Supramolecular organic nanotubes: how to utilize the inner nanospace and the outer space

Kameta, Naohiro; Minamikawa, Hiroyuki; Masuda, Mitsutoshi

doi:10.1039/c0sm01559h

Cited by 135 publications

(123 citation statements)

References 150 publications

Supporting

Mentioning

120

Contrasting

Order By: Relevance

“…In particular, the use of sugars is of specific interest because of their biologically-relevant functionality 40,41 occurring in cell-cell agglutination mechanisms, but new nanotechbased applications are also being explored. 42,24 Among this class of compounds, sophorolipids, natural bolaform glycolipids, can be obtained from the fermentation process of the yeast Starmerella bombicola (Figure 1a) and are the best bioderived candidates to substitute their synthetic counterparts previously studied, 43,44 both in terms of properties and conditions of productions. 45,46 Even if predictions cannot be done, it has been empirically observed that fibers with nanoscale chirality can be formed in glycolipid-based systems if specific sugar-to-lipid linkers like phenyl, 15 phenylamide 47 or amidopyridine 48 groups are used over simple ether bonding.…”

Section: Introductionmentioning

confidence: 99%

“…24 In the case of sophorolipids, nanoscale chirality has never been reported even if giant ribbons seem to be formed from an elaidic acid (C18:1-trans) based compound while contradictory results exists (giant ribbons versus micelles) on the behavior of oleic acid derived (C18:1-cis) sophorolipids. 50,51,52,53 In the present paper, we present the pHtriggered formation of self-assembled fibers with nanoscale chirality using a saturated sophorolipid (C18:0 sophorolipids, Figure 1b) Preparation of the supramolecular assemblies: Different amounts of acidic C18:0 sophorolipids (c= 2 mg/mL and 5 mg/mL) were solubilized in deionized water.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

pH-triggered formation of nanoribbons from yeast-derived glycolipid biosurfactants

et al. 2014

View full text Add to dashboard Cite

International audienceIn the present paper, we show that the saturated form of acidic sophorolipids, a family of industrially scaled bolaform microbial glycolipids, unexpectedly forms chiral nanofibers only at pH below 7.5. In particular, we illustrate that this phenomenon derives from a subtle cooperative effect of molecular chirality, hydrogen bonding, van der Waals forces and steric hindrance. The pH-responsive behaviour was shown by Dynamic Light Scattering (DLS), pH-titration and Field Emission Scanning Electron Microscopy (FE-SEM) while the nanoscale chirality was evidenced by Circular Dichroism (CD) and cryo Transmission Electron Microscopy (cryo-TEM). The packing of sophorolipids within the ribbons was studied using Small Angle Neutron Scattering (SANS), Wide Angle X-ray Scattering (WAXS) and 2D H-1-H-1 through-space correlations via Nuclear Magnetic Resonance under very fast (67 kHz) Magic Angle Spinning (MAS-NMR)

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

pH-triggered formation of nanoribbons from yeast-derived glycolipid biosurfactants

et al. 2014

View full text Add to dashboard Cite

show abstract

“…Given the importance of carbohydrates in glycobiology and medicine, 29,30 and the richness of carbohydrate chemistry, the applications of glycolipids are potentially broader than those for engineered amphiphiles. 31 In addition, the biobased microbial origin of the glycolipids selected for this study makes them interesting alternative candidates to both petroleum-based compounds. Microbial glycolipids, also known as "biosurfactants", have a good biodegradability, low cytotoxicity, and numerous applications as antimicrobial, antibiofilm, anticancer, emulsifying, and stabilizing agents already exist.…”

Section: ■ Introductionmentioning

confidence: 99%

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

et al. 2016

View full text Add to dashboard Cite

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.

show abstract

“…Furthermore, most glycolipids have additional chemical functions like acetylenic, carboxylic, 4,5 hydroxy 4 in their aliphatic moiety, thus increasing the level of complexity and functionality of these compounds and making them promising precursors for application in advanced material science. 10,11 However, even their simplest structural form hides an underlying complexity in terms of collective supramolecular behaviour.…”

Section: Introductionmentioning

confidence: 99%

pH-Driven Self-Assembly of Acidic Microbial Glycolipids

et al. 2016

View full text Add to dashboard Cite

Microbial glycolipids are a class of well-known compounds, but their self-assembly behavior is still not well understood. While the free carboxylic acid end group makes some of them interesting stimuli-responsive compounds, the sugar hydrophilic group and the nature of the fatty acid chain make the understanding of their self-assembly behavior in water not easy and highly unpredictable. Using cryo-transmission electron microscopy (cryo-TEM) and both pH-dependent in situ and ex situ small angle X-ray scattering (SAXS), we demonstrate that the aqueous self-assembly at room temperature (RT) of a family of β-d-glucose microbial glycolipids bearing a saturated and monounsaturated C18 fatty acid chain cannot be explained on the simple basis of the well-known packing parameter. Using the “pH-jump” process, we find that the molecules bearing a monosaturated fatty acid forms vesicles below pH 6.2, as expected, but the derivative with a saturated fatty acid forms infinite bilayer sheets below pH 7.8, instead of vesicles. We show that this behavior can be explained on the different bilayer membrane elasticity as a function of temperature. Membranes are either flexible or stiff for experiments performed at a temperature respectively above or below the typical melting point, T M, of the lipidic part of each compound. Finally, we also show that the disaccharide-containing acidic cellobioselipid forms a majority of chiral fibers, instead of the expected micelles.

show abstract

Supramolecular organic nanotubes: how to utilize the inner nanospace and the outer space

Cited by 135 publications

References 150 publications

pH-triggered formation of nanoribbons from yeast-derived glycolipid biosurfactants

pH-triggered formation of nanoribbons from yeast-derived glycolipid biosurfactants

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

pH-Driven Self-Assembly of Acidic Microbial Glycolipids

Contact Info

Product

Resources

About