A macrocyclic tetraether bolaamphiphile and an oligoamino .alpha.,.omega.-dicarboxylate combine to form monolayered, porous vesicle membranes, which are reversibly sealed by EDTA and other bulky anions

Fuhrhop, Jürgen‐Hinrich; Liman, Ulrich; Koesling, V.

doi:10.1021/ja00228a037

Cited by 98 publications

(47 citation statements)

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“…This stabilizing approach was adopted from naturally occurring archaebacterial membrane lipids 4,25,26 and its applicability to drug delivery systems for pharmaceutical purposes was confirmed for a variety of natural and artificial bolalipids. [27][28][29][30][31][32][33][34] In our study we combine both, alkyl chain modifications and the introduction of headgroup asymmetry. At first, we synthesized two novel single-chain bolalipids, namely PC-C17pPhC17-PC and PC-C17pPhC17-OH.…”

Section: Introductionmentioning

confidence: 99%

The Headgroup (A)Symmetry Strongly Determines the Aggregation Behavior of Single-Chain Phenylene-Modified Bolalipids and Their Miscibility with Classical Phospholipids

et al. 2014

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In the present work, we describe the synthesis of two single-chain phenylene-modified bolalipids, namely PC-C17pPhC17-PC and PC-C17pPhC17-OH, with either symmetrical (phosphocholine) or asymmetrical (phosphocholine and hydroxyl) headgroups using a Sonogashira cross coupling reaction as key-step. The temperature-dependent aggregation behavior of both bolalipids in aqueous suspension was studied using transmission electron microscopy (TEM), differential scanning calorimetry (DSC), Fourier-transform infrared (FTIR) spectroscopy, small angle neutron scattering (SANS), and X-ray scattering. We show that different headgroup symmetries lead to a change in the aggregation behavior: Whereas PC-C17pPhC17-PC forms nanofibers with a diameter of 5.7 nm that transform into small ellipsoidal micelles at 23 °C, the PC-C17pPhC17-OH self-assembles into lamellae with bolalipid molecules in an antiparallel orientation up to high temperatures. Furthermore, the mixing behavior of both bolalipids with bilayer forming phospholipids (DPPC and DSPC) was studied by means of DSC and TEM. The aim was to stabilize bilayer membranes formed of phospholipids in order to improve these mixed lipid vesicles for drug delivery purposes. We show that the symmetrical PC-C17pPhC17-PC is miscible with DPPC and DSPC, however, closed lipid vesicles are not observed and elongated micelles and bilayer fragments are found instead. In contrast, the asymmetrical PC-C17pPhC17-OH shows no miscibility with phospholipids at all.

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Section: Introductionmentioning

confidence: 99%

The Headgroup (A)Symmetry Strongly Determines the Aggregation Behavior of Single-Chain Phenylene-Modified Bolalipids and Their Miscibility with Classical Phospholipids

et al. 2014

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“…[56,57] By using zwitterions as a bolaamphiphile analogue, switching can be triggered by changing the pH. Since amino acids exist in their zwitterionic form only within a small pH range, so addition of acid as well as base may easily change the aggregation process.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

Advances in Switchable Supramolecular Nanoassemblies

Fenske

Korth

Mohr

et al. 2011

Chemistry A European J

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Supramolecular nanoassemblies are gaining increasing importance as promising new materials with considerable potential for novel and promising applications. Within supramolecular nanoassemblies the connectivity of the monomeric units is based on reversible noncovalent interactions, like van der Waals interactions, hydrogen bonding, or ionic interactions. As the strength of these interactions depends on the molecular surrounding, the formation of nanoassemblies in principle can be controlled externally by changing the environment and/or the molecular shape of the underlying monomer. This way it is not only possible to switch the self-assembly on or off, but also to change between different aggregation states. In this minireview we present some recent selected approaches to supramolecular stimuli-responsive nanoassemblies.

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“…Pioneered by the groups of Tabushi, 46 Fuhrhop, 47 Kobuke,48 and others, the creation of new ion channels and pores has become one of the classical applications of synthetic nanoarchitecture in lipid bilayer membranes. Excellent reviews continuously update this field from different points of view.…”

Section: Ion Channels and Poresmentioning

confidence: 99%

Synthetic Multifunctional Nanoarchitecture in Lipid Bilayers: Ion Channels, Sensors, and Photosystems

Bhosale

Bollot

et al. 2007

Bulletin of the Chemical Society of Japan

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The creation of functional materials such as ion channels, porous sensors, or smart photosystems depends critically on our ability to assemble sophisticated, error-free and self-repairing nanoarchitecture in a predictable manner. To address these challenging topics, we often used lipid bilayer membranes as compartmentalizing platform and have introduced rigid-rod molecules as privileged scaffolds that bypass all folding problems because they do not fold. This approach provides access to motifs such as rigid-rod barrels, helices, stacks, slides, and wires that can act as smart, stimuli-responsive photosystems, pores, ion channels, hosts, sensors, and catalysts. The selected examples focus on naphthalenediimides (NDIs), a compact, organizable, colorizable, and functionalizable n-semiconductor. This versatile module is used in rigid-rod molecules to mediate transmembrane anion transport by anion-interactions, as sticky -clamp within pore sensors to catch otherwise elusive analytes by aromatic electron donor-acceptor interactions, or in blue, transmembrane -stack architecture to collect and convert photonic energy. These specific examples with multifunctional NDI nanoarchitecture are of help to outline, on the one hand, possibilities to contribute to advanced functional materials such as multianalyte sensors or solar cells and, on the other hand, to keep on wondering about an enormous structural and functional space waiting to be explored.In biology, highest sophistication on both the structural and functional level is accomplished with membrane proteins. Ion channels and pores, for instance, function as stimuli-responsive multianalyte sensors that assure perception of and communication with the outside world.

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A macrocyclic tetraether bolaamphiphile and an oligoamino .alpha.,.omega.-dicarboxylate combine to form monolayered, porous vesicle membranes, which are reversibly sealed by EDTA and other bulky anions

Cited by 98 publications

References 0 publications

The Headgroup (A)Symmetry Strongly Determines the Aggregation Behavior of Single-Chain Phenylene-Modified Bolalipids and Their Miscibility with Classical Phospholipids

The Headgroup (A)Symmetry Strongly Determines the Aggregation Behavior of Single-Chain Phenylene-Modified Bolalipids and Their Miscibility with Classical Phospholipids

Advances in Switchable Supramolecular Nanoassemblies

Synthetic Multifunctional Nanoarchitecture in Lipid Bilayers: Ion Channels, Sensors, and Photosystems

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