2011
DOI: 10.1016/j.jfluchem.2011.01.004
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Evaluation of the hydrophobicity of perfluoroalkyl chains in amphiphilic compounds that are incorporated into cell membrane

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Cited by 63 publications
(48 citation statements)
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“…We further investigated the effect of fluorination on cytosolic protein delivery. It was reported that the contribution of a CF 2 group to hydrophobicity was about 1.5 times that of a CH 2 group 39 , and thus the hydrophobicity of F3 and F4 could be roughly equivalent to that of A3 and A4, respectively. In this case, A4-1 and A3-3 in the library can be used as non-fluorinated controls for F4-1 and F3-3, respectively.…”
Section: Resultsmentioning
confidence: 99%
“…We further investigated the effect of fluorination on cytosolic protein delivery. It was reported that the contribution of a CF 2 group to hydrophobicity was about 1.5 times that of a CH 2 group 39 , and thus the hydrophobicity of F3 and F4 could be roughly equivalent to that of A3 and A4, respectively. In this case, A4-1 and A3-3 in the library can be used as non-fluorinated controls for F4-1 and F3-3, respectively.…”
Section: Resultsmentioning
confidence: 99%
“…Fluorinated compounds are both hydrophobic and lipophobic, and have a high phase-separation tendency in both polar and non-polar environments 25,26 . Therefore, fluorination can improve the affinity of polymers to cell membrane 27 and across the lipid bilayer of the cell membrane, as well as the endosome/lysosome membrane 28 , facilitating endosomal escape of the polymers. In addition, fluorinated polymers have low surface energy and prefer to associate with each other at low concentrations [29][30][31] , allowing the formation of polyplexes with nucleic acid at low nitrogen to phosphorus (N/P) ratios.…”
mentioning
confidence: 99%
“…Spontaneous phase separation in supramolecular aggregates of F/H amphiphiles is well documented for several such systems (e.g., micelles, Langmuir, and Langmuir–Blodgett films), including 2D SAMs on gold surfaces . Furthermore, fluorinated amphiphiles are receiving increasing interest for biological/biomedical applications as they confer useful properties to the materials they are linked to, such as inertness, facilitated cellular uptake, avoidance of protein denaturation, and reduced toxicity . Additionally, being NMR active, fluorine nuclei also assist in probing biological interactions and may lead to novel supramolecular contrast agents for bioimaging .…”
Section: Introductionmentioning
confidence: 99%
“…[31] Furthermore, fluorinated amphiphiles are receiving increasing interest for biological/biomedical applications [32] as they confer useful properties to the materials they are linked to, such as inertness, facilitated cellular uptake, avoidance of protein denaturation, and reduced toxicity. [33][34][35][36] Additionally, being NMR active, fluorine nuclei also assist in probing biological interactions [37] and may lead to novel supramolecular contrast agents for bioimaging. [38][39][40] This calls for a more in-depth investigation on the role of fluorinated ligands in monolayer-protected nanoparticles in modulating interactions with biological environments such as cellular membranes and cells.…”
mentioning
confidence: 99%