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Langmuir. 2017 May 23;33(20):4960-4973. doi: 10.1021/acs.langmuir.7b00228. Epub 2017 May 10.

Azide-Modified Membrane Lipids: Synthesis, Properties, and Reactivity.

Author information

1
Institute of Pharmacy - Pharmaceutical Chemistry and Bioanalytics, Martin Luther University (MLU) Halle-Wittenberg , Wolfgang-Langenbeck-Strasse 4, 06120 Halle (Saale), Germany.
2
Institute of Pharmacy - Biophysical Pharmacy, MLU Halle-Wittenberg , Wolfgang-Langenbeck-Strasse 4, 06120 Halle (Saale), Germany.
3
Helmholtz-Zentrum Geesthacht: Zentrum für Material und Küstenforschung GmbH (HZG), Max-Planck-Strasse 1, 21502 Geesthacht, Germany.
4
Fraunhofer Institute for Cell Therapy and Immunology IZI , Weinbergweg 22, 06120 Halle (Saale), Germany.
5
Biocenter, MLU Halle-Wittenberg , Weinbergweg 22, 06120 Halle (Saale), Germany.
6
Institute of Chemistry and Institute of Biochemistry and Biotechnology, MLU Halle-Wittenberg , von-Danckelmann-Platz 4, 06120 Halle (Saale), Germany.

Abstract

In the present work, we describe the synthesis and the temperature-dependent behavior of photoreactive membrane lipids as well as their capability to study peptide/lipid interactions. The modified phospholipids contain an azide group either in the middle part or at the end of an alkyl chain and also differ in the linkage (ester vs ether) of the second alkyl chain. The temperature-dependent aggregation behavior of the azidolipids was studied using differential scanning calorimetry (DSC), Fourier-transform infrared (FTIR) spectroscopy, and small-angle X-ray scattering (SAXS). Aggregate structures were visualized by stain and cryo transmission electron microscopy (TEM) and were further characterized by dynamic light scattering (DLS). We show that the position of the azide group and the type of linkage of the alkyl chain at the sn-2 position of the glycerol influences the type of aggregates formed as well as their long-term stability: P10AzSPC and r12AzSHPC show the formation of extrudable liposomes, which are stable in size during storage. In contrast, azidolipids that carry a terminal azido moiety either form extrudable liposomes, which show time-dependent vesicle fusion (P15AzPdPC), or self-assemble in large sheet-like, nonextrudable aggregates (r15AzPdHPC) where the lipid molecules are arranged in an interdigitated orientation at temperatures below Tm (LβI phase). Finally, a P10AzSPC:DMPC mixture was used for photochemically induced cross-linking experiments with a transmembrane peptide (WAL-peptide) to demonstrate the applicability of the azidolipids for the analysis of peptide/lipid interactions. The efficiency of photo-cross-linking was monitored by attenuated total reflection infrared (ATR-IR) spectroscopy and mass spectrometry (MS).

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