ACS Publications. Most Trusted. Most Cited. Most Read

OR SEARCH CITATIONS

My Activity
Publications
CONTENT TYPES

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:Langmuir 2011, 27, 23, 14078-14090
RETURN TO ISSUEPREVArticleNEXT

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

View Author Information
† †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]
Cite this: Langmuir 2011, 27, 23, 14078–14090
Publication Date (Web):September 20, 2011
https://doi.org/10.1021/la203057b
Copyright © 2011 American Chemical Society
Request reuse permissions

    Article Views

    1257

    Altmetric

    -

    Citations

    38
    LEARN ABOUT THESE METRICS
    Other access options
    Get e-Alerts
    Supporting Info (1)»
    SUBJECTS:

    Abstract

    Abstract Image

    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.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Supporting Information

    ARTICLE SECTIONS
    Jump To

    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.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    This article is cited by 38 publications.

    1. Alexia Martin, Carmelo Tempra, Yuefan Yu, Juho Liekkinen, Roma Thakker, Hayoung Lee, Berta de Santos Moreno, Ilpo Vattulainen, Christos Rossios, Matti Javanainen, Jorge Bernardino de la Serna. Exposure to Aldehyde Cherry e-Liquid Flavoring and Its Vaping Byproduct Disrupt Pulmonary Surfactant Biophysical Function. Environmental Science & Technology 2024, 58 (3) , 1495-1508. https://doi.org/10.1021/acs.est.3c07874
    2. Zachary R. Cohen, Zoe R. Todd, Nicholas Wogan, Roy A. Black, Sarah L. Keller, David C. Catling. Plausible Sources of Membrane-Forming Fatty Acids on the Early Earth: A Review of the Literature and an Estimation of Amounts. ACS Earth and Space Chemistry 2023, 7 (1) , 11-27. https://doi.org/10.1021/acsearthspacechem.2c00168
    3. Ehsan FrozandehMehr, Aliakbar Tarlani, Saeed Farhadi. Cetyltrimethylammonium Bromide (CTAB) Bloated Micelles and Merged CTAB/Bolaamphiphiles Self-Assembled Vesicles toward the Generation of Highly Porous Alumina as Efficacious Inorganic Adsorbents. Langmuir 2019, 35 (34) , 11188-11199. https://doi.org/10.1021/acs.langmuir.9b01934
    4. Niloy Kundu, Debasis Banik, Nilmoni Sarkar. Self-Assembly of Amphiphiles into Vesicles and Fibrils: Investigation of Structure and Dynamics Using Spectroscopy and Microscopy Techniques. Langmuir 2018, 34 (39) , 11637-11654. https://doi.org/10.1021/acs.langmuir.7b04355
    5. Michael C. Wamberg, Pernille L. Pedersen, Philipp M. G. Löffler, Anders N. Albertsen, Sarah E. Maurer, Kent A. Nielsen, and Pierre-Alain Monnard . Synthesis of Lipophilic Guanine N-9 Derivatives: Membrane Anchoring of Nucleobases Tailored to Fatty Acid Vesicles. Bioconjugate Chemistry 2017, 28 (7) , 1893-1905. https://doi.org/10.1021/acs.bioconjchem.7b00228
    6. Valerio Pereno, Dario Carugo, Luca Bau, Erdinc Sezgin, Jorge Bernardino de la Serna, Christian Eggeling, and Eleanor Stride . Electroformation of Giant Unilamellar Vesicles on Stainless Steel Electrodes. ACS Omega 2017, 2 (3) , 994-1002. https://doi.org/10.1021/acsomega.6b00395
    7. Niloy Kundu, Pavel Banerjee, Sangita Kundu, Rupam Dutta, and Nilmoni Sarkar . Sodium Chloride Triggered the Fusion of Vesicle Composed of Fatty Acid Modified Protic Ionic Liquid: A New Insight into the Membrane Fusion Monitored through Fluorescence Lifetime Imaging Microscopy. The Journal of Physical Chemistry B 2017, 121 (1) , 24-34. https://doi.org/10.1021/acs.jpcb.6b09298
    8. Wenlong Xu, Heng Zhang, Yingping Zhong, Liwen Jiang, Mengxin Xu, Xionglu Zhu, and Jingcheng Hao . Bilayers at High pH in the Fatty Acid Soap Systems and the Applications for the Formation of Foams and Emulsions. The Journal of Physical Chemistry B 2015, 119 (33) , 10760-10767. https://doi.org/10.1021/acs.jpcb.5b04553
    9. Wenlong Xu, Hongyao Gu, Xionglu Zhu, Yingping Zhong, Liwen Jiang, Mengxin Xu, Aixin Song, and Jingcheng Hao . CO2-Controllable Foaming and Emulsification Properties of the Stearic Acid Soap Systems. Langmuir 2015, 31 (21) , 5758-5766. https://doi.org/10.1021/acs.langmuir.5b01295
    10. Keishi Suga, Tomoya Yokoi, Dai Kondo, Keita Hayashi, Seiichi Morita, Yukihiro Okamoto, Toshinori Shimanouchi, and Hiroshi Umakoshi . Systematical Characterization of Phase Behaviors and Membrane Properties of Fatty Acid/Didecyldimethylammonium Bromide Vesicles. Langmuir 2014, 30 (43) , 12721-12728. https://doi.org/10.1021/la503331r
    11. Wenlong Xu, Heng Zhang, Shuli Dong, and Jingcheng Hao . 133Cs NMR and Molecular Dynamics Simulation on Bilayers of Cs+ Ion Binding to Aggregates of Fatty Acid Soap at High pH. Langmuir 2014, 30 (39) , 11567-11573. https://doi.org/10.1021/la503193h
    12. Michael C. Wamberg, Rafał Wieczorek, Søren Bo Brier, Jan Willem de Vries, Minseok Kwak, Andreas Herrmann, and Pierre-Alain Monnard . Functionalization of Fatty Acid Vesicles through Newly Synthesized Bolaamphiphile–DNA Conjugates. Bioconjugate Chemistry 2014, 25 (9) , 1678-1688. https://doi.org/10.1021/bc500289u
    13. Animesh Pan, Pallabi Sil, Sounak Dutta, Prasanta Kumar Das, Subhash Chandra Bhattacharya, Animesh Kumar Rakshit, Vinod Kumar Aswal, and Satya Priya Moulik . Micellization of Cetyltrimethylammonium Bromide: Effect of Small Chain Bola Electrolytes. The Journal of Physical Chemistry B 2014, 118 (11) , 3041-3052. https://doi.org/10.1021/jp4108427
    14. Wenlong Xu, Aixin Song, Shuli Dong, Jingfei Chen, and Jingcheng Hao . A Systematic Investigation and Insight into the Formation Mechanism of Bilayers of Fatty Acid/Soap Mixtures in Aqueous Solutions. Langmuir 2013, 29 (40) , 12380-12388. https://doi.org/10.1021/la403008d
    15. Wenlong Xu, Xiaolin Wang, Zhenhuan Zhong, Aixin Song, and Jingcheng Hao . Influence of Counterions on Lauric Acid Vesicles and Theoretical Consideration of Vesicle Stability. The Journal of Physical Chemistry B 2013, 117 (1) , 242-251. https://doi.org/10.1021/jp306630n
    16. Yuxi Gong, Wei Yang, Chao Wu, Xinyu Fan, Xiangyu Zhang, Jinlian Li, Dongmei Wu. Design of Tween80/oleic acid composite vesicle and its application in controlled release of vitamin C. Colloid and Polymer Science 2024, 302 (4) , 561-571. https://doi.org/10.1007/s00396-023-05212-z
    17. Isabella Lago, Lissa Black, Maximillian Wilfinger, Sarah E. Maurer. Synthesis and Characterization of Amino Acid Decyl Esters as Early Membranes for the Origins of Life. Membranes 2022, 12 (9) , 858. https://doi.org/10.3390/membranes12090858
    18. Lei Li, Yun Fang, Yongmei Xia, Chunling Bo, Ye Fan. Monosaccharides driving the formation of conjugated linoleic acid vesicles in near-neutral solutions via weak noncovalent bonding interactions. Journal of Molecular Liquids 2022, 351 , 118656. https://doi.org/10.1016/j.molliq.2022.118656
    19. Niloy Kundu, Dipankar Mondal, Nilmoni Sarkar. Dynamics of the vesicles composed of fatty acids and other amphiphile mixtures: unveiling the role of fatty acids as a model protocell membrane. Biophysical Reviews 2020, 12 (5) , 1117-1131. https://doi.org/10.1007/s12551-020-00753-x
    20. , Anna Wang, Jack W. Szostak. Lipid constituents of model protocell membranes. Emerging Topics in Life Sciences 2019, 3 (5) , 537-542. https://doi.org/10.1042/ETLS20190021
    21. Li-Chun Chen, Ke-Xian Chen, Xi-ying Huang, Jian Lou, Jing-Yuan Li, Shao-Ping Deng. Vesicles from the self-assembly of the ultra-small fatty acids with amino acids under aqueous conditions. Colloids and Surfaces B: Biointerfaces 2019, 173 , 69-76. https://doi.org/10.1016/j.colsurfb.2018.07.007
    22. Martin M. Hanczyc, Pierre‐Alain Monnard. Self‐Assembly and Primitive Membrane Formation: Between Stability and Dynamism. 2018, 101-136. https://doi.org/10.1002/9781119001379.ch4
    23. Sarah Maurer. The Impact of Salts on Single Chain Amphiphile Membranes and Implications for the Location of the Origin of Life. Life 2017, 7 (4) , 44. https://doi.org/10.3390/life7040044
    24. Vivek V. Dhawan, Mangal S. Nagarsenker. Catanionic systems in nanotherapeutics – Biophysical aspects and novel trends in drug delivery applications. Journal of Controlled Release 2017, 266 , 331-345. https://doi.org/10.1016/j.jconrel.2017.09.040
    25. Martin M Hanczyc, Pierre-Alain Monnard. Primordial membranes: more than simple container boundaries. Current Opinion in Chemical Biology 2017, 40 , 78-86. https://doi.org/10.1016/j.cbpa.2017.07.009
    26. Yue Hong, Wenlong Xu, Yuanyuan Hu, Guihua Li, Mengjun Chen, Jingcheng Hao, Shuli Dong. Multi-responsive emulsion of stearic acid soap aqueous solution. Colloids and Surfaces A: Physicochemical and Engineering Aspects 2017, 522 , 652-657. https://doi.org/10.1016/j.colsurfa.2017.03.053
    27. Beibei Hu, Yue Yuan, Yun Yan, Xiaoping Zhou, Yue Li, Qiming Kan, Sanming Li. Preparation and evaluation of a novel anticancer drug delivery carrier for 5-Fluorouracil using synthetic bola-amphiphile based on lysine as polar heads. Materials Science and Engineering: C 2017, 75 , 637-645. https://doi.org/10.1016/j.msec.2017.02.106
    28. Steen Rasmussen, Adi Constantinescu, Carsten Svaneborg. Generating minimal living systems from non-living materials and increasing their evolutionary abilities. Philosophical Transactions of the Royal Society B: Biological Sciences 2016, 371 (1701) , 20150440. https://doi.org/10.1098/rstb.2015.0440
    29. Wenlong Xu, Huizhong Liu, Aixin Song, Jingcheng Hao. Bilayers and wormlike micelles at high pH in fatty acid soap systems. Journal of Colloid and Interface Science 2016, 465 , 304-310. https://doi.org/10.1016/j.jcis.2015.12.006
    30. Yi Li, Xincheng Wang, Jing Jing, Baorong Xie, Sihui Zhan. Optimal Conditions for Existence of Vesicles Under Electric Field. Journal of Dispersion Science and Technology 2015, 36 (11) , 1564-1568. https://doi.org/10.1080/01932691.2014.975817
    31. Diana Paiva, Thomas Markowski, Bodo Dobner, Gerald Brezesinski, Helmuth Möhwald, Maria do Carmo Pereira, Sandra Rocha. Synthesis and study of the complex formation of a cationic alkyl-chain bola amino alcohol with DNA: in vitro transfection efficiency. Colloid and Polymer Science 2015, 293 (11) , 3167-3175. https://doi.org/10.1007/s00396-015-3710-9
    32. Pierre-Alain Monnard, Peter Walde. Current Ideas about Prebiological Compartmentalization. Life 2015, 5 (2) , 1239-1263. https://doi.org/10.3390/life5021239
    33. Sandra G. Silva, M. Luísa C. do Vale, Eduardo F. Marques. Size, Charge, and Stability of Fully Serine‐Based Catanionic Vesicles: Towards Versatile Biocompatible Nanocarriers. Chemistry – A European Journal 2015, 21 (10) , 4092-4101. https://doi.org/10.1002/chem.201406111
    34. Jung Lee, Chien-Hsiang Chang. DNA association-enhanced physical stability of catanionic vesicles composed of ion pair amphiphile with double-chain cationic surfactant. Colloids and Surfaces B: Biointerfaces 2014, 121 , 171-177. https://doi.org/10.1016/j.colsurfb.2014.06.005
    35. A.N. Albertsen, C.D. Duffy, J.D. Sutherland, P.-A. Monnard. Self-Assembly of Phosphate Amphiphiles in Mixtures of Prebiotically Plausible Surfactants. Astrobiology 2014, 14 (6) , 462-472. https://doi.org/10.1089/ast.2013.1111
    36. F. Olasagasti, M.-C. Maurel, D.W. Deamer, , . Physico-chemical interactions between compartment-forming lipids and other prebiotically relevant biomolecules. BIO Web of Conferences 2014, 2 , 05001. https://doi.org/10.1051/bioconf/20140205001
    37. Yi Li, Jing Jing, Xuejun Zhang, Jie Cao, Yiwei Li, Sihui Zhan. Great application prospect in vivo: Efficient electroformation of giant vesicles on novel carbon fiber microelectrode. Electrochemistry Communications 2012, 25 , 151-154. https://doi.org/10.1016/j.elecom.2012.10.008
    38. Lin-Hao Sun, Song Wang, Wei-Lin Shi, Shuming Zhang, Xi Chen, Qiang Cai. A new type of anionic surfactant with four carboxylates for the preparation of mesoporous materials. Frontiers of Materials Science 2012, 6 (3) , 268-277. https://doi.org/10.1007/s11706-012-0173-5
    Download PDF

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    MENDELEY PAIRING EXPIRED
    Your Mendeley pairing has expired. Please reconnect