Abstract
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.
Highlights
The interaction of a partially fluorinated longchain 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
We used a combination of monolayer and differential scanning calorimetry (DSC) studies to gain a better insight into the interaction of DPPC, an important biological phospholipid, and several long-chain nicotinates
The present study investigates the mixing behavior of a partially fluorinated nicotinate (F-NA18) with DPPC in insoluble monolayers at the air-water interface
Summary
The interaction of a partially fluorinated longchain 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. The introduction of such a perfluorinated segment into the hydrophobic tail of a long-chain nicotinate would likely introduce a strong dipole moment resulting from the CH2CF2 linkage and a larger cross-sectional area of the hydrophobic tail resulting from the larger van der Waals radius of the perfluoroalkyl group Both factors are known to influence the phase behavior of mixtures of phosphatidylcholines with partially fluorinated long-chain carboxylic acids [17,18,19]. The aim of this study was to understand the extent to which the introduction of a perfluoroalkyl group alters the phase behavior of nicotinate-DPPC mixtures For this purpose, we used a combination of monolayer and differential scanning calorimetry (DSC) studies to gain a better insight into the interaction of DPPC, an important biological phospholipid, and several long-chain nicotinates. The combination of these two different approaches will further our understanding of phospholipid-nicotinate interactions and contribute to the rational design of fluorinated nicotinates for a variety of biomedical applications [8]
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