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Stable Vesicles Composed of Monocarboxylic or Dicarboxylic Fatty Acids and Trimethylammonium Amphiphiles

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    Stable Vesicles Composed of Monocarboxylic or Dicarboxylic Fatty Acids and Trimethylammonium Amphiphiles
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    † †FLinT (Center for Fundamental Living Technology), Institute of Physics and Chemistry, ‡Membrane Biophysics and Biophotonis Group/MEMPHYS (Center for Biomembrane Physics), Department of Biochemistry and Molecular Biology, and §Department of Physics and Chemistry, University of Southern Denmark, Campusvej 55, DK-5230 Odense M, Denmark
    Phone: +45 6550 4437. Fax: + 45 6615 8760. E-mail: [email protected]
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    Langmuir

    Cite this: Langmuir 2011, 27, 23, 14078–14090
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    https://doi.org/10.1021/la203057b
    Published September 20, 2011
    Copyright © 2011 American Chemical Society
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    Abstract

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    The self-assembly of cationic and anionic amphiphile mixtures into vesicles in aqueous media was studied using two different systems: (i) decanoic acid and trimethyldecylammonium bromide and (ii) hexadecanedioic acid (a simple bola-amphiphile) and trimethyldecylammonium bromide. The resulting vesicles with varying amphiphile ratios were characterized using parameters such as the critical vesicle concentration, pH sensitivity, and encapsulation efficiency. We also produced and observed giant vesicles from these mixtures using the electroformation method and confocal microscopy. The mixed catanionic vesicles were shown to be more stable than those formed by pure fatty acids. Those containing bola-amphiphile even showed the encapsulation of a small hydrophilic solute (8-hydroxypyrene-1,3,6-trisulfonic-acid), suggesting a denser packing of the amphiphiles. Compression and kinetics analysis of monolayers composed of these amphiphiles mixtures at the air/water interface suggests that the stabilization of the structures can be attributed to two main interactions between headgroups, predominantly the formation of hydrogen bonds between protonated and deprotonated acids and the additional electrostatic interactions between ammonium and acid headgroups.

    Copyright © 2011 American Chemical Society

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    Calibration data for the quantification of DTAB in solution by the bromothymol blue colorimetric assay. DLS measurements showing the impact of ultrafiltration on the bulk composition. Controls for the quantification of DTAB and the carboxylic acid amphiphiles. Micrographs of DA/DTAB-supported membranes and other bilayer morphologies and C16:0-dioic acid/DTAB vesicles that encapsulate HPTS after 1:10 dilution. Graphs of the compression isotherms of the different formulations at different pH values. Biexponential decay values obtained after fitting the interfacial film relaxation kinetics graphs to y = y0 + A1e(−x/t1) + A2e(−x/t2). Filtrate concentration data for various concentrations of amphiphile mixtures. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Langmuir

    Cite this: Langmuir 2011, 27, 23, 14078–14090
    Click to copy citationCitation copied!
    https://doi.org/10.1021/la203057b
    Published September 20, 2011
    Copyright © 2011 American Chemical Society
    Request reuse permissions

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