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Novel Approaches to PET Imaging Neurodegeneration by Sean

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Novel Approaches to PET Imaging Neurodegeneration by Sean Novel Approaches to PET Imaging Neurodegeneration by Sean Tanzey A dissertation submitted in partial fulfillment Of the requirements for the degree of Doctor of Philosophy (Medicinal Chemistry) in the University of Michigan 2021 Doctoral Committee: Associate Professor, Peter J.H. Scott, Chair Professor Timothy A. Cernak Professor Robert A. Koeppe Professor Andy White Sean Tanzey [email protected] ORCID id: 0000-0002-7423-6142 © Sean Tanzey 2021 DEDICATION This work is dedicated to my father, Terry Tanzey, my true mentor in life. You will be missed. ii ACKNOWLEDGEMENTS This work could not have been made possible without the help of so many that I have crossed paths with. I would first like to thank my mentor, Professor Peter J.H. Scott for accepting me into his lab where I have met the finest group of scientists. His relaxed approach made things very easy-going during times that could have otherwise been very stressful during the PhD process. Thank you for being a friend. My most fond memory will be driving all the way across Michigan to see Slayer!!! My first organic chemistry mentor, Dr. Andy Mossine showed me the ropes and taught me so much than I could have ever asked for. Thank you for your friendship as well. Dr. Allen F. Brooks, who I like to refer to as the walking-talking encyclopedia, has given me such tremendous insight into all these projects. Thank you for the endless conversations, friendship, and all the beers we shared together. I developed a very close relationship with Dr. Xia Shao, my scientist mother, the most kind and funny person I have worked with in this process. Without her, all my work with carbon-11 would have been even more of a struggle. All the biochemistry performed in this work was taught to me by the eccentric Timothy Desmond, who provided the best smiles and jokes in the lab for me. Dr. Stefan Verhoog, a fellow metal head, has given me more votes of self-confidence in chemistry than anyone and has helped me to edit this work. I would also like to thank Robert Koeppe for his mentorship and allowing me the opportunity to travel abroad and learn from the experts in PET imaging analysis. I have appreciated my time in this Taj Mahal of PET centers, where I have worked alongside some of the most fun individuals in this field including the Gallium-68 crew Missy Rodnick, Jeremiah Alicea, Laura Bruton, and iii Mara Clark, the animal imaging crew, Jenelle Stauff, Janna Arteaga, and Phil Sherman, the postdocs that have ventured into our lab, Stephen Thompson, Tanpreet Kaur, So Jeong Lee, Jay Wright, Ryan Pakula, and Sean Preshlock, my graduate student sisters Megan Stewart, Allie Sowa/Dumond, and Lindsey Drake and finally the undergraduates, Isaac Jackson, Tony Mufarreh, Jonathan Pham, Wade Winton, and the student I got to mentor, Jake Sypniewski. I hope to continue to work with these amazing individuals in my future career as a PhD radiochemist. Every single one of them has provided comic relief, interesting conversations, and memories that will be cherished. Getting through these past 4 years was challenging, but I had the support of many loved ones. My strong, independent mother has taught me the virtue of working diligently and how to weather any storm. I will always look up to you. iv TABLE OF CONTENTS DEDICATION ................................................................................................................................ ii ACKNOWLEDGEMENTS ........................................................................................................... iii LIST OF FIGURES ..................................................................................................................... viii LIST OF TABLES ......................................................................................................................... xi LIST OF SCHEMES..................................................................................................................... xii ABSTRACT ............................................................................................................................... xiiiii CHAPTER 1: Application of Positron Emission Tomography (PET) as a Molecular Imaging Tool to Investigate the Metal Hypothesis of Neurodegeneration ................................................... 1 1.1. Introduction .......................................................................................................................... 1 1.2. What Makes a Good CNS PET Target? ............................................................................... 5 1.3. Current Neurodegeneration Imaging Approaches and their Limitations ............................. 7 1.3.1. Alzheimer’s Disease .................................................................................................. 8 1.3.2. Parkinson’s Disease ................................................................................................. 11 1.3.3. Neuroinflammation .................................................................................................. 12 1.4. Metal Ions as a Target for PET .......................................................................................... 14 1.4.1. Iron as a Target for PET........................................................................................... 15 1.4.2. Copper as a Target for PET ..................................................................................... 34 1.4.3. Zinc as a Target for PET .......................................................................................... 49 1.5. What Makes a Good CNS PET Tracer? ............................................................................. 61 1.6. Metal Chelators as PET Tracers ......................................................................................... 64 1.6.1. Iron Chelators as PET Tracers ................................................................................. 65 1.6.2. Copper/Zinc Chelators as PET Tracers .................................................................... 70 1.7. Measuring Metal Dyshomeostasis with MRI ..................................................................... 75 1.8. Summary ............................................................................................................................ 77 1.9. REFERENCES .................................................................................................................. 79 CHAPTER 2: Development of Iron Chelating PET Radiotracers in Assessing Neurodegenerative Diseases......................................................................................................................................... 99 2.1. Introduction ........................................................................................................................ 99 2.2. Results and Discussion ..................................................................................................... 101 2.2.1. First synthesis of [11C]DFP with a nonprotected precursor ................................... 101 2.2.2. Solving the Issue of Radiolysis .............................................................................. 105 2.2.3. Synthesis of [11C]DFP with a benzyl protected precursor ..................................... 106 2.2.4. Semi-preparative HPLC Development .................................................................. 108 v 2.2.5. Preclinical Imaging Analysis ................................................................................. 111 2.3. Conclusions ...................................................................................................................... 115 2.4. Materials and Methods ..................................................................................................... 116 2.4.1. Organic Chemistry ................................................................................................. 120 2.4.2. Radiochemistry ...................................................................................................... 120 2.4.3. Quality Control of [11C]DFP .................................................................................. 127 2.4.4. Preclinical PET Imaging ........................................................................................ 129 2.5. REFERENCES ................................................................................................................. 132 CHAPTER 3: Development of Copper/Zinc Chelating Scaffolds as PET Radiotracers in Assessing Neurodegenerative Diseases ...................................................................................... 135 3.1. Introduction ...................................................................................................................... 135 3.2. Results and Discussion ..................................................................................................... 139 3.2.1. [18F]FHQ415 .......................................................................................................... 139 3.2.2. [18F]FL2-b .............................................................................................................. 143 3.3. Conclusion ........................................................................................................................ 146 3.4. Materials and Methods ..................................................................................................... 147 3.4.1. Synthesis of HQ415 Precursors and Standards ...................................................... 147 3.4.2. Radiochemical
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