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Polymers 2017, 9(11), 573; https://doi.org/10.3390/polym9110573

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

1
Institute of Pharmacy—Biochemical Pharmacy, 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
Institute of Chemistry—Biophysical Chemistry, MLU Halle-Wittenberg, von-Danckelmann-Platz 4, 06120 Halle (Saale), Germany
4
Institute of Biochemistry and Biotechnology, MLU Halle-Wittenberg, Kurt-Mothes-Strasse 3, 06120 Halle (Saale), Germany
Thomas Markowski and Sindy Müller contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 28 September 2017 / Revised: 25 October 2017 / Accepted: 31 October 2017 / Published: 3 November 2017
(This article belongs to the Special Issue From Amphiphilic to Polyphilic Polymers)
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Abstract

Investigations regarding the self-assembly of (bola)phospholipids in aqueous media are crucial to understand the complex relationship between chemical structure of lipids and the shape and size of their aggregates in water. Here, we introduce a new asymmetrical glycerol diether bolaphospholipid, the compound Me2PE-Gly(2C16)C32-OH. This bolalipid contains a long (C32) ω-hydroxy alkyl chain bond to glycerol in the sn-3 position, a C16 alkyl chain at the sn-2 position, and a protonable phosphodimethylethanolamine (Me2PE) headgroup at the sn-1 position of the glycerol. The aggregation behavior of this bolalipid was studied as a function of temperature and pH using transmission electron microscopy (TEM), differential scanning calorimetry (DSC), and Fourier transform infrared (FTIR) spectroscopy. We show that this bolalipid aggregates into condensed lamellar sheets in acidic milieu and in large sheet-like aggregates at neutral pH-value. By contrast, at a pH-value of 10, where the Me2PE headgroup is only partially protonated, small lipid disks with diameter 50–100 nm were additionally found. Moreover, the miscibility of this asymmetrical bolalipid with the bilayer-forming phosphatidylcholine DPPC was investigated by means of DSC and TEM. The incorporation of bolalipids into phospholipid membranes could result in stabilized liposomes applicable for drug delivery purposes. We show that mixtures of DPPC and Me2PE-Gly(2C16)C32-OH form large lamellar aggregates at pH of 5, 7, and 10. However, closed lipid vesicles (liposomes) with an increased thermal stability were not found. View Full-Text
Keywords: bolaamphiphile; bolalipid; aggregation behavior; lipids; mixing behavior; pH; membranes bolaamphiphile; bolalipid; aggregation behavior; lipids; mixing behavior; pH; membranes
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Markowski, T.; Müller, S.; Dobner, B.; Meister, A.; Blume, A.; Drescher, S. An Asymmetrical Glycerol Diether Bolalipid with Protonable Phosphodimethylethanolamine Headgroup: The Impact of pH on Aggregation Behavior and Miscibility with DPPC. Polymers 2017, 9, 573.

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