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Search for "cytotoxicity" in Full Text gives 281 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Clustering and curation of electropherograms: an efficient method for analyzing large cohorts of capillary electrophoresis glycomic profiles for bioprocessing operations
Beilstein J. Org. Chem. 2020, 16, 2087–2099, doi:10.3762/bjoc.16.176
- fucosylation or increase in galactosylation is needed for either antibody dependent cell cytotoxicity [1][2] or complement-dependent cytotoxicity [3][4], respectively, whilst additionally, antibody mannosylation is important for clearance [5]. For these reasons, glycosylation is a critical quality attribute
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
- ), here exemplified by asparagusic acid. A persistent challenge in this evolution is the simultaneous and quantitative detection of cytosolic delivery and cytotoxicity in a high-throughput format. Here, we show that the combination of the HaloTag-based chloroalkane penetration assay (CAPA) with automated
- 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
- transfection results. In contrast to the linear Schmuck peptides, the inactivity of a bafilomycin treatment in gene transfection processes indicates the nonendocytic cellular uptake pathway. Among the central challenges with CPPs in general are the cytotoxicity and the endosomal capture, particularly with an
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
- )-configuration of the 3-hydroxy acid components in 1–4. These compounds showed no cytotoxicity but were weakly antibacterial against a fish ulcer pathogen, Tenacibaculum maritimum. The (2Z)-enoic acyl termini in 1–4 are precedented by 5, discovered from another Vibrio bacterium, and the (R)-configured short
- . 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
Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida)
Beilstein J. Org. Chem. 2020, 16, 1596–1605, doi:10.3762/bjoc.16.132
- sponge prey availability [41]. The isolated metabolites showed various biological activities, such as cytotoxicity, antimicrobial, antiviral and antitumor activities, inhibition of transactivation for the farnesoid X receptor, inhibition of mammalian phospholipase A2, and ichthyotoxicity against the
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
- activity, with IC50 value for the xL3 motility improved to 0.38 µM and for the L4 development to 0.7 nM, with a similar activity for the corresponding fluoropyrazole derivative 24. These latter two compounds 23 and 24 showed high selectivity for the parasite, with low or no cytotoxicity. The authors went
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
- examined in antimicrobial and cytotoxicity assays (Table 3). Pseudosporamide (1) was not active against all microorganisms tested in this study. Pseudosporamicin 2–4 were selectively active against the Gram-positive bacterium Kocuria rhizophila and the filamentous fungus Glomerella cingulate, but were
- inactive against Staphylococcus aureus, Escherichia coli, Rhizobium radiobacter, and Candida albicans. The antimicrobial potency of 2 and 3 were similar, implying that the acyl side chain at C13 of compound 2 had no influence on the activity. In addition, compounds 1–4 showed moderate cytotoxicity against
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
- Figure 6, 2f also exhibited cytotoxicity against U251 human glioblastoma cells and HKBMM human malignant meningioma cells. Importantly, the diselenide 2f was more cytotoxic toward HeLa cancer cells than to human brain microvascular endothelial (HBME) cells, which are noncancerous (Figure 7). Hence, the
Efficient synthesis of piperazinyl amides of 18β-glycyrrhetinic acid
Beilstein J. Org. Chem. 2020, 16, 798–808, doi:10.3762/bjoc.16.73
- modifications at the C3-OH group of 18β-glycyrrhetinic acid are identified to be relatively common and effective. The modification of the C3-OH group, altering the molecular polarity of 18β-glycyrrhetinic acid, may be an advantage in achieving better cytotoxicity or antiproliferative activity [8][9][10]. For
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
- constitute a broad family of natural macrolides that act as powerful cytotoxic agents against various cancer cell lines. Due to the stereochemical intricacy and high cytotoxicity, these compounds have attracted a great deal of attention from synthetic chemists. The application of an intermolecular enyne
- highly critical parameter for their activity, while certain alterations of the side chain do not affect the cytotoxicity to a notable extent. Anthramycin In an interesting approach to the protected precursor 8 of (+)-anthramycin (8a), a compound with strong antitumor activity having a
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
- 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
- . The tests were done in triplicates, and the absorbance at a wavelength of 650 nm was measured with the help of a microplate reader. Cytotoxicity assay The cytotoxicity assay was carried out in a similar manner as described in [17]. P388 murine leukemia cells were maintained in RPMI-1640 medium
Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo
Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14
- future in vivo studies. We also noted that the para-hydroxy HITubs featured ca. 30% residual (Z)-HITub at PSS λ = 450 nm in cell-free measurements, and that for HITub-2–4, the PSS isomer mixture's cellular cytotoxicity at that wavelength was on average 3.3-fold lower than the cytotoxicity of the
Photocontrolled DNA minor groove interactions of imidazole/pyrrole polyamides
Beilstein J. Org. Chem. 2020, 16, 60–70, doi:10.3762/bjoc.16.8
- to modulate gene expression in an organism has attracted considerable interest in molecular medicine [1]. However, the missing selectivity of chemical agents, such as chemotherapeutics, often results in undesirable cytotoxicity, harming healthy cells, and thereby inducing a multitude of side effects
Light-controllable dithienylethene-modified cyclic peptides: photoswitching the in vivo toxicity in zebrafish embryos
Beilstein J. Org. Chem. 2020, 16, 39–49, doi:10.3762/bjoc.16.6
- , we noticed that there was generally a poor correlation between the antibacterial activity on the one side, and the cytotoxicity against HeLa cells on the other side, and erythrocytes as a third scenario. Different compounds could thus be regarded as potential leads for chemotherapy of either
- cells may not be the leading cause of in vivo toxicity for these membranolytic peptides. Based on the results described above, we wondered whether the cytotoxicity against epithelial cells should be considered as an important safety aspect for applications in humans, and whether it should be monitored
- such comparisons are known for peptides or peptidomimetics. When plotting the D. rerio embryotoxicity LD50 values of the ring-open (activated, ON) photoforms against the in vitro HeLa cytotoxicity indicators, namely against IC50 [30] of the ring-closed (deactivated, OFF) photoforms (Figure 5A), the
Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica
Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293
- cholesterol acyltransferase (ACAT) inhibitors [35], insecticides, antimicrobial agents, and immunomodulators [36]. In the current study, beauverolide N (4) displayed weak antibiofilm activity against S. aureus DSM1104 (MIC 250 μg/mL) and weak cytotoxicity against KB3.1 cells (IC50 16 μg/mL), while
- against Caenorhabditis elegans was investigated using a microtiter plate assay according to Helaly and co-workers [9], while the cytotoxicity was tested against murine fibroblast (L929) and human HeLa (KB3.1) cell lines according to Chepkirui and co-workers [50]. The isolated compounds were also tested
- Department in Thailand is gratefully acknowledged for permission to conduct a study in the protected area. We also thank Wera Collisi, Christel Kakoschke, and Donnaya Thanakitpipattana for conducting the cytotoxicity assay, NMR spectroscopic measurements, and providing some sequence data, respectively
Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis
Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286
- , cytotoxicity and antibiotic activity, the selectivity profile of this class of compounds should be considered for optimization of future antibacterials. The first total synthesis was reported by Ley and co-workers [14] for argyrin B in 18 linear steps, followed by an alternative strategy towards argyrin F (6
Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa
Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270
- during this cytotoxicity study [6]. Conclusion In summary, five previously undescribed tyromycin A derivatives 1–5 could be isolated from Skeletocutis sp. fruiting bodies. These metabolites are closely related to the skelotocutins that were previously reported as isolates from liquid cultures. Compounds
- albicans (C. albicans) DSM1665 were applied. The assays were conducted in 96-well plates and Mueller–Hinton Broth (MHB) for bacteria, or yeast, malt, and gluocse (YMG) medium for filamentous fungus and yeasts. Cytotoxicity assay In vitro cytotoxicity, using IC50 values as a measure, was evaluated against
- ITS sequences of the producing strain. Acknowledgements We are grateful to W. Collisi for conducting the cytotoxicity assays, C. Kakoschke for recording NMR data, and C. Schwager as well as E. Surges for recording HPLC–MS data. Financial support by the ASAFEM project (Grant no. IC-070) under the
Diversity-oriented synthesis of spirothiazolidinediones and their biological evaluation
Beilstein J. Org. Chem. 2019, 15, 2774–2781, doi:10.3762/bjoc.15.269
- dormancy) of drug candidates and toxic compounds. In vitro cytotoxicity was assessed using a standard MTT colorimetric assay in a similar manner as described in [60][61]. HEK293 cells were plated in 96-well microassay culture plates (1 × 104 cells per well) and grown overnight at 37 °C in a 5% CO2
- , the formazan crystals were dissolved in 150 μL of DMSO, and the absorbance was determined at 595 nm using a microplate spectrophotometer. The IC50 value was determined from plots of percent viability against the dose of the compound added. Cytotoxicity assay: Viability (live/dead) assessment was
Plasma membrane imaging with a fluorescent benzothiadiazole derivative
Beilstein J. Org. Chem. 2019, 15, 2644–2654, doi:10.3762/bjoc.15.257
- (GGA level) and ωB97XD (long range-corrected hybrid level) XCFs were employed. Both B97D3 and ωB97XD were strongly recommended by a thoroughly benchmarking of DFT methods for thermochemistry by Goerik and Grimme [55]. The new dye was then submitted to an MTT assay to investigate possible cytotoxicity
Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis
Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256
- , sponges, molluscs and other fungi as well and possess a wide range of bioactivities [24]. The drimane sesquiterpenoids isolated from Aspergillus spp. have exhibited in vitro anti-inflammatory [5] and antiviral [22] activities as well as cytotoxicity against several mammalian cell lines [4][16][22
- activity observed for 2, 3, 6 and 8. Compounds 2, 5, 8, 9 and 10 exhibited low levels of cytotoxicity against the four mammalian cell lines tested, while 3, 6 and 7 were considerably more cytotoxic. Notably, 4 showed strong activity against the mouse myeloma NS-1 cell line, but no activity against the
- activity against human and murine tumour cell lines. This suggests that the regioisomeric lactone moiety could play an important role in the observed cytotoxicity. Interestingly, 3 (SF002-96-1 [4]) was previously shown to inhibit survivin, which is a member of the inhibitor of apoptosis (IAP) family and a
Synthesis of novel sulfide-based cyclic peptidomimetic analogues to solonamides
Beilstein J. Org. Chem. 2019, 15, 2544–2551, doi:10.3762/bjoc.15.247
- cell viability assay on human fibroblasts (Detroit 551 cell line) was performed for compounds 9e and 9g in order to observe their eventual cytotoxicity to normal cells (see Supporting Information File 1, assay 4). The concentration range tested was 6.25 to 200 µM for 9e and 9.38 to 300 µM for 9g
α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA
Beilstein J. Org. Chem. 2019, 15, 2524–2533, doi:10.3762/bjoc.15.245
- preliminarily evaluated for anticancer activity towards HeLa cells. The administration of the analogues caused a significant decrease in the proliferation of HeLa cells. Furthermore, one of the analogues showed a maximum cytotoxicity with a minimum GI50 value of 2.5 µg/mL and the generation of reactive oxygen
- clearly the truncated analogue 11g is less effective. Loss of cell viability by LDH assay LDH assays quantitatively measures lactate dehydrogenase (LDH) released into the media from damaged cells as a biomarker for cellular cytotoxicity [35][36]. Hence, to further characterize compound-induced HeLa cell
- a minimal effect of cytotoxicity (≈9.1% necrotic as well as apoptotic cells, respectively), by observing the morphology of the cells under a microscope at a concentration of 15 μg/mL. ROS generation study by DCFDA (2′,7′-dichlorodihydrofluorescein diacetate) by FACS (fluorescence-activated cell
Current understanding and biotechnological application of the bacterial diterpene synthase CotB2
Beilstein J. Org. Chem. 2019, 15, 2355–2368, doi:10.3762/bjoc.15.228
- hydrolysis of the fatty acid ester bonds of lysophospholipids [31][41]. Moreover, cyclooctatin (5) was shown to be effective against Plasmodium falciparum with an IC50 of 7.14 µg/mL along with very low cytotoxicity [42]. CotB2 belongs to the class of cyclopentane-forming diterpene synthases [46], a class of
- cytotoxicity [82]. Further, thunbergol (18) is reported to repel aphids within 48 h by 70%, if wheat seedlings are topically treated with a 0.25% (w/w) solution in ethyl acetate, compared to untreated plants [25]. During application in agriculture a negative impact on useful insects, like bees, should be
Synthesis of a dihalogenated pyridinyl silicon rhodamine for mitochondrial imaging by a halogen dance rearrangement
Beilstein J. Org. Chem. 2019, 15, 2333–2343, doi:10.3762/bjoc.15.226
- only nano- or picomolar amounts of the radiopharmaceutical compound are needed, medical applications of fluorescence dyes (e.g., fluorescence-guided interventions) require larger amounts of material. Therefore, cytotoxicity testing is necessary for our proposed bimodal imaging agent 16 and its
- , without dye: 0.32 ± 0.06 divisions per cell, for division duration see Figure S7, Supporting Information File 1). These results are supported by cell count and confluency analysis (Figure S9, Supporting Information File 1). In summary, we conclude that dye 15 does not show any significant cytotoxicity in
- undisturbed cell proliferation in U2OS cells incubated with 1 µM of dye 15 for 1 h compared to untreated U2OS cells are given. Supporting Information File 442: Experimental and analytical data, spectra, live cell imaging and assessment of cytotoxicity. Supporting Information File 443: Independent experiment
Isolation of fungi using the diffusion chamber device FIND technology
Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216
- the appropriate test organism was significantly inhibited compared to a negative control; total inhibition: no growth at all in the appropriate zone. Benzylpenicillin (1 mg/mL MeOH), streptomycin (1 mg/mL MeOH) and miconazole (0.5 mg/mL DCM) were used as positive controls. Cytotoxicity assay HEK293
An overview of the cycloaddition chemistry of fulvenes and emerging applications
Beilstein J. Org. Chem. 2019, 15, 2113–2132, doi:10.3762/bjoc.15.209
- temperatures, as well as low levels of cytotoxicity against mouse fibroblast 3T3 cells [191]. With these characteristics in mind, the outlook for these hydrogels having therapeutic applications is promising, with further optimisation [236]. Pentafulvenes have also been used to prepare monomers for ring-opening
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