Vesicles composed of one simple single-tailed surfactant

Du, Na; Song, Ruiying; Zhu, Xiaoyu; Hou, Wanguo; Li, Haiping; Zhang, Renjie

doi:10.1039/c4cc02047b

Cited by 22 publications

(43 citation statements)

References 33 publications

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“…At pH 4, and also at pH 7 with Triton X-100 added, the diffusion time of the slow component was reduced substantially, indicating disruption of the MSDH vesicles ( Figure 5B and Table 1). 31 , but also gemini surfactants 32,33,34 , catanionic 35,36 or other binary amphiphile systems 37, 38 39 , and indeed also some single-tailed amphiphiles 40,41,42,43,44,45 volume, into which molecules can be entrapped.…”

Section: Msdh Vesicles Can Be Efficiently Loaded At Neutral Ph and Rmentioning

confidence: 99%

Spontaneous Vesiculation and pH-Induced Disassembly of a Lysosomotropic Detergent: Impacts on Lysosomotropism and Lysosomal Delivery

et al. 2016

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Lysosomotropic detergents (LDs) selectively rupture lysosomal membranes through mechanisms that have yet to be characterized. A consensus view, currently, holds that LDs, which are weakly basic, diffuse across cellular membranes as monomers in an uncharged state, and via protonation in the acidic lysosomal compartment, they become trapped, accumulate, and subsequently solubilize the membrane and induce lysosomal membrane permeabilization. Here we demonstrate that the lysosomotropic detergent O-methyl-serine dodecylamide hydrochloride (MSDH) spontaneously assembles into vesicles at, and above, cytosolic pH, and that the vesicles disassemble as the pH reaches 6.4 or lower. The aggregation commences at concentrations below the range of those used in cell studies. Assembly and disassembly of the vesicles was studied via dynamic light scattering, zeta potential measurements, cryo-TEM, and fluorescence correlation spectroscopy and was found to be reversible via control of the pH. Aggregation of MSDH into closed vesicles under cytosolic conditions is at variance with the commonly held view of LD behavior, and we propose that endocytotic pathways should be considered as possible routes of LD entry into lysosomes. We further demonstrate that MSDH vesicles can be loaded with fluorophores via a solution transition from low to high pH, for subsequent release when the pH is lowered again. The ability to encapsulate molecular cargo into MSDH vesicles together with its ability to disaggregate at low pH and to permeabilize the lysosomal membrane presents an intriguing possibility to use MSDH as a delivery system.

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Section: Msdh Vesicles Can Be Efficiently Loaded At Neutral Ph and Rmentioning

confidence: 99%

Spontaneous Vesiculation and pH-Induced Disassembly of a Lysosomotropic Detergent: Impacts on Lysosomotropism and Lysosomal Delivery

et al. 2016

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“…21 Hence, interfaces provide platforms for unexpected properties of surface-active entities, being unparalleled in bulk. 22,23,49 We have reported on the prevention of self-assembly of so-called miktoarm stars by architecture-induced complexation in bulk water. 24 Within one molecule, 25 different poly(propylene oxide) (PPO) and poly(dimethylaminoethyl methacrylate) (PDMAEMA) arms interacted due to the increased mutual segment density close to the center of these star-shaped polymers.…”

Section: Introductionmentioning

confidence: 99%

Interface-enforced complexation between copolymer blocks

Steinschulte

Draber

et al. 2015

Soft Matter

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Binary diblock copolymers and corresponding ternary miktoarm stars are studied at oil-water interfaces. All polymers contain oil-soluble poly(propylene oxide) PPO, water-soluble poly(dimethylaminoethyl methacrylate) PDMAEMA and/or poly(ethylene oxide) PEO. The features of their Langmuir compression isotherms are well related to the ones of the corresponding homopolymers. Within the Langmuir-trough, PEO-b-PPO acts as the most effective amphiphile compared to the other PPO-containing copolymers. In contrast, the compression isotherms show a complexation of PPO and PDMAEMA for PPO-b-PDMAEMA and the star, reducing their overall amphiphilicity. Such complex formation between the blocks of PPO-b-PDMAEMA is prevented in bulk water but facilitated at the interface. The weakly-interacting blocks of PPO-b-PDMAEMA form a complex due to their enhanced proximity in such confined environments. Scanning force microscopy and Monte Carlo simulations with varying confinement support our results, which are regarded as compliant with the mathematical random walk theorem by Pólya. Finally, the results are expected to be of relevance for e.g. emulsion formulation and macromolecular engineering.

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“…This corroborated the data obtained with turbidity measurements (Figure ). However, the introduction of even a small percentage of dodecyl groups (∼2%) was responsible for overcoming the electrostatic repulsion of charged amino groups and led to the formation of aggregates, whose probed polarities ( I 1 / I 3 ≈ 1.1–1.2) were lower than those obtained with the cationic surfactant dodecyltrimethylammonium bromide (DTAB) . As the pH increased from 5.0 to 7.4, the CAC values decreased approximately 30%; this was attributed to the deprotonation of the amino groups.…”

Section: Resultsmentioning

confidence: 95%

Synthesis and self‐assembly study of zwitterionic amphiphilic derivatives of chitosan

Barbosa

Lima

Taboga

et al. 2016

J of Applied Polymer Sci

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New zwitterionic derivatives of chitosan (CH) were synthesized through the Michael addition reaction of 1‐(3‐sulfopropyl)‐2‐vinylpyridine hydroxide (SPP) with primary amines of deacetylated CHs (with weight‐average molecular weights of 46 and 216 kDa) to obtain SPP‐substituted CHs. The hydrophilic derivatives were subsequently modified with 2.1, 4.6, and 9.7% of dodecyl groups [degree of substitution by dodecyl groups (DSDod)]. The SPP‐substituted CH derivatives were characterized by 1H‐NMR, Fourier transform infrared spectroscopy, and gel permeation chromatography. Aqueous solutions of SPP‐substituted CH samples remained clear, independently of the pH (3.0 < pH < 12.0). The self‐association study of the amphiphilic derivatives was performed in aqueous buffered solution at pH 5.0 and 7.4, and the critical aggregation concentration values varied from 5.6 × 10−3 to 0.02 g/L. The measurements of dynamic light scattering and ζ potentials showed that the self‐assembly behavior was dependent on the pH and DSDod. At pH 7.4, the measured ζ potentials were near zero, and colloidal stability was provided by the hydrated zwitterionic shell of the aggregates. Transmission electron microscopy revealed spherelike microsized particles of broad distribution. The amphiphilic SPP‐substituted CH samples were shown to be nontoxic with a 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide assay performed with HeLa cells. The remarkable water solubility and nontoxicity displayed by the new SPP‐substituted CH derivatives showed promising properties for the design of CH‐based biomaterials and nanoparticles. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2016, 133, 44176.

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Vesicles composed of one simple single-tailed surfactant

Cited by 22 publications

References 33 publications

Spontaneous Vesiculation and pH-Induced Disassembly of a Lysosomotropic Detergent: Impacts on Lysosomotropism and Lysosomal Delivery

Spontaneous Vesiculation and pH-Induced Disassembly of a Lysosomotropic Detergent: Impacts on Lysosomotropism and Lysosomal Delivery

Interface-enforced complexation between copolymer blocks

Synthesis and self‐assembly study of zwitterionic amphiphilic derivatives of chitosan

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