Self-assembled vesicles of monocarboxylic acids and alcohols: Conditions for stability and for the encapsulation of biopolymers
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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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Addition of long chain alcohols or monoglycerides has a significant stabilizing effect on fatty acid membranes by reducing their lability to salt and divalent cations.
“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]
Section 3.4 reports that adding nonanol markedly stabilizes fatty-acid vesicles, extending the pH range for vesicle formation and lowering the fatty-acid concentration required. It does not establish that alcohol reduces membrane lability to salt or divalent cations, and the passages found do not report a stabilizing effect of monoglycerides. Section 3.5 tests KCl permeability, not resistance to salt-induced instability; page numbers were not available in our copy. (LLM, conf=0.87)
Experimental — accuracy not yet measuredIt is possible to reduce the effect of pH by adding fatty alcohols or monoglycerides or even cationic alkyl amines, but it is uncertain whether any of these would be available in the prebiotic environment.
“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]
Section 3.4 reports that adding a fatty alcohol increased the pH range over which fatty-acid vesicles remained stable. The cited paper does not report the corresponding effect for monoglycerides. The alkyl-amine claim has a different citation, and the sentence’s uncertainty about prebiotic availability is not attributed specifically to this paper. (LLM, conf=0.86)
Experimental — accuracy not yet measuredLipid-encapsulated polymers can be synthesized by cycles of hydration and dehydration to form protocells.
“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
Section 2.3 describes dehydrating and rehydrating vesicles mixed with pre-existing macromolecules, and Section 3.6 reports DNA encapsulation. Section 4.2 connects such vesicles to prebiotic membranes, but the paper does not show polymers being synthesized by hydration–dehydration cycles or demonstrate the formation of protocells. (LLM, conf=0.87)
Experimental — accuracy not yet measuredIn water, the simplest amphiphiles spontaneously self-organize into bipolar membrane sheets that close into spherical structures known as vesicles.
“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
The Discussion reports that simple monocarboxylic acids self-assemble into bilayer vesicles in water, but only at defined pH and sufficiently high concentrations. Section 3.3 says the vesicles may appear spherical or tubular; our copy does not describe membrane sheets closing into spheres. Page numbers are unavailable in the indexed passages. (LLM, conf=0.88)
Experimental — accuracy not yet measuredMixed amphiphile compositions can be more stable than membranes composed of pure lipids.
“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]
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; stabilization results from hydrogen bonding between the head groups.
“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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- 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 › Organic 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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