Highly fluorinated amphiphilic molecules and self-assemblies with biomedical potential

Riess, Jean G.

doi:10.1016/j.cocis.2009.05.008

Cited by 125 publications

(78 citation statements)

References 184 publications

(159 reference statements)

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“…[7,8] In particular, most of the commercially available injectable soft-shell bubbles contain a perfluoro compound in the gas phase. [3,[9][10][11][12] In these systems, monolayers of PLs generally constitute the bubble or emulsion droplet walls. Formulations containing FC or a combination of PLs and FCs have also been proposed to serve as new lung surfactant substitutes [13] and for the treatment of lung diseases.…”

Section: Introductionmentioning

confidence: 99%

A Nonpolar, Nonamphiphilic Molecule Can Accelerate Adsorption of Phospholipids and Lower Their Surface Tension at the Air/Water Interface

et al. 2011

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The adsorption dynamics of a series of phospholipids (PLs) at the interface between an aqueous solution or dispersion of the PL and a gas phase containing the nonpolar, nonamphiphilic linear perfluorocarbon perfluorohexane (PFH) was studied by bubble profile analysis tensiometry. The PLs investigated were dioctanoylphosphatidylcholine (DiC(8)-PC), dilaurylphosphatidylcholine, dimyristoylphosphatidylcholine, and dipalmitoylphosphatidylcholine. The gas phase consisted of air or air saturated with PFH. The perfluorocarbon gas was found to have an unexpected, strong effect on both the adsorption rate and the equilibrium interfacial tension (γ(eq)) of the PLs. First, for all of the PLs, and at all concentrations investigated, the γ(eq) values were significantly lower (by up to 10 mN m(-1)) when PFH was present in the gas phase. The efficacy of PFH in decreasing γ(eq) depends on the ability of PLs to form micelles or vesicles in water. For vesicles, it also depends on the gel or fluid state of the membranes. Second, the adsorption rates of all the PLs at the interface (as assessed by the time required for the initial interfacial tension to be reduced by 30%) are significantly accelerated (by up to fivefold) by the presence of PFH for the lower PL concentrations. Both the surface-tension reducing effect and the adsorption rate increasing effect establish that PFH has a strong interaction with the PL monolayer and acts as a cosurfactant at the interface, despite the absence of any amphiphilic character. Fitting the adsorption profiles of DiC(8)-PC at the PFH-saturated air/aqueous solution interface with the modified Frumkin model indicated that the PFH molecule lay horizontally at the interface.

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Section: Introductionmentioning

confidence: 99%

A Nonpolar, Nonamphiphilic Molecule Can Accelerate Adsorption of Phospholipids and Lower Their Surface Tension at the Air/Water Interface

et al. 2011

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“…Moreover, the interfacial properties of similar alcohols have been reported previously 13 . However, there are very few reports on the mechanisms of interaction between partially fluorinated compounds and biomembrane components 8,14 . In particular, there are fewer reports on the biophysical interplay incorporated by the shorter F-chains n F ≤ 6 .…”

Section: Introductionmentioning

confidence: 99%

Monolayer Compression Induces Fluidization in Binary System of Partially Fluorinated Alcohol (F4H11OH) with DPPC

et al. 2013

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“…As a consequence of their chemical stability, these compounds exhibit an environmental stability and are transmitted into the mammal food chain [3]. Due to their tendency to bioaccumulate, the compounds affect properties of cell membranes, causing developmental and reproductive disorders [2,4]. It is of particular interest to understand the effect of perfluorinated compounds not only on cellular membranes [5,6], but also on their biomimetic counterparts [7].…”

mentioning

confidence: 99%

“…Similar to the effect evoked by cholesterol, we attribute the observed lipid bilayer stiffening to a condensing effect of the perfluorinated compound on the membrane. Perfluorinated compounds (PFCs) are fully fluorinated fatty acid analogs commonly used in a wide range of applications, such as the production of fire-extinguishing foams, anticorrosion agents, lubricants, or cosmetics [1,2]. As a consequence of their chemical stability, these compounds exhibit an environmental stability and are transmitted into the mammal food chain [3].…”

mentioning

confidence: 99%

Perfluorooctanoic acid rigidifies a model lipid membrane

Brüning

Faragó

2014

Phys. Rev. E

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We report a combined dynamic light scattering and neutron spin-echo (NSE) study on vesicles composed of the phospholipid 1,2-dimyristoyl-sn-glycero-3-phosphatidylcholine under the influence of varying amounts of perfluorooctanoic acid. We study local lipid bilayer undulations using NSE on time scales up to 200 ns. Similar to the effect evoked by cholesterol, we attribute the observed lipid bilayer stiffening to a condensing effect of the perfluorinated compound on the membrane. Perfluorinated compounds (PFCs) are fully fluorinated fatty acid analogs commonly used in a wide range of applications, such as the production of fire-extinguishing foams, anticorrosion agents, lubricants, or cosmetics [1,2]. As a consequence of their chemical stability, these compounds exhibit an environmental stability and are transmitted into the mammal food chain [3]. Due to their tendency to bioaccumulate, the compounds affect properties of cell membranes, causing developmental and reproductive disorders [2,4]. It is of particular interest to understand the effect of perfluorinated compounds not only on cellular membranes [5,6], but also on their biomimetic counterparts [7]. In mammal organisms, vesicular membranes often serve as natural carriers. It is assumed that functional properties of a membrane depend likewise on its composition-dependent structure and dynamics [8,9]. In order to gain insight into membrane function, specific material properties, such as, e.g., the bilayer bending rigidity κ can be aimfully influenced. Several studies have addressed the insertion of perfluorinated compounds into binary model membranes. Oriented mono-and bilayers were investigated by Matyszewska et al. using methods including surface pressure and potential measurements, infrared spectroscopy (IR), nuclear magnetic resonance (NMR) techniques, and molecular dynamics (MD) simulations [4,10,11]. While the phospholipid head group tilt against the bilayer normal decreases with rising amounts of inserted perfluorooctanoic acid (PFOA), the lipid acyl chain order increases. Lateral molecule diffusion in the membrane plane changes nonuniformly as the ratio of the components in the binary mixture is varied [10]. Lehmler et al. study liposomes containing binary mixtures of varying phospholipids and perfluorinated surfactants [12][13][14][15]. They use fluorescence spectroscopy and differential scanning calorimetry measurements to study the partitioning of surfactants into the phospholipid bilayer and find that it is independent of the lipid acyl chain length. While the phase behavior is largely independent of the type of phospholipid, PFOA itself is found to partition more readily into lipid bilayers in their fluid phase [13]. Several studies have taken advantage of a combination of dynamic light scattering (DLS) and long-wavelength NSE for the investigation of the local bilayer undulation dynamics in unilamellar lipid vesicles (ULVs) [16][17][18][19][20][21]. Here, we cover a window of more than 200 ns. The membrane dynamics was investigated by NSE using w...

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Highly fluorinated amphiphilic molecules and self-assemblies with biomedical potential

Cited by 125 publications

References 184 publications

A Nonpolar, Nonamphiphilic Molecule Can Accelerate Adsorption of Phospholipids and Lower Their Surface Tension at the Air/Water Interface

A Nonpolar, Nonamphiphilic Molecule Can Accelerate Adsorption of Phospholipids and Lower Their Surface Tension at the Air/Water Interface

Monolayer Compression Induces Fluidization in Binary System of Partially Fluorinated Alcohol (F4H11OH) with DPPC

Perfluorooctanoic acid rigidifies a model lipid membrane

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