Dry Thermotropic Glycolipid Self-Assembly:A Review

Hashim, Roslan; Zahid, N. Idayu; Velayutham, Thamil Selvi; Aripin, Nurul Fadhilah Kamalul; Ogawa, Shigesaburo; Sugimura, Akihiko

doi:10.5650/jos.ess17261

Cited by 28 publications

(29 citation statements)

References 95 publications

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“…The biological activity of this panel of compounds as TLR4 antagonists, combined with the tendency to spontaneously form vesicular aggregates, make this type of carboxylate-based lipid A analogues interesting in the perspective to exploit the self-assembled aggregates structures to modulate their pharmacokinetic and biodistribution properties in biomedical and pharmacological contexts 61–64 .…”

Section: Discussionmentioning

confidence: 99%

Novel carboxylate-based glycolipids: TLR4 antagonism, MD-2 binding and self-assembly properties

Cochet

Facchini

Zaffaroni

et al. 2019

Sci Rep

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New monosaccharide-based lipid A analogues were rationally designed through MD-2 docking studies. A panel of compounds with two carboxylate groups as phosphates bioisosteres, was synthesized with the same glucosamine-bis-succinyl core linked to different unsaturated and saturated fatty acid chains. The binding of the synthetic compounds to purified, functional recombinant human MD-2 was studied by four independent methods. All compounds bound to MD-2 with similar affinities and inhibited in a concentration-dependent manner the LPS-stimulated TLR4 signaling in human and murine cells, while being inactive as TLR4 agonists when provided alone. A compound of the panel was tested in vivo and was not able to inhibit the production of proinflammatory cytokines in animals. This lack of activity is probably due to strong binding to serum albumin, as suggested by cell experiments in the presence of the serum. The interesting self-assembly property in solution of this type of compounds was investigated by computational methods and microscopy, and formation of large vesicles was observed by cryo-TEM microscopy.

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Section: Discussionmentioning

confidence: 99%

Novel carboxylate-based glycolipids: TLR4 antagonism, MD-2 binding and self-assembly properties

Cochet

Facchini

Zaffaroni

et al. 2019

Sci Rep

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“…Immiscible solutions consisting of high-and low-concentration solutions of β-OGlu have been exploited for membrane protein purification [2]. The glass-transition behavior both in the absence and presence of ice, and the water-cluster-like responsive behavior under magnetic and electric fields have been demonstrated for the LC phases [23,25,26,[28][29][30]. These physical properties of β-OGlu self-assembly must be directly or indirectly related to the specific features of individual β-OGlu interactions with proteins-and/or surrounding the proteins with self-assembling membrane domains-and they may further advance its use.…”

Section: Introductionmentioning

confidence: 99%

Unveiling the Uniqueness of Crystal Structure and Crystalline Phase Behavior of Anhydrous Octyl β-D-Glucoside Using Aligned Assembly on a Surface

Ogawa

Takahashi

2020

Polymers

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Although the anomalous low crystallinity of octyl β-D-glucoside (β-OGlu) was first proposed more than 30 years ago, many fundamental aspects of its crystal structure and of the crystalline phase behavior of the pure substance have remained uncertain. In this paper, we employ grazing-incidence wide-angle X-ray-diffraction measurements using a two-dimensional detector (2D-GI-WAXD) and perpendicularly aligned crystalline films to demonstrate that β-OGlu forms crystal structures consisting of an intermediate phase-like a ripple phase with two large crystal-lattice constants, a and c, comparable to the lengths of its bilayer structures. Furthermore, solid-to-solid phase transitions accompanied by latent heat confirm the existence of a solid-solution-like phase consisting of a crystalline and a liquid-crystal (LC) phase, which persists over a 20 • C temperature range, in a single-component system. In addition, the system forms a superlattice, accompanied by a change in packing of the component sugars in the partial-melting state; this shift is different from the gel-crystal transition observed for a typical lipid system. These facts indicate that even in the crystalline phase formed from a single component, each individual β-OGlu molecule in a single-component phase plays a versatile role in the crystallisation and melting processes. These findings must somewhat explain the specific co-assembling features with proteins of β-OGlu, which has long been used empirically in biochemistry.

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“…We note, however, that the exhibition of liquid J o u r n a l P r e -p r o o f crystalline phases is not based on the formation of new "rod-like" or "disc-like" moieties by hydrogen-bonding, but instead on segregation due to the amphiphilic character of the glycosides, including hydrogen-bonding between the sugar heads. Carbohydrate liquid crystals experienced a fast development in the 1980's and 1990's [26][27][28] , and the mesomorphic behaviour of new glycosides continues to be the object of systematic investigation by varying their composition and stereochemistry [30][31][32][33] .…”

Section: Introductionmentioning

confidence: 99%

Unveiling the hydrogen bonding network in liquid crystalline natural-based glycosides containing polymeric complexes: Experimental and theoretical assessment

Aripin

Heap

Piñol

et al. 2020

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Unveiling the hydrogen bonding network in liquid crystalline natural-based glycosides containing polymeric complexes: experimental and theoretical assessment Nurul Fadhilah Kamalul Aripin (Conceptualization) (Data curation) (Writing -original draft) (Writing -review and editing) (Funding acquisition), Jonathan Heap (Data curation) (Formal analysis), Rafael Piñol (Data curation) (Methodology), Vijayan M. Achari (Data curation) (Formal analysis) (Writing -original draft), Alfonso Martinez-Felipe (Conceptualization) (Investigation) (Writingoriginal draft) (Writing -review and editing) (Funding acquisition

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Dry Thermotropic Glycolipid Self-Assembly:A Review

Cited by 28 publications

References 95 publications

Novel carboxylate-based glycolipids: TLR4 antagonism, MD-2 binding and self-assembly properties

Novel carboxylate-based glycolipids: TLR4 antagonism, MD-2 binding and self-assembly properties

Unveiling the Uniqueness of Crystal Structure and Crystalline Phase Behavior of Anhydrous Octyl β-D-Glucoside Using Aligned Assembly on a Surface

Unveiling the hydrogen bonding network in liquid crystalline natural-based glycosides containing polymeric complexes: Experimental and theoretical assessment

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