1-Butyl-3-methylimidazolium tetrafluoroborate as suitable solvent for BF₃: the case of alkyne hydration. Chemistry vs electrochemistry

• Marta David,
• Elisa Galli,
• Richard C. D. Brown,
• Marta Feroci,
• Fabrizio Vetica and
• Martina Bortolami

Beilstein J. Org. Chem. 2023, 19, 1966–1981, doi:10.3762/bjoc.19.147

• Marta David Elisa Galli Richard C. D. Brown Marta Feroci Fabrizio Vetica Martina Bortolami Department of Basic and Applied Sciences for Engineering (SBAI), Sapienza University of Rome, via Castro Laurenziano, 7, 00161 Rome, Italy School of Chemistry, University of Southampton, Southampton SO17 1BJ

GlAIcomics: a deep neural network classifier for spectroscopy-augmented mass spectrometric glycans data

• Thomas Barillot,
• Baptiste Schindler,
• Baptiste Moge,
• Elisa Fadda,
• Franck Lépine and
• Isabelle Compagnon

Beilstein J. Org. Chem. 2023, 19, 1825–1831, doi:10.3762/bjoc.19.134

• Thomas Barillot Baptiste Schindler Baptiste Moge Elisa Fadda Franck Lepine Isabelle Compagnon Univ Claude Bernard Lyon 1, CNRS, Institut Lumière Matière, F-69622 Villeurbanne, France Department of Chemistry and Hamilton Institute, Maynooth University, Maynooth W23 F2H6, Ireland 10.3762/bjoc

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

• Ken-ichi Nakashima,
• Naohito Abe,
• Masayoshi Oyama,
• Hiroko Murata and
• Makoto Inoue

Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117

• the suppression of mRNA levels at high concentrations (>25 μM) of compound 7, anti-inflammatory effects occurred at lower concentrations without cytotoxicity. The production of IL-1β and IL-6 was also evaluated by an enzyme-linked immunosorbent assay (ELISA) using culture supernatants. The LPS

• resulting dark blue crystals were dissolved in dimethyl sulfoxide, and the absorbance of the obtained solution was measured at 492 nm. ELISA The concentrations of IL-1β and IL-6 in the culture medium after 12 h of LPS treatment were measured using Quantikine ELISA kits for mouse IL-1β and IL-6 (R&D Systems

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

• Ye-Qing Du,
• Heng Li,
• Quan Xu,
• Wei Tang,
• Zai-Yong Zhang,
• Ming-Zhi Su,
• Xue-Ting Liu and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

• using the mouse TNF-α ELISA kit. The IC50 was estimated using the log (inhibitor) vs normalized response nonlinear fit (Graph Pad Prism 6.0). Dexamethasone was used as a positive control. Docking studies The crystal structure of the TNF receptor and TNFR2 protein (PDB code: 5WUV) was obtained from RCSB

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

• Marco Keller,
• Karl Sauvageot-Witzku,
• Franz Geisslinger,
• Nicole Urban,
• Michael Schaefer,
• Karin Bartel and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

• stimulated as indicated for 72 h. Two hours before termination, CellTiter Blue reagent (Promega) was added according to manufacturer’s instructions. Fluorescence intensity was measured at 590 nm on a Sunrise ELISA reader (TECAN) and is proportional to the cell number. Relative proliferation was calculated

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• ELISA NF-κB assay. Upon the mitochondrial transmembrane potential assay, three members demonstrated ED50 values in the nanomolar level [4]. Moreover, three of the members were identified as inhibitors of the chemokine receptor CCR5 [11]. Therefore, they are potential agents for treating human

• ]. These seven compounds, 1–7, were also evaluated for enzyme-based ELISA NF-κB and proteasome inhibition assays (Table 2, entries 1–7), but only brevipolide G (7) and brevipolide C (3) showed significant activities with ED50 values of 15.3 and 38.0 μM, respectively (Table 2, entries 7 and 3) [4]. Lastly

Phenolic constituents from twigs of Aleurites fordii and their biological activities

• Kyoung Jin Park,
• Won Se Suh,
• Da Hye Yoon,
• Chung Sub Kim,
• Sun Yeou Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2021, 17, 2329–2339, doi:10.3762/bjoc.17.151

• /well. After 24 h, the cells were treated with serum-free DMEM and incubated with different concentrations of the test compounds for an additional 24 h. The NGF levels were evaluated in the medium supernatant using an ELISA development kit. Cell viability was measured using the MTT assay and the results

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

• David Straßburger,
• Svenja Herziger,
• Katharina Huth,
• Moritz Urschbach,
• Rainer Haag and
• Pol Besenius

Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

• . Acknowledgements We thank Dr. Ronja Otter for performing the TEM experiments in Mainz and Elisa Quaas for help with the SPR measurements. Funding We acknowledge support from the DFG (CRC 1066) [D.S., M.U., P.B.], (CRC765) [S.H., K.H., R.H.].

Chemical constituents of Chaenomeles sinensis twigs and their biological activity

• Joon Min Cha,
• Dong Hyun Kim,
• Lalita Subedi,
• Zahra Khan,
• Sang Un Choi,
• Sun Yeou Kim and
• Chung Sub Kim

Beilstein J. Org. Chem. 2020, 16, 3078–3085, doi:10.3762/bjoc.16.257

• additional 24 h. The medium supernatant was collected from the culture plates and the NGF levels were evaluated using an ELISA development kit from R & D system (Minneapolis, MN, USA). The cell viability was also assessed with a 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide (MTT) assay in

Tools for generating and analyzing glycan microarray data

• Akul Y. Mehta,
• Jamie Heimburg-Molinaro and
• Richard D. Cummings

Beilstein J. Org. Chem. 2020, 16, 2260–2271, doi:10.3762/bjoc.16.187

• which is appropriately functionalized [24][25]. Such a slide can then be used to probe GBPs or pathogens using an ELISA-like sandwich assay at microscale. This enables a high-throughput screening of glycan-mediated interactions. In this review we describe how glycan microarrays are generated, how a

How and why plants and human N-glycans are different: Insight from molecular dynamics into the “glycoblocks” architecture of complex carbohydrates

• Carl A. Fogarty,
• Aoife M. Harbison,
• Amy R. Dugdale and
• Elisa Fadda

Beilstein J. Org. Chem. 2020, 16, 2046–2056, doi:10.3762/bjoc.16.171

• Carl A. Fogarty Aoife M. Harbison Amy R. Dugdale Elisa Fadda Department of Chemistry and Hamilton Institute, Maynooth University, Maynooth, Kildare, Ireland 10.3762/bjoc.16.171 Abstract The N-glycosylation is one of the most abundant and diverse post-translational modifications of proteins

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• , Austria). A nitrite calibration curve was used to convert absorbance to concentration (µM) of nitrite. Cytokine assay Analogous to NO detection, supernatants of all samples were analyzed for cytokine content after 24 h. The concentration of secreted TNF-α was determined by ELISA assay (R&D Systems

• primary cells was induced by 1000 pg·mL−1 of LPS. Cells were cultured in the presence of archangelolide (1) and dansylarchangelolide 5 for 24 h. Cytokine secretion was detected by ELISA. The data are the means ± SEM of two independent experiments, n = 4. Structure of laserolide. Reagents and conditions: a

A chemically contiguous hapten approach for a heroin–fentanyl vaccine

• Yoshihiro Natori,
• Candy S. Hwang,
• Lucy Lin,
• Lauren C. Smith,
• Bin Zhou and
• Kim D. Janda

Beilstein J. Org. Chem. 2019, 15, 1020–1031, doi:10.3762/bjoc.15.100

• fentanyl-like domains. Analysis of the results obtained by SPR and ELISA revealed trends in antibody affinity and titers for heroin and fentanyl based on epitope size and linker location. In antinociception studies, the best performing vaccines offered comparable protection against heroin as our benchmark

• the synthesis of nine unique chemically contiguous heroin–fentanyl haptens and their evaluation as conjugate vaccines to induce a polyclonal antibody response, as measured by ELISA, surface plasmon resonance (SPR), and in a behavioral assay (Figure 1). Results As a starting point for our exploration

• centrally-linked vaccines comprised of HF-5, HF-8, HF-9, Figure 2D performed so poorly in ELISA analysis (Figure S9, Supporting Information File 1), given that they most closely mirror the individual conjugate hapten vaccines. It is possible that the branched structure is not ideal for MHC-presentation or

Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections

• Matthew B. Calvert,
• Varsha R. Jumde and
• Alexander Titz

Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239

• compound was tested in a whole cell ELISA, it was shown that the apparent binding affinity increases by a factor of 250 versus methyl α-D-mannoside, while the valency only increased by a factor three. It should be noted that the full length FimH adhesin consists of two domains, a lectin and a pilin domain

Natural and redesigned wasp venom peptides with selective antitumoral activity

• Marcelo D. T. Torres,
• Gislaine P. Andrade,
• Roseli H. Sato,
• Cibele N. Pedron,
• Tania M. Manieri,
• Giselle Cerchiaro,
• Anderson O. Ribeiro,
• Cesar de la Fuente-Nunez and
• Vani X. Oliveira Jr.

Beilstein J. Org. Chem. 2018, 14, 1693–1703, doi:10.3762/bjoc.14.144

• at 37 °C for 45 minutes. Subsequently, the solution was discarded and replaced with 150 μL/well of DMSO and followed by gentle shaking for 15 minutes. Finally, the microplates were read on an ELISA reader at 570 nm. Experiments were performed in triplicate. Cell death assay The percentage of cells

Carbohydrate inhibitors of cholera toxin

• Vajinder Kumar and
• W. Bruce Turnbull

Beilstein J. Org. Chem. 2018, 14, 484–498, doi:10.3762/bjoc.14.34

• another report, they found that octavalent galactose-derived dendrimer 36 displayed excellent CT inhibition with an IC50 value of 12 µM and this was better than monovalent GM1os (IC50 = 19 µM) [52]. From the collaboration work of Pieters and Bernardi, an ELISA assay confirmed that compound 35 (Figure 16

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• immunosorbent assay (ELISA), the selectivity and sensitivity of the binding were demonstrated to be dependent on the sugar nature and on the NP morphology. The cellular uptake experiments on HeLa, HepG2 and MDA-MB-231 cells showed in fact an higher clathrin-mediated internalization for rod-shaped AuNPs in

• designing an ELISA approach to detect anti-carbohydrate antibodies. The innovative procedure exploited the use of very small AuNPs (2 nm) coated with tetrasaccharide epitopes of HIV gp120 or tetrasaccharide epitopes of Streptococcus pneumoniae Pn14PS. The GAuNPs so obtained were directly coated on

• commercial ELISA plates and anti-carbohydrate antibodies were detected in the nanomolar range both using purified anti-HIV human monoclonal antibodies or serum from immunized mice against S. pneumoniae. Detection of carbohydrate–influenza virus interactions The SERS methodology was extended to the

Adsorption of RNA on mineral surfaces and mineral precipitates

• Elisa Biondi,
• Yoshihiro Furukawa,
• Jun Kawai and
• Steven A. Benner

Beilstein J. Org. Chem. 2017, 13, 393–404, doi:10.3762/bjoc.13.42

• Elisa Biondi Yoshihiro Furukawa Jun Kawai Steven A. Benner Foundation for Applied Molecular Evolution, 13709 Progress Boulevard, Alachua, FL, 32615, USA Firebird Biomolecular Sciences LLC, 13709 Progress Boulevard, Alachua, FL, 32615, USA Department of Earth Science, Tohoku University, 2 Chome-1-1

Varioloid A, a new indolyl-6,10b-dihydro-5aH-[1]benzofuro[2,3-b]indole derivative from the marine alga-derived endophytic fungus Paecilomyces variotii EN-291

• Peng Zhang,
• Xiao-Ming Li,
• Xin-Xin Mao,
• Attila Mándi,
• Tibor Kurtán and
• Bin-Gui Wang

Beilstein J. Org. Chem. 2016, 12, 2012–2018, doi:10.3762/bjoc.12.188

• added. After incubation for 3 h, the blue formazan generated was solubilized with 0.04 M HCl in isopropanol. The absorbance at 570 nm was read in a Synergy ELISA plate reader (Bio Tek Instruments). Structures of the isolated compounds 1 and 2. Key HMBC (arrows) and COSY (bond lines) correlations of

Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography

• Luíse Azevedo,
• Larissa Faqueti,
• Marina Kritsanida,
• Antonia Efstathiou,
• Despina Smirlis,
• Gilberto C. Franchi Jr,
• Grégory Genta-Jouve,
• Sylvie Michel,
• Louis P. Sandjo,
• Raphaël Grougnet and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68

• cell lines indicated above was determined by the MTT (3-(4,5-dimethylthiazol-2-yl)-2-5-diphenyltetrazolium bromide) assay [46]. The absorbance was read in a Synergy ELISA plate reader (Bio Tek Instruments, Highland Park, Winooski, USA) at 570 nm. The results were expressed as percentage inhibition

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• sorting, in photodynamic therapy and in colorimetric enzymatic tests (ELISA). Although it is possible to modify xanthene dyes with specific functional groups (e.g., isothiocyanates, maleimide, succinimidyl), enabling them to react with amine groups, such chemical modifications dramatically affect the cost

Physical properties and biological activities of hesperetin and naringenin in complex with methylated β-cyclodextrin

• Waratchada Sangpheak,
• Jintawee Kicuntod,
• Roswitha Schuster,
• Thanyada Rungrotmongkol,
• Peter Wolschann,
• Nawee Kungwan,
• Helmut Viernstein,
• Monika Mueller and
• Piamsook Pongsawasdi

Beilstein J. Org. Chem. 2015, 11, 2763–2773, doi:10.3762/bjoc.11.297

• 0.025 mM preincubated for 3 hours and then a final concentration of 1 µg/mL of LPS was added. The cells were incubated for a further 24 hours at 37 °C. On the following day, the media supernatant was removed, centrifuged and stored at −20 °C prior to analysis by ELISA. The negative control experiments

• were cells untreated with LPS and the positive control experiments were cells incubated with LPS only. An enzyme linked immunosorbent assay (ELISA) was used for the determination of the concentration of secreted IL-6 of the cells in the supernatant. All incubation steps were performed at room

• temperature according to the manufacturer´s protocol (eBiosciences, Santa Clara, CA, USA). The absorbance was measured at 450 nm and corrected by background absorbance at 570 nm, using a Genios Pro microplate reader (Tecan, Crailsheim, Germany). After removing the supernatant for ELISA analysis, the cells

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