Archaeabacteria bipolar lipid analogues: structure, synthesis and lyotropic properties

Benvegnu, Thierry; Brard, Mickaëlle; Plusquellec, Daniel

doi:10.1016/j.cocis.2004.01.005

Cited by 101 publications

(75 citation statements)

References 48 publications

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“…Archaea membranes have high stability in harsh environments (Benvegnu et al 2004;Ulrih et al 2009) and as such are very good candidates for use as liposomes for drug delivery (Hanford and Peeples 2002;Ulrih et al 2009). Their stability is probably due to several factors that directly relate to the peculiar chemical structure of the lipids of which they are composed.…”

Section: Introductionmentioning

confidence: 99%

On the Electroporation Thresholds of Lipid Bilayers: Molecular Dynamics Simulation Investigations

et al. 2013

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Electroporation relates to the cascade of events that follows the application of high electric fields and that leads to cell membrane permeabilization. Despite a wide range of applications, little is known about the electroporation threshold, which varies with membrane lipid composition. Here, using molecular dynamics simulations, we studied the response of dipalmitoyl-phosphatidylcholine, diphytanoyl-phosphocholine-ester and diphytanoylphosphocholine-ether lipid bilayers to an applied electric field. Comparing between lipids with acyl chains and methyl branched chains and between lipids with ether and ester linkages, which change drastically the membrane dipole potential, we found that in both cases the electroporation threshold differed substantially. We show, for the first time, that the electroporation threshold of a lipid bilayer depends not only on the ''electrical'' properties of the membrane, i.e., its dipole potential, but also on the properties of its component hydrophobic tails.

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Section: Introductionmentioning

confidence: 99%

On the Electroporation Thresholds of Lipid Bilayers: Molecular Dynamics Simulation Investigations

et al. 2013

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“…[2,3] Since well defined, natural bolaphospholipids are difficult to isolate from natural membranes, considerable efforts have been devoted to the synthesis of novel bipolar lipids. [4,5] Unexpectedly, the simplification of these model compounds to bipolar lipids with just one long alkyl chain gave rise to new aggregate structures, such as nanofibres and nanoparticles of self-assembled single-chain bolaphospholipids. [6,7] Recently, we reported the synthesis and temperature-dependent aggregation behaviour of symmetrical single-chain polymethylene-1,w-bis(phosphocholines) with hydrocarbon chain lengths of 22 to 32 carbon atoms and two phosphocholine headgroups attached at both ends (PC-Cn-PC).…”

Section: Introductionmentioning

confidence: 99%

General Synthesis and Aggregation Behaviour of New Single‐Chain Bolaphospholipids: Variations in Chain and Headgroup Structures

Drescher

Meister

Graf

et al. 2008

Chemistry A European J

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The chemical structures of polymethylene-1,omega-bis(phosphocholines) that self-assemble into nanofibres was modified on the one hand in the hydrophobic chain region, by introduction of sulfur and oxygen atoms, and on the other hand by variation of the polar headgroup structure with functionalised tertiary amines. The temperature-dependent self-assembly of these novel bolaphospholipids into nanofibres and spherical micelles was investigated by differential scanning calorimetry (DSC) and transmission electron microscopy (TEM). The thermal stabilities of the nanofibres strongly depend on the chemical compositions of the headgroups and of the hydrophobic chains. The insertion of new functionalities in the headgroup region by click chemistry makes these substances interesting for potential applications in bioscience and materials science.

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“…These unique physical properties of archaeal lipids are of great interest for biotechnological and pharmaceutical applications (3,17,18), and the synthesis of archaeal lipid analogs represents an exciting challenge (see for instance Ref. 19 and citations therein).…”

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confidence: 99%

A molecular dynamics study of an archaeal tetraether lipid membrane: Comparison with a dipalmitoylphosphatidylcholine lipid bilayer

Nicolas

2005

Lipids

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Molecular dynamics simulations of an archaeal membrane made up of bipolar tetraether lipids and a dipalmitoylphosphatidylcholine (DPPC) lipid membrane were performed and compared for the first time. The simulated archaeal membrane consists of a pure monolayer of asymmetrical lipids, analogous to the main polar lipid [MPL; Swain, M., Brisson, J.-R., Sprott, G.D., Cooper, F.P., and Patel, G.B., (1997) Identification of beta-L-Gulose as the Sugar Moiety of the Main Polar Lipid of Thermoplasma acidophilum, Biochim. Biophys. Acta 1345, 56-64] found in T. acidophilum, an extremophile archaeal organism. This simulated membrane lipid contains two cyclopentane rings located on one of the two aliphatic chains of the lipid. The archaeal membrane is simulated at 62degreesC, slightly above the optimal growth temperature of T. acidophilum. We compared the organization of this tetraether lipid monolayer with a DPPC bilayer simulated at 50degreesC, both of them being modeled in a partially hydrated state. Our results assess the singularity of the tetraether lipid organization, in particular the influence of the spanning structure on the molecular ordering within the archaeal membrane.

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Archaeabacteria bipolar lipid analogues: structure, synthesis and lyotropic properties

Cited by 101 publications

References 48 publications

On the Electroporation Thresholds of Lipid Bilayers: Molecular Dynamics Simulation Investigations

On the Electroporation Thresholds of Lipid Bilayers: Molecular Dynamics Simulation Investigations

General Synthesis and Aggregation Behaviour of New Single‐Chain Bolaphospholipids: Variations in Chain and Headgroup Structures

A molecular dynamics study of an archaeal tetraether lipid membrane: Comparison with a dipalmitoylphosphatidylcholine lipid bilayer

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