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Making Energetic Materials Safer

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Making Energetic Materials Safer University of Rhode Island DigitalCommons@URI Open Access Dissertations 2020 MAKING ENERGETIC MATERIALS SAFER Michelle D. Gonsalves University of Rhode Island, [email protected] Follow this and additional works at: https://digitalcommons.uri.edu/oa_diss Recommended Citation Gonsalves, Michelle D., "MAKING ENERGETIC MATERIALS SAFER" (2020). Open Access Dissertations. Paper 1217. https://digitalcommons.uri.edu/oa_diss/1217 This Dissertation is brought to you for free and open access by DigitalCommons@URI. It has been accepted for inclusion in Open Access Dissertations by an authorized administrator of DigitalCommons@URI. For more information, please contact [email protected]. MAKING ENERGETIC MATERIALS SAFER BY MICHELLE D`ASSUMPSOA GONSALVES A DISSERTATION SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN CHEMISTRY UNIVERSITY OF RHODE ISLAND 2020 DOCTOR OF PHILOSOPHY IN CHEMISTRY DISSERTATION OF MICHELLE D`ASSUMPSOA GONSALVES APPROVED: Dissertation Committee: Major Professor Jimmie C. Oxley Co-Major Professor James L. Smith Louis Kirschenbaum Otto Gregory Brenton DeBoef DEAN OF THE GRADUATE SCHOOL UNIVERSITY OF RHODE ISLAND 2020 ABSTRACT Canine (K9) units and scientists developing explosives trace detection devices (ETDs) work with and are exposed to energetic materials when imprinting the dog or building instrument libraries. However, access to extremely hazardous materials, such as explosives, is limited, with a great need for training aids that provide a safe-handling and long shelf-life material. In order to address these needs, encapsulation of energetic materials, such as triacetone triperoxide (TATP), erythritol tetranitrate (ETN) and trinitrotoluene (TNT) in a polymer matrix have been developed, and extensively characterized to ensure explosive desensitization, controlled released, clean background odor and delivery of the pure explosive as effective training aids. Although, peroxide explosives, such as TATP and hexamethylene triperoxide diamine (HMTD) are a prominent threat, and their detection a priority within K9 units and ETD manufacturers, their absorption, distribution, metabolism and excretion (ADME) in the body have not been investigated. TATP is volatile and HMTD is lipophilic allowing for their inhalation and dermal absorption. Their distribution to the body was evaluated with blood incubations, which determined that TATP is stable for at least a week, while HMTD is degraded within minutes. Hepatic metabolism was investigated with microsomal and recombinant enzyme incubations. The metabolism of TATP undergoes hydroxylation catalyzed by cytochrome P450 2B6 (CYP2B6) to form TATP-OH, which undergoes glucuronidation catalyzed by uridine diphosphoglucuronosyltransferase 2B7 (UGT2B7) to form TATP-O-glucuronide, which was excreted in the urine of laboratory personnel and bomb-sniffing dogs exposed to TATP. Detection of these peroxide explosives and/or their metabolites in biological matrices (e.g. blood and urine) can be used as forensic evidence to exposure; therefore, paper spray ionization mass spectrometry was exploited as a robust analytical method for the analysis of peroxide explosives in in vitro and in vivo biological samples. ACKNOWLEDGMENTS Thank you to my advisors, Jimmie Oxley and James Smith, for teaching and guiding me, for supporting my bio-related projects and for developing my scientific mind. I would like to recognize the amazing time I had at the University of Rhode Island and thank my committee and the funding agencies that supported this work. Thank you to my colleagues for all of their support throughout these long years, from coaching me when I first started to later allowing me to share my own knowledge with the new labmates. I would like to recognize the co-authors of the manuscripts presented in this dissertation: Kevin Colizza, Alexander Yevdokimov, Audreyana Nash, Lindsay McLennan and professor Angela Slitt. iv DEDICATION I would like to dedicate this dissertation to my family; my parents Marcos Antonio Gonçalves da Silva and Marcia d’Assumpção Gonçalves, my brother Marcos Antonio Gonçalves da Silva Filho, and my grandmother Maria da Conceição Fuina d’Assumpção, for encouraging me to pursue this degree and for bearing with me every step of the way. v PREFACE This dissertation has been prepared in manuscript format in accordance with the guidelines of the Graduate School of the University of Rhode Island. The broad topic “Making energetic materials safer” was focused into four manuscripts. The first manuscript, “Characterization of Encapsulated Energetic Materials for Trace Explosives Aids for Scent (TEAS),” was submitted to the Journal of Energetic Materials. The second manuscript, “In vitro and in vivo studies of triacetone triperoxide (TATP) metabolism in humans,” has been published in the journal Forensic Toxicology. The third manuscript, “Paper spray ionization – high resolution mass spectrometry (PSI-HRMS) of peroxide explosives in biological matrices” was submitted to the journal Analytical and Bioanalytical Chemistry. The fourth manuscript, “In vitro blood stability and toxicity of peroxide explosives in canines and humans” will be submitted to the journal Xenobiotica. vi TABLE OF CONTENTS ABSTRACT .................................................................................................................. ii ACKNOWLEDGMENTS .......................................................................................... iv DEDICATION............................................................................................................... v PREFACE .................................................................................................................... vi TABLE OF CONTENTS .......................................................................................... vii LIST OF TABLES ...................................................................................................... ix LIST OF FIGURES .................................................................................................... xi LIST OF ABBREVIATIONS .................................................................................. xix MANUSCRIPT 1 .......................................................................................................... 1 Abstract ........................................................................................................................... 2 Introduction ..................................................................................................................... 3 Materials and Methods .................................................................................................... 6 Results and Discussion .................................................................................................. 15 Conclusions ................................................................................................................... 45 References ..................................................................................................................... 47 MANUSCRIPT 2 ........................................................................................................ 55 Abstract ......................................................................................................................... 56 Introduction ................................................................................................................... 58 Materials and Methods .................................................................................................. 61 Results ........................................................................................................................... 71 Discussion ..................................................................................................................... 94 Conclusions ................................................................................................................... 97 References ..................................................................................................................... 98 vii MANUSCRIPT 3 ...................................................................................................... 107 Abstract ....................................................................................................................... 108 Introduction ................................................................................................................. 109 Materials and Methods ................................................................................................ 114 Results ......................................................................................................................... 119 Discussion ................................................................................................................... 137 Conclusions ................................................................................................................. 139 References ................................................................................................................... 141 MANUSCRIPT 4 ...................................................................................................... 149 Abstract ....................................................................................................................... 150 Introduction ................................................................................................................. 151
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