Relationship between molecular structure and supramolecular morphology of DODA-EO2-biotin and related lipids

Abstract

Relationship between molecular structure and supramolecular morphology of DODA-EO2-biotin and related lipids Huetz, P.; van Neuren, S.; Ringler, P.; Kremer, F.; van Breemen, J.F.L.; Wagenaar, A.; Engberts, Jan; Fraaije, J.G E M; Brisson, A. Link to publication in University of Groningen/UMCG research database Citation for published version (APA): Huetz, P., van Neuren, S., Ringler, P., Kremer, F., van Breemen, J. F. L., Wagenaar, A., ... Brisson, A. (1997). Relationship between molecular structure and supramolecular morphology of DODA-EO2-biotin and related lipids. Chemistry and Physics of Lipids, 89(1), 15-30. DOI: 10.1016/S0009-3084(97)00055-8 Copyright Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons).Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim.Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. AbstractWe have recently reported that a biotinylated lipid molecule, called DODA-EO 2 -biotin, forms tubular lipid structures upon hydration, which act as a matrix for the formation of ordered helical arrays of streptavidin as well as for secondary macromolecular recognition reactions involving biotinylated structures (Ringler et al., 1997). In the present study, the supramolecular structures formed by the compounds obtained during the synthesis of DODA-EO 2 -biotin and of compounds structurally related to DODA-EO 2 -biotin were investigated by transmission electron microscopy, with the objective being to understand the relationship between molecular structure and supramolecular morphology. From the eight lipid molecules investigated, only DODA-EO 2 -biotin formed tubular structures. Several structural parameters were identified as playing a role in the formation of DODA-EO 2 -biotin tubes, such as the chirality of the biotin moiety, the saturated nature of the lipid chains, the presence of amide bonds and the correct length and structure of the hydrophilic spacer. In addition, helical crystals of streptavidin were only obtained upon binding of streptavidin to the supramolecular assemblies formed by DODA-EO 2 -biotin. © 1997 Elsevier Science Ireland Ltd.

Self-assembling properties of a series of homologous ester-diamides – from ribbons to nanotubes

“…The form factor of long hollow cylinders (e.g. for which L [ 10r ext , with L the length of the nanotubes) can be written as Pðq; r ext ; eÞ ¼ p qL r ext J 1 ðqr ext Þ À ðr ext À eÞJ 1 ðqðr ext À eÞÞ qeðr ext À e=2Þ 2 (5) with r ext the external radius of the tube, e the thickness of the wall and J 1 the Bessel function of rst kind and rst order. This single tube model reproduces the main experimental features of the experimental curve (Fig.…”

“…1 The diameters of the resulting tubes depend on the nature of the molecule and range from 10 to 500 nm. Due to their unique shape and their high aspect ratio, these nanotubes nd applications for instance as scaffolds for cell growth, 2 as supports for 2-D crystallization of proteins [3][4][5] or as templates to form silica nanotubes [6][7][8] and mesopores in organic matrices. 9 They also have triggered much theoretical research by physicists to understand the mechanism of their self-assembly.…”

Ab initio study of the influence of conformation on partial charge distribution of dioctadecylamine

“…We have shown [8] that DODA molecules spontaneously form plates in aqueous solution, some of them presenting a regular geometry, with clues in favor of a crystalline gel state of the lipids. Such behaviour is a purely collective property.…”

“…In a previous work [8], we have shown experimentally that DODA molecules spontaneously self-organize in plate-like structures in aqueous solution. This dynamics at the mesoscopic level was simulated with a functional Langevin model [9], and several features observed by electron microscopy could be qualitatively reproduced.…”

Structure of Nanotubes Self-Assembled from a Monoamide Organogelator

“…We have shown that the tubes are metastable, and they transform into crystals after 28 h. Such transformations in organogels, have been observed for other gelators [ 25 , 26 ]. Given the shape of the aggregates, it is relevant to compare HUB-4 also with lipid compounds self-assembling in metastable nanotubes [ 27 ]. As Gubitosi et al have shown lately, kinetically stable tubes formed by lithocholic acid have been proved to be thermodynamically metastable [ 28 ].…”