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Search for "cytotoxicity" in Full Text gives 281 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Synthesis of multi-lactose-appended β-cyclodextrin and its cholesterol-lowering effects in Niemann–Pick type C disease-like HepG2 cells
Beilstein J. Org. Chem. 2017, 13, 10–18, doi:10.3762/bjoc.13.2
- -Lac-β-CD had an average degree of substitution of lactose (DSL) of 5.6. This newly synthesized multi-Lac-β-CD was found to significantly decrease the concentration of intracellular cholesterol with negligible cytotoxicity as compared to HP-β-CD. An increased internalization of TRITC-multi-Lac-β-CD
- (Figure 2B). These results indicate the successful synthesis of multi-Lac-β-CD (DSL5.6). Cytotoxicity of multi-Lac-β-CD (DSL5.6) To evaluate the cytotoxicity of multi-Lac-β-CD (DSL5.6), cell viability was examined after treatment with multi-Lac-β-CD (DSL5.6) by the water-soluble tetrazolium (WST)-1 method
- (Figure 3). U18666A-treated HepG2 cells were used as NPC-like cells in this experiment because U18666A can inhibit cholesterol trafficking in cells and simulate NPC disease phenotypes [18]. No significant changes in cytotoxicity were observed in NPC-like HepG2 cells after treatment with 0.01–1 mM multi
Synthesis of spiro[isoindole-1,5’-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction
Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278
- . Assessment of cell proliferation was also performed cytofluorimetrically by the BrdU assay, [48] obtaining results that reflect data from MTS test (Figure 7b). Cytotoxic effect The cytotoxic effect induced by 6a–f was evaluated by an LDH assay [49], revealing that significant cytotoxicity was exerted only at
Interactions between cyclodextrins and cellular components: Towards greener medical applications?
Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261
- , the final effect is the same (i.e., hemolysis). It should be noted that this cholesterol and/or phospholipids extraction is not limited to erythrocytes. Indeed, all eukaryotic or prokaryotic cells are affected by the presence of CDs. For instance, the cytotoxicity of native, methylated, and
- cholesterol content in blood–brain barrier cells compared to erythrocytes. Indeed, the cholesterol fraction is markedly higher in erythrocytes than in other cells. As for hemolysis, the presence of hydrophilic substituents (e.g., 2-hydroxypropyl and sulfobutyl ether) annihilates the cytotoxicity while the
- consequences of this phenomenon (e.g., hemolysis or cytotoxicity, see section above). Since the nineties, β-CDs are known to have a high affinity, in vitro, for sterols as compared to other lipids [58][115]. Consequently, these molecules can be used to manipulate the cellular cholesterol content, to modify
A self-assembled cyclodextrin nanocarrier for photoreactive squaraine
Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248
- cytotoxicity. Santos et al. postulated the production of singlet oxygen as a result of interaction between the squaraines and the ground state of oxygen [19][20]. A few years later, Salice et al. showed that squaraines are not efficient singlet oxygen producing agents, but can be applied successfully as
Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B
Beilstein J. Org. Chem. 2016, 12, 2523–2534, doi:10.3762/bjoc.12.247
- towards CNS cytotoxic activity on undifferentiated SH-SY5Y neuroblastoma cells. None of the two isomeric compounds exerted cytotoxicity on this cell line (IC50 > 150 μM for both compounds), which rules out their potential CNS antitumor activity and it also suggests them as non-neurotoxic substances. On
Facile synthesis of indolo[3,2-a]carbazoles via Pd-catalyzed twofold oxidative cyclization
Beilstein J. Org. Chem. 2016, 12, 2490–2494, doi:10.3762/bjoc.12.243
- in 2002 [1]. Up to now, four members of this family were isolated from marine organisms (Figure 1) [1][2][3]. Preliminary results of the antimicrobial and cytotoxicity assays indicated that these compounds have medicinal potentiality to target neurological and psychiatric disorders [1][2]. Several
Enduracididine, a rare amino acid component of peptide antibiotics: Natural products and synthesis
Beilstein J. Org. Chem. 2016, 12, 2325–2342, doi:10.3762/bjoc.12.226
- the unique enduracididine-containing bromoindole metabolite 11 (Figure 4). This was the first time the enduracididine motif had been isolated from a marine source. The exact compound responsible for the observed cytotoxicity was not determined. Mannopeptimycins Mannopeptimycins α–ε (12–16, Figure 5
An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy
Beilstein J. Org. Chem. 2016, 12, 2240–2249, doi:10.3762/bjoc.12.216
- viruses [35], anti-HIV and anticancer [36][37], antimicrobial and antifungal activities as well as cytotoxicity to MCF-7 cells [38][39]. Based on these observations we therefore aimed at combining the spiropyrrolidinyloxindole motif with hetero-annelated 1,2,4-triazine scaffolds. Recently, we have already
The direct oxidative diene cyclization and related reactions in natural product synthesis
Beilstein J. Org. Chem. 2016, 12, 2104–2123, doi:10.3762/bjoc.12.200
- contrast to other representatives of this subgroup of acetogenins they are lacking one of the secondary alcohols usually framing the bis-THF core (Scheme 14). They were isolated from the leaves of Rollinia mucosa [108] and shown to exhibit cytotoxicity against six human tumor cell lines. Rollidecin C (69
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
Beilstein J. Org. Chem. 2016, 12, 2012–2018, doi:10.3762/bjoc.12.188
- varioloid B (2). Both compounds 1 and 2 exhibited cytotoxicity against A549, HCT116, and HepG2 cell lines, with IC50 values ranging from 2.6 to 8.2 µg/mL. Keywords: bisindolyl benzenoid derivatives; cytotoxicity; marine alga-derived fungus; Paecilomyces variotii; TDDFT-ECD calculation; Introduction The
- elucidation including the assignment of the absolute configuration, and the cytotoxicity studies of these compounds. Results and Discussion Varioloid A (1), obtained as a light brown solid, has the molecular formula C26H24N2O5 as established from a prominent pseudomolecular ion peak at m/z 445.1766 [M + H
- the same as that of 1. Both compounds 1 and 2 were evaluated for their cytotoxic activity using a panel of three tumor cell lines, A549 (human lung adenocarcinoma cells), HCT116 (human colon carcinoma cells), and HepG2 (human hepatoma cells). Both compounds exhibited relevant cytotoxicity. Compound 1
Rearrangements of organic peroxides and related processes
Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162
Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates
Beilstein J. Org. Chem. 2016, 12, 1229–1235, doi:10.3762/bjoc.12.117
- normal lymphocytes (IC50 = 230.8 µM). Keywords: aminophosphonic derivatives; cytotoxicity; fluorescence properties; MTT test; pyrene-1-carboxaldehyde; Introduction The biological activity of aminophosphonic systems is very well known and described, in aspect of their crop protective [1], antibacterial
- cytotoxicity against both tested cancer cell lines HT29 (IC50 = 24.2 µM) as well as HCT116 (IC50 = 20.8 µM) cells, and it simultaneously was not strongly toxic for normal human lymphocytes (IC50 = 230.8 µM). However, HT29 cells were more resistant to 3Ad than HCT116 cells. Therefore, the aminophosphonate 3Ad
- showed a carcinoma-specific cytotoxicity against human colon cancer cells. A similar correlation was observed for the aminophosphonic derivative 3Ac, which was strongly cytotoxic against both colon cancer cell lines, but in contrast to 3Ad, was also toxic for lymphocytes. Paradoxally, compound 3Ac
Antibacterial structure–activity relationship studies of several tricyclic sulfur-containing flavonoids
Beilstein J. Org. Chem. 2016, 12, 1065–1071, doi:10.3762/bjoc.12.100
- indicated that the newly synthesized tricyclic flavanoids exhibit similar or even better antimicrobial properties. However, due to the lack of cytotoxicity results one may assume that the investigated structures represent a promising class of compounds. In summary, the newly synthesized compounds exhibit
Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites
Beilstein J. Org. Chem. 2016, 12, 969–984, doi:10.3762/bjoc.12.96
- ), Candida albicans (DSM 1665) and Mucor hiemalis (DSM 2656, 33.3 μg mL−1 in each case). Significant cytotoxic activity was revealed for 22 towards SKOV-3 (IC50 = 2.4 μM), KB3-1 (IC50 = 5.3 μM), as well as A431 (IC50 = 8.45 μM), while 23 showed remarkable cytotoxicity against cell lines HUVEC and KB3-1 (IC50
Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents
Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77
- essential for bacterial survival or growth and offers selectivity to strike only bacterial cells (without cytotoxicity to human cells). There are mainly four classical target processes for antibiotics: bacterial cell wall biosynthesis, bacterial protein biosynthesis, DNA replication and folate metabolism
- ). These values were comparable to those of the naturally occurring congeners of the A and B series [22]. Generally, derivatives with the naturally occurring L-configuration in the leucine moiety showed slightly better activities. These lipophilic analogues were also tested for cytotoxicity towards Hep G2
- cells and showed no cytotoxicity (IC50 > 100 μg/mL) [114]. In another series of analogues with different peptide units, the pentadecyl side chain of 91a was kept. The L-epicapreomycidine (L-epi-Cpm) unit of 91a was replaced by L-capreomycidine (L-Cpm, 92a), L-arginine (L-Arg, 92b) and L-ornithine (L-Orn
Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine
Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75
- focused on the synthesis of acetylated 3-deoxy-3-fluoro, 4-deoxy-4-fluoro and 3,4-dideoxy-3,4-difluoro analogs of D-glucosamine and D-galactosamine via 1,6-anhydrohexopyranose chemistry. Moreover, the cytotoxicity of the target compounds towards selected cancer cells is determined. Results: Introduction
- -2-azido-hexopyranoses have potential as synthons in oligosaccharide assembly. Keywords: amino sugars; cytotoxicity; fluorinated carbohydrates; fluorine; hexosamines; Introduction Derivatives of D-glucosamine (GlcN) and D-galactosamine (GalN) are essential amino sugar components of glycans in
- ][29]. Herein we also report on the cytotoxicity of prepared fluoro analogs in the human ovarian cancer A2780 and prostate cancer PC-3 cell lines. Preliminary results for the synthesis of compounds 5 and 6 were communicated earlier in a letter [30]. Results and Discussion Synthesis The synthesis
Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography
Beilstein J. Org. Chem. 2016, 12, 674–683, doi:10.3762/bjoc.12.68
- against L. donovani, L. infantum and L. amazonensis (promastigotes and intracellular amastigotes). The cytotoxicity of the butanol fraction in murine macrophages was found weak, with an IC50 value at 290 μg/mL. However, the butanol fraction displayed activity against L. amazonensis intracellular
- cytotoxicity against murine macrophages and the leukemic cancer cell lines. Experimental Solvents, materials and instruments Ethanol for extraction and organic solvents for partitioning (hexane, dichloromethane, ethyl acetate, and butanol) as well as for CPC were pro-analysis grade (p.a.). Water was distilled
- experiments were performed at least three independent times in triplicate. In vitro cytotoxicity against leukemic cells The cell lines used in this study were HL60 (Acute Promyelocytic Leukemia), JURKAT (Acute T cell Leukemia) and REH (Acute Lymphocytic Leukemia non-T; non-B). The cells were grown in plastic
Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins
Beilstein J. Org. Chem. 2016, 12, 662–669, doi:10.3762/bjoc.12.66
- like leprosy caused by M. leprae. Recently, hydnocarpin (isolated from Brucea javanica; which was named as (−)-hydnocarpin, even though the enantiomeric purity was not determined) has been described as potentiator of vincristine’s cytotoxicity due to MDR inhibition [18]. Furthermore, 5
Biosynthesis of α-pyrones
Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56
- inhibited 10 out of the 24 kinases tested. The results of the MTT and the kinase assay showed a similar pattern, and hence it was concluded that protein kinase inhibition should be one mechanism leading to the cytotoxicity of 17. In a study using human colon carcinoma cells to elucidate the cell death mode
A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy
Beilstein J. Org. Chem. 2016, 12, 125–138, doi:10.3762/bjoc.12.14
- Hergenrother and it was found to have low cytotoxicity, enter DM1 model cells, dissolved the MBNL1 foci and partially corrected the missplicing of two key pre-mRNAs, cTNT and IR. A terrific collaboration with Professor Edwin Chan’s group at the Chinese University of Hong Kong allowed the compounds to be tested
Physical properties and biological activities of hesperetin and naringenin in complex with methylated β-cyclodextrin
Beilstein J. Org. Chem. 2015, 11, 2763–2773, doi:10.3762/bjoc.11.297
- inclusion complexes. The data obtained by the dissolution method showed that complexation with RAMEB resulted in a better release of both flavanones to aqueous solution. The flavanones-β-CD/DM-β-CD complexes demonstrated a similar or a slight increase in anti-inflammatory activity and cytotoxicity towards
- to increase water solubility, stability and bioavailability of those drugs [56][57]. In such a way, the bioavailability of genistein was found to be increased by complexation with CDs [58]. Cytotoxicity to cancer cell lines The cytotoxicity of flavanones and their inclusion complexes against three
- -loaded nanoparticles which exhibited significant cytotoxicity at high concentrations (30, 40 and 50 μg/mL) [59]. At low concentration (0.025 mM), naringenin complexed with DM-β-CD exerted a higher effect on MCF-7 and HeLa cells than free naringenin. However, for CaCo-2 cells, the effect of the naringenin
Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry
Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276
- CuSO4·5H2O and sodium ascorbate in DMF [35][36]. All the obtained compounds were evaluated for in vitro cytotoxicity against a panel of five human cancer cell lines, where compounds 45 and 46 displayed the highest and broadest spectrum activity against all five cancer cell lines under study (Scheme 16
Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa
Beilstein J. Org. Chem. 2015, 11, 2334–2342, doi:10.3762/bjoc.11.254
- of 1 and 2 were confirmed by an 1,1-ADEQUATE experiment. Compounds 1 and 2 showed a mild to moderate cytotoxic activities against KB-31 and FS4-LTM cell lines. Only aplysinin A (2) exhibited cytotoxicity against MCF-7 cells. Keywords: alkaloids; Aplysina lacunosa; bromotyrosine; marine natural
- luteus; Gram-negative: Peumonia aruginosa and Klebsiella pneumonia] and antifungal Candida albicans using microdilution technique. The MIC was defined as lowest concentration that shows 50% growth inhibition after 24 hour incubation. Cytotoxicity assay The cytotoxicity was determined using WST-1 cell
- ), hexadellin B (10), and diacetylhexadellin B (20). NMR data of aplysinin B (3) (600 MHz, DMSO-d6) and compound 21. Cytotoxicity of the isolated compounds (IC50).a Supporting Information Supporting Information File 448: 1D, 2D NMR, and CD spectra of three new compounds. 1D NMR, mass and CD spetra of all known
Cholesterol lowering effects of mono-lactose-appended β-cyclodextrin in Niemann–Pick type C disease-like HepG2 cells
Beilstein J. Org. Chem. 2015, 11, 2079–2086, doi:10.3762/bjoc.11.224
- preliminary result suggests that the inclusion ability of Lac-β-CyD is still maintained. Cytotoxicity of Lac-β-CyD To reveal the cytotoxicity of Lac-β-CyD, we examined the WST-1 method (Figure 3). Here, we used U18666A-treated HepG2 cells as NPC-like cells, because U18666A inhibits an intracellular
- cholesterol trafficking and has the potential to induce NPC disease phenotype [16]. No significant cytotoxicity of Lac-β-CyD was observed in U18666A-treated HepG2 cells at 1 mM for 24 h. The following studies were performed under the experimental conditions. Cellular uptake of TRITC-Lac-β-CyD To reveal
- cells, which accumulate the cholesterol and sphingolipids in cells, were prepared by the treatment with DMEM containing 1.25 μM U18666A for 48 h. Cytotoxicity In a similar manner as described in [30], cytotoxicity was assayed by the WST-1 method. Briefly, U18666A-treated HepG2 cells were seeded at 3
The marine sponge Agelas citrina as a source of the new pyrrole–imidazole alkaloids citrinamines A–D and N-methylagelongine
Beilstein J. Org. Chem. 2015, 11, 2029–2037, doi:10.3762/bjoc.11.220
- mice fibroblasts. Only minor antimicrobial activities were obtained for citrinamines B–D (2–4) whereas no activities were found in the cytotoxicity assay for citrinamines A–D (1–4). Experimental General experimental procedures 1H, 13C, and 15N NMR spectra were conducted on Bruker Avance I 400 MHz
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