Learning from the unexpected in life and DNA self-assembly

• Jennifer M. Heemstra

Beilstein J. Org. Chem. 2015, 11, 2713–2720, doi:10.3762/bjoc.11.292

• were specifically drawn to the enzyme-linked immunosorbent assay (ELISA) that is the current gold standard in this field. As shown in Figure 3, we constructed our enzyme-linked assay by immobilizing one fragment of the split aptamer on the surface of a microplate, then adding the test sample along with

Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope

• Manuel Johannes,
• Maximilian Reindl,
• Bastian Gerlitzki,
• Edgar Schmitt and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15

• epitopes. Use of tetanus toxoid (TTox) and bovine serum albumin (BSA) as immunogenic carrier proteins allows application of these conjugates in immunization studies and diagnostic ELISA experiments [44]. Results and Discussion Chemical synthesis of the 4’-fluoro-TF neo-glycoconjugate The synthesis of the 4

• molecule of BSA, whereas the corresponding antigen loading of the larger TTox conjugate 18b was not likewise feasible. However, antigen loadings of >20 molecules of glycopeptide antigen per molecule of protein were estimated by ELISA binding data for similar MUC1 conjugates in earlier studies by the Kunz

• with incomplete Freund’s adjuvant (IFA) were performed by intraperitoneal applications at intervals of 21 days. Five days following the final immunization, serum antibody levels were determined by an enzyme-linked immunosorbent assay (ELISA). Therefore, blood was drawn from tail veins of the mice and

Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals

• Éva Rajnavölgyi,
• Renáta Laczik,
• Viktor Kun,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

• -10 and IL-12 cytokines we measured the expression levels of moDC-derived IL-10 and IL-12 by ELISA. However, the treatment of PUFAs in our hands did not cause such a decrease in cytokine secretion, although the secretion of both cytokines was increased upon activation by LPS or Poly(I:C), and no

• ELISA studies were analyzed by one-way ANOVA with Bonferroni post-hoc test using the GraphPad Prism v.6 software (GraphPad Software Inc., La Jolla, CA, USA). Differences were considered to be statistically significant at p < 0.05. Structure of RAMEA. Structures of ALA, EPA and DHA. Solubility of n−3

Synthesis and immunological evaluation of protein conjugates of Neisseria meningitidis X capsular polysaccharide fragments

• Laura Morelli,
• Damiano Cancogni,
• Marta Tontini,
• Alberto Nilo,
• Sara Filippini,
• Paolo Costantino,
• Maria Rosaria Romano,
• Francesco Berti,
• Roberto Adamo and
• Luigi Lay

Beilstein J. Org. Chem. 2014, 10, 2367–2376, doi:10.3762/bjoc.10.247

• (BS(PEG)5) linker was used to rule out the interference of the spacer (details are reported in Supporting Information File 1). ELISA analysis using HSA conjugates as coating reagent demonstrated that the conjugated monomer 1 and the dimer 2 at the present dose elicited extremely low levels of

• antibodies against themselves and were, therefore, scarcely antigenic. By contrast, the trimer 3 was the only fragment which evoked a robust antibody production against its own structure (Figure 3A). Surprisingly, when the trimer-HSA conjugate was used as coating reagent for the ELISA analysis (Figure 3B

• assay (rSBA) titers were determined using pooled sera from mice immunized with the conjugated monomer 14, dimer 15, trimer 16 and MenXDP15 17. As it can be seen from Table 2, rSBA titers showed a trend similar to the measured ELISA IgG levels. Only pooled sera from mice immunized with the conjugated

Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions

• Yoann M. Chabre,
• Alex Papadopoulos,
• Alexandre A. Arnold and
• René Roy

Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157

• precipitation of the complexes [30][31]. Alternatively, the application of surface plasmon resonance (SPR) also creates artificial situations not sufficiently related to the natural cellular events, thus requiring complex mathematical algorithms [32]. Most solid-phase immunoassays (ELLA, ELISA) also fall under

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• tanks. Following the synthesis, the peptides remain on the polymer carrier enabling a fast and parallel screening for antibody binding by ELISA (enzyme-linked immunosorbent assay) (‘PepScan’). Although quality control is not possible using this strategy, it is suitable for fast epitope mapping. In

Recent progress in the discovery of small molecules for the treatment of amyotrophic lateral sclerosis (ALS)

• Allison S. Limpert,
• Margrith E. Mattmann and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2013, 9, 717–732, doi:10.3762/bjoc.9.82

• translational level, one strategy for increasing EAAT2 activity is to use small molecules to increase the translation of EAAT2 mRNA [6]. This strategy, employed by Colton et al. [6], prompted the screening of a library of 140,000 compounds by using an ELISA-based assay for EAAT2 protein expression. This screen

Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors

• Francesca Pertici,
• Norbert Varga,
• Arnoud van Duijn,
• Matias Rey-Carrizo,
• Anna Bernardi and
• Roland J. Pieters

Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25

• 24 is a mimic for DC-SIGN inhibition and its bioactivity will be tested elsewhere. Inhibition studies The inhibitory potency of 22 for LecA was studied in an ELISA type assay by using a glycochip as the solid phase [10]. In this assay an IC50 value of 0.9 μM was determined (Table 1). This compared

Peptides presenting the binding site of human CD4 for the HIV-1 envelope glycoprotein gp120

• Julia Meier,
• Kristin Kassler,
• Heinrich Sticht and
• Jutta Eichler

Beilstein J. Org. Chem. 2012, 8, 1858–1866, doi:10.3762/bjoc.8.214

• to gp120 The seven CD4-derived peptides (Table 1) were tested in an ELISA type binding assay for their ability to bind to recombinant gp120 from HIV-1 strain IIIB (Figure 3, left). Of the two linear peptides (CD4-M1 and CD4-M4), only the longer peptide CD4-M1 is recognized by gp120, illustrating the

• for mass spectrometry data). Binding assays Direct ELISA (Figure 3): The following buffers were used: Coupling buffer: 0.01 M KCl; blocking buffer: 5% BSA in 0.1 M phosphate buffer pH 7.2; sample buffer: 0.1% BSA and 0.01% Tween 20 in 0.1 M phosphate buffer pH 7.2; washing buffer: phosphate buffer pH

Synthesis of 4” manipulated Lewis X trisaccharide analogues

• Christopher J. Moore and
• France-Isabelle Auzanneau

Beilstein J. Org. Chem. 2012, 8, 1134–1143, doi:10.3762/bjoc.8.126

• trisaccharide [16][17][18][19][20][21]. The relative affinity of the anti-Lex monoclonal antibody SH1 [6] for the native Lex antigen 1 and our Lex analogues [12][13][14] was examined by competitive ELISA experiments using a Lex-BSA glycoconjugate as the immobilized ligand [15][22][23][24]. It was discovered

• leading to a balance between favourable enthalpic and unfavourable entropic contributions [25][26][27][28][29]. Thus, only additional competitive ELISA studies with Lex-OMe analogue inhibitors containing strategic manipulations at the 4” site will provide further insight into specific binding interactions

• . Overall, this study also confirms our observation [68], that galactosylations at position 4 of N-acetylglucosamine acceptors are usually less successful than glucosylations [14][67]. The final Lex-OMe analogues will be used as competitive inhibitors in future ELISA experiments to provide a better

An easily accessible sulfated saccharide mimetic inhibits in vitro human tumor cell adhesion and angiogenesis of vascular endothelial cells

• Grazia Marano,
• Claas Gronewold,
• Martin Frank,
• Anette Merling,
• Christian Kliem,
• Sandra Sauer,
• Manfred Wiessler,
• Eva Frei and
• Reinhard Schwartz-Albiez

Beilstein J. Org. Chem. 2012, 8, 787–803, doi:10.3762/bjoc.8.89

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

• Elena A. Khatuntseva,
• Vladimir M. Men’shov,
• Alexander S. Shashkov,
• Yury E. Tsvetkov,
• Rodion N. Stepanenko,
• Raymonda Ya. Vlasenko,
• Elvira E. Shults,
• Genrikh A. Tolstikov,
• Tatjana G. Tolstikova,
• Dimitri S. Baev,
• Vasiliy A. Kaledin,
• Nelli A. Popova,
• Valeriy P. Nikolin,
• Pavel P. Laktionov,
• Anna V. Cherepanova,
• Tatiana V. Kulakovskaya,
• Ekaterina V. Kulakovskaya and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2012, 8, 763–775, doi:10.3762/bjoc.8.87

• ). Cells were incubated in IMDM-FBS for 24 h, culture medium was removed, and cells were centrifuged at 1500g and preserved at −20 °С. The IL-6 concentration in the samples was determined by using a commercial ELISA kit (Vector-Best, Russia, A-8768) according to the protocol suggested by the manufacturer

• : Four groups of seven mice each were immunized intramuscularly thrice, on days 0, 14, and 84 with a mixture of 40 μg of conjugate and 50 μg of different saponins (or without adjuvant for the control group) in PBS as a vehicle in a total vaccine volume of 200 μL. ELISA: Sera from inoculated mice were

• collected on day 91 post-inoculation (p.v.) of the first dose of vaccine and pooled. The titers for IgG and IgM against α-NeuAc-(2→3)-β-Galp-(1→4)-β-Glcp were determined in an indirect ELISA as previously described [31]. ELISA plates (96-well, Nunc Maxisorp) were coated with a cover polyacrylamide antigen

Formation of carbohydrate-functionalised polystyrene and glass slides and their analysis by MALDI-TOF MS

• Martin J. Weissenborn,
• Johannes W. Wehner,
• Christopher J. Gray,
• Robert Šardzík,
• Claire E. Eyers,
• Thisbe K. Lindhorst and
• Sabine L. Flitsch

Beilstein J. Org. Chem. 2012, 8, 753–762, doi:10.3762/bjoc.8.86

• coupling and analysis of the attached ligands to ensure quality control. Noncovalent attachment of biomolecules to hydrophobic surfaces has been used for a long time in ELISA assays and is attractive because no coupling reagents are required. However, it requires inherent hydrophobicity in the biomolecule

Synthesis of multivalent host and guest molecules for the construction of multithreaded diamide pseudorotaxanes

• Nora L. Löw,
• Egor V. Dzyuba,
• Boris Brusilowskij,
• Lena Kaufmann,
• Elisa Franzmann,
• Wolfgang Maison,
• Emily Brandt,
• Daniel Aicher,
• Arno Wiehe and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2012, 8, 234–245, doi:10.3762/bjoc.8.24

• Nora L. Low Egor V. Dzyuba Boris Brusilowskij Lena Kaufmann Elisa Franzmann Wolfgang Maison Emily Brandt Daniel Aicher Arno Wiehe Christoph A. Schalley Institut für Chemie und Biochemie der Freien Universität Berlin, Takustr. 3, 14195 Berlin, Germany Pharmazeutische und Medizinische Chemie

The interplay of configuration and conformation in helical perylenequinones: Insights from chirality induction in liquid crystals and calculations

• Elisa Frezza,
• Silvia Pieraccini,
• Stefania Mazzini,
• Alberta Ferrarini and
• Gian Piero Spada

Beilstein J. Org. Chem. 2012, 8, 155–163, doi:10.3762/bjoc.8.16

• Elisa Frezza Silvia Pieraccini Stefania Mazzini Alberta Ferrarini Gian Piero Spada Department of Chemical Sciences, University of Padova, via Marzolo 1, 35131 Padova, Italy Dipartimento di Chimica Organica “A. Mangini”, Alma Mater Studiorum – Università di Bologna, via San Giacomo 11, 40126

Pyridinium based amphiphilic hydrogelators as potential antibacterial agents

• Sayanti Brahmachari,
• Sisir Debnath,
• Sounak Dutta and
• Prasanta Kumar Das

Beilstein J. Org. Chem. 2010, 6, 859–868, doi:10.3762/bjoc.6.101

• . Then, 15μL of MTT stock solution (5 mg/mL) in phosphate buffer saline was added to the above mixture and the cells were further incubated for another 4 h. The precipitated formazan was dissolved in DMSO and absorbance at 570 nm was measured using BioTek® Elisa Reader. The number of surviving cells were

En route to photoaffinity labeling of the bacterial lectin FimH

• Thisbe K. Lindhorst,
• Michaela Märten,
• Andreas Fuchs and
• Stefan D. Knight

Beilstein J. Org. Chem. 2010, 6, 810–822, doi:10.3762/bjoc.6.91

• -mannoside (pNPMan), respectively (Table 1). When these mannosides were tested as inhibitors of type 1 fimbriae-mediated bacterial adhesion to a mannan-coated surface in an ELISA [21][22], IC50-values were obtained, which reflect the concentration of the derivative employed, that leads to 50% inhibition of

• 2, 3 and 5 are the most potent ligands of FimH in the tested series, which was not confirmed experimentally. On the other hand, it has to be kept in mind that the employed ELISA is not based on pure FimH, but rather on type 1-fimbriated bacteria, a dissimilar more complex system. The binding studies

• sugar ligand was allowed to change its conformation freely under the influence of the force field. ELISA ELISAs to determine IC50-values of the various FimH ligands were carried out with E. coli bacteria of strain HB101pPKL4 and mannan-coated microtiter plates as described earlier [21][22]. Mass

A bivalent glycopeptide to target two putative carbohydrate binding sites on FimH

• Thisbe K. Lindhorst,
• Kathrin Bruegge,
• Andreas Fuchs and
• Oliver Sperling

Beilstein J. Org. Chem. 2010, 6, 801–809, doi:10.3762/bjoc.6.90

• requires further investigation to be conclusive. Keywords: bacterial adhesion; bivalent ligand; ELISA; FimH; glycopeptides; Introduction Bacterial adhesion is a phenomenon which occurs on the surface of host cells as well as on the surface of surgical implants, where it can lead to the formation of

• -mediated bacterial adhesion The synthesis of the bivalent glycopeptide 1 was not optimized in order to improve all the individual yields, because it has been the primary goal of this study to test the anti-adhesive properties of this type of ligand. An ELISA was performed as reported earlier [32][33

• dilutions. This leads to inhibition curves, from which IC50-values can be deduced. The IC50-values reflect the inhibitor concentration that causes 50% inhibition of bacterial binding to mannan. ELISA measurements typically lead to IC50-values covering a broad range of absolute values. Therefore, highly

Synthesis of 6-PEtN-α-D-GalpNAc-(1–>6)-β-D-Galp-(1–>4)-β-D-GlcpNAc-(1–>3)-β-D-Galp-(1–>4)-β-D-Glcp, a Haemophilus influenzae lipopolysacharide structure, and biotin and protein conjugates thereof

• Andreas Sundgren,
• Martina Lahmann and
• Stefan Oscarson

Beilstein J. Org. Chem. 2010, 6, 704–708, doi:10.3762/bjoc.6.80

• examined. Compound 23 was also biotinylated for use in ELISA-screening of antibodies raised against native LPS. Reaction with the commercial NHS-activated ester of biotin followed by TFA-treatment to remove the Boc-group afforded derivative 25. The H. influenzae outer core target structure. i. BH3, Bu2BOTf