Functionalized Polyether Block Copolymers

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Jan 26, 2018 - Tobias C. Majdanski, David Pretzel, Justyna A. Czaplewska, Jürgen Vitz, ... T. C. Majdanski, Dr. D. Pretzel, Dr. J. A. Czaplewska, Dr. J. Vitz,.

Full  Paper Fructosylated Worms

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Spherical and Worm-Like Micelles from FructoseFunctionalized Polyether Block Copolymers Tobias C. Majdanski, David Pretzel, Justyna A. Czaplewska, Jürgen Vitz, Pelin Sungur, Stephanie Höppener, Stephanie Schubert, Felix H. Schacher, Ulrich S. Schubert, and Michael Gottschaldt* generate well-defined micelles with tunable properties, several different polymer classes have been investigated.[3] Among all, poly(ethylene glycol)s (PEG)s are a family of hydrophilic polymers with several benefits, such as low toxicity, and solubility both in aqueous media as well as in organic solvents. It is reported as the gold standard for polymers showing stealth behavior, a term describing the escape of a foreign substance from immunological recognition leading to a prolonged blood circulation time of a substance or a nanocarrier. Various PEGs[4] are FDA approved for different applications, and several nanocarriers based on PEG block copolymers entered clinical trials.[5] To induce micelle formation with the above mentioned PEG as hydrophilic shell, different monomers can be used for the synthesis of the hydrophobic blocks. Due to the commercial availability and variety, glycidyl ethers are frequently applied for this purpose in order to introduce functional groups or hydrophobic side chains. In particular, ethyl hexyl glycidyl ether (EHG) revealed several beneficial properties for the presented synthesis: A very hydrophobic side chain, high chemical stability, for example, toward strong acids, and nondegradability by enzymes or hydrolytic cleavage. In literature, acrylic polymers with ethyl hexyl side chains are described, but to the best of our knowledge no polymers with a polyether backbone.[6] For a long time, research in the field of micelle applications focused on spherical nanostructures. However, current findings demonstrate that other properties, such as the shape of the nanostructures, are also highly relevant. In this context, worm-like micelles, in analogy to filoviruses also termed filomicelles, are of particular interest. Due to their phenotype they showed a high loading capacity and increased in vivo circulation time by overcoming biological processes responsible for clearance of nanocarriers, such as the fast renal excretion of very small nanostructures (