Hydrophilic spacer groups in polymerizable lipids: formation of biomembrane models from bulk polymerized lipids

Elbert, R.; Laschewsky, André; Ringsdorf, Helmut

doi:10.1021/ja00300a007

Cited by 122 publications

(56 citation statements)

References 4 publications

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“…4 an interlayer spacing of 29,4 A was calculated for i-PODMA and a-PODMA multilayers. The length of an extended C18chain, in zig-zag conformation, is approximately 23 Å. Electron diffraction of an i-PODMA multilayer revealed 11)a hexagonally packed structure of the side chains with a lattice spacing of 4,19 Å. This value is well known from the crystallization of the bulk polymers 18, 19).…”

Section: Cos2qn(e=o) (Gir)mentioning

confidence: 77%

“…The value to be expected for a hexagonally packed side chain lattice with a lattice spacing of 4,19 Å is 20,3 Å 2. The result for i-PODMA differs somewhat from this number.…”

Section: Cos2qn(e=o) (Gir)mentioning

confidence: 95%

“…Elbert et al 4) investigated the layer spacings of Y-type multilayers of prepolymerized synthetic lipids and concluded that the structure of the layers was comparable to the ones formed by first spreading the monomeric lipids followed by polymerization in the multilayer. Nakahara et al 5) and Kawaguchi et al 6) investigated mono-and multilayers of cellulose esters and concluded that the glucose-rings lay flat on the water surface and that the aliphatic side chains were oriented perpendicular to the layer plane.…”

Section: Introductionmentioning

confidence: 99%

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Langmuir‐Blodgett mono‐ and multilayers of preformed poly(octadecyl methacrylate)s, 2. Structural studies by IR spectroscopy and small‐angle X‐ray scattering

Arndt¹,

Schouten²,

Schmidt³

et al. 1991

Makromol. Chem.

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Langmuir‐Blodgett (LB) mono‐ and multilayers of preformed atactic and isotactic poly(octadecyl methacrylate)s were studied on gold surfaces and silicon wafers. The average orientation of the carbonyl bond of the ester group was found to be about 50° with respect to the normal to the substrate, and the side chains were concluded to be oriented perpendicular to the substrate. Furthermore, the degree of side chain orientation increased on going from a single monolayer to a multilayer. This is explained by an interdigitation of the side chains during or after the transfer process. A peculiar transfer behavior of the atactic samples is discussed in terms of the effect of disorder of the first layer on the transfer process. On heating multilayers of the polymers, melting of the crystalline domains formed by the side chains was observed at temperatures of about 35°C to 40°C. However, the layer structure appeared to be stable up to 100°C. The oriented structure was completely recovered after cooling down to room temperature.

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Section: Cos2qn(e=o) (Gir)mentioning

confidence: 77%

“…The value to be expected for a hexagonally packed side chain lattice with a lattice spacing of 4,19 Å is 20,3 Å 2. The result for i-PODMA differs somewhat from this number.…”

Section: Cos2qn(e=o) (Gir)mentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

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Langmuir‐Blodgett mono‐ and multilayers of preformed poly(octadecyl methacrylate)s, 2. Structural studies by IR spectroscopy and small‐angle X‐ray scattering

Arndt¹,

Schouten²,

Schmidt³

et al. 1991

Makromol. Chem.

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“…The column consisted of four types of styrenedivinylbenzene copolymer gels (Shodex KF-S02, KF-S03, KF-S04, and KF-S05 with exclusion limits of 5 x 10 3 , 7 X 10 4 ,4 X 105, and 4 x 10 6 , respectively). A calibration curve for molecular weights was obtained by using standard polystyrene samples (Showa Denko Co.): Mn=3.6x10 6 The phase transition behavior was studied with a differential scanning calorimeter (Seiko Instruments SSCj560). Unpolymerized aqueous dispersions (20 mM) were prepared by sonication, and were used after aging overnight.…”

Section: Measurementsmentioning

confidence: 99%

“…We showed that this approach is effective for bilayer formation from prepolymerized amphiphiles, 5 Elbert, Laschewsky and Ringsdorf similarly succeeded in decoupling of the motion of these two portions in single-component bilayer membranes. 6 We found recently that the presence of ether oxygen in the alkyl tail e.g., 1 and 2, imparted the aggregation morphology with surprising flexibility without losing the regular side-chain alignment. 7 It was perceived that the ether oxygen in the alkyl tail is efficient for decoupling of the motion of the polymeric chain and the alkyl tail more than the Bis(2-dodecyloxyethyl)-L-glutamate hydrochloride (1.0 g, 0.0016mol) and triethylamine (0.65 g, 0.0065 mol) were dissolved in dry tetrahydrofuran (THF), and the mixture was stirred at room temperature.…”

mentioning

confidence: 99%

Aqueous Bilayers of Glutamate-Based Double-Chain Ammonium Amphiphiles II. Improvement of Polymerization and Membrane Characteristics by Ether-Linked Alkyl Tails

Katō

Kunitake

1991

Polym J

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ABSTRACT:Photopolymerization was conducted for aqueous bilayer membranes of glutamate-based double-chain ammonium amphiphiles which have the ether linkage in the alkyl tail portion and the acrylate moiety attached to the ammonium head. The polymerization readily proceeded to completion 10 7 ) in contrast to that of related bilayers which lack the ether linkage. The reactivity difference was particularly large in the polymerization in the crystalline state. According to DSC measurement, circular dichroism, and fluorescence spectroscopy, the bilayer polymerized in the liquid crystalline state showed lessened side chain alignment, whereas regular side-chain packing was maintained in the polymerization in the crystalline state. Re-dispersion in water was not possible for the former polymer, though possible for the latter. These different properties may be attributed to the steric difference in the main chain portion which, however, could not be detected by 400 MHz 'H-NMR spectroscopy.KEY WORDS Bilayer Membrane I Polymerized Bilayer I Amphiphile I Phase Transition I Electron Microscopy I Molecular Organization I It has been expected that covalent linking of component molecules by polymerization would stabilize aqueous bilayer vesicles and facilitate their uses in practical applications such as controlled drug delivery,3,4 Many of the past examples of polymerized vesicles faced a dilemma of efficient polymerization at the expense of lost bilayer characteristics, In our previous investigation on this topic, 2 we introduced the acrylate unit at the hydrophilic head of glutamate-based double-chain ammonium amphiphiles and scrutinized the molecular organization of the polymerized bilayers by a combination of thermal and spectral measurements. The polymerization was suppressed in crystalline bilayer states. The polymerized bilayers in water showed large hystereses, These results suggested that the polymer chain in the hydrophilic region interferred with facile organization of the side chain alkyl groups.

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Influence of spacer groups on grafting ability, curing ability, and film properties of water-based radiation curable latexes

Odeberg¹,

Rassing

Jönsson

et al. 1998

J. Appl. Polym. Sci.

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Film-forming polystyrene/poly(n-butyl acrylate-co-glycidyl methacrylate) [PS/P(BA-co-GMA)] core-shell latex particles were prepared via a two-stage emulsion polymerization procedure using a PS latex seed. A delayed addition of GMA was used to locate the functional epoxy groups near the surface of the particles. The surfacebound epoxy groups were used as grafting sites for unsaturated carboxyl functional monomers having the unsaturated groups and the carboxylic group separated by 1, 5, or 10 oxyethylene units. Grafting and curing characteristics and film properties after irradiation were investigated as a function of the number of oxyethylene units. A BA-GMA [P(BA-co-GMA)] copolymer was used as a model system for the core-shell latex particles for quantification of the grafting reactions. The grafting was demonstrated by FTIR and 1 H-NMR spectroscopy. The effects of crosslinking was studied by thermal mechanical analysis and dynamical mechanical analysis. Differential photocalorimetry was also used for evaluation of the curing ability. It was demonstrated that the reagent having five oxyethylene units in the spacer group was grafted onto the polymer backbones to a larger extent than the other two reagents, and a more thoroughly cured film was obtained upon irradiation.

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Hydrophilic spacer groups in polymerizable lipids: formation of biomembrane models from bulk polymerized lipids

Cited by 122 publications

References 4 publications

Langmuir‐Blodgett mono‐ and multilayers of preformed poly(octadecyl methacrylate)s, 2. Structural studies by IR spectroscopy and small‐angle X‐ray scattering

Langmuir‐Blodgett mono‐ and multilayers of preformed poly(octadecyl methacrylate)s, 2. Structural studies by IR spectroscopy and small‐angle X‐ray scattering

Aqueous Bilayers of Glutamate-Based Double-Chain Ammonium Amphiphiles II. Improvement of Polymerization and Membrane Characteristics by Ether-Linked Alkyl Tails

Influence of spacer groups on grafting ability, curing ability, and film properties of water-based radiation curable latexes

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