Chameleonic amphiphile: The unique multiple self-assembly properties of a natural glycolipid in excess of water

Baccile, Niki; Poirier, Alexandre; Seyrig, Chloé; Griel, Patrick Le; Pérez, Javier; Hermida‐Merino, Daniel; Pernot, Pétra; Roelants, Sophie; Soetaert, Wim

doi:10.1016/j.jcis.2022.07.130

Cited by 26 publications

(55 citation statements)

References 87 publications

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“…Alkali metal cations are found in the form of free ions in water at pH between 5 and 8, at which most of the studies reported in Table S1 are presumably performed. In this case, the assumption of metal–ligand interactions between amphiphiles and cations is reasonable, and they are actually proved here by means of 13 C solid-state nuclear magnetic resonance experiments, shown elsewhere. , This may not be the case for most studies performed on transition metal cations, which display complex speciation diagrams between pH 4 and 10. Multiple hydroxo species, each having a different charge, generally coexist at the same time. , Each species cannot only undergo coulombic interactions with amphiphiles but also specific metal–hydroxo–ligand complexes could potentially form, making the complete understanding more complex than expected.…”

Section: Discussionmentioning

confidence: 56%

“…May they be wormlike micelles or fibers, each of these phases enriches the phase diagram of G-C18:1, making this molecule unique, not only compared to any other known biosurfactant but also to many other amphiphiles, including LMW gelators, peptide-based compounds, or surfactants (Table S1). This aspect was specifically discussed in ref .…”

Section: Discussionmentioning

confidence: 99%

“…The ability of G-C18:1 to form metallogels occurs with a number of both alkaline earth and transition metal ions (Table ), also in agreement with many other amphiphiles (Table S1). Metal-induced gelation adds further complexity to the phase diagram of G-C18:1 . Top of Figure gives an illustration of the metal-free, pH-dependent self-assembly of G-C18:1 in water.…”

Section: Discussionmentioning

confidence: 99%

“…Schematic representation of the self-assembly of G-C18:1 microbial glycolipid at room temperature in water as a function of pH and in the presence of ions at pH ≥ 8. For a broader insight of the phase behavior of G-C18:1 under diluted conditions in water, refer to ref .…”

Section: Discussionmentioning

confidence: 99%

“…This work does not only show the metallogel properties of a glycolipid biosurfactant, thus broadening the perspectives of applications for this class of bio-based molecules. It also shows the richness and complexity of their unique phase behavior, which can span, within a contained pH range and type of cation, from micelles to single- and multilamellar wall vesicles but also fibers, setting this unique molecule at the crossroad of lipids, surfactants, and LMW gelators …”

Section: Introductionmentioning

confidence: 99%

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Metallogels from a Glycolipid Biosurfactant

Poirier

Griel

Pérez

et al. 2022

ACS Sustainable Chem. Eng.

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Low-molecular-weight (LMW) molecules of biological origin like microbial glycolipid biosurfactants can selfassemble in water, with a tunable structure by a soft chemistry approach (pH, temperature, and ionic strength). The unique molecular structure of microbial glycolipids gives possible access to a wide variety of aqueous self-assembled structures, although highly unpredictable beforehand. The glycolipid presented here consists in a glucose group linked to a C18:1-cis fatty acid (G-C18:1) and produced by the fermentation of Starmerella bombicola ΔugtB1. Due to the carboxylic group of the fatty acid, the supramolecular self-assembly is pH dependent. In the pH range 5−7, G-C18:1 forms vesicles, while above pH 7, it forms a micellar phase. Adding a wide range of metal salts

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Section: Discussionmentioning

confidence: 56%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Metallogels from a Glycolipid Biosurfactant

Poirier

Griel

Pérez

et al. 2022

ACS Sustainable Chem. Eng.

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Heavy metal removal from water using the metallogelation properties of a new glycolipid biosurfactant

Poirier

Ozkaya

Gredziak

et al. 2022

J Surfact & Detergents

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Water pollution by heavy metals is a problem of both western and developing countries.Heavy metal pollution can be associated to human activity, such as wastewaters from processing of ore mining, but also to simple contamination from metal rich soils. Whichever the case, chemical and physical methods are generally employed to depollute water. Since most chemicals are themselves polluting agents, there is an increasing interest in finding biobased and biodegradable alternative chemicals, both efficient in removing metals and benign to the environment. Biosurfactants are green chemicals produced by fermentation of yeasts and bacteria and with a good environmental score. Among many applications, this class of compounds has been used to remove heavy metals from contaminated soils. Within this framework, we propose a new mechanism of depolluting water using a glucolipid biosurfactant, G-C18:1, composed of glucose (G) and a C18:1 fatty acid (oleic acid). This compound is able to form a metallogel by complexing cations in water, thus trapping heavy metals (Cu 2+ , Ni 2+ , Cr 2+ and Co 2+ ) in the gel phase. This mechanism allows to remove up to 95% for cobalt and 88 ± 10%, 80 ± 3% and 59 ± 6% for Cu 2+ , Ni 2+ and Cr 2+ , respectively. A dedicated structural study shows that this is possible because positively charged species induce gelation of G-C18:1 through a micelle-to-wormlike phase transition, most likely driven by a charge neutralization process. This work shows that wise control of the nanoscale properties of green chemicals can strongly benefit to develop a sustainable future.

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Myelin figures from microbial glycolipid biosurfactant amphiphiles

Roy,

Chaleix,

Parikh

et al. 2024

J Surfact & Detergents

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Myelin figures (MFs)—cylindrical lyotropic liquid crystalline structures consisting of concentric arrays of bilayers and aqueous media—arise from the hydration of the bulk lamellar phase of many common amphiphiles. Prior efforts have concentrated on the formation, structure, and dynamics of myelin produced by phosphatidylcholine (PC)‐based amphiphiles. Here, we study the myelinization of glycolipid microbial amphiphiles, commonly addressed as biosurfactants, produced through the process of fermentation. The hydration characteristics (and phase diagrams) of these biological amphiphiles are atypical (and thus their capacity to form myelin) because unlike typical amphiphiles, their molecular structure is characterized by two hydrophilic groups (sugar, carboxylic acid) on both ends with a hydrophobic moiety in the middle. We tested three different glycolipid molecules: C18:1 sophorolipids and single‐glucose C18:1 and C18:0 glucolipids, all in their nonacetylated acidic form. Neither sophorolipids (too soluble) nor C18:0 glucolipids (too insoluble) displayed myelin growth at room temperature (RT, 25°C). The glucolipid C18:1 (G‐C18:1), on the other hand, showed dense myelin growth at RT below pH 7.0. Examining their growth rates, we find that they display a linear (L, myelin length; t, time) growth rate, suggesting ballistic growth, distinctly different from the dependence, characterizing diffusive growth such as what occurs in more conventional phospholipids. These results offer some insight into lipidic mesophases arising from a previously unexplored class of amphiphiles with potential applications in the field of drug delivery.

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Chameleonic amphiphile: The unique multiple self-assembly properties of a natural glycolipid in excess of water

Cited by 26 publications

References 87 publications

Metallogels from a Glycolipid Biosurfactant

Metallogels from a Glycolipid Biosurfactant

Heavy metal removal from water using the metallogelation properties of a new glycolipid biosurfactant

Myelin figures from microbial glycolipid biosurfactant amphiphiles

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