TY - JOUR A1 - Mertens, Monique A1 - Hilsch, Malte A1 - Haralampiev, Ivan A1 - Volkmer, Rudolf A1 - Wessig, Pablo A1 - Müller, Peter T1 - Synthesis and characterization of a new Bifunctionalized, Fluorescent, and Amphiphilic molecule for recruiting SH-Containing molecules to membranes JF - ChemBioChem N2 - This study describes the synthesis and characterization of an amphiphilic construct intended to recruit SH-containing molecules to membranes. The construct consists of 1)an aliphatic chain to enable anchoring within membranes, 2)a maleimide moiety to react with the sulfhydryl group of a soluble (bio)molecule, and 3)a fluorescence moiety to allow the construct to be followed by fluorescence spectroscopy and microscopy. It is shown that the construct can be incorporated into preformed membranes, thus allowing application of the approach with biological membranes. The close proximity between the fluorophore and the maleimide moiety within the construct causes fluorescence quenching. This allows monitoring of the reaction with SH-containing molecules by measurement of increases in fluorescence intensity and lifetime. Notably, the construct distributes into laterally ordered membrane domains of lipid vesicles, which is probably triggered by the length of its membrane anchor. The advantages of the new construct can be employed for several biological, biotechnological, and medicinal applications. KW - DBD dyes KW - fatty acids KW - liposomes KW - maleimide KW - membranes KW - palmitoylation Y1 - 2018 U6 - https://doi.org/10.1002/cbic.201800268 SN - 1439-4227 SN - 1439-7633 VL - 19 IS - 15 SP - 1643 EP - 1647 PB - Wiley-VCH CY - Weinheim ER - TY - CHAP A1 - Haralampiev, Ivan A1 - Mertens, Monique A1 - Schwarzer, Roland A1 - Herrmann, Andreas A1 - Volkmer, Rudolf A1 - Wessig, Pablo A1 - Müller, Peter T1 - A palmitic acid functionalized with a maleimide group is used to recruit SH-containing peptides to lipid and biological membranes T2 - The FEBS journal Y1 - 2015 SN - 1742-464X SN - 1742-4658 VL - 282 SP - 204 EP - 204 PB - Wiley-Blackwell CY - Hoboken ER - TY - JOUR A1 - Nikolaus, Jörg A1 - Czapla, Sylvia A1 - Möllnitz, Kristian A1 - Höfer, Chris T. A1 - Herrmann, Andreas A1 - Wessig, Pablo A1 - Müller, Peter T1 - New molecular rods - Characterization of their interaction with membranes JF - Biochimica et biophysica acta : Biomembranes N2 - Molecular rods are synthetical molecules consisting of a hydrophobic backbone which are functionalized with varying terminal groups. Here, we report on the interaction of a recently described new class of molecular rods with lipid and biological membranes. In order to characterize this interaction, different fluorescently labeled rods were synthesized allowing for the application of fluorescence spectroscopy and microscopy based approaches. Our data show that the rods are incorporated into membranes with a perpendicular orientation to the membrane surface and enrich preferentially in liquid-disordered lipid domains. These characteristics underline that rods can be applied as stable membrane-associated anchors for functionalizing membrane surfaces. KW - Molecular rod KW - Phospholipid KW - Lipid domain KW - Spiro compound Y1 - 2011 U6 - https://doi.org/10.1016/j.bbamem.2011.08.008 SN - 0005-2736 VL - 1808 IS - 12 SP - 2781 EP - 2788 PB - Elsevier CY - Amsterdam ER - TY - JOUR A1 - Wawrzinek, Robert A1 - Wessig, Pablo A1 - Möllnitz, Kristian A1 - Nikolaus, Joerg A1 - Schwarzer, Roland A1 - Müller, Peter A1 - Herrmann, Andreas T1 - DBD dyes as fluorescent probes for sensing lipophilic environments JF - Bioorganic & medicinal chemistry letters : a Tetrahedron publication for rapid dissemination of preliminary communications on all aspects of bioorganic chemistry, medicinal chemistry and related disciplines N2 - Small fluorescent organic molecules based on [1,3]dioxolo[4,5-f][1,3]benzodioxole (DBD) could be used as probes for lipophillic microenvironments in aqueous solutions by indicating the critical micelles concentration of detergents and staining cell organelles. Their fluorescence lifetime decreases drastically by the amount of water in their direct environment. Therefore they are potential probes for fluorescence lifetime imaging microscopy (FLIM). KW - Fluorescence lifetime probes KW - FLIM KW - Cell staining KW - Lysotrackers KW - Detergents Y1 - 2012 U6 - https://doi.org/10.1016/j.bmcl.2012.07.056 SN - 0960-894X VL - 22 IS - 17 SP - 5367 EP - 5371 PB - Elsevier CY - Oxford ER - TY - JOUR A1 - Grimm, Christiane A1 - Meyer, Thomas A1 - Czapla, Sylvia A1 - Nikolaus, Jörg A1 - Scheidt, Holger A. A1 - Vogel, Alexander A1 - Herrmann, Andreas A1 - Wessig, Pablo A1 - Huster, Daniel A1 - Müller, Peter T1 - Structure and dynamics of molecular rods in membranes application of a Spin-Labeled rod JF - Chemistry - a European journal N2 - Molecular rods consisting of a hydrophobic backbone and terminally varying functional groups have been synthesized for applications for the functionalization of membranes. In the present study, we employ a spin-labeled analogue of a recently described new class of molecular rods to characterize their dynamic interactions with membranes. By using the different approaches of ESR and NMR spectroscopy, we show that the spin moiety of the membrane-embedded spin-labeled rod is localized in the upper chain/glycerol region of membranes of different compositions. The rod is embedded within the membrane in a tilted orientation to adjust for the varying hydrophobic thicknesses of these bilayers. This orientation does not perturb the membrane structure. The water solubility of the rod is increased significantly in the presence of certain cyclodextrins. These cyclodextrins also allow the rods to be extracted from the membrane and incorporated into preformed membranes. The latter will improve the future applications of these rods in cellular systems as stable membrane-associated anchors for the functionalization of membrane surfaces. KW - hydrophobic mismatch KW - membranes KW - molecular rods KW - phospholipids KW - spiro compounds Y1 - 2013 U6 - https://doi.org/10.1002/chem.201202500 SN - 0947-6539 VL - 19 IS - 8 SP - 2703 EP - 2710 PB - Wiley-VCH CY - Weinheim ER - TY - JOUR A1 - Müller, Peter A1 - Nikolaus, Jörg A1 - Schiller, Sabine A1 - Herrmann, Andreas A1 - Moellnitz, Kristian A1 - Czapla, Sylvia A1 - Wessig, Pablo T1 - Molecular rods with oligospiroketal backbones as anchors in biological membranes N2 - Getting stuck in: A hydrophobic molecular rod with terminal fluorescent moieties has been synthesized. The insertion of the rod into membranes was investigated and shown to incorporate efficiently into model and biological membranes (see picture; gray C, blue N, red O). Those rods can be used as stable membrane-associated anchors for functionalization of membrane surfaces. Y1 - 2009 UR - http://www3.interscience.wiley.com/cgi-bin/jhome/26737/ U6 - https://doi.org/10.1002/anie.200901133 SN - 1433-7851 ER -