Aggregation Behaviour of a Single-chain, Phenylene-modified Bolalipid and Its Miscibility with Classical Phospholipids

Overview

Journal Beilstein J Org Chem

Specialty Chemistry

Date 2017 Jul 8

PMID 28684979

Citations 3

Authors

Simon Drescher

Vasil M Garamus

Christopher J Garvey

Annette Meister

Alfred Blume

Affiliations

Soon will be listed here.

Abstract

In the present work, we describe the synthesis of a single-chain, phenylene-modified bolalipid with two phosphocholine headgroups, PC-C18pPhC18-PC, using a Sonogashira cross-coupling reaction as a key step. The aggregation behaviour was studied as a function of temperature using transmission electron microscopy (TEM), differential scanning calorimetry (DSC), Fourier-transform infrared (FTIR) spectroscopy, and small angle neutron scattering (SANS). We show that our new bolalipid self-assembles into nanofibres, which transform into flexible nanofibres at 27 °C and further to small elongated micelles at 45 °C. Furthermore, the miscibility of the bolalipid with bilayer-forming phosphatidylcholines (DMPC, DPPC, and DSPC) was investigated by means of DSC, TEM, FTIR, and small angle X-ray scattering (SAXS). We could show that the PC-C18pPhC18-PC is partially miscible with saturated phosphatidylcholines; however, closed lipid vesicles with an increased thermal stability were not found. Instead, bilayer fragments and disk-like aggregates are formed.

Citing Articles

Bolalipid-Doped Liposomes: Can Bolalipids Increase the Integrity of Liposomes Exposed to Gastrointestinal Fluids?.

Muller S, Gruhle K, Meister A, Hause G, Drescher S Pharmaceutics. 2019; 11(12).

PMID: 31816937 PMC: 6956191. DOI: 10.3390/pharmaceutics11120646.

An Asymmetrical Glycerol Diether Bolalipid with Protonable Phosphodimethylethanolamine Headgroup: The Impact of pH on Aggregation Behavior and Miscibility with DPPC.

Markowski T, Muller S, Dobner B, Meister A, Blume A, Drescher S Polymers (Basel). 2019; 9(11).

PMID: 30965876 PMC: 6418739. DOI: 10.3390/polym9110573.

(Cryo)Transmission Electron Microscopy of Phospholipid Model Membranes Interacting with Amphiphilic and Polyphilic Molecules.

Meister A, Blume A Polymers (Basel). 2019; 9(10).

PMID: 30965829 PMC: 6418595. DOI: 10.3390/polym9100521.

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