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Structure and interactive properties of highly fluorinated phospholipid bilayers.

Publication ,  Journal Article
McIntosh, TJ; Simon, SA; Vierling, P; Santaella, C; Ravily, V
Published in: Biophys J
October 1996

Because liposomes containing fluoroalkylated phospholipids are being developed for in vivo drug delivery, the structure and interactive properties of several fluoroalkylated glycerophosphocholines (PCs) were investigated by x-ray diffraction/osmotic stress, dipole potential, and hydrophobic ion binding measurements. The lipids included PCs with highly fluorinated tails on both alkyl chains and PCs with one hydrocarbon chain and one fluoroalkylated chain. Electron density profiles showed high electron density peaks in the center of the bilayer corresponding to the fluorine atoms. The height and width of these high density peaks varied systematically, depending on the number of fluorines and their position on the alkyl chains, and on whether the bilayer was in the gel or liquid crystalline phase. Wide-angle diffraction showed that in both gel and liquid crystalline bilayers the distance between adjacent alkyl chains was greater in fluoroalkylated PCs than in analogous hydrocarbon PCs. For interbilayer separations of less than about 8 A, pressure-distance relations for fluoroalkylated PCs were similar to those previously obtained from PC bilayers with hydrocarbon chains. However, for bilayer separations greater than 8A, the total repulsive pressure depended on whether the fluoroalkylated PC was in a gel or liquid-crystalline phase. We argue that these pressure-distance relations contain contributions from both hydration and entropic repulsive pressures. Dipole potentials ranged from -680 mV for PCs with both chains fluoroalkylated to -180 mV for PCs with one chain fluoroalkylated, compared to +415 mV for egg PC. The change in dipole potential as a function of subphase concentration of tetraphenyl-boron was much larger for egg PC than for fluorinated PC monolayers, indicating that the fluorine atoms modified the binding of this hydrophobic anion. Thus, compared to conventional liposomes, liposomes made from fluoroalkylated PCs have different binding properties, which may be relevant to their use as drug carriers.

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Published In

Biophys J

DOI

ISSN

0006-3495

Publication Date

October 1996

Volume

71

Issue

4

Start / End Page

1853 / 1868

Location

United States

Related Subject Headings

  • X-Ray Diffraction
  • Tetraphenylborate
  • Structure-Activity Relationship
  • Potentiometry
  • Phosphatidylcholines
  • Molecular Conformation
  • Models, Theoretical
  • Lipid Bilayers
  • Isomerism
  • Fluorescent Dyes
 

Citation

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McIntosh, T. J., Simon, S. A., Vierling, P., Santaella, C., & Ravily, V. (1996). Structure and interactive properties of highly fluorinated phospholipid bilayers. Biophys J, 71(4), 1853–1868. https://doi.org/10.1016/S0006-3495(96)79385-2
McIntosh, T. J., S. A. Simon, P. Vierling, C. Santaella, and V. Ravily. “Structure and interactive properties of highly fluorinated phospholipid bilayers.Biophys J 71, no. 4 (October 1996): 1853–68. https://doi.org/10.1016/S0006-3495(96)79385-2.
McIntosh TJ, Simon SA, Vierling P, Santaella C, Ravily V. Structure and interactive properties of highly fluorinated phospholipid bilayers. Biophys J. 1996 Oct;71(4):1853–68.
McIntosh, T. J., et al. “Structure and interactive properties of highly fluorinated phospholipid bilayers.Biophys J, vol. 71, no. 4, Oct. 1996, pp. 1853–68. Pubmed, doi:10.1016/S0006-3495(96)79385-2.
McIntosh TJ, Simon SA, Vierling P, Santaella C, Ravily V. Structure and interactive properties of highly fluorinated phospholipid bilayers. Biophys J. 1996 Oct;71(4):1853–1868.
Journal cover image

Published In

Biophys J

DOI

ISSN

0006-3495

Publication Date

October 1996

Volume

71

Issue

4

Start / End Page

1853 / 1868

Location

United States

Related Subject Headings

  • X-Ray Diffraction
  • Tetraphenylborate
  • Structure-Activity Relationship
  • Potentiometry
  • Phosphatidylcholines
  • Molecular Conformation
  • Models, Theoretical
  • Lipid Bilayers
  • Isomerism
  • Fluorescent Dyes