Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst

• Abhijit Paul,
• Debnath Chatterjee,
• Srirupa Banerjee and
• Somnath Yadav

Beilstein J. Org. Chem. 2020, 16, 140–148, doi:10.3762/bjoc.16.16

• . Mechanistic studies have unambiguously proven the heterogeneous nature of the catalysis. The ability of the nanocatalyst to activate the C–H bond is due to the presence of minimal stabilising groups on its surface. Studies of the surface morphology of the catalyst have revealed the presence of surface oxides

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

• Alexander Sailer,
• Franziska Ermer,
• Yvonne Kraus,
• Rebekkah Bingham,
• Ferdinand H. Lutter,
• Julia Ahlfeld and
• Oliver Thorn-Seshold

Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

• network within cells treated with HITubs and documented the resulting disruption of the physiological MT network integrity, and consequently also changes in cell morphology by confocal microscopy. Cells exposed to HITub-4 (1 μM) in the dark or under λ = 530 nm illumination (to maintain exclusively Z

Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles

• Sara Tejera,
• Giada Caniglia,
• Rosa L. Dorta,
• Andrea Favero,
• Javier González-Platas and
• Jesús T. Vázquez

Beilstein J. Org. Chem. 2019, 15, 2881–2888, doi:10.3762/bjoc.15.282

• thin and short fibers. The xerogel of compound 12 showed long, thin, and relatively straight fibers, with lack of torsion, as well as regularity of the network. Its cis stereoisomer 14 showed a fibrous network, but of much shorter length. However, the gel of compound 10 showed a different morphology

Carbazole-functionalized hyper-cross-linked polymers for CO₂ uptake based on Friedel–Crafts polymerization on 9-phenylcarbazole

• Dandan Fang,
• Xiaodong Li,
• Meishuai Zou,
• Xiaoyan Guo and
• Aijuan Zhang

Beilstein J. Org. Chem. 2019, 15, 2856–2863, doi:10.3762/bjoc.15.279

• the temperature raised up to 800 °C (Supporting Information File 1, Table S1), demonstrated the splendid thermal stability of P1–P11 as reported for microporous polymers [34]. Morphology analysis The morphology of P1–P11 was investigated by SEM images (Figure 4), which showed that HCPs were composed

• than many carbazole-based HCPs with similar BET specific surface area [19][20][24]. We conjecture that the concentration of FDA can affect the formation process and morphology of the polymers, when polymer particles agglomerate and stack together (Figure 4). We reached the conclusion that when varying

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

• Lorenzo Sansalone,
• Jun Zhao,
• Matthew T. Richers and
• Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

• an internal solution containing (in mM): 135 potassium gluconate, 4 MgCl2, 10 HEPES, 4 Na2-ATP, 0.4 Na2-GTP, 10 Na2-phosphocreatine, pH 7.35. The red fluorescent dye Alexa 594 (0.05 mM, ThermoFisher Scientific, Waltham, MA, USA) was added to visualize the morphology of the neurons. Normal ACSF was

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

• plasma membranes in live cells is still one of the most promising strategies to investigate their roles, functions and to relate them with specific cellular responses [7]. The selective imaging of plasma membranes allows the tracking of the cell morphology, the cell status, cellular division step, signal

• cells. (A) Plasma membranes stained with the designed BTD-4APTEG. (B) Overlay of (A) and (C) showing the orange emission as the result of both green and red emissions. (C) Plasma membranes stained with the commercially available CellMask. (D) Shows the normal morphology of the cells by phase contrast

α,ß-Didehydrosuberoylanilide hydroxamic acid (DDSAHA) as precursor and possible analogue of the anticancer drug SAHA

• Shital K. Chattopadhyay,
• Subhankar Ghosh,
• Sarita Sarkar and
• Kakali Bhadra

Beilstein J. Org. Chem. 2019, 15, 2524–2533, doi:10.3762/bjoc.15.245

• a minimal effect of cytotoxicity (≈9.1% necrotic as well as apoptotic cells, respectively), by observing the morphology of the cells under a microscope at a concentration of 15 μg/mL. ROS generation study by DCFDA (2′,7′-dichlorodihydrofluorescein diacetate) by FACS (fluorescence-activated cell

Targeted photoswitchable imaging of intracellular glutathione by a photochromic glycosheet sensor

• Xianzhi Chai,
• Hai-Hao Han,
• Yi Zang,
• Jia Li,
• Xiao-Peng He,
• Junji Zhang and
• He Tian

Beilstein J. Org. Chem. 2019, 15, 2380–2389, doi:10.3762/bjoc.15.230

• activities [1][2]. Nonetheless, conventional fluorescence sensors always encounter background signal interferences during cell imaging, which are usually generated from bioluminescence and light scattering in the intracellular environment [3]. This may lead to the deviation in judging the morphology and

• obvious morphology of nanosheets which presented a large 2D and ultrathin plane with a diameter of ca. 200 nm (Figure 2B) [33][34]. By virtue of the expansive surface, 2D MnO2 nanosheets possess the ability to load dozens of fluorophores. An array of fluorescent reporters thus formed, which facilitate

Synthesis of a dihalogenated pyridinyl silicon rhodamine for mitochondrial imaging by a halogen dance rearrangement

• Jessica Matthias,
• Thines Kanagasundaram,
• Klaus Kopka and
• Carsten S. Kramer

Beilstein J. Org. Chem. 2019, 15, 2333–2343, doi:10.3762/bjoc.15.226

• example, Giedt et al. could show that analysis of mitochondrial morphology can be used as a biomarker for cancer phenotype assignment and for drug response analysis [54]. For STED imaging, HeLa cells were stained for 1 h with 1 µM of dye 15, washed and imaged live. Figure 2 and Figure S5, Supporting

Isolation of fungi using the diffusion chamber device FIND technology

• Benjamin Libor,
• Henrik Harms,
• Stefan Kehraus,
• Ekaterina Egereva,
• Max Crüsemann and
• Gabriele M. König

Beilstein J. Org. Chem. 2019, 15, 2191–2203, doi:10.3762/bjoc.15.216

• earlier. Alternatively, a stamp can be used to punch all agar plugs simultaneously into the wells of a 96 well plate. Fermentation on agar plates was performed in an incubator at 25 °C for another four weeks. Morphology of the axenic colonies was then analysed microscopically, and their taxonomy was

Morphology-tunable and pH-responsive supramolecular self-assemblies based on AB₂-type host–guest-conjugated amphiphilic molecules for controlled drug delivery

• Yang Bai,
• Cai-ping Liu,
• Di Chen,
• Long-hai Zhuo,
• Huai-tian Bu and
• Wei Tian

Beilstein J. Org. Chem. 2019, 15, 1925–1932, doi:10.3762/bjoc.15.188

• -responsive supramolecular self-assemblies have been constructed, the controlled drug delivery induced by morphology transitions of these supramolecular self-assemblies on the basis of host–guest-conjugated monomers (HGCMs) are few reported. In this paper, the self-assembly behaviors of AB2-type HGCMs, e.g

• spherical supramolecular self-assemblies with a size of 52 nm under acidic conditions. This morphology transition process was utilized to conduct a two-stage DOX delivery under neutral and acidic pH. Basic cell experiments demonstrated that the drug-loaded β-CD-BM2-based supramolecular self-assemblies with

• varied morphology could inhibit cancer cell proliferation, indicating their potential application in the field of drug delivery. Keywords: β-cyclodextrin; controlled drug delivery; host–guest interaction; stimuli-responsive; supramolecular self-assemblies; Introduction Supramolecular self-assemblies

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

• Piyali Sarkar,
• Sayan Sarkar and
• Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

• apoptotic cells, the investigation of the morphology of nuclei, the direct counting of cultivable bacteria, DNA intercalators, etc. [1][2][3][4]. Pyrrole, another biologically active heterocyclic compound, when fused with acridines affords promising bioactive pyrroloacridinone moieties demonstrating

Self-assembly behaviors of perylene- and naphthalene-crown macrocycle conjugates in aqueous medium

• Xin Shen,
• Bo Li,
• Tiezheng Pan,
• Jianfeng Wu,
• Yangxin Wang,
• Jie Shang,
• Yan Ge,
• Lin Jin and
• Zhenhui Qi

Beilstein J. Org. Chem. 2019, 15, 1203–1209, doi:10.3762/bjoc.15.117

• the weaker π–π stacking of 2 leading to a less regular packing arrangement, no regular morphology was observed when CHCl3 or MeCN was used as solvent (Figure 2d and 2e), and only a short nanobelt was observed in H2O/MeCN (v/v = 10:1, Figure 2f). The TEM characterization result was corroborated well by

Mechanochemical synthesis of hyper-crosslinked polymers: influences on their pore structure and adsorption behaviour for organic vapors

• Sven Grätz,
• Sebastian Zink,
• Hanna Kraffczyk,
• Marcus Rose and
• Lars Borchardt

Beilstein J. Org. Chem. 2019, 15, 1154–1161, doi:10.3762/bjoc.15.112

• contents below the limit of detection (Supporting Information File 1, Figure S3). Scattering electron microscopy also revealed an agglomerated morphology of the samples (Supporting Information File 1, Figure S4). After successfully establishing the occurrence of the cross-linking reaction and investigating

Fabrication, characterization and adsorption properties of cucurbit[7]uril-functionalized polycaprolactone electrospun nanofibrous membranes

• Changzhong Chen,
• Fengbo Liu,
• Xiongzhi Zhang,
• Zhiyong Zhao and
• Simin Liu

Beilstein J. Org. Chem. 2019, 15, 992–999, doi:10.3762/bjoc.15.97

• , Xiangnan University, Chenzhou 423000, China 10.3762/bjoc.15.97 Abstract The fabrication of electrospun nanofibers comprising cucurbit[7]uril (CB[7]) and poly(ε-caprolactone) (PCL) is reported. Various techniques such as SEM, FTIR, XRD, DSC and TG were utilized to characterize the morphology, composition

• or some low-molecular weight organic compounds [1][2][3][4][5]. With the unique advantages of ultrafine diameter, high specific surface area, controllable morphology, and easy functionalization, electrospun nanofibers have potential applications in various areas including drug delivery and tissue

• morphology of the PCL/CB[5], PCL/CB[6], and PCL/CB[8] composite nanofibers as observed by SEM are supplied in Supporting Information File 1 (Figures S2–S4). In contrast, CB[7] was quite soluble in formic acid and the maximum CB[7] mass percentage in the composite nanofibers could be up to 66.67% (the mass

Application of olefin metathesis in the synthesis of functionalized polyhedral oligomeric silsesquioxanes (POSS) and POSS-containing polymeric materials

• Patrycja Żak and
• Cezary Pietraszuk

Beilstein J. Org. Chem. 2019, 15, 310–332, doi:10.3762/bjoc.15.28

• the range of 1.3–1.9. The surface morphology and thermal properties of hybrids were found to be affected by the POSS macromer. TEM analysis of copolymer films revealed the presence of POSS agglomerates. An analogous macromer bearing POSS-bound via phenylene linker was used in the synthesis of a series

Repurposing the anticancer drug cisplatin with the aim of developing novel Pseudomonas aeruginosa infection control agents

• Mingjun Yuan,
• Song Lin Chua,
• Yang Liu,
• Daniela I. Drautz-Moses,
• Joey Kuok Hoong Yam,
• Thet Tun Aung,
• Roger W. Beuerman,
• May Margarette Santillan Salido,
• Stephan C. Schuster,
• Choon-Hong Tan,
• Michael Givskov,
• Liang Yang and
• Thomas E. Nielsen

Beilstein J. Org. Chem. 2018, 14, 3059–3069, doi:10.3762/bjoc.14.284

• vivo P. aeruginosa infections using a mouse model of keratitis, where P. aeruginosa cells have biofilm-like morphology [26][27] and employ type III secretion during infections [43]. We firstly confirmed that cisplatin was not toxic and did not interfere with wound healing, with no observable

MoO₃ on zeolites MCM-22, MCM-56 and 2D-MFI as catalysts for 1-octene metathesis

• Hynek Balcar,
• Martin Kubů,
• Naděžda Žilková and
• Mariya Shamzhy

Beilstein J. Org. Chem. 2018, 14, 2931–2939, doi:10.3762/bjoc.14.272

• cups as we assume host MoOx species. Although MCM-56(13) as 2D zeolite consists of very thin layers, these layers may be curled and packed, which prevents the access of substrate molecules to the most of 12MR cups (for MCM-56(13) morphology see Supporting Information File 1, Figure S8). This may

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

• Eszter Lajkó,
• Sarah Spring,
• Rózsa Hegedüs,
• Beáta Biri-Kovács,
• Sven Ingebrandt,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

• because of difficulty in realizing adhesion contacts to the substrate [53]. Our present results about the chemorepellent character of the conjugates appeared to be well-correlated to their effect on cell adhesion and cellular morphology of A2058 cells. Next, the chemokinetic activities (inducing random

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

• Ana-Maria Preda,
• Małgorzata Krasowska,
• Lydia Wrobel,
• Philipp Kitschke,
• Phil C. Andrews,
• Jonathan G. MacLellan,
• Lutz Mertens,
• Marcus Korb,
• Tobias Rüffer,
• Heinrich Lang,
• Alexander A. Auer and
• Michael Mehring

Beilstein J. Org. Chem. 2018, 14, 2125–2145, doi:10.3762/bjoc.14.187

• rarely a more compact morphology. Both types of crystals of 2 were suitable for single crystal X-ray diffraction analysis and revealed the formation of two polymorphs 2a (colorless acicular crystals) and 2b (light yellow block-shaped crystals) in the solid state. Polymorph 2a crystallizes in the

Synthesis and supramolecular self-assembly of glutamic acid-based squaramides

• Juan V. Alegre-Requena,
• Marleen Häring,
• Isaac G. Sonsona,
• Alex Abramov,
• Eugenia Marqués-López,
• Raquel P. Herrera and
• David Díaz Díaz

Beilstein J. Org. Chem. 2018, 14, 2065–2073, doi:10.3762/bjoc.14.180

• these images should always be done cautiously. Further detailed investigations with the aid of additional techniques are still necessary in order to clarify the exact molecular mechanism associated with each morphology. Conclusion In conclusion, unsymmetrical glutamic acid-based squaramides 3 and 4 can

Functionalization of graphene: does the organic chemistry matter?

• Artur Kasprzak,
• Agnieszka Zuchowska and
• Magdalena Poplawska

Beilstein J. Org. Chem. 2018, 14, 2018–2026, doi:10.3762/bjoc.14.177

• and hydrogen bonding-dependent adsorption of glucose on the RGO surface results in a shift of the absorption bands coming from the C=O of RGO (from 1724 cm−1 to 1735 cm−1). Another consideration is that this process further influences the obtained material’s morphology, properties and thermal

A self-assembled photoresponsive gel consisting of chiral nanofibers

• Lei Zou,
• Dan Han,
• Zhiyi Yuan,
• Dongdong Chang and
• Xiang Ma

Beilstein J. Org. Chem. 2018, 14, 1994–2001, doi:10.3762/bjoc.14.174

• and the chirality of the nanostructures could both be adjusted by subsequent light irradiation at different wavelengths. The helical nanofiber-like morphology was verified in the internal structure of the gel. The performance of this gel was investigated by a series of methods, such as UV–vis

• conditions [6][17][18][19], such as solvent, light and temperature. These characteristics meet currents demands for conveniently controlling the assembly of materials according to their size, shape, and morphology. Chiral functional materials have aroused much attention for their potential applications. Liu

• process was partially reversible. The compound 3 cycling test, with more than 8 cycles, caused the total disappearance of the CD signal and the process was then no longer reversible (Figure S8, Supporting Information File 1). The morphology of compound 3 was further characterized by scanning electron

Graphitic carbon nitride prepared from urea as a photocatalyst for visible-light carbon dioxide reduction with the aid of a mononuclear ruthenium(II) complex

• Kazuhiko Maeda,
• Daehyeon An,
• Ryo Kuriki,
• Daling Lu and
• Osamu Ishitani

Beilstein J. Org. Chem. 2018, 14, 1806–1812, doi:10.3762/bjoc.14.153

• . The sample synthesized at 773 K had a lot of circular voids having 50–100 nm in size. At 823 K, this void structure was less prominent, and sheet-like morphology started to appear. With a further increase in the synthesis temperature, the synthesized samples consisted of disordered nanosheets. This

• change in particle morphology is in qualitative agreement with that in the specific surface area (see Table 1). Figure 4 shows the UV–visible diffuse reflectance spectra of g-C3N4 synthesized at different temperatures. All of the samples exhibited an absorption edge at 420–450 nm, attributed to electron

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

• attributed to [9 + H]3+, [9 + 2H]4+ and [9 + 3H]5+ by comparison between the experimental and theoretical isotope distributions (see Supporting Information File 1). Molecular modeling simulations were carried out to provide insights into the size and morphology of conjugate 9. An optimized geometry is