Nucleolipids
Lipophilic nucleosides and oligonucleotides have received broad interest.Because of their amphiphilic properties they can form interesting supramolecular structures, such as monolayer films, micelles and/or vesicles, organogels or multilamellar layers. Normally their nucleobases are exposed to the aqueous phase, and they potentially can form complementary Watson–Crick base pairs. The lipophilic substituent can also act as an anchor for fixing lipophilic nucleosides or oligonucleotides in biocompatible lipid membranes, again by exposing the nucleotides to the aqueous phase. Recently we could show that nucleosides with lipid moieties linked to the nucleobase anchor in giant unilamellar vesicles (GUVs) and large unilamellar vesicles (LUVs) composed of unilamellar phospholipid bilayers. Oligonucleotides with two of such lipophilic nucleotides incorporated into the nucleotide chain anchor in both, GUVs and LUVs and were shown to form double-strand DNAs with complementary oligonucleotides in solution.
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Our work is focussed on the Synthesis of New Nucleolipides, for incorporation in Biocompatible Lipid Membran and for the Synthesis of lipophilic DNA. |
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Nucleolipids – Synthesis, Supramolecular Behavior, Membrane Anchoring, Nanobiotechnological Application |
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Surface-functionalized LUV´s |
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LBL-capsules covered with different layers of GUV´s based on recognition of complementary lipidated oligonucleotides |
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Selected Publications
Luisa Losensky, Björn Goldenbogen, Gudrun Holland, Michael Laue, Anca Petran, Jürgen Liebscher, Holger A. Scheidt, Alexander Vogel, Daniel Huster, Edda Klipp, Anna Arbuzova: "Micro- and nano-tubules built from loosely and tightly rolled up thin sheets"
PhysChemChemPhys, 2016, 18, 1292-1301. DOI 10.1039/c5cp06084b
Luisa Losensky, Salvo Chiantia, Gudrun Holland, Michael Laue, Anca Petran, Jürgen Liebscher, Anna Arbuzova: "Self-assembly of a cholesteryl-modified nucleoside into tubular structures from giant unilamellar vesicles"
RSC Advances, 2015, 4502-4510, DOI 10.1039/C4RA11289J
Daniela Serien, Christiane Grimm, Jürgen Liebscher, Andreas Herrmann, Anna Arbuzova: "DNA-controlled aggregation of virus like particles – mimicking a tetherin-like mechanism"
New J. Chem., 2014, 38, 5181-5185. DOI 10.1039/c4nj00724g.
Matthias Schade, Andrea Knoll, Alexander Vogel, Oliver Seitz, Jürgen Liebscher, Daniel Huster, Andreas Herrmann, Anna Arbuzova: "Remote control of lipophilic nucleic acids domain partitioning by DNA hybridization and enzymatic cleavage"
J. Am. Chem. Soc., 2012, 134, 20490-20497
E. A. Montanha, L. Caseli, O. Kaczmarek, J. Liebscher, D. Huster, O. N. Oliveira: "Comparative Study of Liponucleosides in Langmuir Monolayers as Cell Membrane Models"
Biophysic. Chem., 2011, 153, 154-158
Björn Goldenbogen, Nicolai Brodersen, Andrea Gramatica, Martin Loew, Jürgen Liebscher, Andreas Herrmann, Holger Egger, Bastian Budde, Anna Arbuzova: "Reduction-Sensitive Liposomes from a Multifunctional Lipid Conjugate and natural Phospholipids: Reduction and Release Kinetics and Cellular Uptake"
Langmuir, 2011, 27, 10820-10829
Martin Loew, Paula Pescador, M. Schade, J. Appelfeller, Jürgen Liebscher, Oliver Seitz, Daniel Huster, Andreas Herrmann, Anna Arbuzova: "Controlled self-assemply and membrane organization of lipophilic nucleosides and nucleic acids: perspectives for applications"
European Biophysics Journal with Biophysics Letters, 2011, 40, 72-72
Paula Pescador, Nicolai Brodersen, Holger A. Scheidt, Martin Loew, Jürgen Liebscher, Andreas Herrmann, Daniel Huster, and Anna Arbuzova: "Microtubes self-assembled from a cholesterol-based nucleoside"
Chem. Commun., 2010, 46, 5358-5360
Martin Loew, Ralph Springer, Silvia Scolari, Frank Altenbrunn, Oliver Seitz, Jürgen Liebscher, Daniel Huster, Andreas Herrmann, Anna Arbuzova: "Lipid domain specific recruitment of palmitoylated peptide nucleic acid – a key for switchable functionalization of (biological) membranes"
J. Am. Chem. Soc., 2010, 132, 16066-16072
O. Kaczmarek, H. A. Scheidt, A. Bunge, D. Föse, S. Karsten, A. Arbuzova, D. Huster, J. Liebscher: "2´-Linking of Lipids and Other Functions to Uridine via 1,2,3-Triazoles and Membrane Anchoring of Amphiphilic Products"
Eur. J. Org. Chem., 2010, 1579 – 1586
É. A Montanha, F. J. Pavinatto, L. Caseli, O. Kaczmarek, J. Liebscher, D. Huster, O. N. Oliveira Jr: "Properties of lipophilic nucleoside monolayers at the air-water"
Colloid Surface B, 2010, 77, 161-165
Martin Loew, Jing Kang, Lars Dähne, Ruth Hendus-Altenburger, Oliver Kaczmarek, Jürgen Liebscher, Daniel Huster, Kai Ludwig, Christoph Böttcher, Andreas Herrmann, Anna Arbuzova: "Controlled Assembly of Vesicle-based Nanocontainers on Layer-by-Layer Particles via DNS Hybridisation"
SMALL, 2009, 5, 320-323
Oliver Kaczmarek, Nicolai Brodersen, Andreas Bunge, Ludwig Löser, Daniel Huster, Andreas Herrmann, Anna Arbuzova, Jürgen Liebscher "Synthesis of Nucleosides with 2´-Fixed Lipid Anchors and Their Behavior in Phospholipid Membranes"
Eur.J.Org.Chem, 2008, 1917-1928
Andreas Bunge, Anke Kurz, Anne-Kathrin Windeck, Thomas Korte, Wolfgang Flasche, Jürgen Liebscher, Andreas Herrmann, Daniel Huster:"Lipophilic Oligonucleotides Spontaneously Insert into Lipid Membranes, Bind Complementary DNA Strands, and Sequester into Lipid Disordered Domains"
Langmuir, 2007, 4455-4464
Anke Kurz, Andreas Bunge, Anne-Katrin Windeck, Maximilian Rost, Wolfgang Flasche, Anna Arbuzova, Denise Strohbach, Sabine Müller, Jürgen Liebscher, Daniel Huster, Andreas Herrmann: "Lipid-Anchored Oligonucleotides for Stable Double Helix Formation in Distinct Membrane Domains"
Angew. Chem., 2006, 4550-4554