Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes
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 latt...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-09-01
|
| Series: | Cells |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4409/9/10/2213 |
| _version_ | 1797552214177218560 |
|---|---|
| author | Lukas Gleue Jonathan Schupp Niklas Zimmer Eyleen Becker Holger Frey Andrea Tuettenberg Mark Helm |
| author_facet | Lukas Gleue Jonathan Schupp Niklas Zimmer Eyleen Becker Holger Frey Andrea Tuettenberg Mark Helm |
| author_sort | Lukas Gleue |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T15:56:47Z |
| format | Article |
| id | doaj.art-5aec340c5bff4558ace6d4975a731f94 |
| institution | Directory Open Access Journal |
| issn | 2073-4409 |
| language | English |
| last_indexed | 2024-03-10T15:56:47Z |
| publishDate | 2020-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Cells |
| spelling | doaj.art-5aec340c5bff4558ace6d4975a731f942023-11-20T15:34:22ZengMDPI AGCells2073-44092020-09-01910221310.3390/cells9102213Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal MembranesLukas Gleue0Jonathan Schupp1Niklas Zimmer2Eyleen Becker3Holger Frey4Andrea Tuettenberg5Mark Helm6Institute of Pharmaceutical and Biomedical Science, Johannes Gutenberg-University Mainz, 55128 Mainz, GermanyDepartment of Dermatology, University Medical Center, Johannes Gutenberg-University Mainz, 55131 Mainz, GermanyDepartment of Dermatology, University Medical Center, Johannes Gutenberg-University Mainz, 55131 Mainz, GermanyDepartment of Chemistry, Johannes Gutenberg-University Mainz, 55128 Mainz, GermanyDepartment of Chemistry, Johannes Gutenberg-University Mainz, 55128 Mainz, GermanyDepartment of Dermatology, University Medical Center, Johannes Gutenberg-University Mainz, 55131 Mainz, GermanyInstitute of Pharmaceutical and Biomedical Science, Johannes Gutenberg-University Mainz, 55128 Mainz, GermanyLipid 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.https://www.mdpi.com/2073-4409/9/10/2213liposomesclick chemistrypolyglycerolbioconjugatesdrug delivery |
| spellingShingle | Lukas Gleue Jonathan Schupp Niklas Zimmer Eyleen Becker Holger Frey Andrea Tuettenberg Mark Helm Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes Cells liposomes click chemistry polyglycerol bioconjugates drug delivery |
| title | Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes |
| title_full | Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes |
| title_fullStr | Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes |
| title_full_unstemmed | Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes |
| title_short | Stability of Alkyl Chain-Mediated Lipid Anchoring in Liposomal Membranes |
| title_sort | stability of alkyl chain mediated lipid anchoring in liposomal membranes |
| topic | liposomes click chemistry polyglycerol bioconjugates drug delivery |
| url | https://www.mdpi.com/2073-4409/9/10/2213 |
| work_keys_str_mv | AT lukasgleue stabilityofalkylchainmediatedlipidanchoringinliposomalmembranes AT jonathanschupp stabilityofalkylchainmediatedlipidanchoringinliposomalmembranes AT niklaszimmer stabilityofalkylchainmediatedlipidanchoringinliposomalmembranes AT eyleenbecker stabilityofalkylchainmediatedlipidanchoringinliposomalmembranes AT holgerfrey stabilityofalkylchainmediatedlipidanchoringinliposomalmembranes AT andreatuettenberg stabilityofalkylchainmediatedlipidanchoringinliposomalmembranes AT markhelm stabilityofalkylchainmediatedlipidanchoringinliposomalmembranes |