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

• showed mild toxicity against the breast cancer cell line MCF-7 and to FS4-LTM conditional immortalization human fibroblasts (IC50 = 78 and 32 µM, respectively). The cytotoxicities of the known compounds (4–17) are also listed in Table 5. None of the isolated compounds showed any antimicrobial activity

• proliferation assays. Targeting cell lines are L929 mouse fibroblasts, KB-31 epidermoid carcinoma, and MCF-7 breast cancer cell lines which were incubated for 5 days with the test substances. The acute toxicity was determined using the FS4-LTM conditional immortalization human fibroblasts cell line which was

Total synthesis of panicein A₂

• Lili Yeung,
• Lisa I. Pilkington,
• Melissa M. Cadelis,
• Brent R. Copp and
• David Barker

Beilstein J. Org. Chem. 2015, 11, 1991–1996, doi:10.3762/bjoc.11.215

• their developmental therapeutics program. Interestingly, at the tested concentration of 10 μM, panicein A2 (5) showed very little activity against most cell lines. The best performance of panicein A2 (5) was against T-47D, a breast cancer cell line, in which it showed a 43% reduction of growth when

Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

• Louis P. Sandjo,
• Victor Kuete and
• Maique W. Biavatti

Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183

• cells, causing an extensive reduction of the MCF-7 breast cancer cells in the G2/M phase [85]. Two skeletons, including 9H-pyrido[4,3,2-mn]thiazolo[4,5-b]acridin-9-one and 8H-pyrido[4,3,2-mn]thiazolo[4,5-b]acridine (Figure 15), are found in kuanoniamine structures (60, 86–88). The first one associated

Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo

• Alireza Shakoori,
• John B. Bremner,
• Mohammed K. Abdel-Hamid,
• Anthony C. Willis,
• Rachada Haritakun and
• Paul A. Keller

Beilstein J. Org. Chem. 2015, 11, 481–492, doi:10.3762/bjoc.11.54

• , selected compounds were assessed for in vitro antiplasmodial (Plasmodium falciparum; drug resistant K1 strain) activity [15], cell-based anticancer activity (cell lines: NCI-H187 small cell lung cancer, KB oral cavity cancer, and MCF-7 breast cancer) [16], and in vitro antitubercular activity

• , respectively), but not against the more refractory MCF-7 breast cancer cell line [16]. Additionally, 17 exhibited some antitubercular activity (MIC 12.5 µg/mL, 38.6 µM), providing a basis for further structurally novel lead development of anti-TB compounds. The need for such compounds is a pressing one with

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

• capable of binding to the native MUC1 antigen structures present on MCF-7 human breast cancer cells. Moreover, selective deoxyfluorination at the antigenic carbohydrate determinant might be used to improve the metabolic stability of the saccharide epitope, as was showcased by the enhanced resistance of

Efficient deprotection of F-BODIPY derivatives: removal of BF₂ using Brønsted acids

• Mingfeng Yu,
• Joseph K.-H. Wong,
• Cyril Tang,
• Peter Turner,
• Matthew H. Todd and
• Peter J. Rutledge

Beilstein J. Org. Chem. 2015, 11, 37–41, doi:10.3762/bjoc.11.6

• –18; LC–MS trace of crude 18. Supporting Information File 8: CIF file of 8, CCDC 1018518. Acknowledgements We thank the National Breast Cancer Foundation for a Novel Concept Grant (NC-10-69) and the Australian Research Council for funding (DP120104035). M. Yu was supported by a University of Sydney

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

• )diphenol. The in vitro cytotoxic activities of compounds 1–4 against HL-60 (human leukemia), HeLa (human cervical carcinoma), and MCF-7 (human breast cancer) cells were evaluated using an MTT assay. As shown in Table 4, compounds 1–3 exerted moderate cytotoxic effects against HL-60 cells with IC50 values

Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3

• Zhi Kai Guo,
• Rong Wang,
• Wei Huang,
• Xiao Nian Li,
• Rong Jiang,
• Ren Xiang Tan and
• Hui Ming Ge

Beilstein J. Org. Chem. 2014, 10, 2677–2682, doi:10.3762/bjoc.10.282

• myeloid leukemia, SH-SY5Y neuroblastoma, SGC-7901 gastric adenocarcinoma, HepG2, SMMC-7721 hepatocellular carcinoma, A549 lung cancer, MCF-7, MDA-MB-231 breast cancer, HCT116, SW480 colon cancer, HT29 colorectal cancer. However, no significant activity was detected (IC50 > 50 μM). It also displayed no

• desposit@ccdc.cam.ac.uk. Biological assays Cytotoxic activity against 11 human cancer cell lines, K562 myeloid leukemia, SH-SY5Y beuroblastoma, SGC-7901 gastric adenocarcinoma, HepG2, SMMC-7721 hepatocellular carcinoma, A549 lung cancer, MCF-7, MDA-MB-231 breast cancer, HCT116, SW480 colon cancer, HT29

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• such as cancer [133][134] and obesity [99], automated SPPS also offers a versatile repertoire. As an example, a method to produce radiolabeled Y1-receptor preferring agonists of NPY has been described, which could selectively target breast cancer cells and allowed specific tumor diagnosis. Here, the Nα

Synthesis of zearalenone-16-β,D-glucoside and zearalenone-16-sulfate: A tale of protecting resorcylic acid lactones for regiocontrolled conjugation

• Hannes Mikula,
• Julia Weber,
• Dennis Svatunek,
• Philipp Skrinjar,
• Gerhard Adam,
• Rudolf Krska,
• Christian Hametner and
• Johannes Fröhlich

Beilstein J. Org. Chem. 2014, 10, 1129–1134, doi:10.3762/bjoc.10.112

• cause problems of the reproductive tract (e.g., impaired fertility) in animals [7]. Physiological studies revealed binding of ZEN to recombinant human estrogen receptors [8] and have furthermore shown a ZEN-induced stimulation of the growth of human breast cancer cells [9]. Additionally, masked

New sesquiterpene hydroquinones from the Caribbean sponge Aka coralliphagum

• Qun Göthel and
• Matthias Köck

Beilstein J. Org. Chem. 2014, 10, 613–621, doi:10.3762/bjoc.10.52

• (4) exhibited mild antiproliferation activity against L929 mouse fibroblast, KB-31 epidermoid carcinoma, and MCF-7 breast cancer cell lines, while siphondictyal E3 (3) and cyclosiphonodictyol A (5) showed moderate activity against Gram-positive bacteria. Keywords: Aka coralliphagum; bioassay

• ) show cytotoxic activity against the L929 mouse fibroblasts, KB-31 epidermoid carcinoma, and the breast cancer cell line MCF7, although none of them showed activity in the antimicrobial assays against Gram-negative bacteria and the fungus Candida albicans. Many of the isolated compounds from Aka

• , targeting cell lines L929 mouse fibroblasts, KB-31 epidermoid carcinoma, MCF-7 breast cancer, and FS4-LTM conditional immortalization human fibroblasts, respectively. The FS4-LTM cell line was incubated for 24 hours with the tested substances. The other cell lines were incubated for 5 days with the tested

Total synthesis and cytotoxicity of the marine natural product malevamide D and a photoreactive analog

• Werner Telle,
• Gerhard Kelter,
• Heinz-Herbert Fiebig,
• Peter G. Jones and
• Thomas Lindel

Beilstein J. Org. Chem. 2014, 10, 316–322, doi:10.3762/bjoc.10.29

• than that of paclitaxel. The breast cancer cell lines MAXF-401 (IC70 0.2 nM) and MCF-7 (0.5 nM), the colon cancer cell lines HT-29 (0.3 nM) and RKO (0.5 nM), the lung cancer cell line H460 (0.7 nM), the liver cancer cell line LIXF-575 (0.6 nM), and the renal cancer cell line RXF-393 (0.4 nM) all proved

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

Amyloid-β probes: Review of structure–activity and brain-kinetics relationships

• Todd J. Eckroat,
• Abdelrahman S. Mayhoub and
• Sylvie Garneau-Tsodikova

Beilstein J. Org. Chem. 2013, 9, 1012–1044, doi:10.3762/bjoc.9.116

• . Between 2000 and 2008, the number of deaths caused by AD increased by 66%, a dramatic rise, especially when compared to other causes of death, such as heart disease, stroke, prostate and breast cancer, and HIV, which decreased by 3–29% during that time period [1]. As these numbers indicate, AD represents

Synthesis and evaluation of cell-permeable biotinylated PU-H71 derivatives as tumor Hsp90 probes

• Tony Taldone,
• Anna Rodina,
• Erica M. DaGama Gomes,
• Matthew Riolo,
• Hardik J. Patel,
• Raul Alonso-Sabadell,
• Danuta Zatorska,
• Maulik R. Patel,
• Sarah Kishinevsky and
• Gabriela Chiosis

Beilstein J. Org. Chem. 2013, 9, 544–556, doi:10.3762/bjoc.9.60

• still retained affinity for tumor Hsp90, they were each evaluated in a fluorescence polarization (FP) assay by using a cancer-cell homogenate (i.e., SKBr3 human breast cancer lysate). This assay measures competitive binding to tumor cell Hsp90 complexes [23]. Each compound retained a good affinity for

• , Breast Cancer Research Fund, W.H. Goodwin and A. Goodwin and the Commonwealth Cancer Foundation for Research, The Experimental Therapeutics Center of Memorial Sloan-Kettering Cancer Center (MSKCC), 1U01 AG032969-01A1, 1R21 CA158609-01A1, 1R21 AI090501 and 1R01 CA155226-01. T.T. is funded by Susan G

• . Komen for the Cure (KG091313) and the Department of Defense, Breast Cancer Research Program (PDF-BC093421). We also thank Dr. George Sukenick and Dr. Hui Liu of the NMR Analytical Core Facility at MSKCC for expert mass spectral analysis.

Thioester derivatives of the natural product psammaplin A as potent histone deacetylase inhibitors

• Matthias G. J. Baud,
• Thomas Leiser,
• Vanessa Petrucci,
• Mekala Gunaratnam,
• Stephen Neidle,
• Franz-Josef Meyer-Almes and
• Matthew J. Fuchter

Beilstein J. Org. Chem. 2013, 9, 81–88, doi:10.3762/bjoc.9.11

• potency ranking for the AB system: NOH > NOMe > O. The most sensitive cell line to treatment was the MCF7 breast cancer cell line, with the most potent thioester 8 displaying an IC50 of 3.2 μM. Such sensitivity correlates with previous SAR data [20]. While being moderately potent against MCF7 cells (21 μM

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

• available on the market. Nanosponge formulation could thus increase the bioavailability of itraconazole. The solubilisation efficiency of nanosponges with regard to tamoxifen, a nonsteroidal anti-estrogen molecule used for treating and preventing breast cancer, was observed by using a 0.5% aqueous

Modulating the activity of short arginine-tryptophan containing antibacterial peptides with N-terminal metallocenoyl groups

• H. Bauke Albada,
• Alina-Iulia Chiriac,
• Michaela Wenzel,
• Maya Penkova,
• Julia E. Bandow,
• Hans-Georg Sahl and
• Nils Metzler-Nolte

Beilstein J. Org. Chem. 2012, 8, 1753–1764, doi:10.3762/bjoc.8.200

• )3 and RcCO-W(RW)2 synAMPs against human red blood cells (hRBCs). IC50 values (in µM) of both (RW)3 and RcCO-W(RW)2 against human liver carcinoma (HepG2), human colon cancer (HT29) and human breast cancer (MCF7) cell lines. Acknowledgements We thank Annegret Knüfer for determining the IC50 values of

Synthesis and characterization of Sant-75 derivatives as Hedgehog-pathway inhibitors

• Chao Che,
• Song Li,
• Bo Yang,
• Shengchang Xin,
• Zhixiong Yu,
• Taofeng Shao,
• Chuanye Tao,
• Shuo Lin and
• Zhen Yang

Beilstein J. Org. Chem. 2012, 8, 841–849, doi:10.3762/bjoc.8.94

• cancer, breast cancer and multiple myeloma [4][5][6][7][8][9]. Taken together, the development of Hh pathway antagonists has thus represented an attractive strategy for anticancer therapy [10][11]. Because mutated Ptch or Smo proteins are mostly responsible for the abnormal activation of Hh related to

Synthetic glycopeptides and glycoproteins with applications in biological research

• Ulrika Westerlind

Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90

• present in the vaccines. FACS analysis with serum antibodies induced by the MUC1 vaccines 7–10 showed that they all recognize MCF-7 breast-cancer cells. The serum from mice immunized with vaccine 9 was further evaluated through mammary carcinoma tissue-staining experiments. A gradual increase of the

• of a MUC1 TN-glycopeptide, a polio peptide T-cell epitope and the Pam3CSK4 lipopeptide immune-stimulant was prepared by liposome-mediated native chemical ligation. Mice immunized with the three-component vaccine were injected with breast-cancer tumor cells, and were found to be significantly more

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

• tested the bioactivity against the human breast-cancer cell line MCF-7, using the XTT assay [18], and against insect hemocytes from the greater wax moth Galleria melonella according to the method described by Proschak et al. [19]. Three oxazole compounds show LD50 [µg ml−1] values against Galleria

Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities

• Hany M. Mohamed,
• Ashraf H. F. Abd EL-Wahab,
• Ahmed M. EL-Agrody,
• Ahmed H. Bedair,
• Fathy A. Eid,
• Mostafa M. Khafagy and
• Kamal A. Abd-EL-Rehem

Beilstein J. Org. Chem. 2011, 7, 1688–1696, doi:10.3762/bjoc.7.199

• their antidepressant, antithrombotic, antipsychotic (for the central nervous system, CNS) and anti-breast-cancer activities [13]. In view of the important biological properties of the diiodocoumarin derivatives and iodo-organic compounds as medical agents, we planned to synthesize some new

Efficient syntheses of 25,26-dihydrodictyostatin and 25,26-dihydro-6-epi-dictyostatin, two potent new microtubule-stabilizing agents

• María Jiménez,
• Wei Zhu,
• Andreas Vogt,
• Billy W. Day and
• Dennis P. Curran

Beilstein J. Org. Chem. 2011, 7, 1372–1378, doi:10.3762/bjoc.7.161

• -up and in vivo testing [28]. Indeed, 1b proved to be more effective than paclitaxel in treating mice bearing human breast cancer xenografts. Encouraged by these results, we have pursued both new analogs and improved synthetic routes. We recently reported a streamlined synthesis of dictyostatin (1a

• comparable to (−)-dictyostatin and discodermolide. Each compound also inhibited the growth of cell lines resistant to paclitaxel and epothilone B at low nanomolar concentrations, synergized with paclitaxel in MDA-MB-231 human breast cancer cells, and had anti-angiogenic activity in transgenic zebra fish

An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals

• Marcus Baumann,
• Ian R. Baxendale,
• Steven V. Ley and
• Nikzad Nikbin

Beilstein J. Org. Chem. 2011, 7, 442–495, doi:10.3762/bjoc.7.57

• the heterocycle. In general, the triazole containing drugs belong to two groups of therapeutic agents: selective and non-steroidal aromatase inhibitors which are used in the treatment of early and advanced breast cancer in postmenopausal women, e.g., letrozole (256, Femara) and anastrozole (257

Michael-type addition of azoles of broad-scale acidity to methyl acrylate

• Sławomir Boncel,
• Kinga Saletra,
• Barbara Hefczyc and
• Krzysztof Z. Walczak

Beilstein J. Org. Chem. 2011, 7, 173–178, doi:10.3762/bjoc.7.24

• -3,5-diyl)diphenol (IV) and its derivatives are known modulators of receptors regulating the secretion of estrogens crucial in the pathogenesis of breast cancer [4]. 4-(Benzo[d][1,3]dioxol-5-ylmethyl)-1-(3-methoxybenzyl)-3-phenyl-pyrazole-5-carboxylic acid (V) is an antagonist of endothelial receptors