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Polysarcosine-Based Lipids: From Lipopolypeptoid Micelles to Stealth-Like Lipids in Langmuir Blodgett Monolayers

Institute of Organic Chemistry, Johannes Gutenberg University of Mainz, Duesbergweg 10-14, 55128 Mainz, Germany
Department of Pharmaceutical Technology and Biopharmacy, Institute of Pharmaceutical Sciences, Albert Ludwigs University of Freiburg, Sonnenstraße 5, 79104 Freiburg im Breisgau, Germany
Author to whom correspondence should be addressed.
Academic Editor: Alexander Böker
Polymers 2016, 8(12), 427;
Received: 17 October 2016 / Revised: 24 November 2016 / Accepted: 2 December 2016 / Published: 9 December 2016
(This article belongs to the Special Issue Young Talents in Polymer Science)
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Amphiphiles and, in particular, PEGylated lipids or alkyl ethers represent an important class of non-ionic surfactants and have become key ingredients for long-circulating (“stealth”) liposomes. While poly-(ethylene glycol) (PEG) can be considered the gold standard for stealth-like materials, it is known to be neither a bio-based nor biodegradable material. In contrast to PEG, polysarcosine (PSar) is based on the endogenous amino acid sarcosine (N-methylated glycine), but has also demonstrated stealth-like properties in vitro, as well as in vivo. In this respect, we report on the synthesis and characterization of polysarcosine based lipids with C14 and C18 hydrocarbon chains and their end group functionalization. Size exclusion chromatography (SEC) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) analysis reveals that lipopeptoids with a degree of polymerization between 10 and 100, dispersity indices around 1.1, and the absence of detectable side products are directly accessible by nucleophilic ring opening polymerization (ROP). The values for the critical micelle concentration for these lipopolymers are between 27 and 1181 mg/L for the ones with C18 hydrocarbon chain or even higher for the C14 counterparts. The lipopolypeptoid based micelles have hydrodynamic diameters between 10 and 25 nm, in which the size scales with the length of the PSar block. In addition, C18PSar50 can be incorporated in 1,2-distearoyl-sn-glycero-3-phosphocholine (DSPC) monolayers up to a polymer content of 3%. Cyclic compression and expansion of the monolayer showed no significant loss of polymer, indicating a stable monolayer. Therefore, lipopolypeptoids can not only be synthesized under living conditions, but my also provide a platform to substitute PEG-based lipopolymers as excipients and/or in lipid formulations. View Full-Text
Keywords: polysarcosine; polypeptoids; surfactants; lipids; NCA polymerization; PSarcosinylated lipids polysarcosine; polypeptoids; surfactants; lipids; NCA polymerization; PSarcosinylated lipids

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Weber, B.; Seidl, C.; Schwiertz, D.; Scherer, M.; Bleher, S.; Süss, R.; Barz, M. Polysarcosine-Based Lipids: From Lipopolypeptoid Micelles to Stealth-Like Lipids in Langmuir Blodgett Monolayers. Polymers 2016, 8, 427.

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