Distribution of BODIPY-labelled phosphatidylethanolamines in lipid bilayers exhibiting different curvatures

Phys Chem Chem Phys. 2011 Jun 28;13(24):11694-701. doi: 10.1039/c1cp20608g. Epub 2011 May 19.

Abstract

In this paper we have investigated the behaviour of newly synthesised mono-palmitoyl- and dipalmitoyl-phosphatidylethanolamine probes (abbreviated as mPE and dPE, respectively) labelled in the polar headgroup region by either the FL-BODIPY or the 564/570-BODIPY fluorophore and solubilised in lipid systems that exhibit different curvatures. Because of the bulky BODIPY-groups, the monoacyl-form derivatives have a conic-like shape, whereas that for the diacyl derivatives is rather cylindrical. A careful analysis of time-resolved resonance energy transfer experiments by means of analytical models as well as Monte Carlo simulations shows that the mPE derivatives have a comparable affinity to highly curved bilayer regions (torroidal pores formed by magainin-2 in lipid bilayers, or the rims of discoid bicelles) and to planar bilayer regions (i.e. the flat region of lipid bilayers and bicelles). Furthermore, the monoacyl-probes are as compared to the diacyl-probes effectively closer to each other in a lipid bilayer, while none of these probes seems to be randomly distributed. Self-aggregation is most efficiently induced by the larger aromatic 564/570-BODIPY chromophore, but it is suppressed when using the diacyl instead of the monoacyl-form, and/or by attaching BODIPY-groups to the acyl-chain.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Boron Compounds / chemistry*
  • Energy Transfer
  • Lipid Bilayers / chemistry*
  • Magainins / chemistry
  • Monte Carlo Method
  • Phosphatidylcholines / chemistry
  • Phosphatidylethanolamines / chemistry*
  • Spectrometry, Fluorescence
  • Xenopus / metabolism
  • Xenopus Proteins / chemistry

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Lipid Bilayers
  • Magainins
  • Phosphatidylcholines
  • Phosphatidylethanolamines
  • Xenopus Proteins
  • magainin 2 peptide, Xenopus
  • 1,2-oleoylphosphatidylcholine