Synthesis of the 1,5-disubstituted tetrazole-methanesulfonylindole hybrid system via high-order multicomponent reaction

• Cesia M. Aguilar-Morales,
• América A. Frías-López,
• Nadia V. Emilio-Velázquez,
• Alejandro Islas-Jácome,
• Angelica Judith Granados-López,
• Jorge Gustavo Araujo-Huitrado,
• Yamilé López-Hernández,
• Hiram Hernández-López,
• Luis Chacón-García,
• Jesús Adrián López and
• Carlos J. Cortés-García

Beilstein J. Org. Chem. 2024, 20, 3077–3084, doi:10.3762/bjoc.20.256

• efficiency and creating six new bonds (two C–C, three C–N, and one N–N). Additionally, the products were evaluated against breast cancer MCF-7 cells, finding moderate activity in the compounds substituted with fluorine and chlorine. Keywords: 1,5-disubstituted tetrazoles; high-order multicomponent reaction

• with greater efficacy and selectivity against targets related to BC. Thus, the 1,5-disubstituted tetrazole-indole hybrids, presented different effects on cell proliferation inhibition in MCF-7 cells (Figure 1) that could be attributable to the molecular background of cells [46][47][48][49]. The

• proposing new structures with improved activity. Differential effect of the 1,5-disubstituted tetrazole-indole hybrid compounds 18a–j on proliferation of MCF-7 cell line. MCF-7 cells were treated with increasing doses of compounds 18a–j. Controls were cells treated with DMSO. Synthetic approaches to obtain

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

• was shown to decrease after 24 hours in a cholesterol extraction assay from MCF-7 cells. Poly-β-CD-C6 nanoparticles, on the other hand, removed three times more cholesterol from cells in 48 hours than anionic CD nanoparticles. In addition to surface charges, the molecular weight, and number of

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• ), and the highest cytotoxicity against MCF-7 was obtained for brevipolide G (7) with ED50 values ranging between 3.6–5.1 μM (Table 1, entry 7). The remaining members of brevipolides were evaluated in vitro against MCF-7 cells (Table 1, entries 9–15), and the best result was obtained for brevipolide J

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• reaction between 54 and 55 was performed in anhydrous methanol under an argon atmosphere to construct 56. The study on the in vitro drug release showed enhanced drug release at an acidic pH value in comparison to a neutral pH value. Importantly, the amount of DOX required for MCF-7 cells was decreased

Plasma membrane imaging with a fluorescent benzothiadiazole derivative

• Pedro H. P. R. Carvalho,
• Jose R. Correa,
• Karen L. R. Paiva,
• Daniel F. S. Machado,
• Jackson D. Scholten and
• Brenno A. D. Neto

Beilstein J. Org. Chem. 2019, 15, 2644–2654, doi:10.3762/bjoc.15.257

• , that is at a concentration 100-fold lower than that of the cytotoxic effect. The new compound was then tested as bioimaging probe in live and fixed cells (Figure 6). As can be seen, the green fluorescent dye BTD-4APTEG was found most concentrated at the plasma membranes of the MCF-7 cells in both, live

• MTT analysis after 24 h treatment with the developed dye BTD-4APTEG. No statistically significant cytotoxic effect was observed after 24 h incubation with the new dye BTD-4APTEG at 10 μM. However, the dye induced strong cytotoxic effects in all tested cell lines at 100 µM (p < 0.05). MCF-7 cells

• accumulated in the peripheral region of the cellular membrane (white arrows) in both samples. The letter N indicates the nuclei of the cells (scale bar of 10 μm). Co-staining experiments using the commercially available CellMask (red emission) and BTD-4APTEG (green emission) in (I) live and (II) fixed MCF-7

Fluorescent phosphorus dendrimers excited by two photons: synthesis, two-photon absorption properties and biological uses

• Anne-Marie Caminade,
• Artem Zibarov,
• Eduardo Cueto Diaz,
• Aurélien Hameau,
• Maxime Klausen,
• Kathleen Moineau-Chane Ching,
• Jean-Pierre Majoral,
• Jean-Baptiste Verlhac,
• Olivier Mongin and
• Mireille Blanchard-Desce

Beilstein J. Org. Chem. 2019, 15, 2287–2303, doi:10.3762/bjoc.15.221

• performed with a confocal microscope; cells were irradiated at 760 nm (in the near IR) by three scans of 1.57 s each at an average power of 80 mW. The percentage of living cells was determined two days after irradiation. 78% cell death was obtained under two-photon irradiation of MCF-7 cells incubated with

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

• Andrejs Šišuļins,
• Jonas Bucevičius,
• Yu-Ting Tseng,
• Irina Novosjolova,
• Kaspars Traskovskis,
• Ērika Bizdēna,
• Huan-Tsung Chang,
• Sigitas Tumkevičius and
• Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

• in the cytoplasm. The representative fluorescent image of the labeled MCF-7 cells with compound 9 is shown in Figure 8 (for other examples see Figure S82 in Supporting Information File 1). Based on the recent investigation of metabolic labelling of DNA [30][56] by deaza-7-ethenyl-2'-deoxyguanosine

• ) Quantum yield dependence on the Dimroth–Reichardt polarity parameter ET(30) with a linear fit for compounds 8c and 11c. Energy diagram for the frontier molecular orbitals of compounds 8a, 8c, 11a and 11c. Labeled MCF-7 cells using compound 9 (C,D) and unlabeled MCF-7 cells (A,B) in microscope (2 h, c(9

• -7 cells were cultured in RPMI medium supplemented with fetal bovine serum (10%), antibiotic–antimycotic (1.0%). MCF-10A cells were cultured in α-MEM supplemented with FBS (10%), and antibiotic–antimycotic (1.0%). All cells were cultured in an environment equilibrated with 5% CO2 at 37 °C. The cell

Natural and redesigned wasp venom peptides with selective antitumoral activity

• Marcelo D. T. Torres,
• Gislaine P. Andrade,
• Roseli H. Sato,
• Cibele N. Pedron,
• Tania M. Manieri,
• Giselle Cerchiaro,
• Anderson O. Ribeiro,
• Cesar de la Fuente-Nunez and
• Vani X. Oliveira Jr.

Beilstein J. Org. Chem. 2018, 14, 1693–1703, doi:10.3762/bjoc.14.144

• low as 12.5 μmol L−1 for the selective targeting of MCF-7 breast cancer cells. Flow cytometry assays further revealed that treatment with wild-type (WT) peptide Dec-NH2 led to necrosis of MCF-7 cells. Additional atomic force microscopy (AFM) measurements indicated that the roughness of cancer cell

• of selective anticancer peptide therapeutics. Keywords: breast cancer; decoralin; MCF-7 cells; peptide design; selective anticancer peptides; structure–activity relationships; Introduction Approximately 12% of U.S. women develop breast cancer according to the U.S. Breast Cancer website (http

• concentrations (≈100 μmol L−1). On the other hand, [Leu]8-Dec-NH2 did not present significant activity against MCF-7 cells when compared to the negative control (Figure 2), and intriguingly was cytotoxic towards normal MCF-10A cells even at the lowest concentration tested (25 μmol L−1, Figure 3). This

Design and biological characterization of novel cell-penetrating peptides preferentially targeting cell nuclei and subnuclear regions

• Anja Gronewold,
• Mareike Horn and
• Ines Neundorf

Beilstein J. Org. Chem. 2018, 14, 1378–1388, doi:10.3762/bjoc.14.116

• peptides when incubated with MCF-7 cells up to a concentration of 100 μM. Also after treating HeLa cells with the peptides up to a concentration of 50 μM, no significant toxicity could be observed for sC18*, N50, N50-sC18* and NrTP. Besides N50, all other peptide sequences did lower the amount of viable

• , Supporting Information File 1), not even after a longer incubation period of two hours (data not shown). For NrTP alone, a slight fluorescent signal was visible in the nucleoli of MCF-7 cells (Figure S6, Supporting Information File 1). Notably, N50-sC18* was distributed within the whole cell cytosol, and

• also accumulated in the cell nuclei and nucleoli. This observation supported the idea of cellular entry via direct penetration when using a concentration of 10 µM. In MCF-7 cells, NrTP-sC18* was also evenly distributed throughout the whole cell, including strong accumulation in the nuclei. Notably, N50

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery

• Sabine Schuster,
• Beáta Biri-Kovács,
• Bálint Szeder,
• Viktor Farkas,
• László Buday,
• Zsuzsanna Szabó,
• Gábor Halmos and
• Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64

• stock solutions. Unfortunately, the lower concentration range with a maximum of 10 µM was not sufficient to achieve the dose-response. Nevertheless, both D-Trp-containing compounds provided a decreased cell viability at the highest concentration (10 µM) on HT-29 (58% (3) and 55% (6)) and MCF-7 cells (69

• -29 cells at 160 µM concentration was higher than 90% for all bioconjugates except compound 5 (83%). The same effect could be observed on MCF-7 cells, whereby the uptake of bioconjugate 5 was 76%. At 40 µM, K2 was taken up by MCF-7 cells more effectively (61.2%) than the other compounds. Apart from

• cytometry, the cellular uptake and localization of K1, K2, 1, 2, 4 and 5 were studied on MCF-7 cells by CLSM. After 6 h incubation with the GnRH-III–Dau conjugates (c = 10 µM, 40 µM and 160 µM), MCF-7 cells were fixed and prepared for confocal laser scanning imaging. In order to gain insight into a possible

An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

• Alexei N. Izmest’ev,
• Galina A. Gazieva,
• Natalya V. Sigay,
• Sergei A. Serkov,
• Valentina A. Karnoukhova,
• Vadim V. Kachala,
• Alexander S. Shashkov,
• Igor E. Zanin,
• Angelina N. Kravchenko and
• Nina N. Makhova

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

Physical properties and biological activities of hesperetin and naringenin in complex with methylated β-cyclodextrin

• Waratchada Sangpheak,
• Jintawee Kicuntod,
• Roswitha Schuster,
• Thanyada Rungrotmongkol,
• Peter Wolschann,
• Nawee Kungwan,
• Helmut Viernstein,
• Monika Mueller and
• Piamsook Pongsawasdi

Beilstein J. Org. Chem. 2015, 11, 2763–2773, doi:10.3762/bjoc.11.297

• effects when compared to the control (Figure 6A). This result is consistent with a previous study of Harmon et al. who suggested that naringenin inhibits the proliferation of MCF-7 cells via impaired glucose uptake [26]. Krishnakumar et al. showed the cytotoxic effects between naringenin and naringenin

• , USA). Anti-Mouse IL-6 was purchased from eBioscience Inc. (San Diego, CA, USA). Human colon cancer (Caco-2) cells, breast cancer (MCF-7) cells and human cervical carcinoma (HeLa) cells were obtained from the American Type Cell Culture Collection (ATCC), USA. Methods Binding free energy calculation

• standard deviation. Cytotoxicity towards cancer cell lines: An MTT assay was performed to determine the cell viability and thus the cytotoxicity of the test compounds towards three different cancer cell lines (HeLa, CaCo-2, MCF-7). Cells were seeded into 96-well plates at a density of 2 × 106 cells/mL and

Bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina lacunosa

• Qun Göthel,
• Thanchanok Sirirak and
• Matthias Köck

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

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• the mean results ± SD (n = 4). Viability of MCF-7 cells cultured with CPT loaded 6OCAPRO and CS-6OCAPRO nanocapsules in comparison with CPT in solution form at the same concentration. Data represents the mean results ± SD (n = 4). P < 0.05 indicates a significant difference between formulations

Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope

• Manuel Johannes,
• Maximilian Reindl,
• Bastian Gerlitzki,
• Edgar Schmitt and
• Anja Hoffmann-Röder

Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15

• (20)-TTox vaccine 18b (antiserum of mice 2; for more details cf. Supporting Information File 1). FACS analysis of the binding of MCF-7 tumor cells by the antiserum of mouse 2 induced by vaccination with 18b: cells treated with buffer solution (top); MCF-7 cells treated with antiserum of mouse 2

Trogopterins A–C: Three new neolignans from feces of Trogopterus xanthipes

• Soyoon Baek,
• Xuikui Xia,
• Byung Sun Min,
• Chanil Park and
• Sang Hee Shim

Beilstein J. Org. Chem. 2014, 10, 2955–2962, doi:10.3762/bjoc.10.313

• of 34.77–45.68 μM using adriamycin as a positive control (IC50 = 0.18 μM). Additionally, compound 1 showed very weak cytotoxic activity against MCF-7 cells with an IC50 of 94.69 μM. None of the compounds affected the HeLa cells. Conclusion In summary, two novel neoligans (trogopterins A and B) and a

• compounds 1–4 (δ, ppm, and coupling constant J in Hz). 13C–NMR data for compounds 1–4. Interproton distances (Å) for trogopterin C (compound 3) in the MM2-minimized model. Cytotoxic effects of compounds 1–4 against HL-60, HeLa, and MCF-7 cells. Supporting Information Supporting Information File 340: NMR

Flow synthesis of a versatile fructosamine mimic and quenching studies of a fructose transport probe

• Matthew B. Plutschack,
• D. Tyler McQuade,
• Giulio Valenti and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 2022–2027, doi:10.3762/bjoc.9.238

• the uptake of NBDM into MCF-7 cells, we measured uptake as a function of concentration over a range of 1–40 μM (Figure 2) [17]. While we did not expect to observe significant self-quenching over this range, we measured the fluorescent intensity of NBDM from 1–40 μM (1X phosphate buffer solution). As

Synthesis and physicochemical characterization of novel phenotypic probes targeting the nuclear factor-kappa B signaling pathway

• Paul M. Hershberger,
• Satyamaheshwar Peddibhotla,
• E. Hampton Sessions,
• Daniela B. Divlianska,
• Ricardo G. Correa,
• Anthony B. Pinkerton,
• John C. Reed and
• Gregory P. Roth

Beilstein J. Org. Chem. 2013, 9, 900–907, doi:10.3762/bjoc.9.103

• studies, selectively inhibited IL-8 secretion and the biologically relevant terminal effect of NOD1 (γ-tri-DAP) dependent NF-κB activation. Additionally, they neither inhibited NOD2-dependent nor TNF-α-dependent IL-8 secretion in biologically relevant MCF-7 cells. While 13 is the more potent and selective

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• showing an interaction between the drug and the nanosponge structure, despite the hydrophilicity of the drug. Moreover, encapsulation of 5-fluorouracile in nanosponges protected the drug and maintained its cytotoxicity against MCF-7 cells. Another paradigmatic example was established with the

Dimerization of a cell-penetrating peptide leads to enhanced cellular uptake and drug delivery

• Jan Hoyer,
• Ulrich Schatzschneider,
• Michaela Schulz-Siegmund and
• Ines Neundorf

Beilstein J. Org. Chem. 2012, 8, 1788–1797, doi:10.3762/bjoc.8.204

• failed to internalize at this concentration. In human embryonic kidney (HEK-293) cells and MCF-7 cells (human breast adenocarcinoma) the uptake rate of (sC18)2 at 1 µM was significantly higher even when compared to sC18 at a concentration of 10 µM (p ≤ 0.05). When comparing the different cell lines, the

• that is sufficient for very efficient peptide internalization. Cytotoxicity of (sC18)2 The effect of the dimeric sC18 on the survival of HEK-293, HT-29 and MCF-7 cells was determined by means of a resazurin-based cell viability assay. After 24 h incubation, a cell-type-dependent cytotoxicity profile of

• (sC18)2 was observed (Figure 3). While HEK-293 cells remained unharmed even at high peptide concentrations up to 100 µM, a steady decrease of cell viability was induced in the tumor cell lines, which was particularly obvious in MCF-7 cells. At least for HEK-293 and MCF-7, this effect seemed to be in no

Identification and isolation of insecticidal oxazoles from Pseudomonas spp.

• Florian Grundmann,
• Veronika Dill,
• Andrea Dowling,
• Aunchalee Thanwisai,
• Edna Bode,
• Narisara Chantratita,
• Richard ffrench-Constant and
• Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 749–752, doi:10.3762/bjoc.8.85

• activity against the MCF-7 cells with 24 being the most potent compound (1.02 µg ml−1). Interestingly, 26 also showed activity against Galleria hemocytes, although its oxazole derivative 10 did not, which may point to different targets for both compound classes. The class of oxazole compounds, which were