J. Lipid Res. Neurobiology of Lipids (ISSN1683-5506)
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Originally published In Press as doi:10.1194/jlr.M500231-JLR200 on September 8, 2005

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Journal of Lipid Research, Vol. 46, 2415-2422, November 2005
Copyright © 2005 by American Society for Biochemistry and Molecular Biology

Interaction of a partially fluorinated long-chain nicotinate with dipalmitoylphosphatidylcholine

Hans-Joachim Lehmler1,* and Paul M. Bummer{dagger}

* Department of Occupational and Environmental Health, University of Iowa, Iowa City, IA 52242
{dagger} College of Pharmacy, University of Kentucky, Lexington, KY 40536

Published, JLR Papers in Press, September 8, 2005. DOI 10.1194/jlr.M500231-JLR200

1 To whom correspondence should be addressed. e-mail: 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 with 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 differential scanning calorimetry studies, only one major phase transition was observed for F-NA18-DPPC mixtures, whereas NA18-DPPC mixtures exhibited 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.

Therefore, for biomedical applications, the use of a partially fluorinated tail may offer advantages over simple hydrocarbon systems because, in addition to the chain length, the position and degree of fluorination can be adjusted.

Supplementary key words differential scanning calorimetry • Langmuir monolayer • liposomes • lipid phase transition • head-tail mismatch


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