Synthesis and photophysical studies of a multivalent photoreactive Ru^II-calix[4]arene complex bearing RGD-containing cyclopentapeptides

• Sofia Kajouj,
• Lionel Marcelis,
• Alice Mattiuzzi,
• Adrien Grassin,
• Damien Dufour,
• Pierre Van Antwerpen,
• Didier Boturyn,
• Eric Defrancq,
• Mathieu Surin,
• Julien De Winter,
• Pascal Gerbaux,
• Ivan Jabin and
• Cécile Moucheron

Beilstein J. Org. Chem. 2018, 14, 1758–1768, doi:10.3762/bjoc.14.150

• photophysical and photochemical characterizations of this Ru(II)–calixarene conjugate as well as the study of its photoreactivity in the presence of guanosine monophosphate have been achieved. The results show that the ruthenium complex should be able to perform efficiently its photoinduced cytotoxic activity

• cytotoxic activity, once incorporated into targeted cancer cells thanks to the multivalent platform. In cellulo studies are currently under investigation and will be reported in the near future. Experimental General: All the solvents and reagents for the syntheses were at least reagent grade quality and

Lanyamycin, a macrolide antibiotic from Sorangium cellulosum, strain Soce 481 (Myxobacteria)

• Lucky S. Mulwa,
• Rolf Jansen,
• Dimas F. Praditya,
• Kathrin I. Mohr,
• Patrick W. Okanya,
• Joachim Wink,
• Eike Steinmann and
• Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 1554–1562, doi:10.3762/bjoc.14.132

• their macrolactone ring was assigned based on NOE and vicinal 1H NMR coupling constants and by calculation of a 3D model. Lanyamycin inhibited HCV infection into mammalian liver cells with an IC50 value of 11.8 µM, and exhibited a moderate cytotoxic activity against the mouse fibroblast cell line L929

• (KB3.1), colon carcinoma cells (HCT-116), and glioblastoma (U87MG). It exhibited cytotoxic activity with IC50 values of 3.1 and 1.5 µM against L929 and KB3.1 cell cultures, respectively, while it was not active against the other cell lines according to the limits of the National Cancer Institute (active

• activities on a Berthold Technologies Centro XS3 Microplate Luminometer as indicators of viral genome replication and cell viability, respectively, as previously described [18]. Cytotoxic activity The cytotoxicity was evaluated by measuring the effect produced on cell morphology including the nuclei and cell

Hyper-reticulated calixarene polymers: a new example of entirely synthetic nanosponge materials

• Alberto Spinella,
• Marco Russo,
• Antonella Di Vincenzo,
• Delia Chillura Martino and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2018, 14, 1498–1507, doi:10.3762/bjoc.14.127

• composites loaded with quercetin may show improved cytotoxic activity towards some human breast cancer cell lines [32], likely due to a synergistic action between the polyphenol nutraceutic guest molecule and triazole derivatives coming from the progressive disgregation of the co-polymer carrier. From the

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

• ][40]. The benzoyl nitrogen mustard (BAM) to the formyl end of the distamycin acts as an alkylating moiety whereas the distamycin framework acts as a DNA binding domain. Therefore, due to the installation of the alkylating moiety, TAM has higher cytotoxic activity in comparison to distamycin, and shows

• structure–activity relationship. It has been observed that the number and position of pyrrole rings are crucial for antileukemic activity. The presence of pyrrole rings close to the alkylating BAM moiety is responsible for better cytotoxic activity both in vitro and in vivo, whereas a pyrazole ring in close

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

• rationally installed taking into consideration the final derivative of the cytotoxic agent to retain the original cytotoxic activity. The sections below summarize the basic design principles of peptide–drug conjugates to selectively target the malignant cells. Selecting the proper tumor-targeting peptide to

• -amino group of the D-Lys side chain of the peptide D-Lys6-LHRH. Notably, both conjugates fully preserved the cytotoxic activity of the parent drugs, DOX or 2-pyrrolino-DOX, respectively, in vitro and also retained the high binding affinity of their peptide carrier to receptors for LHRH on rat pituitary

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

• % (3) and 53% (6)), demonstrating that all measured compounds displayed an in vitro cytotoxic activity. Nevertheless, the replacement of 6Asp by D-Asp, D-Glu or D-Trp led to a decreased cytostatic effect on the estimated cancer cell lines. Considering the determined IC50 values, no relevant differences

Mannich base-connected syntheses mediated by ortho-quinone methides

• Petra Barta,
• Ferenc Fülöp and
• István Szatmári

Beilstein J. Org. Chem. 2018, 14, 560–575, doi:10.3762/bjoc.14.43

• active zwitterionic species via an o-QM intermediate. Dimmock et al. subsequently examined the cytotoxic activity of phenolic azobenzene Mannich bases [92]. Correlations were found between structures and activities against murine P388DI and L1210 cells, human T-lymphocyte cell lines and, in some cases

5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines

• Ranjana Aggarwal and
• Suresh Kumar

Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15

• ). Interestingly, high yields of the corresponding pyrazolo[3,4-b]pyridines 34 were obtained when reactions were carried under solvent-free microwave irradiation. The synthesized pyrazolo[3,4-b]pyridines have shown potential cytotoxic activity against cervical HeLa and prostate DU 205 cancer cell lines. A similar

• screened for their cytotoxic activity against human colon carcinoma (Colo-205) cell lines (Scheme 35). Buriol et al. [92] described the reaction of 5-aminopyrazole 16 with 4-alkoxy-1,1,1-trifluoro-3-alken-2-ones 129 to yield pyrazolo[1,5-a]pyrimidine derivatives 130 in acetic acid and ethanol using

Volatiles from the tropical ascomycete Daldinia clavata (Hypoxylaceae, Xylariales)

• Tao Wang,
• Kathrin I. Mohr,
• Marc Stadler and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2018, 14, 135–147, doi:10.3762/bjoc.14.9

• -5,6-dihydro-2H-pyran-2-one (9) and 6-nonyl-2H-pyran-2-one (17). Volatiles from Daldinia clavata MUCL 47436. 13C NMR data (chemical shifts in ppm) for 11a–d (125 MHz, C6D6). In vitro antibacterial, antifungal and cytotoxic activity of compounds 9, 14 and 17 in comparison with positive controls

A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines

• Benedikt C. Melzer and
• Franz Bracher

Beilstein J. Org. Chem. 2017, 13, 1564–1571, doi:10.3762/bjoc.13.156

• oxoisoaporphine alkaloids and the isomers 18 and 19 showed significant cytotoxic activity. IC50 values of alkaloid 3 and of compounds 18 and 19 are ranging from 3–6 µM. Very strong cytotoxicity was determined for 6-O-demethylmenisporphine (4) with an IC50 value of 0.06 µM and for dauriporphinoline (5) with 0.23

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• cytotoxic activity toward lymphoma cells, resulting active at a very low micromolar range [101]. With the aim to activate the human immune system against self-tumor cells, Schlecht and co-workers designed the synthesis of AuNPs functionalized with Mucin1(MUC1)-glycopeptide antigens [102]. Mucins are a

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

• keto-oximes 179 and 2-amino derivatives 180 are β2-adrenergic agonists tested for bronchodilating activity. The pterosin family are sesquiterpenoids naturally occurring in bracken fern (Pteridium aquilinum), some of them exhibit antibacterial and cytotoxic activity. A practical synthesis of pterosin A

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

• Naganna Narra,
• Shiva Shanker Kaki,
• Rachapudi Badari Narayana Prasad,
• Sunil Misra,
• Koude Dhevendar,
• Venkateshwarlu Kontham and
• Padmaja V. Korlipara

Beilstein J. Org. Chem. 2017, 13, 26–32, doi:10.3762/bjoc.13.4

• calorimetry (DSC). The prepared compounds were also screened for their cytotoxic activity against five cell lines. It was observed that the lipoconjugates of caffeic acid, sinapic acid, ferulic acid, and coumaric acid displayed anticancer and anti-oxidant properties. The anticancer properties of these

• due to different media used for the assays; the DPPH assay is conducted in a polar medium but the linoleic acid oxidation study is conducted in a non-polar environment. Cytotoxic activity As there were studies reported on the cytotoxicity of phenolic lipids, we have further screened the prepared

Synthesis of spiro[isoindole-1,5’-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction

• Salvatore V. Giofrè,
• Santa Cirmi,
• Raffaella Mancuso,
• Francesco Nicolò,
• Giuseppe Lanza,
• Laura Legnani,
• Agata Campisi,
• Maria A. Chiacchio,
• Michele Navarra,
• Bartolo Gabriele and
• Roberto Romeo

Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278

• 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

• from of independent experiments performed in eightplicate (MTS assay) or in triplicate (BrdU test). *P < 0.05, **P < 0.01 and ***P < 0.001 vs untreated cells. Cytotoxic effect of 6e. The cytotoxic activity of 6e was assessed in terms of both LDH release (a) and cell death (b). LDH levels are

Biomimetic synthesis and HPLC–ECD analysis of the isomers of dracocephins A and B

• Viktor Ilkei,
• András Spaits,
• Anita Prechl,
• Áron Szigetvári,
• Zoltán Béni,
• Miklós Dékány,
• Csaba Szántay Jr,
• Judit Müller,
• Árpád Könczöl,
• Ádám Szappanos,
• Attila Mándi,
• Sándor Antus,
• Ana Martins,
• Attila Hunyadi,
• György Tibor Balogh,
• György Kalaus (†),
• Hedvig Bölcskei,
• László Hazai and
• Tibor Kurtán

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

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

• Mikhail Yu. Ievlev,
• Oleg V. Ershov,
• Mikhail Yu. Belikov,
• Angelina G. Milovidova,
• Viktor A. Tafeenko and
• Oleg E. Nasakin

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

• Peng Zhang,
• Xiao-Ming Li,
• Xin-Xin Mao,
• Attila Mándi,
• Tibor Kurtán and
• Bin-Gui Wang

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

Cyclisation mechanisms in the biosynthesis of ribosomally synthesised and post-translationally modified peptides

• Andrew W. Truman

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

Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites

• Antonio Dávila-Céspedes,
• Peter Hufendiek,
• Max Crüsemann,
• Till F. Schäberle and
• Gabriele M. König

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

Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine

• Štěpán Horník,
• Lucie Červenková Šťastná,
• Petra Cuřínová,
• Jan Sýkora,
• Kateřina Káňová,
• Roman Hrstka,
• Ivana Císařová,
• Martin Dračínský and
• Jindřich Karban

Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75

• 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

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• 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

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• 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

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

• , the cytotoxic activity on CaCo-2, HeLa and MCF-7 carcinoma cell lines of inclusion complexes was also determined. Results and Discussion The binding free energy of inclusion complexes between naringenin with β-CD and DM-β-CD has been previously reported by our group [40]. In the present work, we

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

• activity. Aplysinin B (3) was not subjected to any biological activity test due to the minute amount and its existence as the minor compound of a mixture. The results showed that 1 and 2 exhibited mild cytotoxic activity against KB-31 epidermoid carcinoma cells (IC50 = 69 and 26 µM, respectively). Only 2

Cu(I)-catalyzed N,N’-diarylation of natural diamines and polyamines with aryl iodides

• Svetlana P. Panchenko,
• Alexei D. Averin,
• Maksim V. Anokhin,
• Olga A. Maloshitskaya and
• Irina P. Beletskaya

Beilstein J. Org. Chem. 2015, 11, 2297–2305, doi:10.3762/bjoc.11.250

• found to possess respiratory stimulating effects [12], N-substituted putrescine and cadaverine have shown antiproliferative and cytotoxic activity [13][14], N-decyl and N-dodecyl derivatives of putrescine, N-(p-tolyl) derivatives of cadaverine and hexane-1,6-diamine have demonstrated affinity to NMDA