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Dissertation Photodegradation Of DISSERTATION PHOTODEGRADATION OF SELECTED ENDOCRINE AND PHARMACEUTICALLY ACTIVE COMPOUNDS UNDER ENVIRONMENTALLY RELEVANT CONDITIONS – PROCESSES AND PRODUCTS Submitted by Robert B. Young Department of Soil and Crop Sciences In partial fulfillment of the requirements For the Degree of Doctor of Philosophy Colorado State University Fort Collins, Colorado Spring 2014 Doctoral Committee: Advisor: Thomas Borch Jessica G. Davis James L. Gray Charles S. Henry Copyright by Robert B. Young 2014 All Rights Reserved ABSTRACT PHOTODEGRADATION OF SELECTED ENDOCRINE AND PHARMACEUTICALLY ACTIVE COMPOUNDS UNDER ENVIRONMENTALLY RELEVANT CONDITIONS – PROCESSES AND PRODUCTS Within the past few decades, books such as Silent Spring and Our Stolen Future have done much to raise the public’s awareness of the threat to human and ecosystem health from chronic exposure to chemical pollution, and considerable effort has been made to identify priority pollutants, understand their toxicological effects, and examine their presence and fate within the environment. Two classes of chemical pollutant that can induce biological effects at extremely low concentrations are pharmaceuticals and steroid hormones. Each has been linked to adverse health effects in humans or wildlife, and each has been detected in surface waters throughout the world, from sources including wastewater treatment plants and agricultural operations. Once present in surface waters, pharmaceuticals and steroid hormones are subject to various transformation and removal processes, including biodegradation, photodegradation, and sorption to colloids or sediments. Because biodegradation and sorption are the primary removal processes during wastewater treatment, photodegradation might be especially important in surface waters, at least for those pharmaceuticals and steroid hormones that have survived wastewater treatment. This dissertation examines the photodegradation of selected pharmaceuticals and steroid hormones (androstenedione, testosterone, and lamotrigine) under environmentally relevant conditions, including natural or simulated sunlight, aqueous solutions at different pH, and the presence of dissolved organic matter. ii Chapter 1 of the dissertation provides a brief introduction to surface water pollution and environmental photochemistry. In addition, chapter 1 lists the dissertation objectives and the publications, presentations, and outreach efforts derived from it. Chapter 2 of the dissertation reviews existing literature on the presence of steroid hormones in freshwater ecosystems, their sources, and their potential fate. Chapter 2 compiles information about the physical and chemical properties of selected steroid hormones, and considers how biodegradation, photodegradation, and sorption influence steroid hormone fate in freshwater ecosystems. In addition, chapter 2 offers suggestions for future research. Chapter 3 of the dissertation examines the direct photodegradation of lamotrigine (LTG), an antiepileptic and mood stabilizing drug that has been detected in wastewater, groundwater, surface water and drinking water. Because LTG is a weak base (pKa = 5.7) that appears in two protonation states in natural waters, chapter 3 examines the photodegradation of LTG under simulated sunlight in buffered aqueous solutions at pH 3.3 (99.6% protonated), pH 5.3 (71.5% protonated) and pH 7.7 (1% protonated). Lamotrigine’s half-life varied little (100 ± 3 to 112 ± 2 h) with solution pH, but its specific light absorption rate was 12 times higher, and its reaction quantum yield was 13 times lower, at pH 7.7 versus pH 3.3. Using these reaction quantum yields and a spectral radiation model (SMARTS v 2.9.5), LTG’s estimated photodegradation rate in the estimated midday, midsummer sunlight of Denver, CO, USA (latitude 39.8617 °N) was more than twice as fast at pH 7.7 versus pH 3.3, demonstrating that solution pH can have a substantial effect on LTG’s photodegradation in natural waters, depending on lighting and other environmental conditions. Lamotrigine’s photoproducts were detected by liquid chromatography-UV diode array detection and time-of-flight mass spectrometry. Solution pH was shown to affect both the identities and relative abundances of iii LTG’s photoproducts. As a result, different reaction mechanisms were proposed. Finally, LTG’s reaction quantum yield (2.51 ± 0.07 × 10−5 mol einstein−1 at pH 7.7) and other results suggested that LTG and three photoproducts are approximately as resistant to direct photodegradation as carbamazepine, a frequently detected and relatively recalcitrant pharmaceutical in surface waters. Chapter 4 of the dissertation compares the direct photodegradation of dilute (<10 μg L−1) aqueous solutions of androstenedione (AD) and testosterone (T), two commonly observed male sex hormones, and evaluates the endocrine-disrupting potential of the resulting solutions. In addition, Chapter 4 examines the effect of dissolved organic matter (DOM) on AD photodegradation. During spring and summer at Henderson, NV, USA (latitude 36.04 °N), AD and T underwent direct photodegradation, with half-lives ranging from 3.7 to 10.8 h. In three model DOM solutions (Suwannee River fulvic acid, Suwannee River humic acid, and Nordic Reservoir natural organic matter), AD’s half-life increased by 11 to 35%. Using screening factors to eliminate DOM’s inner filter effect, quantum yield calculations suggested that light screening was primarily responsible for AD’s increased half-life, and that physical quenching further inhibited AD’s photodegradation in two out of three DOM solutions (Suwannee River fulvic acid and Suwannee River humic acid). In vitro androgenic activity of the AD and T solutions decreased approximately as fast as AD and T were removed, suggesting that solar photodegradation reduces the risk of endocrine disruption in surface waters impacted by AD or T, subject to continuing inputs. Finally, the reduced in vitro androgenic activity appeared to be related to steroid ring cleavage and the formation of highly oxidized photoproducts. iv Chapter 5 of the dissertation presents broad conclusions from the research described in the dissertation, and suggests future work to advance the understanding of pollutant persistence and environmental photodegradation processes. v ACKNOWLEDGMENTS The phrase “long and winding road” has new meaning to me now. The transition from business lawyer to environmental scientist was more difficult than expected, but it has been rewarding, and I have many people to thank. First, I would like to thank Melissa Young, my former wife and closest friend, for inspiring me with the statement “If you really cared that much about clean water and the environment, you would do something about it”. Nobody ever challenged me like Melissa, and she encouraged me the entire way. I also want to thank my parents, Bob and Pat Young, who have been extremely supportive, in every way, throughout my life. My belief that I can learn almost anything with time and effort is a direct result of my life with them. I only wish that my father had lived to see me complete this dissertation. Others who have encouraged me most include my brother, Bryan Young, my friends, Jens Blotevogel and Mike Massey, and my advisor, Dr. Thomas Borch, who gave me the opportunity to pursue this path with almost no scientific experience. More than anybody, Thomas made the change from business lawyer to environmental scientist possible for me. Similarly, the people I have worked with at Colorado State University (especially in Dr. Borch’s research group), and at the Applied Research and Development Center of the Southern Nevada Water Authority, have made my career change worthwhile and enjoyable. Each of these friends and colleagues has made me feel like I belong, and inspired or encouraged me along the way. In particular, I want to thank Dr. Shane Snyder for giving me the opportunity to work with the Southern Nevada Water Authority as a graduate student intern. vi In addition, I want to thank several individuals who shared their technical expertise, and taught me the technical skills I now use. Dr. James Gray and Don Dick introduced me to environmental analysis and mass spectrometry, and Dr. Doug Mawhinney contributed more than anyone to my current understanding. He was always available to answer my questions, sometimes with the cryptic answer “42”. I learned a lot about sample preparation from Janie Holady, and much about liquid chromatography-mass spectrometry from Dr. Imma Ferrer, Dr. Mike Thurman, and Dr. Yury Desyaterik. I also want to thank the Finkner-Hale Undergraduate Internship program, the Colorado Water Institute, the SeaCrest Group, the United States – Israel Binational Agricultural Research and Development Fund, the Borch-Hoppess Fund for Environmental Contaminant Research, and Karl Hoppess, in particular, for their financial support along the way. Karl Hoppess made it possible for me to come home when my father was sick, and I never will forget it. I also want to thank Dr. Ken Barbarick for allowing me to work as his graduate student teaching assistant. I can’t imagine a better model for teaching science. Finally, I want to thank the members of my Ph.D. committee for their time, effort and guidance on completing this dissertation and the entire Ph.D. process. It’s an important milestone in my career and life, and I appreciate their investment in me, this dissertation, and the graduate education process. vii TABLE OF CONTENTS ABSTRACT ...................................................................................................................................
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