@article{MertensHilschHaralampievetal.2018, author = {Mertens, Monique and Hilsch, Malte and Haralampiev, Ivan and Volkmer, Rudolf and Wessig, Pablo and M{\"u}ller, Peter}, title = {Synthesis and characterization of a new Bifunctionalized, Fluorescent, and Amphiphilic molecule for recruiting SH-Containing molecules to membranes}, series = {ChemBioChem}, volume = {19}, journal = {ChemBioChem}, number = {15}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1439-4227}, doi = {10.1002/cbic.201800268}, pages = {1643 -- 1647}, year = {2018}, abstract = {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.}, language = {en} } @article{CzarneckiWessig2018, author = {Czarnecki, Maciej and Wessig, Pablo}, title = {Scaling Up UV-Mediated Intramolecular Photodehydro-Diels-Alder Reactions Using a Homemade High-Performance Annular Continuous-Flow Reactor}, series = {Organic Process Research \& Development}, volume = {22}, journal = {Organic Process Research \& Development}, number = {12}, publisher = {American Chemical Society}, address = {Washington}, issn = {1083-6160}, doi = {10.1021/acs.oprd.8b00353}, pages = {1823 -- 1827}, year = {2018}, abstract = {Here we present a self-made annular continuous-flow reactor that can be used in the UV/vis range in an internal numbering-up manner. As a model reaction, we chose a powerful batch-scale-limited benzoannelation method, namely, an intramolecular photodehydro-Diels-Alder (IMPDDA) reaction. The scale-up potential of this particular photochemical benchmark reaction toward the preparation of macrocylic (1,7)naphthalenophanes by variation of selected flow parameters is presented.}, language = {en} } @article{WessigJohnMertens2018, author = {Wessig, Pablo and John, Leonard and Mertens, Monique}, title = {Extending the Class of [1,3]-Dioxolo[4.5-f]benzodioxole (DBD) Fluorescent Dyes}, series = {European journal of organic chemistry}, volume = {2018}, journal = {European journal of organic chemistry}, number = {14}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {1434-193X}, doi = {10.1002/ejoc.201800002}, pages = {1674 -- 1681}, year = {2018}, abstract = {Synthetic routes to a collection of new fluorescent dyes are described, which are based on the [1,3]-dioxolo[4.5-f]benzodioxole (DBD) core. By introducing different electron withdrawing groups in 4- and 8-position of the DBD moiety the emission wavelength could be adjusted over a large spectral range from blue to orange light.}, language = {en} } @article{BuechnerJohnMertensetal.2018, author = {B{\"u}chner, D{\"o}rthe and John, Leonard and Mertens, Monique and Wessig, Pablo}, title = {Detection of dsDNA with [1,3]Dioxolo[4,5-f]benzodioxol (DBD) Dyes}, series = {Chemistry - a European journal}, volume = {24}, journal = {Chemistry - a European journal}, number = {60}, publisher = {Wiley-VCH}, address = {Weinheim}, issn = {0947-6539}, doi = {10.1002/chem.201804057}, pages = {16183 -- 16190}, year = {2018}, abstract = {DBD fluorescent dyes have proven to be useful in numerous applications. To widen the range of biological applications, we propose three different types of DBD molecules that have been modified in such a way that DNA interaction becomes probable. After the successful synthesis of all three compounds, we tested their fluorescent properties and their DNA binding abilities. Two of the three probes exhibit an interaction with dsDNA with subsequent fluorescence enhancement. The determined binding constants of the two new DNA dyes are comparable to other minorgroove-binding dyes. Their large Stokes shifts and their long fluorescent lifetimes are outstanding features of these dyes.}, language = {en} } @article{HoangMertensWessigetal.2018, author = {Hoang, Hoa T. and Mertens, Monique and Wessig, Pablo and Sellrie, Frank and Schenk, J{\"o}rg A. and Kumke, Michael Uwe}, title = {Antibody Binding at the Liposome-Water Interface}, series = {ACS Omega}, volume = {3}, journal = {ACS Omega}, number = {12}, publisher = {American Chemical Society}, address = {Washington}, issn = {2470-1343}, doi = {10.1021/acsomega.8b03016}, pages = {18109 -- 18116}, year = {2018}, abstract = {Different signal amplification strategies to improve the detection sensitivity of immunoassays have been applied which utilize enzymatic reactions, nanomaterials, or liposomes. The latter are very attractive materials for signal amplification because liposomes can be loaded with a large amount of signaling molecules, leading to a high sensitivity. In addition, liposomes can be used as a cell-like "bioscaffold" to directly test recognition schemes aiming at cell-related processes. This study demonstrates an easy and fast approach to link the novel hydrophobic optical probe based on [1,3]dioxolo[4,5-f]-[1,3]benzodioxole (DBD dye mm239) with tunable optical properties to hydrophilic recognition elements (e.g., antibodies) using liposomes for signal amplification and as carrier of the hydrophobic dye. The fluorescence properties of mm239 (e.g., long fluorescence lifetime, large Stokes shift, high photostability, and high quantum yield), its high hydrophobicity for efficient anchoring in liposomes, and a maleimide bioreactive group were applied in a unique combination to build a concept for the coupling of antibodies or other protein markers to liposomes (coupling to membranes can be envisaged). The concept further allowed us to avoid multiple dye labeling of the antibody. Here, anti-TAMRA-antibody (DC7-Ab) was attached to the liposomes. In proof-of-concept, steady-state as well as time-resolved fluorescence measurements (e.g., fluorescence depolarization) in combination with single molecule detection (fluorescence correlation spectroscopy, FCS) were used to analyze the binding interaction between DC7-Ab and liposomes as well as the binding of the antigen rhodamine 6G (R6G) to the antibody. Here, the Forster resonance energy transfer (FRET) between mm239 and R6G was monitored. In addition to ensemble FRET data, single-molecule FRET (PIE-FRET) experiments using pulsed interleaved excitation were used to characterize in detail the binding on a single-molecule level to avoid averaging out effects.}, language = {en} }