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Search for "cells" in Full Text gives 784 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
How and why plants and human N-glycans are different: Insight from molecular dynamics into the “glycoblocks” architecture of complex carbohydrates
Beilstein J. Org. Chem. 2020, 16, 2046–2056, doi:10.3762/bjoc.16.171
- , implicated in protein folding and structural stability, and mediating interactions with receptors and with the environment. All N-glycans share a common core from which linear or branched arms stem from, with functionalization specific to different species and to the cells’ health and disease state. This
- )-linked fucose and one with both core α(1-3)- and α(1-6)-linked fucose, a characteristic “double-fucose” glycosylation found in worm and fly cells [30]. As shown in Supporting Information File 1, Table S12 unlike in plants N-glycans, the α(1-3)-Fuc alone does not affect the A2G2 (1-6) arm equilibrium [24
Automated high-content imaging for cellular uptake, from the Schmuck cation to the latest cyclic oligochalcogenides
Beilstein J. Org. Chem. 2020, 16, 2007–2016, doi:10.3762/bjoc.16.167
- chemistry tools to deliver into living cells has seen a shift of attention from counterion-mediated uptake of cell-penetrating peptides (CPPs) and their mimics, particularly the Schmuck cation, toward thiol-mediated uptake with cell-penetrating poly(disulfide)s (CPDs) and cyclic oligochalcogenides (COCs
- high-content (HC) microscopy can satisfy this need. The automated imaging of thousands of cells per condition in multiwell plates allows us to obtain quantitative data on not only the fluorescence intensity but also on the localization in a very short time. Quantitative and statistically relevant
- results can be obtained from dose–response curves of the targeted delivery to selected cells and the cytotoxicity in the same experiment, even with poorly optimized cellular systems. Keywords: automation; cell-penetrating peptides; cellular uptake; cytosolic delivery; cytotoxicity; high-content imaging
Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio
Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154
- (3), and 25 μg/mL (4), respectively. None of the compounds showed cytotoxicity against 3Y1 rat embryonic fibroblastic cells below 50 μg/mL. Conclusion In summary, the known O-isocrotonyl-3-hydroxybutyric acid (4) and its three new congeners with different alkyl chain lengths, O-isocrotonyl-3
- . Antibacterial assay The antibacterial activity was evaluated by a microculture technique described previously [20], except for a 1:100 reduction of the seeding density of T. maritimum NBRC16015. Cytotoxicity assay 3Y1 rat embryonic fibroblastic cells were maintained in low-glucose DMEM medium containing ʟ
- cells were seeded in each well of a 96-well culture plate at a density of 2500 cells/well. Meanwhile, the compounds 1–4 and doxorubicin hydrochloride as a positive control were serially diluted 1:3.16 (half-log dilution) by the same medium in a different microtiter plate. After incubating the cell
Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides
Beilstein J. Org. Chem. 2020, 16, 1820–1829, doi:10.3762/bjoc.16.149
- absorption spectra were recorded on a Varian Cary 100 spectrophotometer. The irradiation of acetonitrile solutions in quartz cells (l = 10 mm, V = 2.mL) with a high pressure Hg lamp (250 W) was performed on a Newport 66941 equipment supplied with a set of interferential light filters. The intensity of light
One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway
Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148
- pharmaceutical products [15]. Moreover, they are used as electrolyte components in Li-ion rechargeable cells and as aprotic polar solvent with high boiling point as alternative of dangerous solvents because of their good biodegradability and low toxicity [16][17][18]. Synthetic intermediates for ring-opening
- purification. Melting points were determined on a melting-point apparatus (Gallenkamp; WA11373) and are uncorrected. IR spectra were obtained from solutions in 0.1 mm cells and in CH2Cl2 with a Perkin–Elmer spectrophotometer. 1H and 13C NMR spectra were recorded on Varian and Bruker spectrometers at 400 and
Models of necessity
Beilstein J. Org. Chem. 2020, 16, 1649–1661, doi:10.3762/bjoc.16.137
- layer of imperfection. Biological systems are even more complex, with an extraordinarily large concentration of molecules in, for instance, cells. In such systems, the necessity to sample all possible geometrical configurations of the system becomes the second major hurdle to accurate simulations. Even
Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells
Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133
- arylhydrazono-DHBERs and -THBERs has been evaluated on NCI-H1975 lung cancer cells. Keywords: antiproliferative agent; dihydroberberine; hydrazones; reduction; tetrahydroberberine; Introduction The rhizome of Coptis chinensis Franch. is a common remedy in traditional oriental medicine for the treatment of
- ]. Evaluation of the antiproliferative activity of hydrazono-DHBERs 2 and hydrazono-THBERs 3 As regards the in vitro experiments on lung cancer cells, two different tests were applied to evaluate the effects of hydrazono-DHBERs 2a–n and hydrazono-THBERs 3a–g,i–n [70] on the NCI-H1975 cell proliferation. Both
- WST-8 [2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetrazolium, monosodium salt] (Figure 5) and SRB (sulforhodamine B) (Figure 6) assays revealed that DHBER significantly reduced the cancer cell proliferation as compared to untreated cells both at 24 and 48 h of incubation
Heterogeneous photocatalysis in flow chemical reactors
Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125
- be irradiated at different wavelengths and inject electrons to the photocatalyst or vice versa. The same methodology is commonly applied in dye-sensitised solar cells [102]. Additionally, as only the surface of the support is functionalised with photoactive units, they are more likely to be
4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity
Beilstein J. Org. Chem. 2020, 16, 1489–1494, doi:10.3762/bjoc.16.124
- tuberculosis H37Ra at IC90 6.8 μM while weakly cytotoxic to MRC-5 human lung-derived fibroblasts with GI50 84.7 μM [30]. It did not inhibit the production of nitric oxide in RAW 264.7 murine macrophage-like cells [31]. In our hands, 1 was inactive against any of the tested strains including Staphylococcus
- reactive oxygen species (ROS), is implemented in eukaryotic cells, including protists [32], as an innate immune response to deactivate foreign substances or as part of phagocytic digestion of internalized nutrients [33]. Pathogenic microbes are equipped with a multitude of strategies to circumvent host
Photocatalyzed syntheses of phenanthrenes and their aza-analogues. A review
Beilstein J. Org. Chem. 2020, 16, 1476–1488, doi:10.3762/bjoc.16.123
- the design of dye-sensitized solar cells (DSSC) [4]. Typical methods for the construction of a phenanthrene core involve transition-metal-catalyzed cycloisomerizations starting from arynes [5][6], o-alkynyl-biaryls [7][8], or substituted N-tosylhydrazones [9]. However, since the introduction in 1964
One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol
Beilstein J. Org. Chem. 2020, 16, 1456–1464, doi:10.3762/bjoc.16.121
- IV inhibitor carmegliptin (2, DPP IV) with potential for the treatment of type-II diabetes [3][4]. A comparative study on novel classes of anticancer drugs identified benzo[a]quinolizines 3 and 4 (Figure 1) to be useful for a specific inhibition of heat shock response in cancer cells, which strongly
- enhances the treatment by sensitizing cancer cells to anticancer drugs [5]. The presence of such structural pattern has driven the development of various approaches for its obtaining – based either on isolation from naturally occurring sources or through multistep synthetic routes [6]. The pyrrolo[2,1-a
Anthelmintic drug discovery: target identification, screening methods and the role of open science
Beilstein J. Org. Chem. 2020, 16, 1203–1224, doi:10.3762/bjoc.16.105
- cells, is the only one for which a complete wiring diagram is known [87], facilitating studies on neural signalling and nervous and neuromuscular disorders [88] as well as research in understanding the anthelmintic drug action [89][90]. To grow and maintain C. elegans in the laboratory is relatively
- cells and zebrafish). By this means, they identified 30 structurally distinct anthelmintic lead molecules [94]. They also determined the target (complex II of the electron transport chain) of one lead compound, that showed nematode specificity and nanomolar potency. This work shows that C. elegans can
A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA
Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100
- two aptamers mentioned above was tested on full-length mRNA [26]. To investigate the ability of the proposed SDFS to selectively detect a full-length AR RNA we performed experiments on total RNA that was extracted from human dermal papilla cells (HDPC) obtained from the cell culture collection of the
- Koltsov Institute of Developmental Biology of the Russian Academy of Sciences (Moscow, Russia). These cells demonstrated a high level of AR mRNA expression (Figure S5, Supporting Information File 1) and by that were considered as a good model for our study. Extracted total RNA of HDPC was added to the
- samples. As a negative control samples containing total RNA from HeLa cells, which referred to be steroid receptor negative [27], with SDFS and malachite green dye were incubated and measured as well (Figure 3). A comparison of the fluorescence data presented above showed that the signal from samples
A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium
Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97
- Glomerella cingulata. All compounds showed moderate cytotoxicity against P388 murine leukemia cells with IC50 values in the micromolar to submicromolar ranges. These results exemplified the validity of phylogeny-focused strain selection combined with biosynthetic gene-directed genome mining for the efficient
- P388 murine leukemia cells with IC50 values of 11, 0.12, 0.35, and 3.7 μM, respectively. Conclusion Many unique features differentiate compounds 1–4 from known metabolites: a tripeptide sequence Tyr–Pro–Trp in 1 is shared with several opiate class endogeneous neuropeptides [28], but not with secondary
- File 310: Copies of NMR chemical shifts calculation for compound 1. Acknowledgements P388 cells were obtained from JCRB Cell Bank under an accession code JCRB0017 (Lot. 06252002). Funding This work was supported by JSPS KAKENHI Grant Number 19K05848 to Y. I.
Synthesis and anticancer activity of bis(2-arylimidazo[1,2-a]pyridin-3-yl) selenides and diselenides: the copper-catalyzed tandem C–H selenation of 2-arylimidazo[1,2-a]pyridine with selenium
Beilstein J. Org. Chem. 2020, 16, 1075–1083, doi:10.3762/bjoc.16.94
- appropriate quantity under otherwise identical reaction conditions. The prepared selenides and diselenides bearing two imidazo[1,2-a]pyridine rings were all novel compounds. Among the prepared diselenides and selenides that exhibited cytotoxicity against cancer cells, bis[2-(4-methoxyphenyl)imidazo[1,2-a
- ]pyridin-3-yl] diselenide showed an excellent anticancer activity and low cytotoxicity toward noncancer cells, suggesting that this diselenide is a potential lead compound for anticancer therapy. Keywords: anticancer activity; copper catalyst; diselenide; imidazopyridine; selenide; selenium; Introduction
- reductive elimination to afford the diselenide 2. The anticancer activity of the novel synthesized bis(2-arylimidazo[1,2-a]pyridin-3-yl) diselenides 2 and selenides 3 was evaluated in human cervical cancer HeLa cells (Figure 5). At 25 µM, each compound significantly decreased the cell viability compared to
Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties
Beilstein J. Org. Chem. 2020, 16, 1066–1074, doi:10.3762/bjoc.16.93
- synthesised solar cells (DSSCs) and sensors [1][2]. In OLEDs, carbazole derivatives are frequently used as host materials [3][4][5]. In this respect the most frequently used host materials are 1,3-bis(N-carbazolyl)benzene (mCP) [6] and polyvinylcarbazole (PVK) [7]. Carbazole derivatives, either just by
- multifunctionalisation [31]. In this work, we designed two novel 2-(N-hexylcarbazol-3’-yl)-4/5-formylpyridine compounds (7a and 7b), where 4/5-pyridinecarboxyaldehyde was attached to the 3-position of carbazole via the 2-position of the pyridine ring. These two compounds (7a and 7b) can be used in OLEDs, solar cells and
Fluorinated phenylalanines: synthesis and pharmaceutical applications
Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91
- ][127] (Figure 10). 5.2.6. The glucagon-like peptide-1 receptor (GLP1R): 3’-Fluorophenylalanine is a key motif in the structure of the glucagon-like peptide-1 receptor (GLP1R, 188, Figure 11). GLP1R is a receptor protein found on beta cells of the pancreas and on neurons of the brain. It is
Cation-induced ring-opening and oxidation reaction of photoreluctant spirooxazine–quinolizinium conjugates
Beilstein J. Org. Chem. 2020, 16, 904–916, doi:10.3762/bjoc.16.82
- = 7.27, δC = 77.0; CD3CN: δH = 1.94, δC = 1.34). The chemical shifts are given in ppm. Absorption spectra were recorded with a Cary 100 Bio or with an Analytik Jena Specord S 600 spectrophotometer in Hellma quartz cells 110-QS or 114B-QS (10 mm), with baseline correction at 20 °C. Emission spectra were
- collected with a Cary Eclipse spectrophotometer in Hellma quartz cells 114F-QS (10 mm × 4 mm) at 20 °C. Elemental analyses data were determined with a HEKAtech EUROEA combustion analyzer by Mr. Rochus Breuer (Universität Siegen, Organische Chemie I). Mass spectra (ESI) were recorded on a Finnigan LCQ Deca
- respective solvent. For spectrometric titrations, aliquots of the spirooxazine solutions were placed into quartz cells and titrated with the metal salt solutions in intervals of 0.15–0.25 equivalents, and after an equilibration time of 3 min absorption spectra were recorded. The titrations were stopped when
Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid
Beilstein J. Org. Chem. 2020, 16, 798–808, doi:10.3762/bjoc.16.73
- instance, the hydroxy group can be converted into an oxime, acyloxyimino, alkoxyimino, alkoxy and 3-oxo group [9]. As a proteasome inhibitor, compound a suppresses the chymotrypsin-like activity of the proteasome in MT4 cells with an IC50 of 0.22 μM, nearly 100-fold more potent than 18β-glycyrrhetinic acid
Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules
Beilstein J. Org. Chem. 2020, 16, 738–755, doi:10.3762/bjoc.16.68
- , thereby affording the triene intermediate in a substantial yield. Additional transformations using conventional methods efficiently provided (−)-amphidinolide E (3). Amphidinolide K, another important bioactive macrolide endowed with specific cytotoxic activity against L1210 and KB cancer cells, was also
- K562 cells [87][88]. In this innovative work, the authors effectively combined an enyne metathesis promoted by the Grubbs first-generation catalyst and an alkene cross-metathesis induced by the Grubbs second-generation catalyst with reverse electron-demand Diels–Alder cycloadditions (Scheme 20). In
Design and synthesis of diazine-based panobinostat analogues for HDAC8 inhibition
Beilstein J. Org. Chem. 2020, 16, 628–637, doi:10.3762/bjoc.16.59
- classified as highly potent amongst traditional HDACis [11]. According to previous reports, panobinostat not only induces apoptosis in cells, but also stimulates cell growth inhibition, and cell-cycle arrest in a time- and dose-dependent manner. Thus, panobinostat has demonstrated high therapeutic potential
A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions
Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52
- and capable to perform over a wide temperature range, increases the attractiveness of carbon nanomaterials [56]. Carbon materials have been used in different areas, including water purification, gas separation, fuel cells, photocatalysis, catalyst supports, etc. [57][58][59][60][61][62]. Different
Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus
Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29
- unambiguously determined to be E. α-Keto fatty acids are characterized by the presence of a keto group at the α-position of a carboxylic acid moiety. They are present in all living cells and play crucial roles in biological systems as they are involved in the Krebs cycle and glycolysis [20]. In contrast, keto
- eggplant calyx induces apoptosis in human ovarian cancer cells, leading to cell death [33]. One example of a keto fatty acid from the animal kingdom is (E)-9-oxo-2-decenoic acid, a sex pheromone found in royal jelly. Queen honey bees use this fatty acid to control the activity of worker bees [34]. (E)-7
- cytotoxicity against murine leukemia P388 cells at 100 µM. Additionally, compounds 1 and 2 were evaluated for agonist activity to peroxisome proliferator-activated receptors (PPARs) because similar oxo fatty acids are known to act as PPAR agonists [42]. PPARs are ligand-activated transcription factors playing
Synthesis of 4-(2-fluorophenyl)-7-methoxycoumarin: experimental and computational evidence for intramolecular and intermolecular C–F···H–C bonds
Beilstein J. Org. Chem. 2020, 16, 190–199, doi:10.3762/bjoc.16.22
- coumarins have been identified from natural sources [1][2]. Coumarins have been reported to play a vital role as food and cosmetics constituents, cigarette additives, and dye-sensitized solar cells [3][4]. In addition, coumarins possess some biological activities such as anti-inflammatory [5], antitumor [6
Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo
Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14
- (Figure 1a). Indanocine is a cytotoxic indanone-based CDI (EC50 ≈ 10–40 nM) [22] with similar cell culture potency to colchicine (EC50 ≈ 3–20 nM) [23] that likewise disrupts MTs, arrests cells in the G2/M phase, and induces apoptosis. Although the size and geometry of thioindoxyl and indanone rings differ
- nm), photoswitching could not be observed either, which we presumed to be due to fast thermal relaxation. However, noting that typical CDIs are substantially biolocalised into lipid environments within cells [31], we decided to explore photoswitching-based cellular assays with these compounds
- lighting conditions (Figure 4). Inhibitors of tubulin polymerisation act as antimitotic cytotoxins in cell culture by preventing formation of a functional mitotic spindle, resulting in mitotic arrest and eventually cell death. The reduction of resazurin by viable cells serves as a fluorogenic proxy readout
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