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- W2766532127 abstract "Recently developed lipids with the trans-2-aminocyclohexanol (TACH) moiety represent unique pH-sensitive conformational switches (“flipids”) that can trigger the membrane of liposome-based drug delivery systems at lowered pH as seen in many pathological scenarios. A library of flipids with various TACH-based headgroups and hydrocarbon tails were designed, prepared, and characterized to systematically elucidate the relationship between their chemical structures and their ability to form and to trigger liposomes. Liposomes (fliposomes) consisting of a flipid, POPC and PEG-ceramide were stable at 4 °C, pH 7.4 for up to several months and yet released the encapsulated fluorophore in seconds upon acidification. The colloidal properties and encapsulation efficiencies of the fliposomes depended on the structure features of the flipids such as the polarity of the headgroups and the shape and fluidity of the lipid tails. The pH-triggered release also depended on the flipid structure, where shorter linear tails yielded more efficient release. The release of fliposomes was enhanced at different narrow pH ranges, depending on the basicity of the flipid headgroup, which can be estimated either by calculated pKa or by acid/base titration of the flipids while its conformation is monitored by 1H NMR. The structure-activity relationship of the flipids supports “lipid tail conformational shortening” as the mechanism to disrupt lipid membranes and would provide great flexibility in the design of pH-sensitive drug delivery systems." @default.
- W2766532127 created "2017-11-10" @default.
- W2766532127 creator A5002317234 @default.
- W2766532127 creator A5009080641 @default.
- W2766532127 creator A5021687717 @default.
- W2766532127 creator A5062567330 @default.
- W2766532127 creator A5063581021 @default.
- W2766532127 creator A5084313185 @default.
- W2766532127 date "2018-01-01" @default.
- W2766532127 modified "2023-10-06" @default.
- W2766532127 title "Fliposomes: trans-2-aminocyclohexanol-based amphiphiles as pH-sensitive conformational switches of liposome membrane – a structure-activity relationship study" @default.
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- W2766532127 doi "https://doi.org/10.1016/j.chemphyslip.2017.10.004" @default.