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Masterarbeit / Master's Thesis MASTERARBEIT / MASTER’S THESIS Titel der Masterarbeit / Title of the Master‘s Thesis Optimization of an LC-MS/MS Method for the Determination of Xenobiotics in Biological Matrices verfasst von / submitted by Thomas Jamnik BSc angestrebter akademischer Grad / in partial fulfilment of the requirements for the degree of Master of Science (MSc) Wien, 2020 / Vienna 2020 Studienkennzahl lt. Studienblatt / UA 066 863 degree programme code as it appears on the student record sheet: Studienrichtung lt. Studienblatt / Masterstudium Biologische Chemie degree programme as it appears on the student record sheet: Betreut von / Supervisor: Assoz. Prof. Dipl.-Ing. Dr. Benedikt Warth, Bakk.techn. 1 2 Erklärung Ich erkläre, dass die vorliegende Masterarbeit von mit selbst verfasst wurde und ich keine anderen als die angeführten Behelfe verwendet bzw. mich auch sonst keiner unerlaubter Hilfe bedient habe. Ich versichere, dass diese Arbeit bisher weder im In- noch Ausland in irgendeiner Form als Prüfungsarbeit vorgelegt wurde. Ich habe mich bemüht, sämtliche Inhaber der Bildrechte ausfindig zu machen und ihre Zustimmung zur Verwendung der Bilder in dieser Arbeit eingeholt. Sollte dennoch eine Urheberrechtsverletzung bekannt werden, ersuche ich um Meldung bei mir. Danksagung Ich danke Dr. Benedikt Warth nicht nur für die Möglichkeit diese interessante Masterarbeit verfassen zu dürfen, sondern auch für die gewonnenen Erfahrungen die der Einblick in seine Arbeitsgruppe und das Institut für Lebensmittelchemie erlaubt hat. Besonderer Dank gilt meiner direkten Betreuerin Dipl.-Ing. Mira Flasch, welche stets hilfsbereite Unterweisung in die Praxis als auch Theorie der verwendeten Arbeitsmethoden gab, immer für ausgiebige Diskussionen bereit stand und sich viel Zeit für diverse Korrekturen dieser Arbeit nahm. Zuletzt möchte ich Dr. Dominik Braun für die Unterstützung bei zusätzlichen technischen und theoretischen Anliegen danken. 3 Kurzfassung Der Mensch ist durch seine unmittelbare Umgebung ständig einer Vielzahl von chemischen Einflüssen ausgesetzt. Dazu gehören einerseits künstlich erzeugte Umweltschadstoffe oder Bestandteile von Produkten die wir im täglichen Leben verwenden. Beides ist eine direkte Folge unseres modernen industrialisierten Lebensstils. Andererseits gibt es natürlich vorkommende Substanzen, welchen wir seit Anbeginn der Zeit ausgesetzt sind. Diese Verbindungen kontaminieren die Luft die wir atmen, das Wasser das wir trinken, die Lebensmittel die wir essen und in einigen Fällen schlicht die Dinge die wir berühren. Einige von ihnen können biologische Aktivität mit akuten als auch chronischen negativen Folgen auf die menschliche Gesundheit aufweisen sobald sie in unseren Körper gelangt sind. Sie können das empfindliche Gleichgewicht verschiedener biologischer Prozesse, wie z.B. des Hormon-, Nerven- oder Immunsystems, stören oder direkt wesentliche Vorgänge des Atmungs- oder Kreislaufsystems unterbrechen. Einige können sogar die Grundlage allen Lebens, den genetischen Code, beeinflussen. Human Biomonitoring (HBM) befasst sich mit der direkten Identifizierung und Quantifizierung dieser Substanzen und ihrer Metabolite um geeignete Biomarker der Exposition, sowie Marker für nachfolgende gesundheitliche Auswirkungen, beim Menschen zu bestimmen. Durch die Analyse der effektiven Gesamtbelastung des Körpers durch chemische Giftstoffe und die Kombination mit epidemiologischen und mechanistischen Erkenntnissen über die Krankheitsentstehung will das Biomonitoring den Beitrag dieser Substanzen zur Pathogenese aufklären um damit eine zuverlässigere Risikoabschätzung zu ermöglichen, als es anhand reiner Umweltanalytik oder Lebensmittelanalytik möglich wäre. Nichtsdestotrotz beschäftigt HBM nicht nur die Untersuchung der Exposition auf individueller-, sondern auch auf Bevölkerungsebene. Somit ist es nicht nur ein wissenschaftliches Instrument für den medizinischen Gebrauch, sondern dient auch der Gesetzgebung um besonders gefährdete Gruppen vor schädlichen Expositionen zu schützen. Das Ziel dieses Projekts war die Erweiterung einer umfassenden Flüssigchromatographie-Tandem- Massenspektrometrie Methode zum ganzheitlicheren Human-Biomonitoring einer Vielzahl toxischer Xenobiotika. Eine intern etablierte LC-MS/MS Methode für die Bestimmung von Xeno- und endogenen Östrogenen in menschlichem Urin, Serum und Muttermilch wurde auf ein neues LC-MS- System (Agilent Infinity II gekoppelt an eine Sciex QTrap 6500+) übertragen. Um bestmögliche Sensitivitäten zu erreichen wurden zahlreiche MS und MS/MS-Parameter optimiert. Die LC-Methode und die Probenvorbereitungsprotokolle wurden beibehalten. Die Entwicklung der Methode umfasste insgesamt 95 Substanzen. Davon waren 75 bereits in der zuvor etablierten Methode inkludiert, während 20 neue toxische Xenobiotika mit der aktuellen Methode hinzugefügt wurden. Sensitivitäten wurden im Mittel um den die Faktoren 20, 17 und 25 in Urin, Serum und Muttermilch verbessert. Die mittleren Wiederfindungsraten reichten von 93% in Urin und 87% in Serum bis 54% in Muttermilch. 4 Intern wurden 39 Substanzen erfolgreich in Urin-, 50 in Serum und 15 in Muttermilch anhand aller gestellten Kriterien validiert. Die vollständige Validierung war für 30 Substanzen in Urin, 16 in Serum und 21 in Muttermilch, aufgrund von geringer Wiederholbarkeit und/oder weil die Extraktionsexperimente des niedrigen Konzentrationslevels nicht erfolgreich waren, nicht möglich. In den Fällen dieser Xenobiotika stellt dies keine Beeinträchtigung der Anwendbarkeit der Methode zur Analyse unbekannter biologischer Proben dar. Die Validierung der restlichen Substanzen war aufgrund von mehreren Kriterien nicht erfolgreich. Als Proof Of Concept wurden bei der Analyse von unbekannten Urin-, Serum- und Muttermilchproben jeweils 42, 31 und 29 Substanzen identifiziert und teilweise quantifiziert. Hierbei wurden erstmals toxische Pyrrolizidin- und Tropanalkaloide in menschlicher Brustmilch detektiert. 5 Abstract Humans are constantly exposed to a variety of chemicals through food and environment. On one hand, this includes synthetic substances such as environmental pollutants or components of personal care products. Both are a direct result of our modern industrialised lifestyle. On the other hand, there are naturally occurring substances we have been exposed to since the dawn of humanity. These compounds are contaminating the air we breathe, the water we drink, the foods we eat and in some cases simply the things we touch. Once they have found their way into our body, some of them exhibit biological activity which may lead to acute or chronic effects on health. They might disturb the delicate balances of various biological processes, such as the hormone-, nervous- or immune system, or directly disrupt essential processes of the respiratory or circulatory system. Some may even directly interfere influence our genetic code. Human Biomonitoring (HBM) deals with the direct investigation of these substances and their metabolites by identifying appropriate biomarkers of exposure, as well as markers of subsequent health effects in humans. By analysing the effective total burden of chemical toxicants on the body and combining it with epidemiological and mechanistic knowledge of disease development, biomonitoring intends to elucidate their contribution to pathogenesis, thus allowing for more reliable risk assessment than mere environmental- or food monitoring. However, HBM not only aims to study exposure at an individual, but also at a population level. Hence, it is not only a scientific tool for environmental health research, but also for informed policy making to help protect particularly vulnerable groups from adverse exposures. The general aim of this project was the extension of a comprehensive liquid chromatography tandem mass spectrometry method, originally developed for xenoestrogens, towards a multiclass assay covering various toxic xenobiotics. The in-house established LC-MS/MS method for the determination of xeno- and endogenous estrogens in human urine, serum and breast milk was transferred onto a newly installed LC-MS system (Agilent Infinity II coupled to a Sciex QTrap 6500+). MS and MS/MS parameters were optimised to achieve the best achievable sensitivity, while the LC method remained as originally developed. Method development included 95 substances in total. Among them, 75 had been used in the method by Preindl et al. (278), while 20 new toxic xenobiotics were added. Median improvements in sensitivity through the new LC-MS/MS system were 20-fold in urine, 17-fold in serum and 25-fold in breast milk. Median extraction recoveries ranged from 93% in urine and 87% in serum to 54% in breast milk. Of 95 analytes included in method validation, 39 analytes met all in- house validation criteria in urine, 50 in serum and 15 in breast milk. Validation parameters were not fully met either because of low repeatability and/or validation issues at the low concentration level for 30 analytes in urine, 16 in serum and 21 in breast milk. This does not detract from the methods ability to quantify or screen for these xenobiotics biological samples. Multiple validation parameters were not met for the remaining compounds. The applicability value of the method was clearly demonstrated by 6 the analysis of unknown urine, serum and breast milk samples. Many analytes (42, 31 and 29) were identified, partly for the first time in the respective biological matrix, such as toxic pyrrolizidine- and tropane alkaloids in breast milk. 7 List of abbreviations Abbreviation Definition 3-OH-BaP
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