13 1.9 Single Photon Emission Computed Tomography (SPECT) 14 1.10 Positron Emission Tomography (PET) 15 1.10.1 Early History 15 1.11 Positron Emitters for use in PET 16 1.11.1 Oxygen-15 16 1.11.2 Rubidium-82 Chloride 16 1.11.3 Fluorine-18 Fluorodeoxyglucose 16 1.11.4 Carbon-11 Methionine 17 1.11.5 Nitrogen-13 Ammonia 17 1.11.6 Iodine-124 17 1.12 Physical Principles of PET 18 1.13 PET Detector 19 1.14 Application of PET 21 1.14.1 Oncology 21 1.14.2 Cardiology 21 1.14.3 Neurology 22 1.14.4 Neuropsychology and Cognitive Neuroscience 22 1.14.5 Pharmacology 22 1.15 PET Vs SPECT 23 1.16 Immuno PET 24 1.17 Cell Tracking in Cancer 25 1.18 Indium-111 Oxine and Indium-111 Tropolone 26 1.18.1 Indium-111 Oxine 26 1.18.2 Indium-111 Tropolone 26 1.19 Zirconium 27 vii 1.19.1 An Introduction to Zirconium 27 1.20 Zirconium Chemistry 28 1.20.1 Zirconium Coordination Chemistry 28 1.21 Zirconium Isotopes 29 1.21.2 Zirconium Radioisotopes 29 1.22 The Synthesis and Uses of 89Zr in PET 30 1.22.1 89Zr Production 30 1.22.2 89Zr PET Tracers 30 1.23 Bodily Clearance of Yttrium-89 31 1.24 Properties Required for New Zirconium Radiopharmaceuticals 32 1.24.1 Half Life 32 1.24.2 Biological Properties 32 1.24.3 Diffusion into Cells and Stability 32 1.25 An Overview of the Zirconium Precursor Complexes 33 1.25.1 Zirconium Tetra Chloride 33 1.25.2 Zirconium Tetrakisoxalato 33 1.26 An Overview of the Ligands to be Complexed with Zirconium 34 1.26.1 Introduction 34 1.26.2 Oxine 34 1.26.3 Tropolone 36 1.26.4 Ethyl Maltol 37 1.26.5 Deferiprone 38 1.27 Zirconium Complexes 39 1.27.1 Zirconium Tetrakisoxine 39 1.27.2 Zirconium Tropolone Complexes 41 1.27.3 Zirconium Ethyl Maltol Complexes 41 1.27.4 Zirconium Deferiprone Complexes 42 viii CHAPTER 2 Synthesis and Nuclear
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