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Open AccessArticle

Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes

1
Institute of Pharmaceutical and Biomedical Science, Johannes Gutenberg-University Mainz, 55128 Mainz, Germany
2
Department of Dermatology, University Medical Center, Johannes Gutenberg-University Mainz, 55131 Mainz, Germany
3
Department of Chemistry, Johannes Gutenberg-University Mainz, 55128 Mainz, Germany
*
Authors to whom correspondence should be addressed.
Cells 2020, 9(10), 2213; https://doi.org/10.3390/cells9102213
Received: 30 July 2020 / Revised: 21 September 2020 / Accepted: 24 September 2020 / Published: 29 September 2020
(This article belongs to the Special Issue Nanoparticles in Cancer Immunotherapy)
Lipid exchange among biological membranes, lipoprotein particles, micelles, and liposomes is an important yet underrated phenomenon with repercussions throughout the life sciences. The premature loss of lipid molecules from liposomal formulations severely impacts therapeutic applications of the latter and thus limits the type of lipids and lipid conjugates available for fine-tuning liposomal properties. While cholesterol derivatives, with their irregular lipophilic surface shape, are known to readily undergo lipid exchange and interconvert, e.g., with serum, the situation is unclear for lipids with regular, linear-shaped alkyl chains. This study compares the propensity of fluorescence-labeled lipid conjugates of systematically varied lengths to migrate from liposomal particles consisting mainly of egg phosphatidyl choline 3 (EPC3) and cholesterol into biomembranes. We show that dialkyl glyceryl lipids with chains of 18–20 methylene units are inherently stable in liposomal membranes. In contrast, C16 lipids show some lipid exchange, albeit significantly less than comparable cholesterol conjugates. Remarkably, the C18 chain length, which confers noticeable anchor stability, corresponds to the typical chain length in biological membranes. View Full-Text
Keywords: liposomes; click chemistry; polyglycerol; bioconjugates; drug delivery liposomes; click chemistry; polyglycerol; bioconjugates; drug delivery
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MDPI and ACS Style

Gleue, L.; Schupp, J.; Zimmer, N.; Becker, E.; Frey, H.; Tuettenberg, A.; Helm, M. Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes. Cells 2020, 9, 2213. https://doi.org/10.3390/cells9102213

AMA Style

Gleue L, Schupp J, Zimmer N, Becker E, Frey H, Tuettenberg A, Helm M. Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes. Cells. 2020; 9(10):2213. https://doi.org/10.3390/cells9102213

Chicago/Turabian Style

Gleue, Lukas; Schupp, Jonathan; Zimmer, Niklas; Becker, Eyleen; Frey, Holger; Tuettenberg, Andrea; Helm, Mark. 2020. "Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes" Cells 9, no. 10: 2213. https://doi.org/10.3390/cells9102213

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