“…To find evidence for the coexistence of two distinct lipid phases below T m at a certain interval of fluorotelomer fraction in the membranes, as expected from the DPPC/sterol phase diagram (Supplementary Fig. 1 ), we performed CLSM experiments at room temperature of DPPC/8:2 FTOH giant unilamellar vesicles (GUVs) double stained with ATTO-633-DOPE, a commonly used red-dye which partitions preferentially in disordered lipid environments, and Rh-C 2 H 4 -C 10 F 21 , a synthesized rhodamine based fluorinated fluorescence dye 30 that has been shown to partition preferentially in fluorine rich phases 31 . As it can be seen in Fig.…”
Section: Resultsmentioning
confidence: 99%
“…This indicates that, at room temperature, the 8:2 FTOH-rich phase is more disordered than a pure DPPC phase. Figure 3 CLSM z-stacking images of DPPC and DPPC/8:2 FTOH mixed GUVs using double staining with a synthethised rhodamine based fluorinated fluorescence dye (0.5 mol % Rh-C 2 H 4 -C 10 F 21 , green channel, left) that partitions preferentially in phases containing fluorinated molecules 30 , 31 and a commonly used dye (0.5 mol % ATTO-633-DOPE, red channel, middle) used to stain disordered phases. The images on the right are overlays of both channels.…”
Section: Resultsmentioning
confidence: 99%
“…The phospholipid 1,2-dipalmitoyl- sn -glycero-3-phosphocholine (DPPC) was purchased from Avanti Polar Lipids, the fluorotelomer alcohol 1H,1H,2H,2H-perfluoro-1-decanol (8:2 FTOH), deuterated chloroform (CDCl3) and D 2 O from Sigma-Aldrich, non-deuterated chloroform from Carl Roth, and the fluorescence dye ATTO-633-DOPE from ATTO-TEC GmbH. The rhodamine based fluorinated fluorescence dye Rh-C 2 H 4 -C 10 F 21 was synthesized according to a previously reported procedure 30 .…”
Fluorocarbon amphiphiles are anthropogenic substances widely used in diverse applications such as food packaging, clothing or cookware. Due to their widespread use and non-biodegradability, these chemicals are now ubiquitous in the natural world with high propensity to bioaccumulate in biological membranes, wherein they may affect microscopic properties. Here, we test the hypothesis that a typical fluorocarbon amphiphile can affect lipid membranes similarly to cholesterol by investigating the effect of 1H,1H,2H,2H-perfluoro-1-decanol (8:2 FTOH) on 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) membranes. Using solid-state nuclear magnetic resonance spectroscopy, differential scanning calorimetry and confocal microscopy, we present a consistent set of independent experimental evidences supporting this hypothesis, namely that upon incorporation of 8:2 FTOH, (i) a condensing effect on the acyl chains occurs in the fluid phase, (ii) coexistence of two membrane phases is observed below melting, and (iii) the melting temperature of DPPC varies no more than approximately ±1 °C up to a concentration of 40 mol% of 8:2 FTOH. The condensing effect is quantified by means of advanced dipolar recoupling solid-state NMR experiments and is found to be of approximately half the magnitude of the cholesterol effect at the same concentration.
“…To find evidence for the coexistence of two distinct lipid phases below T m at a certain interval of fluorotelomer fraction in the membranes, as expected from the DPPC/sterol phase diagram (Supplementary Fig. 1 ), we performed CLSM experiments at room temperature of DPPC/8:2 FTOH giant unilamellar vesicles (GUVs) double stained with ATTO-633-DOPE, a commonly used red-dye which partitions preferentially in disordered lipid environments, and Rh-C 2 H 4 -C 10 F 21 , a synthesized rhodamine based fluorinated fluorescence dye 30 that has been shown to partition preferentially in fluorine rich phases 31 . As it can be seen in Fig.…”
Section: Resultsmentioning
confidence: 99%
“…This indicates that, at room temperature, the 8:2 FTOH-rich phase is more disordered than a pure DPPC phase. Figure 3 CLSM z-stacking images of DPPC and DPPC/8:2 FTOH mixed GUVs using double staining with a synthethised rhodamine based fluorinated fluorescence dye (0.5 mol % Rh-C 2 H 4 -C 10 F 21 , green channel, left) that partitions preferentially in phases containing fluorinated molecules 30 , 31 and a commonly used dye (0.5 mol % ATTO-633-DOPE, red channel, middle) used to stain disordered phases. The images on the right are overlays of both channels.…”
Section: Resultsmentioning
confidence: 99%
“…The phospholipid 1,2-dipalmitoyl- sn -glycero-3-phosphocholine (DPPC) was purchased from Avanti Polar Lipids, the fluorotelomer alcohol 1H,1H,2H,2H-perfluoro-1-decanol (8:2 FTOH), deuterated chloroform (CDCl3) and D 2 O from Sigma-Aldrich, non-deuterated chloroform from Carl Roth, and the fluorescence dye ATTO-633-DOPE from ATTO-TEC GmbH. The rhodamine based fluorinated fluorescence dye Rh-C 2 H 4 -C 10 F 21 was synthesized according to a previously reported procedure 30 .…”
Fluorocarbon amphiphiles are anthropogenic substances widely used in diverse applications such as food packaging, clothing or cookware. Due to their widespread use and non-biodegradability, these chemicals are now ubiquitous in the natural world with high propensity to bioaccumulate in biological membranes, wherein they may affect microscopic properties. Here, we test the hypothesis that a typical fluorocarbon amphiphile can affect lipid membranes similarly to cholesterol by investigating the effect of 1H,1H,2H,2H-perfluoro-1-decanol (8:2 FTOH) on 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) membranes. Using solid-state nuclear magnetic resonance spectroscopy, differential scanning calorimetry and confocal microscopy, we present a consistent set of independent experimental evidences supporting this hypothesis, namely that upon incorporation of 8:2 FTOH, (i) a condensing effect on the acyl chains occurs in the fluid phase, (ii) coexistence of two membrane phases is observed below melting, and (iii) the melting temperature of DPPC varies no more than approximately ±1 °C up to a concentration of 40 mol% of 8:2 FTOH. The condensing effect is quantified by means of advanced dipolar recoupling solid-state NMR experiments and is found to be of approximately half the magnitude of the cholesterol effect at the same concentration.
“…As 1-octanol possesses a lipophilic tail and a polar headgroup, it is amphiphilic and resembles the proteins and phospholipids present in the cell membranes, which makes it suitable as a model for investigating the partitioning in such biological systems [29]. In the case of using fluorinated species, a partition coefficient between perfluoro(methylcyclohexane) (PFMC) and toluol ( ln P PFMC/Tol ) is useful, especially when using fluorophilic fluorescence dyes for their determination [32,33].…”
Section: Quantitative Approaches To Philicitiesmentioning
Recent developments in synthetic pathways as simple reversible-deactivation radical polymerization (RDRP) techniques and quantitative post-polymerization reactions, most notoriously ‘click’ reactions, leading to segmented copolymers, have broadened the molecular architectures accessible to polymer chemists as a matter of routine. Segments can be blocks, grafted chains, branchings, telechelic end-groups, covalently attached nanoparticles, nanodomains in networks, even sequences of random copolymers, and so on. In this review, we describe the variety of the segmented synthetic copolymers landscape from the point of view of their chemical affinity, or synonymous philicity, in bulk or with their surroundings, such as solvents, permeant gases, and solid surfaces. We focus on recent contributions, current trends, and perspectives regarding polyphilic copolymers, which have, in addition to hydrophilic and lipophilic segments, other philicities, for example, towards solvents, fluorophilic entities, ions, silicones, metals, nanoparticles, and liquid crystalline moieties.
“…As one of the decomposition products was identified as a hydroxamic acid derivative (formal oxydefluorination at the α-position), we set out to investigate a controllable defluorination. Notably, fluorinated amides are important motifs in biologically active molecules and valuable building blocks for pharmaceuticals, dyes, and functional materials . Only a few synthesis methods for perfluorinated amides are reported; ,, most of them have a limited substrate scope and rely on sensitive acid derivatives or coupling reagents.…”
A one-pot approach to fluorinated hydroxamic acid, amide, and thioamide derivatives is reported. The reaction proceeds via an N-perfluoroalkylation of nitrosoarenes with perfluoroalkanesulfinates, resulting in labile N-perfluoroalkylated hydroxylamines. By the addition of suitable additives, a controllable oxy/thiodefluorination of the fluorinated hydroxylamine intermediates was achieved. The method highlights N-perfluoroalkylated amines as versatile intermediates for further synthesis.
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