J. Lipid Res.
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A more recent version of this article appeared on November 1, 2005

Papers In Press, published online ahead of print September 8, 2005
J. Lipid Res., doi:10.1194/jlr.M500231-JLR200
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Submitted on June 7, 2005
Revised on August 15, 2005
Accepted on August 17, 2005

Interaction of a partially fluorinated long-chain nicotinate with dipalmitoylphosphatidylcholine

Hans-Joachim Lehmler and Paul M. Bummer

Department of Occupational and Environmental Health, University of Iowa, Iowa City, IA 52242

Corresponding Author: hans-joachim-lehmler{at}uiowa.edu

The interaction of a partially fluorinated long-chain nicotinate F-NA18, a compound of interest as a chemopreventive agent, with dipalmitoylphosphatidylcholine (DPPC) was investigated in monolayers at the air-water interface and in fully hydrated bilayers and compared to its hydrocarbon analog NA18. For the monolayer studies, the compression isotherms of mixtures of F-NA18 with DPPC were recorded at various compositions on a hydrochloric acid subphase (pH = 1.9-2.1, 32 ± 2°C). Analysis of the composition dependence of the average molecular area at constant film pressure and of the dependence of the breakpoints of the phase transitions suggests that F-NA18 is miscible with DPPC at the air-water interface whereas NA18 shows some degree of immiscibility. In the DSC studies only one major phase transition can be observed for F-NA18-DPPC mixtures whereas NA18-DPPC mixtures exhibit a complex phase behavior. The differences in the phase behavior of the respective mixtures may be the result of the geometric packing constraints of F-NA18 versus NA18. For biomedical applications, the use of a partially fluorinated tail may, therefore, offer advantages over simple hydrocarbon systems because, in addition to the chain-length, the position and degree of fluorination can be adjusted.


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S. L. Duncan and R. G. Larson
Comparing Experimental and Simulated Pressure-Area Isotherms for DPPC
Biophys. J., April 15, 2008; 94(8): 2965 - 2986.
[Abstract] [Full Text] [PDF]


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