Fatty acid vesicles

Morigaki, Kenichi; Walde, Peter

doi:10.1016/j.cocis.2007.05.005

Cited by 279 publications

(301 citation statements)

References 56 publications

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“…The ionized form corresponds to the negatively charged surfactant. The formation and stability of the vesicles depends on the protonation/ionization ratio of the terminal carboxylic acid which governs the formation of hydrogen bonds [16]. This approach was then extended to disperse…”

Section: 2) Self-assemblies Based On Fatty Acids In Aqueous Solutionmentioning

confidence: 99%

“…various saturated fatty acids under the form of vesicles [16]. Another method consists in mixing fatty acids with cationic surfactants to obtain catanionic systems [17].…”

Section: 2) Self-assemblies Based On Fatty Acids In Aqueous Solutionmentioning

confidence: 99%

“…The pH range for vesicles formation varies as a function of the fatty acid molecules pKa, which is linked to their chemical nature [16]. A modification of the pH medium by adding NaOH or HCl can lead to other kinds of fatty acid self-assemblies than only vesicles or spherical micelles.…”

Section: 1) Ph Effectmentioning

confidence: 99%

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Responsive self-assemblies based on fatty acids

Fameau

Arnould

Saint‐Jalmes

2014

Current Opinion in Colloid & Interface Science

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Section: 2) Self-assemblies Based On Fatty Acids In Aqueous Solutionmentioning

confidence: 99%

“…various saturated fatty acids under the form of vesicles [16]. Another method consists in mixing fatty acids with cationic surfactants to obtain catanionic systems [17].…”

Section: 2) Self-assemblies Based On Fatty Acids In Aqueous Solutionmentioning

confidence: 99%

See 1 more Smart Citation

Responsive self-assemblies based on fatty acids

Fameau

Arnould

Saint‐Jalmes

2014

Current Opinion in Colloid & Interface Science

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“…However, in a narrow pH range between 7 and 9, they are able to form vesicular objects under accurate control of the starting conditions and the COO − /COOH ratio. 5 Phospholi-pids, the major constituent of the cell membrane, generally form planar bilayers. However, upon change of the water osmotic pressure or upon introduction of a cosurfactant (bile salts are often described in the literature), the bilayer membrane curvature can be modified.…”

Section: ■ Introductionmentioning

confidence: 99%

Self-Assembly Mechanism of pH-Responsive Glycolipids: Micelles, Fibers, Vesicles, and Bilayers

et al. 2016

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A set of four structurally related glycolipids are described: two of them have one glucose unit connected to either stearic or oleic acid, and two other ones have a diglucose headgroup (sophorose) similarly connected to either stearic or oleic acid. The self-assembly properties of these compounds, poorly known, are important to know due to their use in various fields of application from cleaning to cosmetics to medical. At basic pH, they all form mainly small micellar aggregates. At acidic pH, the oleic and stearic derivatives of the monoglucose form, respectively, vesicles and bilayer, while the same derivatives of the sophorose headgroup form micelles and twisted ribbons. We use pH-resolved in situ small angle X-ray scattering (SAXS) under synchrotron radiation to characterize the pH-dependent mechanism of evolution from micelles to the more complex aggregates at acidic pH. By pointing out the importance of the COO − /COOH ratio, the melting temperature, T m , of the lipid moieties, hydration of the glycosidic headgroup, the packing parameter, membrane rigidity, and edge stabilization, we are now able to draw a precise picture of the full self-assembly mechanism. This work is a didactical illustration of the complexity of the self-assembly process of a stimuli-responsive amphiphile during which many concomitant parameters play a key role at different stages of the process.

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“…15 Therefore, in alkaline aqueous solutions (pH 7-10), fatty-acid assemblies are composed of two types of amphiphiles: a neutral carboxylic acid form and a carboxylate anion form. [16][17][18][19] The higher pK a app values of assembled fatty acids are due to the interaction between carboxylates 14,15,17 and the characteristic dielectric properties and proton activities around the self-assembly surface. 17 These properties change temporally during the nonequilibrium self-assembly process; thus, the acid dissociation of fatty acids fluctuates greatly.…”

Section: Introductionmentioning

confidence: 99%

Structure and growth behavior of centimeter-sized helical oleate assemblies formed with assistance of medium-length carboxylic acids

et al. 2015

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The nonequilibrium organization of self-assemblies from small building-block molecules offers an attractive and essential means to develop advanced functional materials and to understand the intrinsic nature of life systems. Fatty acids are well-known amphiphiles that form self-assemblies of several shapes. Here, we found that the lengths of helical structures of oleic acid formed in a buffered aqueous solution are dramatically different by the presence or absence of certain amphiphilic carboxylic acids. For example, under the coexistence of a small amount of N-decanoyl-L-alanine, we observed the formation of over 1-centimeter-long helical assemblies of oleate with a regular pitch and radius, whereas mainly less than 100 µm-long helices formed without this additive.Such long helical assemblies are unique in terms of their highly dimensional helical structure and growth dynamics. Results from the real-time observation of self-assembly formation, site-selective small-angle X-ray scattering, high-performance liquid chromatography analysis, and pH titration experiments suggested that the coexisting carboxylates assist in elongation by supplying oleate molecules to a scaffold for oleate helical assembly.

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Fatty acid vesicles

Cited by 279 publications

References 56 publications

Responsive self-assemblies based on fatty acids

Responsive self-assemblies based on fatty acids

Self-Assembly Mechanism of pH-Responsive Glycolipids: Micelles, Fibers, Vesicles, and Bilayers

Structure and growth behavior of centimeter-sized helical oleate assemblies formed with assistance of medium-length carboxylic acids

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