Mixing of Partially Fluorinated Carboxylic Acids with Their Hydrocarbon Analogs at the Air–Water Interface

Lehmler, Hans‐Joachim; Bummer, Paul M.

doi:10.1006/jcis.2002.8282

Cited by 33 publications

(43 citation statements)

References 43 publications

(55 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Concentrated hydrochloric acid was obtained from Fisher Scientific. Deionized water for the monolayer studies was distilled first from basic potassium permanganate followed by distillation from sulfuric acid (16,19,(21)(22)(23). Deionized water for the DSC experiments was obtained from a Purelab Plus water system and had a resistance of у 18 ⍀ (16).…”

Section: Methodsmentioning

confidence: 99%

Interaction of long-chain nicotinates with dipalmitoylphosphatidylcholine

Lehmler

Fortis-Santiago

Nauduri

et al. 2005

Journal of Lipid Research

Self Cite

View full text Add to dashboard Cite

The interaction of four long-chain nicotinates, compounds that are of interest as potential chemopreventive agents, with dipalmitoylphosphatidylcholine (DPPC) was investigated in monolayers at the air-water interface and in fully hydrated bilayers. For the monolayer studies, the compression isotherms of mixtures of the respective nicotinate with DPPC were recorded at various compositions on a hydrochloric acid subphase (pH 1.9-2.1, 37 ؎ 2 ؇ C). The headgroup of the nicotinates (24-29 Å 2 /molecule) is larger than that of the hydrophobic tail (20 Å 2 /molecule). The pure nicotinates exhibit a temperature-and chain lengthdependent transition from an expanded to a condensed phase. Analysis of the concentration dependence of the average molecular area at constant film pressure and the concentration dependence of the breakpoint of the phase transition from the expanded to the condensed state suggests that all four DPPC-nicotinate mixtures are partially miscible at the air-water interface. Although a complex phase behavior with several phase transitions was observed, differential scanning calorimetry studies of the four mixtures are also indicative of the partial miscibility of DPPC and the respective nicotinate.Overall, the complex phase behavior most likely results from the head-tail mismatch of the nicotinates and the geometric packing constraints in the twocomponent lipid bilayer. Nicotinic acid and its alkyl esters are of considerable biological and pharmacological importance. Besides being the precursor of cofactors to many vital enzymes, nicotinic acid is a drug possessing vasodilating and fibrinolytic properties. Nicotinic acid itself has been proven beneficial against bleomycin-and cyclophosphamide-induced lung injury in animal models (1-5). Dietary supplements of nicotinic acid and dermatologic formulations of its longchain esters are under investigation for the prevention and treatment of skin carcinogenesis (6). Therefore, nicotinic acid esters may be useful as a chemopreventive agent for the prevention of lung cancer.Currently, there is significant interest in the pulmonary administration of several chemopreventive agents, such as steroids and retinoids, directly to the lung because of reduced systemic toxicity (7-11). This route of administration may also be advantageous for the administration of nicotinic acid esters, by using either an aerosol or a perfluorocarbon vehicle (12, 13). Although the interaction of various chemopreventive agents, especially retinoids, with phospholipids has been investigated (14, 15), there is no current knowledge about the factors that determine the interaction (i.e., phase behavior) of nicotinates with biological lipids such as the phospholipids present in pulmonary surfactant. A better understanding of these interactions, however, is a prerequisite for the rational design of nicotinates for pulmonary administration, especially using a perfluorocarbon-based drug delivery system (12, 13). The aim of this study is to understand which molecular characteristics influe...

show abstract

Section: Methodsmentioning

confidence: 99%

Interaction of long-chain nicotinates with dipalmitoylphosphatidylcholine

Lehmler

Fortis-Santiago

Nauduri

et al. 2005

Journal of Lipid Research

Self Cite

View full text Add to dashboard Cite

show abstract

“…The perfluorinated terminus of 10-(perfluorohexyl)-decanol is lipophobic, significantly larger compared to an alkyl chain, and the -CF 2 -CH 2 -linkage is highly polar. We and others have suggested that such a structure results in less dense packing at the air-water interface and, thus, weaker chain-chain interactions in monolayers of partially fluorinated amphiphiles [8,20,23,24,40]. This ultimately results in differences in the macroscopic phase behavior of the fluorinated versus the hydrocarbon system at the air-water interface.…”

Section: Mixing Behavior In Monolayers At the Air-water Interfacementioning

confidence: 97%

“…All solvents and chemicals were of HPLC or ACS grade purity and were purchased from Fisher Scientific (Pittsburgh, Pennsylvania, U.S.A.) or VWR (West Chester, Pennsylvania, U.S.A.). Deionized water for the DSC experiments was obtained from a PURELAB Plus water system and had a resistance ≥ 18 meg Ω [13,14] whereas deionized water for the monolayer studies was distilled first from basic potassium permanganate followed by distillation from sulfuric acid [13,14,20].…”

Section: Chemicalsmentioning

confidence: 99%

“…The surface pressure was measured by the Wilhelmy plate method using paper plates (15 × 58 mm) [8,13,14,20,23,24]. Every surface area-surface pressure isotherm was determined on a freshly poured subphase of water, hydrochloric acid (pH = 1.9 to 2.1), sodium chloride (0.15 M) or calcium chloride (2 mM).…”

Section: Monolayer Studies At the Air-water Interfacementioning

confidence: 99%

“…To assess the miscibility of 10-(perfluorohexyl)-decanol and DPPC on the four subphases the concentration dependence of the surface pressure of onset of the liquid expanded-liquid condensed phase transition of the compression isotherms was employed [13,20,24,33,34]. In general, a concentration-dependent surface pressure of the phase transition is indicative of complete miscibility of the two components, whereas concentration independence is a sign of immiscibility of the components [33].…”

Section: Mixing Behavior In Monolayers At the Air-water Interfacementioning

confidence: 99%

See 2 more Smart Citations

Mixing behavior of 10-(perfluorohexyl)-decanol and DPPC

Lehmler

Bummer

2005

Colloids and Surfaces B: Biointerfaces

Self Cite

View full text Add to dashboard Cite

Fluorocarbon alcohol such as 10-(perfluorohexyl)-decanol are of interest for novel pulmonary drug delivery approaches. The purpose of this study was to investigate the mixing behavior of 10-(perfluorohexyl)-decanol with dipalmitoylphosphatidylcholine (DPPC), the major component of lung surfactant, as an aid in assessing usefulness for this and other biomedical applications. The impact of 10-(perfluorohexyl)-decanol on the phase transitions of DPPC bilayers fully hydrated with a 0.15 M sodium chloride solution were studied using differential scanning calorimetry (DSC). No peak corresponding to excess alcohol was observed. The fluorinated alcohol caused DPPC peak broadening, especially below X DPPC < 0.95, and elimination of the pretransition of DPPC at X DPPC ∼ 0.91. The onset of the main phase transition remains constant down to X DPPC ∼ 0.91, suggesting limited miscibility in the gel phase. Hydration of the 10-(perfluorohexyl)-decanol-DPPC mixtures with calcium chloride (2 mM) in place of sodium chloride did not alter the macroscopic phase behavior. In addition to the thermal properties, the miscibility of 10-(perfluorohexyl)-decanol in DPPC in monolayers at the air water interface was investigated on water, sodium chloride (0.15 M), calcium chloride (2 mM) or hydrochloric acid (pH=1.9) subphases. The concentration dependence of the onset pressure of the liquid-expanded to liquid condensed phase transition of DPPC showed a slight change with increasing mole fraction on all four subphases. The surface areamole fraction diagrams of 10-(perfluorohexyl)-decanol and DPPC on water, sodium chloride and calcium chloride showed near ideal behavior with slight negative deviations at higher surface pressure. A more significant negative deviation was observed for the hydrochloric acid subphase. Overall, both the DSC and the monolayer studies suggest that 10-(perfluorohexyl)-decanol and DPPC are partially miscible in biological mono-and bilayers. The macroscopic phase behavior 10-(perfluorohexyl)-decanol-DPPC system is significantly different from the analogous hydrocarbon system, which is attributed to a less favorable packing of the partially fluorinated hydrophobic tails in the mono-and bilayer.

show abstract

Stacking of Self‐Assembled Surface Micelles in Ultrathin Films

et al. 2012

View full text Add to dashboard Cite

Nonpolar fluorophilic/lipophilic tetrablock amphiphiles are investigated on the surface of water and on solid substrates using compression isotherms, Brewster angle microscopy, and atomic force microscopy. At low pressures, the tetrablocks form monolayers of closely packed surface hemimicelles. Further compression causes a 2D/3D transition. At the end of the plateau, half of the deposited material is expelled forming a second monolayer on top of the initially formed monolayer. Both layers of the films consist of surface micelles, thus providing the first example of spontaneous or compression-driven stacking of self-assembled nano-objects.

show abstract

Mixing of Partially Fluorinated Carboxylic Acids with Their Hydrocarbon Analogs at the Air–Water Interface

Cited by 33 publications

References 43 publications

Interaction of long-chain nicotinates with dipalmitoylphosphatidylcholine

Interaction of long-chain nicotinates with dipalmitoylphosphatidylcholine

Mixing behavior of 10-(perfluorohexyl)-decanol and DPPC

Stacking of Self‐Assembled Surface Micelles in Ultrathin Films

Contact Info

Product

Resources

About