Amphiphilic properties of synthetic glycolipids based on amide linkages. I. Electron microscopic studies on aqueous gels

Pfannemüller, B.; Welte, Wolfram

doi:10.1016/0009-3084(85)90011-8

Cited by 144 publications

(100 citation statements)

References 24 publications

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“…As can be seen in Figs. [4][5][6], pitch angles of the helical ribbons were constant and independent of p and w, thus confirming that the pitch angle is determined by the ratio of the two elastic moduli as predicted by Eq. 16.…”

supporting

confidence: 67%

“…4 into Eq. 3 and making notational substitutions, KnC = A12, KPP = A21, KcP = All/2, and K* =-D29 where the subscript n denotes the dependence on the number of bilayers, we obtain an elastic free energy per unit area of a tubule similar to that of Helfrich and Prost (11), Gtubule(PA 13) = Kcccos4p + KPPsin4/3 + (KcP/2)sin22/8 2p2 K*sin 2,B 2p [5] The K"C and KPP terms correspond to the bending of the bilayer along the e and 0 directions, respectively. The K?P and K* terms correspond to the twist of the coordinate system about the k direction.…”

mentioning

confidence: 89%

“…In view of the clinical importance of controlling cholesterol crystallization, we have carried out experimental and theoretical studies of kinetics and energetics of these metastable intermediates in a series of model biles. Although, to our knowledge, helical ribbon structures had not been previously reported in bile, twisted strips, helical ropes, helical ribbons, and tubules have been observed in a variety of systems composed of chiral amphiphiles (4)(5)(6)(7)(8)(9). To understand the extraordinary helical and tubular superstructures formed in bile, we shall adopt and extend previous theoretical models for the elastic free energy ofbilayers whose symmetry is broken by the chirality.…”

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confidence: 96%

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Elastic free energy of anisotropic helical ribbons as metastable intermediates in the crystallization of cholesterol.

Chung

Benedek

Konikoff

et al. 1993

Proc. Natl. Acad. Sci. U.S.A.

163

170

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We report measurements of the geometrical a In 1986, Helfrich (10) proposed a simple elastic model in which the optimal shape of a helical ribbon is controlled by a balance between bending of the ribbon and torsion of its edges, leading to a universal pitch angle of 450 for an elastically isotropic ribbon. Two years later Helfrich and Prost (11) generalized the bending free energy for anisotropic bilayers. To account for the lack of mirror reflection symmetry of bilayers of chiral molecules, they also added a term linear in the surface curvature to the elastic free energy (11).Despite these refinements, the analysis of the pitch angle was made only for an isotropic bilayer and the pitch angle remained 45°. In 1990, Ou-Yang and Liu (12) modeled the The publication costs of this article were defrayed in part by page charge payment. This article must therefore be hereby marked "advertisement" in accordance with 18 U.S.C. §1734 solely to indicate this fact. helical ribbon as a cholesteric liquid crystal layer and also obtained the pitch angle of 45°.Herein, we describe experimentally observed helical ribbon structures with either of two distinctive pitch angles: 540 or 110. We also present a form for the elastic free energy of anisotropic chiral bilayers that provides analytical expressions for the geometrical features and growth of the helical ribbon structures observed in our biles. MATERIALS AND METHODSAll model biles were composed of the common bile salt sodium taurocholate, lecithin, and cholesterol in a molar ratio of 97.5:0.8:1.7. Sodium taurocholate (Sigma) was recrystallized and found to be >98% pure by HPLC and TLC. Cholesterol (Nu Chek Prep, Elysian, MN) was >99% pure by TLC, GC, and HPLC. Grade I egg yolk lecithin (Lipid Products, Nutley, U.K.) was >99% pure by TLC. Synthetic sn-1-16:0-sn-2-18:1 lecithin (lecithin I) and sn-1-16:0-sn-2-16:0 lecithin (lecithin II) were obtained from Avanti Polar Lipids. Model biles A, B, C, and D contained lecithin I, a 1:1 mixture of lecithin I and lecithin II, egg yolk lecithin, and lecithin II, respectively. Native bile was a generous gift from M. Cahalane (Beth Israel Hospital, Boston) (2). Using TLC, no degradation of the components of bile was observed during our experiments.At a total lipid concentration of 70 mg/ml (0.15 M NaCl/3 mM NaN3), all four model biles formed micellar solutions with a mean hydrodynamic radius of 17 ± 5 A (2, 13).Meticulous precautions were taken to reduce the nucleating effect of dust. A 5-ml vial with a Teflon septum cap was acid-cleaned, rinsed, filled with Milli-Q water (Millipore), Abbreviation: ChM, cholesterol monohydrate crystal.§Present address:

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confidence: 67%

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confidence: 89%

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Elastic free energy of anisotropic helical ribbons as metastable intermediates in the crystallization of cholesterol.

Chung

Benedek

Konikoff

et al. 1993

Proc. Natl. Acad. Sci. U.S.A.

163

170

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“…A variety of compounds have been shown to act as building blocks for mesoscopic aggregates with helical or tubular morphology: synthetic compounds such as double-or single-chain amphiphiles with an aminoacid backbone (Nakashima et al, 1984;Yamada et al, 1984;Imae et al, 1992), polymerizable lecithins with diacetylenic fatty acyl chains (Yager and Schoen, 1984;Georger et al, 1987), octyl-aldonamides (Pfannemü ller and Welte, 1985;Fuhrhop et al, 1987;Kö ning et al, 1993), single chain diacetylenic aldonamides (Frankel and O'Brien, 1994), diphenylglycoluril-based amphiphiles (van Nunen et al, 1994), non-ionic or fluorinated surfactants (Uchegbu and Florence, 1995;Giulieri et al, 1994), di-polyprenyl phosphates (Birault et al, 1996), anionic glucophospholipids and natural lipids such as phospholipids (Papahadjopoulos et al, 1975), bile lipids (Kaplun et al, 1994) or galactocerebrosides (Archibald and Yager, 1992). Several structural parameters have been identified as playing an essential role in the formation of tubular assemblies (Schnur, 1993;Nakashima et al, 1984;Frankel and O'Brien, 1994;Singh et al, 1988;Fuhrhop et al, 1988;Kulkarni et al, 1995), such as a highly ordered conformation of the acyl tails (Nakashima et al, 1985;Burke et al, 1988;Chappell and Yager, 1991), the presence of a chiral head group (Nakashima et al, 1984;Singh et al, 1988;Fuhrhop et al, 1988), or the formation of intermolecular amide hydrogen bonds stabilizing the association of polar head groups (Fuhrhop et al, 1987).…”

Section: Introductionmentioning

confidence: 99%

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

Huetz

Neuren

Ringler

et al. 1997

Chemistry and Physics of Lipids

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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.

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“…The aggregation behaviour of N-alkyl-hexonamides and subsequent formation of the characteristic ordered structures has recently been described (Pfannemueller & Welte, 1985;Fuhrhop et al, 1988). Such structures were formed by cooling hot micellar aqueous solutions down to temperatures where amide hydrogen bond chains are formed in a co-operative reaction sequence.…”

Section: Introductionmentioning

confidence: 99%

Assignment of two ultrastructures formed by a mixture of hexonamides using autoradiography and electron microscopy

Boettcher¹,

Boekema²,

Fuhrhop³

1990

Journal of Microscopy

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SUMMARY The combined application of autoradiography and electron microscopy allowed the assignment of molecular components to individual micellar fibres in a mixed gel. Resolution was of the order of 0.1 μm. As a result, it was shown that bimolecular sheets of N‐dodecyl‐l‐mannonamide (= l‐Man‐12) completely separated from helical rods consisting of tritiated N‐octyl‐d‐gluconamide (= d‐Glu‐8). The method should be useful for the analysis of several other synthetic supramolecular systems.

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Amphiphilic properties of synthetic glycolipids based on amide linkages. I. Electron microscopic studies on aqueous gels

Cited by 144 publications

References 24 publications

Elastic free energy of anisotropic helical ribbons as metastable intermediates in the crystallization of cholesterol.

Elastic free energy of anisotropic helical ribbons as metastable intermediates in the crystallization of cholesterol.

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

Assignment of two ultrastructures formed by a mixture of hexonamides using autoradiography and electron microscopy

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