Interaction of a partially fluorinated long-chain nicotinate with dipalmitoylphosphatidylcholine

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, N...

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Bibliographic Details
Published in:Journal of lipid research 2005-11, Vol.46 (11), p.2415-2422
Main Authors: Lehmler, Hans-Joachim, Bummer, Paul M
Format: Article
Language:English
Subjects:
1,2-Dipalmitoylphosphatidylcholine - chemistry
Air
Calorimetry
Calorimetry, Differential Scanning
Chemistry - methods
differential scanning calorimetry
Fluorine - chemistry
head-tail mismatch
Hydrocarbons - chemistry
Hydrogen-Ion Concentration
Langmuir monolayer
Lipid Bilayers - chemistry
lipid phase transition
liposomes
Models, Chemical
Niacin - chemistry
Pressure
Protein Binding
Surface Properties
Temperature
Water
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Summary: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 degrees 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.
ISSN:0022-2275
DOI:10.1194/jlr.M500231-JLR200