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Development of Non-Traditional Platinum Anticancer Agents: Trans-Platinum Planar Amine Compounds and Polynuclear Platinum Compounds

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Development of Non-Traditional Platinum Anticancer Agents: Trans-Platinum Planar Amine Compounds and Polynuclear Platinum Compounds Virginia Commonwealth University VCU Scholars Compass Theses and Dissertations Graduate School 2015 Development of Non-Traditional Platinum Anticancer Agents: trans-Platinum Planar Amine Compounds and Polynuclear Platinum Compounds Daniel E. Lee Virginia Commonwealth University Follow this and additional works at: https://scholarscompass.vcu.edu/etd Part of the Chemical Actions and Uses Commons, Inorganic Chemistry Commons, Medicinal Chemistry and Pharmaceutics Commons, and the Medicinal-Pharmaceutical Chemistry Commons © The Author Downloaded from https://scholarscompass.vcu.edu/etd/3809 This Dissertation is brought to you for free and open access by the Graduate School at VCU Scholars Compass. It has been accepted for inclusion in Theses and Dissertations by an authorized administrator of VCU Scholars Compass. For more information, please contact [email protected]. © 2015 Daniel E. Lee All Rights Reserved DEVELOPMENT OF NON-TRADITIONAL PLATINUM ANTICANCER AGENTS: TRANS- PLATINUM PLANAR AMINE COMPOUNDS AND POLYNUCLEAR PLATINUM COMPOUNDS A Dissertation Submitted in the Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in Chemistry at Virginia Commonwealth University. by Daniel E. Lee B. Sc in Chemistry, Temple University, 2007 Advisor: Nicholas P. Farrell, Professor, Department of Chemistry, College of Humanities and Sciences, Virginia Commonwealth University Virginia Commonwealth University Richmond, VA February, 2015 ACKNOWLEDGEMENTS What a journey it has been! It has been the amazing experience but also probably has been the most difficult time of my life so far. I have met many wonderful individuals throughout the graduate program and I would like to express my sincere gratitude for all the supports and contributions. First of all, I would like to thank Dr. Farrell for his guidance and support throughout the entire program. I would like to thank Samantha Tsotsoros and Sarah Spell (my dear friends, siblings, lab-mates, lunch buddies, and so on). It would not have been the same without you two. I would like to thank Dr.Qu for all of your valuable advice and assistance with NMR. I would like to thank my committee members (Dr. Sidorov, Dr. Collinson, and Dr. Ryan) for all of the guidance and valuable comments. I would like to thank Erica Peterson, Vijay Menon (former biology collaborator) and Samantha Katner (current biology collaborator) for all of your assistance in biological side of the lab. I would like to thank A. Gerard Daniel for all of your inputs based on theoretical chemistry and modeling. I would also like to thank our futures of the lab, Jamie Beaton, Wyatt Johnson, and Eric Ginsburg. Last but not least, I would like to thank my family for always being so faithful, supportive, and loving. ii TABLE OF CONTENTS Acknowledgements ....................................................................................................................... ii Table of Contents ......................................................................................................................... iii List of Figures ............................................................................................................................. viii List of Tables ............................................................................................................................. xvii Abstract ....................................................................................................................................... xxi Chapter 1. Introduction ............................................................................................................. 2 1.1 Cancer .............................................................................................................................. 2 1.2 Treatments ........................................................................................................................ 3 1.3 Platinum-Based Chemotherapeutics ................................................................................ 3 1.4 Mechanism of Action of Cisplatin .................................................................................... 4 1.5 Cisplatin Resistance ......................................................................................................... 6 1.6 Nontraditional Platinum Compounds .............................................................................. 9 1.6.1 trans-Platinum Planar Amine (TPA) Compounds .................................................... 9 1.6.2 Polynuclear Platinum Compounds (PPC) ............................................................... 13 1.6.3 Noncovalently Binding Cationic Polynuclear Platinum Compounds (PPC-NC) ... 15 1.7 Aim and Scope of This Thesis ......................................................................................... 18 Chapter 2. Synthesis, Characterization, and Chemical Property of trans-Platinum Planar Amine Compounds ......................................................................................................... 20 iii 2.1 Structure-Based Rational TPA Drug Design ................................................................. 21 2.1.1 Effects of Planar Amines Carrier Ligands on Cytotoxicity .................................... 21 2.1.2 Effects of Carboxylate Leaving Groups on Cytotoxicity and Cellular Accumulation 22 2.2 Synthesis and Characterization ...................................................................................... 23 2.3 Evaluation of TPA Compounds by Chemical Techniques .............................................. 27 2.3.1 Experimental Condition .......................................................................................... 28 2.3.2 Results ..................................................................................................................... 29 2.4 Binding of TPA Compounds with DNA .......................................................................... 31 2.4.1 Experimental Conditions ........................................................................................ 33 2.4.2 Results ..................................................................................................................... 35 2.5 Contributions .................................................................................................................. 36 Chapter 3. Biological Effect of TPA Compounds ................................................................. 38 3.1 Cytotoxicity, Cellular Accumulation, and Metabolic Stability of TPA Compounds ...... 39 3.1.1 Experimental ........................................................................................................... 39 3.1.2 Results ..................................................................................................................... 41 3.2 Cell Cycle Effects of TPA Compounds ........................................................................... 45 3.2.1 Experimental ........................................................................................................... 45 3.2.2 Cell Cycle Effects ................................................................................................... 45 3.3 Possible Cellular Targets Other Than DNA .................................................................. 46 3.3.1 Ternary Topoisomerase I-DNA Interaction ............................................................ 47 3.3.2 Zinc-Finger Proteins ............................................................................................... 48 iv 3.3.3 Telomerase .............................................................................................................. 49 3.3.4 Nuclear Protein Positive Cofactor PC4................................................................... 49 3.4 Conclusion ...................................................................................................................... 50 3.5 Contributions .................................................................................................................. 51 Chapter 4. Synthesis and Characterization of Polynuclear Platinum Compounds ........... 53 4.1 Synthetic Considerations ................................................................................................ 57 4.1.1 Synthetic Considerations of PPC Chloride Analogs (PPC-Cl) ............................... 57 4.1.2 Synthetic Considerations of PPC-NC ..................................................................... 58 4.2 Synthesis and Characterization of PPC-Cl .................................................................... 60 4.2.1 Synthesis of BBR3464 by New Approach.............................................................. 61 4.2.2 Synthesis of Tetraplatin-Cl ..................................................................................... 62 4.3 Synthesis and Characterization of PPC-NC .................................................................. 62 4.3.1 Synthesis of Monoplatin NC ................................................................................... 62 4.3.2 Synthesis of Diplatin NC, Triplatin NC and Tetraplatin NC .................................. 63 4.4 Contributions .................................................................................................................. 66 Chapter 5. DNA Binding Profiles and Cellular Effects of Polynuclear Platinum Compounds 68 5.1 Determination of Platinum Compound-DNA Interactions ............................................ 69 5.1.1 Background ............................................................................................................
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