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Search for "cytotoxic" in Full Text gives 303 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
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
- -benzylnitrone with isoindolin-3-methylene-1-ones. The regio- and stereoselectivity of the process have been rationalized by computational methods. The obtained compounds show cytotoxic properties and antiproliferative activity in the range of 9–22 μM. Biological tests suggest that the antitumor activity could
- inhibitory [32] and cytotoxic activity. Recently, MDM2-p53 inhibitors based on an isoindolinone scaffold [33][34] have been reported. These latter results demonstrate the versatility of the isoindolinone scaffold as MDM2-p53 inhibitor and show that significant improvements in potency may be gained by modest
- . 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
Symmetry-based approach to oligostilbenoids: Rapid entry to viniferifuran, shoreaphenol, malibatol A, and diptoindonesin G
Beilstein J. Org. Chem. 2016, 12, 2689–2693, doi:10.3762/bjoc.12.266
- diptoindonesin G, a potent cytotoxic and immunosuppressant agent [16][17], by using a highly efficient domino cyclodehydration/intramolecular Friedel–Crafts acylation/regioselective demethylation sequence as a key transformation. Very recently, a dual functional role of diptoindonesin G in modulating α and β
A self-assembled cyclodextrin nanocarrier for photoreactive squaraine
Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248
- Ulrike Kauscher Bart Jan Ravoo Organic Chemistry Institute and Center for Soft Nanoscience, Westfälische Wilhelms-Universität Münster, Corrensstrasse 40, 48149 Münster, Germany 10.3762/bjoc.12.248 Abstract Photoreactive squaraines produce cytotoxic oxygen species under irradiation and have
- interference of the PS with the triplet ground state of oxygen, leading to the production of singlet oxygen. In both mechanisms, the PS harvests the energy of incident light to form reactive oxygen species or singlet oxygen, which are highly cytotoxic [6][7]. Most clinically used PSs are based on porphyrins
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
Inhibition of peptide aggregation by means of enzymatic phosphorylation
Beilstein J. Org. Chem. 2016, 12, 2462–2470, doi:10.3762/bjoc.12.240
- Pmel17 amyloid templates and accelerates the covalent polymerization of reactive small molecules into melanin, an important biopolymer that protects against a broad range of cytotoxic insults, including UV and oxidative damage [11]. While amyloid morphologies and events which induce amyloid formation are
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
- mechanism is operative [31]. Indole metabolite In 1996, during a screening program for biologically active metabolites from marine ascidians, Riguera et al. identified a small group of amino acid containing compounds in a cytotoxic extract of the ascidian Leptoclinides dubius [32]. Among these compounds was
- B (8). Minosaminomycin (9) and related antibiotic kasugamycin (10). Enduracididine-containing compound 11 identified in a cytotoxic extract of Leptoclinides dubius [32]. Mannopeptimycins α–ε (12–16). Regions of the mannopeptimycin structure investigated in structure–activity relationship
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
- ’-spiropyrrolidinyloxindole core show various biological effects such as bactericidal and fungicidal [21], anticancer [22], cytotoxic to MCF-7 and HepG2 cells [23][24], and advanced glycation end (AGE) product formation inhibitory activities [25] (Figure 1). Over the last decade, a lot of publications have been devoted to
- class of promising bioactive polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties. Investigations of cytotoxic activities of the synthesized products against A549, HCT116, RD, and MCF7 cell lines are in progress. Bioactive 2,3
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
- monensin A, another well-known ionophore antibiotic, applying an oxidative cyclization approach using potassium permanganate [64]. Amphidinolide F Amphidinolide F (24) is a marine natural product isolated from the dinoflagellate Amphidinium sp. in 1991 [65]. The macrocyclic core of these highly cytotoxic
- advantage of the meso-geometry of the central THF diol moiety [80]. cis-Sylvaticin cis-Sylvaticin (40), a non-adjacent bis-THF acetogenin [92] (Scheme 10), was discovered in dried fruits of Rollinia sylvatica [93] and leafs of Rollinia mucosa [94]. It has been shown to be cytotoxic against several cancer
- oxide (79) in a further few steps. Teurilene Teurilene (82) is a squalene-derived cytotoxic polyether which was originally extracted from the red algae Laurencia obtusa by Suzuki et al. [138][139]. Though it is CS-symmetric, it is structurally closely related to pentacyclic C2-symmetric glabrescol [140
Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group
Beilstein J. Org. Chem. 2016, 12, 2093–2098, doi:10.3762/bjoc.12.198
- acidic media were observed in the course of the described transformation. Moreover, the intermediate 6-imino-2,7-dioxabicyclo[3.2.1]octane-4,4,5-tricarbonitriles 3 had demonstrated a cytotoxic activity in various cancer cell lines [32], therefore the derived 3,4-dihydro-2H-pyrans 2 are very promising for
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
- DPPH radical scavenging activity [11], and two new prenylated indole alkaloids with cytotoxic activity [12] had been isolated and identified. In an effort to isolate additional analogues that might show similar effects, a larger fermentation was undertaken. This study led to the isolation of two
- 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
- (d) level in vacuo. The MOLEKEL [23] software package was used for visualization of the results. Cytotoxicity assay: The cytotoxic activities against A549, HCT116, and HepG2 cell lines were determined by the MTT (3-(4,5-dimethylthiazol-2-yl)-2-5-diphenyltetrazolium bromide) assay according to
Rearrangements of organic peroxides and related processes
Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162
Biosynthesis of oxygen and nitrogen-containing heterocycles in polyketides
Beilstein J. Org. Chem. 2016, 12, 1512–1550, doi:10.3762/bjoc.12.148
Beta-hydroxyphosphonate ribonucleoside analogues derived from 4-substituted-1,2,3-triazoles as IMP/GMP mimics: synthesis and biological evaluation
Beilstein J. Org. Chem. 2016, 12, 1476–1486, doi:10.3762/bjoc.12.144
- their corresponding nucleosides [2][3]. Recent studies on patients affected by haematological malignancies, such as acute myeloid leukaemia (AML) and myelodysplasic syndrome (MS), have demonstrated the involvement of cN-II in the resistance to cytotoxic drugs such as mercaptopurines and suggested the
Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA
Beilstein J. Org. Chem. 2016, 12, 1348–1360, doi:10.3762/bjoc.12.128
- transformations. So, this reaction is suitable for the synthesis of different biologically important conjugates including polyamide-TFO conjugates and fluorescent probes based on these components. Several methods avoiding the presence of cytotoxic copper ions have been also described [27][28][29]. Baskin et al
Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides
Beilstein J. Org. Chem. 2016, 12, 1250–1268, doi:10.3762/bjoc.12.120
- identified by signature protein domains. Finally, many RiPPs do not possess antimicrobial or cytotoxic activity, so are not identified by classical activity-based screens. Mass spectrometry (MS) represents a relatively unbiased approach to screening for the production of novel RiPPs, although this is non
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
- derivatives on two colon cancer cell lines HT29 and HCT116 was also investigated. The most promising results were obtained for N-(4-methoxyphenyl)amino(pyren-1-yl)methylphosphonate, which was found to be cytotoxic for the HCT116 cancer cell line (IC50 = 20.8 μM), simultaneously showing weak toxicity towards
- -carbimino moiety [21] were found to be fluorescence-based sensors of Cu(II) and Mg(II) cations. Considering all above, we decided to synthesize a series of N-substituted derivatives of C-(pyren-1-yl)phosphonoglycine and to investigate their cytotoxic and fluorescence properties. Results and Discussion
- biological imaging. Investigation of cytotoxic effects of studied compounds The cytotoxic effects of dimethyl aminophosphonates 3Aa, 3Ab, 3Ac, 3Ad, 3Ai and dimethyl [hydroxy(pyren-1-yl)methyl]phosphonate (5A) were investigated with two human colorectal carcinoma cell lines: HT29 and HCT116 and also on the
Towards the total synthesis of keramaphidin B
Beilstein J. Org. Chem. 2016, 12, 1096–1100, doi:10.3762/bjoc.12.104
- addition; keramaphidin B; nitro-Mannich lactamisation cascade; Introduction Keramaphidin B (1) is a marine alkaloid first isolated by Kobayashi in 1994 from the Okinawan marine sponge Amphimedon sp and has been shown to be cytotoxic against KB human epidermoid carcinoma cells (IC50 0.28 μg/mL) and P388
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
- ) and 19 proved to have cytotoxic effects in the lower micromolar range against different cancer cell lines [47]. Nannozinones A (21) and B (22, Figure 9) are produced by N. pusilla strain MNa10913, isolated from a soil sample, collected in Mallorca, Spain [49]. They represent novel pyrazinone type
- ), 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
- corresponding hybrid PKS-NRPS machinery responsible for metabolite biosynthesis [57]. The molecule was shown to have cytotoxic effects towards HeLa-S3 cells (IC50 = 12 μM). The genus Enhygromyxa All Enhygromyxa species isolated to date are halophilic and considered as truly marine myxobacteria. The initial
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
- was also cytotoxic to the human pancreatic cancer cell line KP1-NL (IC50 = 30 μM) [20], and 1 and its 1-O-deacetylated derivative 2 inhibited cell proliferation of the human prostate cancer cell line PC-3 (IC50 61 µM for 2) [2]. Interestingly, while all 4-fluoro analogs 1–3 (Figure 1) reduced the
- cell growth creates an avenue for their use in the development of anticancer drugs, it also limits their utility as agents to modify the cellular glycome [62]. The cytotoxic activity of peracetylated monofluoro analogs 1, and 4–6, their 1-O-deacetylated derivatives 2, and 49–51, difluoro analogs 7 and
- DAST with retention of configuration. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs 51 and 50 of acetylated D-galactosamine were shown to be more cytotoxic in the PC-3 cell line than cisplatin and 5-fluorouracil. Most of the other fluoro analogs displayed moderate to low cytotoxicity. Fluoro
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
- established by using spectroscopic data in comparison to those reported in the literature. Furthermore, the isolates were evaluated for their leishmanicidal and cytotoxic effects. No cytotoxic effect was observed against the three cancer cell lines (HL60, JURKAT and REH), but compound 1 showed a weak
- assess their antileishmanial and cytotoxic effects. To the best of our knowledge, there are no reports dealing with the isolation and structure characterization of glycosylated sesquiterpene derivatives from Jungia sellowii. Results and Discussion CPC separation The aerial parts crude extract of Jungia
Antibiotics from predatory bacteria
Beilstein J. Org. Chem. 2016, 12, 594–607, doi:10.3762/bjoc.12.58
- , respectively. In contrast, the tripeptidic cystobactamid 507 seems to be either a biosynthetic byproduct or a degradation fragment of its larger congeners. All cystobactamids lack antifungal and cytotoxic properties, but they exhibit significant antibacterial activities. Especially derivative 919-2 (19
Biosynthesis of α-pyrones
Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56
- are applied for defense against competitors and predators. The biological activities these compounds exhibit is immense, including antimicrobial [2], antitumor [3][4], and cytotoxic activities [5]. Aflatoxins, produced by several Aspergillus species, are known to cause food poisoning due to their
- cytotoxic activity. They can regularly be found in improperly stored food, hence, entering the food supply chain [6]. Further coumarin derivatives, e.g., umbelliferone (4), esculetin (5), and scopoletin (6), are subject of investigation due to their pharmacological properties, i.e., anticancer effects
- and by inducing the so-called aryl hydrocarbon receptor, apoptosis is mediated by inducing cytochrome P450 1A1 [25]. For alternariol 9-methyl ether (19) and the graphislactone A (21) cytotoxic effects against the human cancer cell line SW1116 with IC50 values between 8.5 and 21 μg/mL were reported [26
Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins
Beilstein J. Org. Chem. 2016, 12, 531–536, doi:10.3762/bjoc.12.52
- cytotoxic properties [6][7][8][9][10][11]. Anthraquinones are well-known as colorants in foods, drugs, and textile industries. They are also used as chemical sensors and liquid crystals [1][2][3][4][5]. Halogenated anthraquinones form a minor group of natural pigments [12][13][14][15]. 7-Bromoemodic acid (1
- ), isolated from the crinoid Holopus rangii, shows remarkable cytotoxic activities. Topopyrone B (2) stabilizes DNA topoisomerase I and DNA topoisomerase II. Haloemodin (3) acts as an antibacterial agent inhibiting DNA gyrase and bacterial topoisomerase I. 6-O-Methyl-7-chloroaveratin (4) displays potent
Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes
Beilstein J. Org. Chem. 2016, 12, 496–504, doi:10.3762/bjoc.12.49
- binding affinity [21], inhibition of hepatic cholesterol [22], inhibition of aldose reductase [23], antiproliferative [24], antiviral, cytotoxic [25], antifungal [26], anti-HIV [27][28][29] and antibacterial activity [30]. Although rare, there are a few natural products, for example, melanervin (5), a
Natural products from microbes associated with insects
Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34
- )), sesquiterpenes with an unprecedented carbon skeleton that are most likely built up by an enzymatic Aldol addition. In a similar example, new cytotoxic furanone analogues (e.g., paraconfuranone A (39)) were obtained from the fungus Paraconiothyrium brasiliense isolated from the gut of the grasshopper Acrida
- amino acid residues, and they exhibit a wide range of interesting biological properties, such as insecticidal, cytotoxic, and moderate antibiotic activity [128]. The secretion of destruxins is weakly correlated to fungal virulence and insecticidal activity, because injection, ingestion or topical
- residues. Beauvericin has antibacterial, antifungal, and insecticidal activities, in addition to its potent cytotoxic activity against human cell lines [130]; attributes which indicate a crucial role in the infection process. The red 1,4-bibenzoquinone derivative oosporein (44) was first identified in the
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