The chiral bilayer effect stabilizes micellar fibers

Fuhrhop, Jürgen‐Hinrich; Schnieder, Peter; Rosenberg, Jörg; Boekema, Egbert J.

doi:10.1021/ja00245a032

Cited by 285 publications

(174 citation statements)

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“…The spectra (IR, 1H-NMR and MS) and elemental analysis (C, H, N) of D-Glu-8 were in agreement with published values (Fuhrhop et al, 1987). L-Man-12 fitted very well with expected spectroscopical data.…”

Section: Methodssupporting

confidence: 87%

“…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. The D-and L-forms of 12) aggregate to form ultrathin helices with diameters of around 7 and 9 nm respectively (Fuhrhop et al, 1987), which continue to rearrange to achieve thicker fibres ( (Fig. lc).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

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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Section: Methodssupporting

confidence: 87%

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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“…The stronger hydrophobicity of 12Lys12 also explains the large surface excess (9.3 mol m −2 ), indicating the affinity of the amphiphile to adsorb at the interface, thus efficiently lowering the surface tension. In addition, the existence of groups where intermolecular hydrogen bonding can occur, namely the N-H and C O groups, can further enhance the surface adsorption [24,[48][49][50]. For instance, comparing this surfactant with a bis(quaternary ammonium) gemini surfactant with four CH 2 spacer groups [46], it can be seen that the lysine derivative attains a much lower surface tension at the cmc (12-4-12: 39.8 mN m −1 ; 12Lys12: 27.1 mN m −1 ).…”

Section: Micellization Propertiesmentioning

confidence: 99%

Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles

Brito

Marques

Silva

et al. 2009

Colloids and Surfaces B: Biointerfaces

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a b s t r a c tThe design of efficient liposomal systems for drug delivery is of considerable biomedical interest. In this context, vesicles prepared from cationic/anionic surfactants may offer several advantages, mainly due to their spontaneity in formation and long-term stability. There is also an impending need to produce less toxic, more biocompatible amphiphiles, while maintaining the desirable aggregation properties. In this work, we present data for acute toxicity to Daphnia magna (IC 50 ), and potential ocular irritation (HC 50 ) for some newly prepared ionic surfactants with dodecyl chains, derived from the amino acids tyrosine (Tyr), serine (Ser), hydroxyproline (Hyp) and lysine (Lys). The micellization behavior of the compounds, evaluated from surface tension measurements, is presented and compared to more conventional ionic amphiphiles. Two types of spontaneouly formed catanionic vesicles, composed either by a dodecyltrimethylammonium bromide (DTAB)/Lys-derivative and or Ser-/Lys-derivative mixture, have also been tested for their ecotoxicity and hemolytic potential. All the micelle-forming surfactants as well as the vesicle-containing mixtures are found to have lower ecotoxicity than the reference surfactant DTAB. Moreover, the results from hemolysis and hemoglobin denaturation tests show that the Tyr-and Lys-derivatives are moderately irritant, whereas the Hyp-and Ser-ones are just slightly irritant. Even more significantly, the vesicle-containing mixtures exhibit lower hemolytic activity than the neat surfactants, a positive result for their potential use in liposomal formulations.

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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). Theories have been elaborated to explain the formation of lipid tubules (Schnur, 1993) based on notions of spontaneous torsion of bilayer edges …”

Section: Introductionmentioning

confidence: 99%

“…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). Theories have been elaborated to explain the formation of lipid tubules (Schnur, 1993) based on notions of spontaneous torsion of bilayer edges (Helfrich, 1986;Helfrich and Prost, 1988;Selinger et al, 1996), curvature energy (Lubensky and Prost, 1992), surface energy reduction (Kö ning et al, 1993), or chiral bilayer effect (Fuhrhop et al, 1987). The picture which has emerged from these papers is that the process of tube formation is driven by the chirality of the constituting molecules and involves a sequential transformation of ribbons into wound sheets, open helices and finally closed lipid cylinders.…”

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 chiral bilayer effect stabilizes micellar fibers

Cited by 285 publications

References 3 publications

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

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

Physicochemical and toxicological properties of novel amino acid-based amphiphiles and their spontaneously formed catanionic vesicles

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

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