Incorporation of a perfluoroalkylalkane (R<sub>F</sub>R<sub>H</sub>) into the phospholipid bilayer of dmpc liposomes results in greater encapsulation stability

Trevino, Leo; Frézard, Frédéric; Postel, M.; Riess, Jean G.

doi:10.3109/08982109409018619

Cited by 18 publications

(12 citation statements)

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“…10 An alternative approach to obtaining fluorinated vesicles consists of using a combination of standard hydrocarbon lipids and semifluorinated alkanes C n F 2n+1 C m H 2m+1 (FnHm diblocks). 1,2,11 FnHm diblocks, because they appear to be well tolerated biologically and are easy to synthesize, have potential as versatile membrane components. 12 FnHm diblocks were shown to be efficient stabilizers of phospholipid-based fluorocarbon emulsions and allowed precise particle size control.…”

Section: Introductionmentioning

confidence: 99%

“…An alternative approach to obtaining fluorinated vesicles consists of using a combination of standard hydrocarbon lipids and semifluorinated alkanes C n F 2 n +1 C m H 2 m +1 (F n H m diblocks). ,, F n H m diblocks, because they appear to be well tolerated biologically and are easy to synthesize, have potential as versatile membrane components , It was recently found that F8H16 substantially decreased the interfacial tension between a phospholipid dispersion and a fluorocarbon pendant drop, revealing the presence of the diblocks at the interface .…”

Section: Introductionmentioning

confidence: 99%

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Fluorinated Vesicles Made from Combinations of Phospholipids and Semifluorinated Alkanes. Direct Experimental Evidence of the Location of the Semifluorinated Alkane within the Bilayer

et al. 2003

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Previous work has demonstrated that codispersion of semifluorinated alkanes CnF2n+1CmH2m+1 (FnHm diblocks) with phospholipids strongly modifies the properties of the resulting vesicles. The hypothetical segregation and ordered self-organization of FnHm diblocks as a continuous film within the bilayer were suggested to account for the observed changes of bilayer behavior; however, no proof of the diblock location and organization was provided. We now report direct experimental evidence of the diblock's presence and organization within the bilayer using cryogenic transmission electron microscopy (cryo-TEM), highsensitivity differential scanning calorimetry (micro-DSC), and small-angle X-ray scattering (SAXS). Cryo-TEM demonstrated that a sonicated codispersion of dioleoylphosphatidylcholine (DOPC) and C 6F13C10H21 (F6H10) (1:1) led to an homogeneous population of small unilamellar vesicles (SUVs) with no F6H10 emulsion droplets present. The bilayer of these SUVs appeared as a single, thick and dark ring, characteristic of the bilayer of vesicles made from fluorinated phospholipids. This aspect, very different from that of the bilayer of DOPC vesicles, which consists of two concentric rings, demonstrated unambiguously the presence of a fluorinated core within the bilayer. The micro-DSC study on dimyristoylphosphatidylcholine (DMPC)/ F6H10 SUVs showed a shift of the DMPC main transition phase temperature to lower values, indicating interdigitation of the H10 hydrogenated segments of the diblock with the fatty acid chains of the DMPC. In addition, F6H10 was observed to undergo a gel-to-fluid transition at ∼25 °C when incorporated in the DMPC bilayer, giving further evidence for an organized fluorinated film within the bilayer (F6H10 is liquid in the bulk). Finally, SAXS experiments were in agreement with a hollow spherelike particle model constituted by a ∼3 nm thick fluorinated shell, indicating that the fluorinated segments are not interdigitated.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Fluorinated Vesicles Made from Combinations of Phospholipids and Semifluorinated Alkanes. Direct Experimental Evidence of the Location of the Semifluorinated Alkane within the Bilayer

et al. 2003

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“…Mixed vesicles obtained by combining standard phospholipids and hydrocarbon/fluorocarbons diblocks indeed show greater stability with respect to usual hydrocarbon vesicles. This proves that the fluorinated segments are tightly organized within the bilayer [15,16]. For recent reviews concerning fluorinated amphiphiles and their use as drug carriers and delivery systems see Refs.…”

Section: Introductionmentioning

confidence: 87%

On the carrier properties of perfluoropolyether–betaine mixed vesicles: the contribution of electron spin resonance spectroscopy

Martini

Balzi

Becciolini

et al. 2004

Journal of Fluorine Chemistry

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“…Previous reports have determined that the e.e. values of calcein in DMPC vesicles 25 and in DMPC-betamethasone vesicles 26 were ca. 20% and 14.5-24.1%, respectively.…”

Section: Evaluation Of the Cargo-carrying Ability Of Obtained Vesiclesmentioning

confidence: 94%

Microfluidic platforms with monolithically integrated hierarchical apertures for the facile and rapid formation of cargo-carrying vesicles

et al. 2015

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Incorporation of a perfluoroalkylalkane (R_FR_H) into the phospholipid bilayer of dmpc liposomes results in greater encapsulation stability

Cited by 18 publications

References 12 publications

Fluorinated Vesicles Made from Combinations of Phospholipids and Semifluorinated Alkanes. Direct Experimental Evidence of the Location of the Semifluorinated Alkane within the Bilayer

Fluorinated Vesicles Made from Combinations of Phospholipids and Semifluorinated Alkanes. Direct Experimental Evidence of the Location of the Semifluorinated Alkane within the Bilayer

On the carrier properties of perfluoropolyether–betaine mixed vesicles: the contribution of electron spin resonance spectroscopy

Microfluidic platforms with monolithically integrated hierarchical apertures for the facile and rapid formation of cargo-carrying vesicles

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Incorporation of a perfluoroalkylalkane (RFRH) into the phospholipid bilayer of dmpc liposomes results in greater encapsulation stability

Cited by 18 publications

References 12 publications

Fluorinated Vesicles Made from Combinations of Phospholipids and Semifluorinated Alkanes. Direct Experimental Evidence of the Location of the Semifluorinated Alkane within the Bilayer

Fluorinated Vesicles Made from Combinations of Phospholipids and Semifluorinated Alkanes. Direct Experimental Evidence of the Location of the Semifluorinated Alkane within the Bilayer

On the carrier properties of perfluoropolyether–betaine mixed vesicles: the contribution of electron spin resonance spectroscopy

Microfluidic platforms with monolithically integrated hierarchical apertures for the facile and rapid formation of cargo-carrying vesicles

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Incorporation of a perfluoroalkylalkane (R_FR_H) into the phospholipid bilayer of dmpc liposomes results in greater encapsulation stability