Cationic Cell Penetrating Oligoprolines and the Effect of Preorganized Charge Display
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1 Research Collection Doctoral Thesis Cationic Cell Penetrating Oligoprolines and the Effect of Preorganized Charge Display Author(s): Raschle, Philipp Stephan Publication Date: 2016 Permanent Link: Rights / License: In Copyright - Non-Commercial Use Permitted This page was generated automatically upon download from the ETH Zurich Research Collection. For more information please consult the Terms of use. ETH Library
2 DISS. ETH Nr Cationic Cell Penetrating Oligoprolines and the Effect of Preorganized Charge Display A dissertation submitted to attain the degree of DOCTOR OF SCIENCES of ETH ZURICH (Dr. sc. ETH Zurich) presented by Philipp Stephan Raschle Master of Science, University of Basel born on citizen of Bütschwil (SG), Switzerland accepted on the recommendation of Prof. Dr. Helma Wennemers, examiner Prof. Dr. Jean-Christophe Leroux, co-examiner 2016
3 Abstract Cell-penetrating peptides (CPPs) are a promising tool for non-invasive delivery of therapeutic and diagnostic molecules into cells, that intrinsically have poor membrane translocation. Intracellular targeting of specific organelles in combination with high proteolytic stability and low cytotoxicity has been a long-standing goal. Several studies have shown that the number and spatial arrangement of the cationic charges are important for efficient cellular uptake. Yet, the structural prerequisites necessary for efficient cellular uptake and intracellular localization are still not well-understood and limit the rational design of more efficient CPPs. Within this thesis, we investigated the effect of preorganized vs. undefined charge display on the cellular uptake of cationic CPPs. We compared the cell-penetrating properties of flexible oligoarginines with conformationally rigid oligoproline-based CPPs bearing guanidinium groups either directly attached to the peptide backbone or via flexible spacers. Furthermore, the influence of the lateral distance between the cationic charges on the cellular uptake was evaluated through the comparison of oligoprolines with different lateral distances, but similar rigidity. Flow cytometry studies showed that preorganization of cationic charges in lateral distances of ~9 Å along the well-defined PPII helix enhances the cellular uptake of CPPs. Binding affinity measurements revealed a tighter binding of oligoproline-based CPPs to heparin and chondroitin compared to flexible CPPs. This finding was further corroborated through cellular uptake studies with mutated CHO cells deficient in heparan or heparan and chondroitin. The influence of the secondary structure was explored by comparing CPPs with different backbone structures. Furthermore, confocal microscopy studies demonstrated that CPPs with preorganized charges along the PPII-helical backbone accumulate in the nucleus of the cell, unlike those with higher flexibility. In summary, this thesis describes our contributions to the field of oligoproline-based CPPs. The experiments revealed the effect of cationic charge preorganization, lateral charge display, and backbone structure on efficient cellular uptake. The gained insights can be used to optimize the structural prerequisites necessary for efficient cellular uptake and intracellular localization. vii
4 Zusammenfassung Zellgängige Peptide sind ein erfolgversprechendes Werkzeug zum nicht-invasiven Transport von therapeutisch und diagnostisch aktiven Molekülen in Zellen, die intrinsisch geringe Membrangängigkeit aufweisen. Das spezifische Ansteuern von Zellorganellen, in Kombination mit hoher proteolytischer Stabilität und geringer Zytotoxizität der zellgängigen Peptide, ist bis heute eine Herausforderung. Die Wichtigkeit von Anzahl und räumlicher Anordnung der kationischen Ladungen für effiziente Aufnahme in die Zelle wurde durch mehrere Studien gezeigt. Allerdings sind die molekularen Voraussetzungen für effiziente zelluläre Aufnahme und intrazelluläre Lokalisation bis heute nicht vollständig verstanden und limitieren das rationelle Design von neuen, effizienteren, zellgängigen Peptiden. In dieser Dissertation untersuchten wir den Effekt von definierter gegenüber undefinierter Ladungsanordung auf die zelluläre Aufnahme von kationischen, zellgängigen Peptiden. Dabei wurde die zelluläre Aufnahme von flexiblen Oligoargininen mit konformationell starren Oligoprolin-basierten, zellgängigen Peptiden verglichen. Hierbei wurden die kationischen Ladungen der Guanidinium-Gruppen direkt oder über einen flexiblen Linker mit dem Peptidrückgrat verknüpft. Der Einfluss des Abstandes der kationischen Ladungen auf die Zellgängigkeit wurde durch den Vergleich von Oligoprolinen mit verschieden Abständen zwischen den kationischen Ladungen untersucht. Durchflusszytometrie-Studien zeigten, dass der definierte Abstand von ungefähr 9 Å der kationischen Ladungen in einer definierten PPII-Helix die Zellgängigkeit der Peptide erhöht. Im Gegensatz zu flexiblen Peptiden zeigten Oligoprolin-basierte, zellgängige Peptide eine stärkere Bindung zu Heparin und Chondroitin in Bindungsaffinitäts-Messungen. Diese stärkere Bindung wurde durch Studien zur Zellgängigkeit mit Heparan-defizitären oder Heparan- sowie Chondroitindefizitären CHO Zellen bestätigt. Verschiedene Rückgratstrukturen bestätigten den Einfluss der Sekundärstruktur auf die zelluläre Aufnahme. Im Gegensatz zu zellgängigen Peptiden mit höherer Flexibilität zeigten zellgängige Peptide mit definierter Ladungsanordnung entlang einer PPII-Helix eine Anreicherung im Zellkern, wie durch konfokale Mikroskopie-Studien gezeigt wurde. ix
5 Zusammenfassend beschreibt diese Dissertation unseren Beitrag zum Feld der kationischen, Oligoprolin-basierten, zellgängigen Peptide. Die Experimente zeigten den Einfluss von definierter, kationischer Ladungsanordnung, dem Ladungsabstand und der Sekundärstruktur für effiziente, zelluläre Aufnahme. Die gewonnenen Erkenntnisse liefern Einblicke in die molekularen Voraussetzungen für eine effiziente Zellgängigkeit und intrazelluläre Lokalisation. x
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