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Surface Modification of Metal-Organic Framework Nanoparticles for Biomedical Applications

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Surface Modification of Metal-Organic Framework Nanoparticles for Biomedical Applications Dissertation zur Erlangung des Doktorgrades der Fakultät für Chemie und Pharmazie der Ludwig-Maximilians-Universität München Surface modification of metal-organic framework nanoparticles for biomedical applications Andreas Zimpel aus Rosenheim, Deutschland 2018 Preface Erklärung Diese Dissertation wurde im Sinne von § 7 der Promotionsordnung vom 28. November 2011 von Herrn Prof. Dr. Thomas Bein betreut. Eidesstattliche Versicherung Diese Dissertation wurde eigenständig und ohne unerlaubte Hilfe bearbeitet. München, den 03. August 2018 ____________________________ Andreas Zimpel Dissertation eingereicht am 28.06.2018 1. Gutachter: Prof. Dr. Thomas Bein 2. Gutachter: Dr. Stefan Wuttke Mündliche Prüfung am 24.07.2018 I Preface Danksagung Zu Beginn meiner Dissertation möchte ich einigen Leuten danken, ohne die das Erlangen meines Doktorgrades niemals zu Stande gekommen wäre. Als erstes möchte ich mich bei meinem Chef, Mentor und Freund Dr. Stefan Wuttke bedanken, ohne den ich ziemlich sicher nie zu diesem, sehr interessanten Forschungsgebiet der „Metall-organischen Gerüstverbindungen“ gekommen wäre. Danke, dass du mich auf meinem wissenschaftlichen Weg, von unserer ersten Begegnung und Zusammenarbeit als F- Praktikant von Christian Dietl in der organischen Chemie, über das PC-F-Praktikum und die Masterarbeit bis hin zu meiner Doktorarbeit, immer angetrieben und unterstützt hast. Besonders herzlicher Dank gilt meinem Doktorvater, Prof. Dr. Thomas Bein für die Möglichkeit meine Dissertation in seiner Arbeitsgruppe anfertigen zu dürfen, für all die finanzielle und wissenschaftliche Unterstützung über die Jahre meiner Promotion, sowie bereits während meiner Masterarbeit. Bei beiden möchte ich mich auch speziell für die Chancen bedanken, meine Forschungsarbeiten auf diversen nationalen und internationalen Konferenzen präsentieren zu dürfen. Diese haben mich nicht nur durch interessante Diskussionen mit anderen Doktoranden wissenschaftlich neu inspiriert, sondern auch menschlich gefestigt, indem ich gezwungen war dadurch meine Kontaktscheu Fremden gegenüber abzulegen. Vielen Dank auch an meine diversen Kooperationspartner, besonders an Ulrich Lächelt, Hanna Engelke und Michael Peller. Ohne eurer Engagement und wissenschaftlichen Input zu den gemeinsamen Projekten wäre diese Arbeit in ihrer jetzigen Form nie zustande gekommen. Dafür möchte ich mich auch speziell bei meinen Kollegen in den verschiedenen Forschungslaboren bedanken, die zusammen mit mir die Vielzahl an Experimenten durchgeführt haben (u.a. Tobias Preiß, Ruth Röder, Konstantin Böll, Miriam Höhn, Nader Danaf, Simone Braig, Michael Ingrisch, Waldemar Schrimpf,...). Danke auch an die Gruppenleiter und Professoren Ernst Wagner, Joachim Rädler, Angelika Vollmar, Don Lamb und Silke Meiners für ihre Ideen, Kommentare und Korrekturen an den gemeinsamen Publikationen. Ein großer Dank gilt auch allen jetzigen und ehemaligen Mitgliedern der MOF/COF- und Mesobio-Subgroups für ihre Kommentare und Anregungen während der vielen Meetings. III Preface All meinen Praktikanten (namentlich Linda, Aylin, Nadine, Luca, Kate und Marina) möchte ich an dieser Stelle für die gute und erfolgreiche Zusammenarbeit bedanken. Durch eure Betreuung habe ich viel für eine spätere Position mit Führungsverantwortung gelernt. Danke an all meine Bürokollegen (Alesja, Andi, Andre, Noggi, Patrick, Sabrina, Stefan und Tina) für die angenehme Büroatmosphäre. Ganz besonderer Dank gilt dabei Noggi, Stefan und Sabrina, welche im Laufe meiner Promotion zu sehr guten Freunden geworden sind. Außerdem danke ich Hans, Mona und Fabi für ihr „Mentoring“ auf den unterschiedlichsten Gebieten während meiner Promotion. Für alles Organisatorische möchte ich mich ganz herzlich bei Tina, Regina und Corinna bedanken. Mein besonderer Dank gilt natürlich auch allen anderen Personen im Arbeitskreis Bein, welche hier nicht namentlich erwähnt worden sind. Ein großes Dankeschön an alle jetzigen und ehemaligen Kollegen und Kolleginnen mit denen ich diese interessanten und spaßigen Jahre verbringen konnte. Meiner Ehefrau Marion danke ich ganz herzlich für all die bisherigen gemeinsamen Jahre, für die aufbauenden Worte und die volle Unterstützung während meiner Promotion. Danke für dein Verständnis für meine schlechte Laune wenn es mal nicht so gut lief (eher selten) und für späteres Heimkommen wenn es mal wieder was zu feiern gab (häufiger). Ich liebe dich! In diesem Zuge möchte ich mich auch bei meiner Schwägerin Andrea bedanken, die durch das mehrmalige Bereitstellen eines Schlafplatzes in ihrer Wohnung in Großhadern auch sehr viel zum Erfolg von Einstands-, Doktor-, Weihnachts- und sonstigen Feiern beigetragen hat. Weiterhin möchte ich mich noch bei meinen Schwiegereltern Renate und Reiner für die nette Aufnahme in die Familie bedanken. Danke vor allem für die mentale Unterstützung in Prüfungszeiten und an „Kapuzentagen“. Meinen beiden Brüdern Fredi und Stefan danke ich für den tollen geschwisterlichen Zusammenhalt, der sehr viel dazu beiträgt, dass ich mich zu Hause sehr wohl fühle und eine sehr große Heimatverbundenheit spüre. In diesem Zusammenhang auch danke an all meine Freunde in Rott am Inn! Der größte Dank gilt meinen Eltern. Ohne die finanzielle und geistige Unterstützung, sowie euer Talent mir das Gefühl zu geben, alles richtig und euch stolz zu machen, hätte ich keinesfalls diesen erfolgreichen akademischen Weg eingeschlagen. IV Preface Abstract Nowadays, cancer is one of the most challenging diseases on earth. Since the 1970s, the number of patients almost doubled, due to the demographic development of mankind. Cancer researcher Robert A. Weinberg put it in a nutshell by claiming, "If we lived long enough, sooner or later we all would get cancer." Therefore, effective and targeted treatment of affected tissue is of immense interest as common chemotherapy suffers from severe side effects. One way towards selective cancer treatment is the implementation of porous nanocarrier systems for the targeted delivery of chemotherapeutics into tumor tissue to minimize side effects. To fulfil all of its ambitious tasks, the nanocarrier has to provide several different properties such as long circulation lifetimes in the bloodstream, a stimuli- responsive capping system which allows drug release at the desired location or targeting ligands on their external surface to enhance preferential uptake in cancer cells. All these properties can be addressed by the functionalization of the external surface of the designated nanocarrier system. In recent years, metal-organic frameworks (MOFs) have attracted great interest in the field of drug delivery. The ability to adjust their pore sizes and to implement functionalities within the pores as well as on their external surface makes this material class a promising candidate. This thesis focuses on the surface modification of MOF nanoparticles (NPs) with regard to prospective biomedical applications. In this context, the uptake potential of porous MOF NPs for guest molecules and the in vitro toxicity of the MOF NPs used in this study are investigated in detail. Further, the possibility for external surface functionalization using different approaches is an important focus of this work. The resulting MOF NPs were fully characterized by various methods to ensure their expected morphology, composition and structure. The final achievement of the work is to evaluate the MOF NPs in the biological context. The work aims at determining how the MOF NP structure and their responsiveness to the surrounding biological environment are related to each other and how this behaviour can be correlated to their toxicity. The first main part (Chapter 3 and 4) demonstrates that the outer surface of MOF NPs can be specifically functionalized with biocompatible polymers to control the interface between colloidally stable MOF NPs and their environment. Chapter 3 is focused on the covalent attachment of different functional polymers on the external surface of the biologically well- tolerated iron based MOF NPs (MIL-100(Fe)). With this approach, it is possible to increase V Preface the chemical and colloidal stability and to provide fluorescence properties by using dye- labeled polymers. The functionalization of the MOF NPs with fluorescent-labeled polymers enables the investigation by fluorescence-based techniques, as demonstrated by fluorescence correlation spectroscopy (FCS) and confocal fluorescence microscopy. Furthermore, the influence of the polymer shell on the intrinsic magnetic resonance imaging (MRI) activity of MIL-100(Fe) is investigated in detail. As already demonstrated in the third chapter, the effective bio-application of MOF NPs is still hampered by limited control of their surface chemistry and insuffucient understanding of their interactions at the biointerface. Using a self-assembly approach, the fourth chapter of the thesis shows that coating of MOF NPs (Zr-fum) with polymers, frequently used for biomedical applications, is a convenient way for peripheral surface functionalization. Detailed investigation of the binding reveals the mechanism to be a self-assembly modulator replacement by the coordinating group-containing polymers. This strong coordinative binding is further used to attach the shielding polymer polysarcosine onto the MOF surface, which results in an exceptionally high colloidal stability of the NPs. The effect of the polymer coatings on the biointerface is investigated with regard to cell interactions and protein binding. An important feature of MOF NPs for their use as nanocarriers
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