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Search for "cytotoxicity" in Full Text gives 281 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.
Synthesis and cytotoxicity studies of novel N-arylbenzo[h]quinazolin-2-amines
Beilstein J. Org. Chem. 2024, 20, 2592–2598, doi:10.3762/bjoc.20.218
- this paper, we report a short and efficient synthesis of novel N-arylbenzo[h]quinazoline-2-amines. We have prepared a focused library of nineteen representative examples which have been submitted to cytotoxicity assays against a representative panel of eight cancer cell lines and several molecules gave
- attractive results in this area. Keywords: Buchwald–Hartwig coupling; cytotoxicity; heterocycles; Pd catalysis; quinazolines; Introduction Nitrogen-containing heterocyclic molecules are ubiquitous in living systems. Among them, quinazolines, and especially the 4-aminoquinazolines (type A molecules, Figure
- compounds with two substituents or with three fluorine atoms. All these compounds have been obtained in fair yields (51–70%) and they have spectral and analytical data in agreement with the indicated structures, as given in the experimental section and Supporting Information File 1. Cytotoxicity studies
Natural resorcylic lactones derived from alternariol
Beilstein J. Org. Chem. 2024, 20, 2171–2207, doi:10.3762/bjoc.20.187
- turned out that induced cytotoxicity [75] is mediated by activation of the mitochondrial pathway of apoptosis in human colon carcinoma cells [76][77] and that cytotoxicity on HCT116 cells is increased, when AOH is combined with 9-O-methylalternariol (2, AME) [78]. AOH further showed to have a detrimental
- tested for cytotoxicity, but turned out to be inactive. Altertenuol (31) has already been mentioned in one of the first reports on metabolites isolated from Alternaria tenuis (synonymous to A. alternata) [42][54]. Its structure was determined by chemical methods and has later been confirmed after total
- weight) [11][74], and showed toxicity against brine shrimp larvae (Artemia salina) with an LD50 value of 375 µg/mL [256][257]. It exhibited cytotoxicity against HeLa cells (ID25: 28 µg/mL) [74], the HCT116 cancer cell line (IC50: 3.13 μM) [232], and against MG-63 cells (IC50: 17.8 µg/mL) [123]. An
Allostreptopyrroles A–E, β-alkylpyrrole derivatives from an actinomycete Allostreptomyces sp. RD068384
Beilstein J. Org. Chem. 2024, 20, 1981–1987, doi:10.3762/bjoc.20.174
- by formyl and carboxyl functionalities. Compounds 1, 4, and 5 showed cytotoxicity against Kasumi-1 human acute myeloblastic leukemia cells with IC50 values of 103, 105, and 105 μM, respectively, which are less active than the anticancer agent cisplatin, with an IC50 value of 70 μM. Keywords
- cytotoxicity against Kasumi-1 human acute myeloblastic leukemia cells with IC50 values of 103, 105, and 105 while 2 and 3 were less active with IC50 values of 200 and 333 μM, respectively. Under the same experimental conditions, cisplatin, a positive control, inhibited the cell growth with an IC50 value of 70
- substitution patterns are different (Figure 1). Natural alkylpyrroles were shown to have cytotoxicity [27], antidiabetic activity [28], anti-lipid peroxidation [12], in vivo antihypoxic activity [12], and antibacterial activity [15]. Though not impressive in cytotoxicity and tyrosinase-inhibitory evaluations
The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)
Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162
Syntheses and medicinal chemistry of spiro heterocyclic steroids
Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152
- with IC50 values ranging from 0.7 to 43 µM, some of them exhibiting significantly more potent activity than the reference compound 5-fluorouracil (5-FU). More recently, similar compounds were evaluated for their cytotoxicity using a brine shrimp bioassay, with LC50 values ranging from 6.19 to 27.2 µg
- /mL. Since the cytotoxicity of the parent 16-arylidene steroids was LC50 > 100 µg/mL, it was concluded that the presence of the pyrrolidine moiety was essential for the activity [28]. Additional derivatives have been reported on different steroidal positions [29] or with variations in the methodology
- . Chromatographic purification was not required post-reaction. Some spiro products exhibited high binding affinity towards DNA, while others showed good cytotoxicity against different cancer cells (A545, MCF-7, HeLa, HL-60, SW480, HepG2, HT-29, and A549) with IC50 values within the micromolar range (2.18–18.54 µM
Methyltransferases from RiPP pathways: shaping the landscape of natural product chemistry
Beilstein J. Org. Chem. 2024, 20, 1652–1670, doi:10.3762/bjoc.20.147
- proteusin family of RiPPs. They are produced by the tunicate symbiont Candidatus Entotheonella factor and exhibit membrane activity against Gram-positive bacteria and are highly cytotoxic. Cytotoxicity was tested with murine leukaemia cells; polytheonamide A, B, and C showed IC50 values between 68 and 78 pg
Polymer degrading marine Microbulbifer bacteria: an un(der)utilized source of chemical and biocatalytic novelty
Beilstein J. Org. Chem. 2024, 20, 1635–1651, doi:10.3762/bjoc.20.146
- Gram-positive bacteria Kocuria rhizophila and S. aureus, Gram-negative bacterium Tenacibaculum maritimum, and a panel of fungi. These molecules also demonstrated moderate cytotoxicity against P388 murine leukemia cells. The bisindole alkaloid violacein (24, Figure 8) was isolated and characterized from
Supramolecular assemblies of amphiphilic donor–acceptor Stenhouse adducts as macroscopic soft scaffolds
Beilstein J. Org. Chem. 2024, 20, 1590–1603, doi:10.3762/bjoc.20.142
- systematically by visible light irradiation. On a macroscopic length scale, the soft DAn scaffolds were able to perform macroscopic structure disassembly upon visible-light irradiation. The biocompatibility of the macroscopic soft DAn scaffolds was investigated, revealing limited cytotoxicity. The current work
- scaffolds were further incubated with hBM-MSCs cells, promoting the attachment of cells onto the surface. The limited cytotoxicity and good stability of DAn macroscopic soft scaffolds points at an application as cell–material interface and even offers opportunities for the fabrication of biomedical
Computation-guided scaffold exploration of 2E,6E-1,10-trans/cis-eunicellanes
Beilstein J. Org. Chem. 2024, 20, 1320–1326, doi:10.3762/bjoc.20.115
- minor products and mostly starting material, hence we decided these products were not worth further purification. The minor isomers of the halogenated derivatives were presumably detected but in too low yields to purify. Since 6/6/6-tricyclic diterpenes are known to show cytotoxicity [26], we tested our
- seven analogs for cytotoxicity against human colon carcinoma HCT-116 cells. Unfortunately, none of the compounds up to 10 μM showed any activity when tested in MTT-based cell viability assays. Conclusion Eunicellane diterpenoids have been known for over 50 years, but it was not until recently that their
Bismuth(III) triflate: an economical and environmentally friendly catalyst for the Nazarov reaction
Beilstein J. Org. Chem. 2024, 20, 1167–1178, doi:10.3762/bjoc.20.99
- ) being active at 5 μg/mL, using a 75% cutoff inhibition at each concentration. On the other hand, MCF-7 and SK-MEL-28 cells were the most resistant ones, with no compound being active at the lower concentration (Figure 5). This evidence of selective cytotoxicity for a specific histological tumor subtype
Switchable molecular tweezers: design and applications
Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45
Green and sustainable approaches for the Friedel–Crafts reaction between aldehydes and indoles
Beilstein J. Org. Chem. 2024, 20, 379–426, doi:10.3762/bjoc.20.36
- ]. DIM has also been found to initiate the expression of tumor suppressing proteins (ATM, p21, p27kip), which control cell growth and protect cells against ionizing radiation, which can cause DNA mutations, decreasing the overall risk of breast cancer [1][5][6]. The cytotoxicity of DIM and BIMs in
Cycloaddition reactions of heterocyclic azides with 2-cyanoacetamidines as a new route to C,N-diheteroarylcarbamidines
Beilstein J. Org. Chem. 2024, 20, 17–24, doi:10.3762/bjoc.20.3
- cells within the concentration range. This indicates the low cytotoxicity of these compounds. Meanwhile, compounds 3m,l are characterized by a borderline inhibition of cell culture viability. Attention is drawn to the increased toxic effect of 3m on cells of tumor origin, in comparison with normal human
- (method A)a; 1 (0.5 mmol), 2 (0.5 mmol), NaOH (0.5 mmol), EtOH (2 mL), 0 °C → rt, 30 min (method B)b. Proposed mechanism for the formation of triazoles 3. Optimization of the reaction of amidine 1a with 6-azidopyrimidine-2,4-dione 2a.a Cytotoxicity index (IC50 ± SE) in µM of the studied compounds on human
Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β-keto amide precursors
Beilstein J. Org. Chem. 2023, 19, 1804–1810, doi:10.3762/bjoc.19.132
- monoamine oxidase [14], cytotoxicity against cancer cell lines [15], activity against nuclear factor of activated T cells [16], and anti-inflammatory activity [17]. Alkaloids with similar structure and anti-inflammatory activity have been isolated from another member of the Rutaceae family – Zanthoxylum
Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups
Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125
- cell membrane integrity [21]. In the context of cancer therapy development, metal complexes of N-acylhydrazones stand out. For example, Firmino et al. demonstrated that gallium(III) complexes of isoniazid-derived hydrazones exhibit strong cytotoxicity against HL-60 and HCT-116 cancer cell lines [22
Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect
Beilstein J. Org. Chem. 2023, 19, 1604–1614, doi:10.3762/bjoc.19.117
- revealed that compound 7 was cytotoxic to RAW 264.7 cells at concentrations above 25 μM (Figure 6d). Furthermore, 7 suppressed the LPS-induced increases in IL-1β and IL-6 transcriptional levels in a concentration-dependent manner from 1 or 2.5 μM (Figure 6e). Thus, while cytotoxicity was likely involved in
- 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
- the LPS-only group)]; d) concentration-dependent cytotoxicity of 7 in RAW 264.7 cells (cell viability was detected by an MTT-based colorimetric assay); e) mRNA levels of IL-1β and IL-6 in RAW 264.7 cells preincubated with different concentrations of compound 7 for 24 h, followed by treatment with LPS
Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials
Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108
- tumor cytotoxicity effects for a number of the berberine derivatives. Keywords: benzylisoquinoline; berberine; chelerythrine; drug discovery; plant-derived antimicrobials; Introduction The isolation, or creation of novel antimicrobial agents is currently at the forefront of modern healthcare due to
- unique compounds at a set concentration against T84 human colon cancer cells has provided useful preliminary comparative cytotoxicity data, which can be directly compared to our previous publication showing the effects of crude A. mexicana extracts against this same cell line [9]. However, further
Synthesis of ether lipids: natural compounds and analogues
Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96
- has similar cell toxicity than edelfosine-C18 on HL-60 leukemic cells [129][130]. The authors also reported that the sulfone 26.5 (Figure 26B) had similar cytotoxicity than edelfosine-C18. In 1987, the group of E. J. Modest reported that the thioether 26.4 featured comparable cytotoxicity than C18
- . The replacement of the oxygen atom located in sn-1 position by a methylamino group corresponds to a compound known as BN52211 (30.6, Figure 30). This compound was used in many studies for its antitumor cytotoxicity [136] or its immunologic properties [137]. To the best of our knowledge, the synthesis
Two new lanostanoid glycosides isolated from a Kenyan polypore Fomitopsis carnea
Beilstein J. Org. Chem. 2023, 19, 1161–1169, doi:10.3762/bjoc.19.84
- (Table S1 in Supporting Information File 1). However, 3-epipachymic acid (3) demonstrated significant cytotoxicity against epidermoid carcinoma cells (A431) (IC50 = 5.7 µM) and HeLa cells (KB-3-1) (IC50 = 7.0 µM). Moderate cytotoxic effects for compound 3 were also recorded against mouse fibroblasts
- cytotoxicity assay. Recent structure–activity relationship (SAR) studies have indicated a key role played by the hydroxy group at C-3 in cytotoxic effects of lanostane triterpenoids [23][36]. According to a study by Wang et al. (2023) [36], synthetic derivatives of pachymic acid demonstrated moderate to high
- hydroxy group [33]. In our case, the C-16 hydroxy group seemed to play a major role in the cytotoxicity instead, as indicated by the active compound 3-epipachymic acid (3). Intriguingly, other compounds lacking the hydroxy group at C-16 were inactive, suggesting the probable role played by a 16-OH in
Five new sesquiterpenoids from agarwood of Aquilaria sinensis
Beilstein J. Org. Chem. 2023, 19, 998–1007, doi:10.3762/bjoc.19.75
- ]. Previous studies have shown that 2-(2-phenylethyl)chromones and sesquiterpenes are the characteristic and main bioactive components of agarwood [5][6]. Various bioactivities, including neuroactive [4], gastrointestinal modulation [7], cytotoxicity [8], antibacterial [9], antifungal, acetylcholinesterase
Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach
Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71
- /instruments. Some of these synthesized N-substituted pyrrole derivatives were evaluated for in vitro cytotoxicity for various cancer cell lines. In 2014, Wang et al. [78] demonstrated a modified Clauson–Kaas reaction to synthesize various N-substituted pyrroles 53 in 75–95% yields by reacting various aromatic
Non-peptide compounds from Kronopolites svenhedini (Verhoeff) and their antitumor and iNOS inhibitory activities
Beilstein J. Org. Chem. 2023, 19, 789–799, doi:10.3762/bjoc.19.59
- compounds, cytotoxic and anti-inflammatory properties were evaluated. In particular, a mouse pancreatic cancer cell line (Panc02-h7-GP-GFP) was used to determine cytotoxicity. Additionally, LPS-induced pro-inflammatory expression of iNOS and COX-2 in RAW264.7 cells was evaluated. Antitumor activity of
Cassane diterpenoids with α-glucosidase inhibitory activity from the fruits of Pterolobium macropterum
Beilstein J. Org. Chem. 2023, 19, 658–665, doi:10.3762/bjoc.19.47
- species known in Thailand [7], and some of them have been applied as antihemorrhoid [8]. Some species of this genus have revealed cassane diterpenoids as mainly secondary metabolites, which have shown interesting biological activities such as cytotoxicity and anti-inflammatory activity [9][10][11
Combretastatins D series and analogues: from isolation, synthetic challenges and biological activities
Beilstein J. Org. Chem. 2023, 19, 399–427, doi:10.3762/bjoc.19.31
- with a median effective dose values (ED50) of 3.3 and 5.2 μg·mL−1 (10.56 and 17.55 μM), respectively [16][17]. Vongvanich and co-workers performed a cytotoxicity assay of combretastatins D-3 (3) and D-4 (4) against human breast cancer cells (BC-1), human epidermoid carcinoma of the mouth (KB), a small
- authors suggested that the presence of hydroxy substituents at C-11 and C-12 played a significant role in the α-glucosidase inhibition [19]. The cytotoxicity of the aforementioned compounds was also evaluated using the sulforhodamine B (SRB) assay against MIAPaCa-2, DU145, MCF-7, and HTC-116 human cancer
- cell lines. The compounds were tested in five different concentrations (ranging from 1 to 100 μM) and showed no in vitro cytotoxicity. However, compound 10 was found to possess anti-inflammatory activity. It showed effects on LPS-induced activation of NF-κB and COX-2 similar to the Bay 11-7082 molecule
CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview
Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29
- albumin and LDL. Furthermore, the Zn and Pd porphyrin complexes revealed a good capability to yield singlet oxygen (quantum yield >70%) and exhibited significant photoinduced cytotoxicity. In another report, Prakash Rao et al. [65] highlighted the click protocol to accomplish the synthesis of hydrogenated
- -soluble nanowires, nanorods, and nanospheres. In addition, these triazoloporphyrins have a wide range of medical applications, including photoinduced cytotoxicity against cancer cells, drug delivery, as phototherapeutic agents, and PDT applications. I believe this review will be useful and encourage
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