The headgroup (A)symmetry strongly determines the aggregation behavior of single-chain phenylene-modified bolalipids and their miscibility with classical phospholipids

Simon Drescher, Bob Dan Lechner, Vasil M. Garamus, L. Almásy, Annette Meister, Alfred Blume

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

In the present work, we describe the synthesis of two single-chain phenylene-modified bolalipids, namely PC-C17pPhC17-PC and PC-C17pPhC17-OH, with either symmetrical (phosphocholine) or asymmetrical (phosphocholine and hydroxyl) headgroups using a Sonogashira cross-coupling reaction as key step. The temperature-dependent aggregation behavior of both bolalipids in aqueous suspension was studied using transmission electron microscopy (TEM), differential scanning calorimetry (DSC), Fourier-transform infrared (FTIR) spectroscopy, small angle neutron scattering (SANS), and X-ray scattering. We show that different headgroup symmetries lead to a change in the aggregation behavior: Whereas PC-C17pPhC17-PC forms nanofibers with a diameter of 5.7 nm that transform into small ellipsoidal micelles at 23 °C, the PC-C17pPhC17-OH self-assembles into lamellae with bolalipid molecules in an antiparallel orientation up to high temperatures. Furthermore, the mixing behavior of both bolalipids with bilayer-forming phospholipids (DPPC and DSPC) was studied by means of DSC and TEM. The aim was to stabilize bilayer membranes formed of phospholipids in order to improve these mixed lipid vesicles for drug delivery purposes. We show that the symmetrical PC-C17pPhC17-PC is miscible with DPPC and DSPC; however, closed lipid vesicles are not observed, and elongated micelles and bilayer fragments are found instead. In contrast, the asymmetrical PC-C17pPhC17-OH shows no miscibility with phospholipids at all.

Original languageEnglish
Pages (from-to)9273-9284
Number of pages12
JournalLangmuir
Volume30
Issue number31
DOIs
Publication statusPublished - Aug 12 2014

Fingerprint

Phospholipids
Phosphorylcholine
Agglomeration
solubility
Solubility
Differential Scanning Calorimetry
Micelles
Lipids
lipids
Differential scanning calorimetry
micelles
symmetry
heat measurement
Small Angle Scattering
Transmission electron microscopy
Nanofibers
Scanning Transmission Electron Microscopy
transmission electron microscopy
Temperature
scanning

ASJC Scopus subject areas

  • Electrochemistry
  • Condensed Matter Physics
  • Surfaces and Interfaces
  • Materials Science(all)
  • Spectroscopy
  • Medicine(all)

Cite this

The headgroup (A)symmetry strongly determines the aggregation behavior of single-chain phenylene-modified bolalipids and their miscibility with classical phospholipids. / Drescher, Simon; Lechner, Bob Dan; Garamus, Vasil M.; Almásy, L.; Meister, Annette; Blume, Alfred.

In: Langmuir, Vol. 30, No. 31, 12.08.2014, p. 9273-9284.

Research output: Contribution to journalArticle

Drescher, Simon ; Lechner, Bob Dan ; Garamus, Vasil M. ; Almásy, L. ; Meister, Annette ; Blume, Alfred. / The headgroup (A)symmetry strongly determines the aggregation behavior of single-chain phenylene-modified bolalipids and their miscibility with classical phospholipids. In: Langmuir. 2014 ; Vol. 30, No. 31. pp. 9273-9284.
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