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University of Florida Thesis Or Dissertation Formatting IMPROVING THE SEPARATION OF DRUG ISOMERS USING CHEMICAL MODIFIERS IN HIGH-FIELD ASYMMETRIC WAVEFORM ION MOBILITY SPECTROMETRY By MICHAEL SHENMING WEI A DISSERTATION PRESENTED TO THE GRADUATE SCHOOL OF THE UNIVERSITY OF FLORIDA IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY UNIVERSITY OF FLORIDA 2019 © 2019 Michael Shenming Wei To my friends and family. Thanks for dealing with me when I needed it. ACKNOWLEDGMENTS I would not be able to present the following research without the advice and support of my friends, family, and colleagues. First and foremost, I want to thank my advisor Dr. Rick Yost for all of the guidance, opportunities, advice, and stories that I got to experience over my time at UF. I would also like to thank the members of my graduate committee: Dr. Kari Basso, Dr. Benjamin Smith, Dr. Timothy Garrett, as well as my previous committee member Dr. Nicholas Polfer. Each motivated and inspired me along my time as a graduate student. Thanks also go out to Dr. Jodie Johnson, whom I learned so much about mass spectrometry instrumentation and troubleshooting from. I want to extend recognition to Dr. George Dubay at Duke University, who first talked mass spectrometry to me and inspired me to pursue a doctorate in analytical chemistry. I want to thank my fellow Yost group members, most notably Robin Kemperman, whom I shared many hours with talking about science and bantering about other topics. Robin has been a critical colleague in my high-field ion mobility research and a great friend. Additional thanks go out to Louis Searcy, Kevin Davis, and my undergrad Christopher Gongar, whom have each helped me out in a huge way during my time in the Yost Group. I also want to give my gratitude to Dr. Elizabeth Dhummakupt for her mentorship during my first year, Dr. Michael Costanzo for his mentorship and collaboration during my second and third, and Dr. Jared Boock for also being a nerd like me (:smileyface:). I want to thank my family for supporting me throughout the years. To my father, I want to give my thanks for the advice and help on so many little life things – car maintenance, cooking, insurance, etc. To my mother, I want to give my thanks for 4 always welcoming me back home with open arms and a hearty meal. To my sister, I want to give my thanks for being someone that I can share stories and experiences with about college. Finally, I want to thank my friends, who challenged me intellectually and with whom I spent many long night gaming with. In particular, I would like to recognize Rodger Zou, Wayne You, and Cullen Wallace. Rodger was instrumental in helping me prepare for my qualification exam presentation and continues to inspire me to learn new skills. Wayne administers the online chat program that has helped me feel connected with so many college friends that I would otherwise not be able to interact with. Cullen has helped me mature so much as a person. From Cullen, I came to truly appreciate the value of keeping one’s eyes on the goal, of seeking out information to make the best possible decisions, of dedication when times get tough, and of practice making perfect. 5 TABLE OF CONTENTS page ACKNOWLEDGMENTS .................................................................................................. 4 LIST OF TABLES ............................................................................................................ 8 LIST OF FIGURES .......................................................................................................... 9 LIST OF ABBREVIATIONS ........................................................................................... 11 ABSTRACT ................................................................................................................... 12 CHAPTER 1 INTRODUCTION .................................................................................................... 14 Ion Mobility and High-Field Ion Mobility Spectrometry ............................................ 14 Principles of High-Field Asymmetric Waveform Ion Mobility Spectrometry ...... 14 FAIMS Instrumentation ..................................................................................... 17 Modifiers for Improving FAIMS Performance .................................................... 20 Ionization and Mass Analysis .................................................................................. 21 Electrospray Ionization ..................................................................................... 21 Quadrupole Ion Trap Mass Spectrometry......................................................... 23 Overview of Research............................................................................................. 24 2 EFFECTS OF SOLVENT VAPOR MODIFIERS FOR THE SEPARATION OF OPIOID ISOMERS IN FAIMS-MS ........................................................................... 32 Introduction ............................................................................................................. 32 Materials and Methods............................................................................................ 34 Chemicals ......................................................................................................... 34 FAIMS-MS Instrumentation and Methods......................................................... 34 Solvent Vapor Procedure ................................................................................. 35 Results and Discussion........................................................................................... 36 FAIMS-MS Separation of Opioids .................................................................... 36 Aprotic Solvents Versus Protic Solvents .......................................................... 41 Conclusions ............................................................................................................ 44 3 FAIMS SEPARATION OF ANABOLIC ANDROGENIC STEROID EPIMER PAIRS USING CATION MODIFIERS ..................................................................... 57 Introduction ............................................................................................................. 57 Materials and Methods............................................................................................ 61 Chemicals ......................................................................................................... 61 FAIMS Instrumentation and Methods ............................................................... 62 Results and Discussion........................................................................................... 63 6 Separation of Testosterone & Epitestosterone using Group 1 Cations ............ 63 Effect of Multimer Cation Complexes on FAIMS Separations .......................... 65 Separation of Androsterone & Trans-androsterone .......................................... 68 Conclusions ............................................................................................................ 68 4 RESOLVING ANDROSTERONE ISOMERS AND ISOBARS USING CATION- MODIFIED FAIMS-MS ............................................................................................ 77 Introduction ............................................................................................................. 77 Materials and Methods............................................................................................ 79 Chemicals ......................................................................................................... 79 FAIMS Instrumentation and Methods ............................................................... 80 Results and Discussion........................................................................................... 81 Resolving Androsterone Epimers ..................................................................... 81 Resolving Non-Epimer Isomers and Isobars .................................................... 83 Effects of DF on CF Peaks ............................................................................... 87 Effects of Cation Size on CF Peaks ................................................................. 90 Cation Concentration Effects ............................................................................ 92 Conclusions ............................................................................................................ 93 5 CONCLUSIONS AND FUTURE WORK ............................................................... 106 LIST OF REFERENCES ............................................................................................. 111 BIOGRAPHICAL SKETCH .......................................................................................... 116 7 LIST OF TABLES Table page 2-1 Average CF peak widths and standard deviations for carrier gas compositions....................................................................................................... 47 4-1 Ionic radii and electronegativities for the cation species used for the separation of androsterone isomers and isobars ................................................ 96 8 LIST OF FIGURES Figure page 1-1 Graph representing an idealized waveform and ion motion for FAIMS ............... 26 1-2 Effects of applying a compensation voltage to the FAIMS waveform ................. 27 1-3 Example FAIMS analysis of morphine [M+H]+ ions ............................................ 28 1-4 Illustration of ion mobility behaviors with increasing electric field strengths ........ 28 1-5
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