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Self-assembled vesicles of monocarboxylic acids and alcohols: conditions for stability and for the encapsulation of biopolymers
Open accessAbstract
We tested the ability of saturated n-monocarboxylic acids ranging from eight to 12 carbons in length to self-assemble into vesicles, and determined the minimal concentrations and chain lengths necessary to form stable bilayer membranes. Under defined conditions of pH and concentrations exceeding 150 mM, an unbranched monocarboxylic acid as short as eight carbons in length (n-octanoic acid) assembled into vesicular structures. Nonanoic acid (85 mM) formed stable vesicles at pH 7.0, the pK of the acid in bilayers, and was chosen for further testing. At pH 6 and below, the vesicles were unstable and the acid was present as droplets. At pH ranges of 8 and above clear solutions of micelles formed. However, addition of small amounts of an alcohol (nonanol) markedly stabilized the bilayers, and vesicles were present at significantly lower concentrations (approximately 20 mM) at pH ranges up to 11. The formation of vesicles near the pK(a) of the acids can be explained by the formation of stable RCOO(-)...HOOCR hydrogen bond networks in the presence of both ionized and neutral acid functions. Similarly, the effects of alcohols at high pH suggests the formation of stable RCOO(-)...HOR hydrogen bond networks when neutral RCOOH groups are absent. The vesicles provided a selective permeability barrier, as indicated by osmotic activity and ionic dye capture, and could encapsulate macromolecules such as DNA and a protein. When catalase was encapsulated in vesicles of decanoic acid and decanol, the enzyme was protected from degradation by protease, and could act as a catalyst for its substrate, hydrogen peroxide, which readily diffused across the membrane. We conclude that membranous vesicles produced by mixed short chain monocarboxylic acids and alcohols are useful models for testing the limits of stabilizing hydrophobic effects in membranes and for prebiotic membrane formation.
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“In later work, it was observed that addition of long chain alcohols or monoglycerides also had a significant stabilizing effect by reducing the lability of fatty acid membranes to salt and divalent cations [33,34].”
From The Role of Lipid Membranes in Life’s Origin (2017) · cites this paper as [33]
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“It is possible to reduce the effect of pH by adding fatty alcohols or monoglycerides [33] or even cationic alkyl amines [35] but it is uncertain whether any of these would be available in the prebiotic environment.”
From The Role of Lipid Membranes in Life’s Origin (2017) · cites this paper as [33]
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“lipid-encapsulated polymers can be synthesized by cycles of hydration and dehydration to form protocells”
From The Hot Spring Hypothesis for an Origin of Life (2020) · cites this paper as Apel et al., 2002
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“In water, the simplest amphiphiles spontaneously self-organize into bipolar membrane sheets that close into spherical structures known as vesicles (Apel et al., 2002).”
From The Astrobiology Primer v2.0 (2016) · cites this paper as Apel et al., 2002
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“A significant point is that mixed compositions can be more stable than membranes composed of pure lipids.”
From The Role of Lipid Membranes in Life’s Origin (2017) · cites this paper as [33]
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“For instance, membranes composed of pure fatty acids are only stable near the pK of the carboxylate group in which there is a mixture of charged and neutral (protonated) head groups. The stabilization results from hydrogen bonding between the head groups, effectively producing the equivalent of transient species having two chains [33].”
From The Role of Lipid Membranes in Life’s Origin (2017) · cites this paper as [33]
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Cites
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Self-citationAutocatalytic self-replicating micelles as models for prebiotic structures
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Ufasomes are stable particles surrounded by unsaturated fatty acid membranes
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Self-citationBoundary structures are formed by organic-components of the Murchison carbonaceous chondrite
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Self-citationSelf-assembling amphiphilic molecules: Synthesis in simulated interstellar/precometary ices
Dworkin, J. P., Deamer, D. W., Sandford, S. A., & Allamandola, L. J. (2001) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.98.3.815 · Cited by 244
Self-citationWalde, P., Goto, A., Monnard, P., Wessicken, M., & Luisi, P. L. (1994) · Journal of the American Chemical Society · doi:10.1021/ja00096a010 · Cited by 237
Diffusion of Small Non-Electrolytes across Liposome Membranes
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A novel method for encapsulation of macromolecules in liposomes
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Self-citationRole of lipids in prebiotic structures
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Short- and medium-chain fatty acids in energy metabolism: the cellular perspective
Schönfeld, P., & Wojtczak, L. (2016) · Journal of Lipid Research · doi:10.1194/jlr.r067629 · Cited by 1,133
Prebiotic Systems Chemistry: New Perspectives for the Origins of Life
Ruiz-Mirazo, K., Briones, C., & de la Escosura, A. (2014) · Chemical Reviews · doi:10.1021/cr2004844 · Cited by 930
Experimental Models of Primitive Cellular Compartments: Encapsulation, Growth, and Division
Hanczyc, M. M., Fujikawa, S. M., & Szostak, J. W. (2003) · Science · doi:10.1126/science.1089904 · Cited by 848
Template-directed synthesis of a genetic polymer in a model protocell
Mansy, S. S., Schrum, J. P., Krishnamurthy, M., Tobé, S., Treco, D. A., & Szostak, J. W. (2008) · Nature · doi:10.1038/nature07018 · Cited by 684
Meot‐Ner, M. (2005) · Chemical Reviews · doi:10.1021/cr9411785 · Cited by 620
Metadata
- Authors
- Apel, C. L., Deamer, D. W., & Mautner, M. N.
- Affiliations
- University of California, Santa Cruz (US)
- Lincoln University (NZ)
- Corresponding author
- Apel, Charles L.
- ORCID
- Deamer, David W.
- Venue
- Biochimica et Biophysica Acta (BBA) - Biomembranes
- Publisher
- Elsevier BV
- Published
- 2002-02
- Volume
- 1559
- Issue
- 1
- Pages
- 1-9
- ISSN
- 0005-2736 (ISSN-L)
- OpenAlex
- W2076968073
- Cited by
- 350
- References
- 15
- Citations by year
- 2026: 14 · 2025: 17 · 2024: 16 · 2023: 22 · 2022: 21 · 2021: 14 · 2020: 9 · 2019: 13 · 2018: 21 · 2017: 20 · 2016: 15 · 2015: 11 · 2014: 23 · 2013: 7 · 2012: 13
- FWCI
- 3.94
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Licence
- Locations
- Biochimica et Biophysica Acta (BBA) - Biomembranes (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Aeronautics and Space Administration (NAG54665)
- Marsden Fund
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Lipid Membrane Structure and Behavior
- Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Surfactants and Colloidal Systems
- Physical Sciences › Chemistry › Organic Chemistry › Advanced Polymer Synthesis and Characterization
- Keywords
- self-assembled vesicles, monocarboxylic acids, alcohol chemistry, octanoic acid, nonanoic acid, capric acid, nonanol, decanol, bilayer stability, pH dependence, hydrogen bonding, selective permeability, DNA encapsulation, protein encapsulation, catalase
- MeSH terms
- Alcohols, Biopolymers, Caprylates, Carboxylic Acids, Catalase, DNA, Fatty Acids, Hydrogen Bonding, Hydrogen-Ion Concentration, Lipid Bilayers, Micelles, Microscopy, Phase-Contrast, Permeability, Spectrophotometry
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