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Design, Synthesis and Physicochemical Analysis of Ruthenium(II) Polypyridyl Complexes for Application in Phototherapy and Nucleic Acid Sensing

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Design, Synthesis and Physicochemical Analysis of Ruthenium(II) Polypyridyl Complexes for Application in Phototherapy and Nucleic Acid Sensing University of Kentucky UKnowledge Theses and Dissertations--Chemistry Chemistry 2016 Design, Synthesis and Physicochemical Analysis of Ruthenium(II) Polypyridyl Complexes for Application in Phototherapy and Nucleic Acid Sensing Erin Melissa Wachter University of Kentucky, erinmelissa24@gmail.com Digital Object Identifier: http://dx.doi.org/10.13023/ETD.2016.229 Right click to open a feedback form in a new tab to let us know how this document benefits ou.y Recommended Citation Wachter, Erin Melissa, "Design, Synthesis and Physicochemical Analysis of Ruthenium(II) Polypyridyl Complexes for Application in Phototherapy and Nucleic Acid Sensing" (2016). Theses and Dissertations-- Chemistry. 60. https://uknowledge.uky.edu/chemistry_etds/60 This Doctoral Dissertation is brought to you for free and open access by the Chemistry at UKnowledge. It has been accepted for inclusion in Theses and Dissertations--Chemistry by an authorized administrator of UKnowledge. For more information, please contact UKnowledge@lsv.uky.edu. STUDENT AGREEMENT: I represent that my thesis or dissertation and abstract are my original work. Proper attribution has been given to all outside sources. I understand that I am solely responsible for obtaining any needed copyright permissions. I have obtained needed written permission statement(s) from the owner(s) of each third-party copyrighted matter to be included in my work, allowing electronic distribution (if such use is not permitted by the fair use doctrine) which will be submitted to UKnowledge as Additional File. I hereby grant to The University of Kentucky and its agents the irrevocable, non-exclusive, and royalty-free license to archive and make accessible my work in whole or in part in all forms of media, now or hereafter known. I agree that the document mentioned above may be made available immediately for worldwide access unless an embargo applies. I retain all other ownership rights to the copyright of my work. I also retain the right to use in future works (such as articles or books) all or part of my work. I understand that I am free to register the copyright to my work. REVIEW, APPROVAL AND ACCEPTANCE The document mentioned above has been reviewed and accepted by the student’s advisor, on behalf of the advisory committee, and by the Director of Graduate Studies (DGS), on behalf of the program; we verify that this is the final, approved version of the student’s thesis including all changes required by the advisory committee. The undersigned agree to abide by the statements above. Erin Melissa Wachter, Student Dr. Edith C. Glazer, Major Professor Dr. Dong-Sheng Yang, Director of Graduate Studies DESIGN, SYNTHESIS AND PHYSICOCHEMICAL ANALYSIS OF RUTHENIUM(II) POLYPYRIDYL COMPLEXES FOR APPLICATION IN PHOTOTHERAPY AND NUCLEIC ACID SENSING _______________________________________________________ DISSERTATION _______________________________________________________ A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the College of Arts and Science at the University of Kentucky By Erin Melissa Wachter Lexington, Kentucky Director: Dr. Edith C. Glazer, Associate Professor of Chemistry Lexington, Kentucky 2016 Copyright © Erin Melissa Wachter 2016 ABSTRACT OF DISSERTATION DESIGN, SYNTHESIS AND PHYSICOCHEMICAL ANALYSIS OF RUTHENIUM(II) POLYPYRIDYL COMPLEXES FOR APPLICATION IN PHOTOTHERAPY AND NUCLEIC ACID SENSING Current chemotherapeutics exhibit debilitating side effects as a result of their toxicity to healthy tissues. Reducing these side effects by developing chemotherapeutics with selectivity for cancer cells is an active area of research. Phototherapy is one promising modality for selective treatment, where drug molecules are “turned on” when irradiated with light, reducing damage to healthy tissues by spatially restricting the areas exposed to irradiation. A second approach to improve selectivity is to exploit the differences in cancerous versus healthy cells, such as increased metabolism and/or upregulation of cell surface receptors. Ruthenium(II) polypyridyl complexes are candidates for phototherapy due to their highly tunable photophysical and photochemical properties. The addition of strain to the metal center is a general approach used to render complexes susceptible to light-induced ligand loss. Upon ejection of a ligand, the Ru(II) center is capable of covalently binding biomolecules within cells to produce a cytotoxic effect. The ligands surrounding the metal center are amenable to chemical modification through the incorporation of pendent functional groups as chemical “handles”, allowing for different directing molecules to be attached. Nucleic acids are important targets for drug discovery, and the development of selective probes to either visualize or selectively damage nucleic acids within the cell is an ongoing area of research. Specifically, G-rich regions are abundant in the human genome, and the presence of G-quadruplexes in telomeres and promoter regions of oncogenes make them potential therapeutic targets. Ru(II) complexes are known to bind nucleic acids, and some have been shown to induce and/or stabilize G-quadruplex Structures. Multiple series of Ru(II) compounds have been synthesized and tested to improve the functional range for Ru(II) complexes for in vivo applications, where they act as “light switches” for DNA. These molecules are “off” when in an aqueous environment but turned “on” in the presence of DNA. Several hit compounds were identified that showed selectivity for specific G-quadruplex structures. KEYWORDS: Ruthenium(II) polypyridyl complexes, cancer, phototherapy, nucleic acid sensing, G-quadruplexes Erin Melissa Wachter 05/12/2016 DESIGN, SYNTHESIS AND PHYSICOCHEMICAL ANALYSIS OF RUTHENIUM(II) POLYPYRIDYL COMPLEXES FOR APPLICATION IN PHOTOTHERAPY AND NUCLEIC ACID SENSING By Erin Melissa Wachter Dr. Edith Glazer Director of Dissertation Dr. Dong-Sheng Yang Director of Graduate Studies 05/12/2016 TO MY FAMILY ACKNOWLEDGMENTS Without the support of many people I would not have been able to accomplish the things I have while pursing my Ph.D. I would first like to thank my advisor, Dr. Edith Glazer, for her continued support, guidance, and inspiration. Over the course of 6 years she has helped me discovery things about myself and become the scientist I am today. Her passion for the research is admirable and I can only hope to show that much passion in my future career. Many other people played an important role in my scientific development. To my committee members Drs. John Selegue, Allan Butterfield, and Ed Pavlik, I would like to thank each of them for their scientific input and encouraging conversations over the years. I would also like to extend my gratitude to Dr. David Heidary for his continued input on my research projects, biological expertise and overall support. Next, I would like to thank each of the Glazer group members, past and present, for the role they played in my Ph.D. career. I would especially like to thank Catherine, for not only being a labmate but a friend who has continuously helped me become a better scientist and person, and Achmad Hidayatullah, for the enjoyable conversations, continued motivational chats and teaching me shorthanded phrasing for everything. Lastly, I would like to thank John May and Tricia Coakley for their guidance and conversations while using the ERTL facilities. Next, I want to thank my family and friends who has been supportive and encouraging since the beginning. Mom and Dad: even though they do not understand all of the science, they still want to read all of my papers and know what I’ve been doing each week in the lab. Siblings: for always being supportive and interested in the entire process. Amber: thank you for all of your “checking in” texts, job postings, and someone to not talk science with. Thy: thank you for being that silly friend that can put you in a good mood no matter how bad the day was. Christine: thank you for the “stimulating” walks and always being there to vent to.. Last but definitely not least, I want to thank Jahmai Turner for being my rock during this process. You’re one of the most supportive people in my life. Thank you for always being my sanity when things were stressful and always finding the positive out of a situation. I have learned countless things from you. iii TABLE OF CONTENTS ACKNOWLEDGMENTS ................................................................................................. iii LIST OF TABLES ........................................................................................................... viii LIST OF FIGURES ........................................................................................................... xi LIST OF SCHEMES...................................................................................................... xviii ABBREVIATIONS ......................................................................................................... xix RESEARCH CONTRIBUTIONS .................................................................................. xxii Chapter 1. Introduction. ...................................................................................................... 1 1.1 What is cancer and how is it treated? ........................................................................ 1 1.2 Metal-based anticancer agents. ................................................................................. 2 1.3 Light-activated therapies. .........................................................................................
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