BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• ). NO production in primary rat macrophages. The cells were treated with Tb, compounds 4, 5, and Tb-construct 6 for 24 h with or without lipopolysaccharide (LPS, 100 pg·mL−1). The results represent the mean ± SEM of 2 independent experiments, n = 4. Statistical significance: *P < 0.05, **P < 0.01, ***P

Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

• Qing Yin,
• Qi Chen,
• Li-Can Lu and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 1212–1221, doi:10.3762/bjoc.13.120

• larger from 2–10 nm (8 h) to 5–20 nm (24 h). The SEM image of the AgNPs/SugPOP-1 composite shows that many AgNPs are loaded onto the surface of the matrix (Figure 3e). The corresponding energy-dispersive X-ray spectroscopy (EDX) technique indicates that AgNPs are successfully loaded in SugPOP-1 (Figure

• ; (d) 24 h. (e) SEM image and (f) the corresponding EDX data of the AgNPs/SugPOP-1 composite obtained after reaction for 24 h. Nitrogen sorption isotherm at 77 K and the pore size distribution profile calculated by NLDFT analysis (inset) of the AgNPs/SugPOP-1 composite. Catalytic performance of the

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

• Gabriel P. Costa,
• Natália Seus,
• Juliano A. Roehrs,
• Raquel G. Jacob,
• Ricardo F. Schumacher,
• Thiago Barcellos,
• Rafael Luque and
• Diego Alves

Beilstein J. Org. Chem. 2017, 13, 694–702, doi:10.3762/bjoc.13.68

• : Experimental and analytical data. Acknowledgements We thank the CNPq (Grants 306430/2013-4, 400150/2014-0 and 447595/2014-8), CAPES and FAPERGS (PRONEM 6/2551-0000240-1) for the financial support. Rafael Luque gratefully acknowledges support from Ciência sem Fronteiras Program (Grant 303415/2014-2) as

Fast and efficient synthesis of microporous polymer nanomembranes via light-induced click reaction

• Qi An,
• Youssef Hassan,
• Xiaotong Yan,
• Peter Krolla-Sidenstein,
• Tawheed Mohammed,
• Mathias Lang,
• Stefan Bräse and
• Manuel Tsotsalas

Beilstein J. Org. Chem. 2017, 13, 558–563, doi:10.3762/bjoc.13.54

• selectively dissolved using cyclohexane. Afterwards we dissolved the sacrificial substrate to obtain the freestanding CMP membranes. To investigate the freestanding CMP nanomembrane we transferred it to a copper grid and recorded scanning electron microscopy (SEM) images. Figure 4 shows the SEM images of the

• electron microscopy (SEM): We recorded SEM images using a FEI Philips XL30 (FEI Co., Eindhoven, NL), a field emission gun environmental scanning electron microscope (FEG-ESEM). Samples have been coated with a thin layer (about 5 nm) of a gold/palladium film in order to avoid charging and improve samples

• using light-induced TYC reaction in the presence of the photoinitiator 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one. IRRA-Spectrum of the CMP thin film on a gold-coated silicon wafer and the corresponding band assignments. AFM image and line-scan across the edge of the CMP thin film. SEM

A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation

• Wangkhem P. Singh and
• Rajkumar S. Singh

Beilstein J. Org. Chem. 2017, 13, 138–149, doi:10.3762/bjoc.13.17

• unit which may be further exploited in the design of small molecule based gelators. Keywords: hydrophobic interactions; organogelator; SEM; triphenylmethyl group; xerogel; Introduction Small organic molecules capable of forming gels are called low molecular weight gelators (LMWGs) [1][2][3]. These

• microscopic structures and morphologies of the gels formed by the gelators, scanning electron microscopy (SEM) studies were performed with the dried gels [33]. Dried gels (xerogels) were obtained from the gels by evaporation of the solvent. The morphologies for TPM-G12 and TPM-G5 are drastically different

• prepared from TPM-G12 in (a) Propan-1-ol and (b) DMSO. SEM images of the dried gels. TPM-G12 in propan-1-ol (a) and (b), in DMSO (c) and (d); TPM-G5 in DMSO (e) and (f). (a), (c), (e) are of lower magnification while (b), (d), (f) are of higher magnification. Stress sweep rheological experiment of TPM-G12

Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• uptake. As this result did not point towards accessible microchannels of the crystal structure, the material was checked for structural and chemical integrity subsequent to activation. As stated, elemental analysis fits very well, so that decomposition is unlikely. Therefore, also SEM investigations by

• in purple and cyan. Synthesis of [60]fullerene dodecaacid C4. Supporting Information Supporting Information File 4: Analytical and crystallographic data; SEM, BET, PXRD and TGA/DTA data. Acknowledgements The authors would like to thank Dr. David Schmidt for PXRD measurements and Dr. Fabian

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

• from 1 to 100 µM for 24, 48 and 72 h reduced the growth rate in a time and concentration-dependent manner. The experiments were performed by the MTS assay (a) and BrdU test (b). Results are expressed as percentages of growth rates of treated cells compared to untreated cultures, and are the means ± SEM

Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I)

• Sem Raj Tamang and
• James D. Hoefelmeyer

Beilstein J. Org. Chem. 2016, 12, 2757–2762, doi:10.3762/bjoc.12.272

• Sem Raj Tamang James D. Hoefelmeyer Department of Chemistry, University of South Dakota, 414 E. Clark St., Vermillion, SD 57069, USA 10.3762/bjoc.12.272 Abstract We report direct arylation of arylhalides with unactivated sp2 C–H bonds in benzene and naphthalene using a copper(I) catalyst

Synthesis of three-dimensional porous hyper-crosslinked polymers via thiol–yne reaction

• Mathias Lang,
• Alexandra Schade and
• Stefan Bräse

Beilstein J. Org. Chem. 2016, 12, 2570–2576, doi:10.3762/bjoc.12.252

• analyses (Table 1) of networks 3 and 5 showed equimolar turnover regarding the number of functional groups of the monomers. Further, TGA measurements showed a high thermal stability of the HCPs. The TGA curves of HCP 3 and 5 are shown in Supporting Information File 1, Figures S5 and S6. The SEM pictures

• (Figure 3) show the amorphous character of the HCPs, which is consistent with the PXRD measurements (see Supporting Information File 1, Figures S3 and S4). The SEM pictures also reveal that HCP 3 consists of particles in the micrometer range while the particle size of HCP 5 is in the sub-micrometre area

• character as the networks are built up by an irreversible reaction leading to kinetically controlled networks with different sizes of the pores, which is in accordance with the PXRD and SEM measurements stated above. The pore-size distributions of HCPs 3 and 5 are illustrated in Supporting Information File

Experimental and theoretical investigations into the stability of cyclic aminals

• Edgar Sawatzky,
• Antonios Drakopoulos,
• Martin Rölz,
• Christoph Sotriffer,
• Bernd Engels and
• Michael Decker

Beilstein J. Org. Chem. 2016, 12, 2280–2292, doi:10.3762/bjoc.12.221

• . All experiments were performed in triplicate (mean ± SEM). Differences in energy along the reaction coordinate using the functional B3LYP-D3 for the hydrolysis of (a) compound 8a and (b) compound 13b in aqueous environment. Reaction equilibrium between tetrahydroquinazoline 1, the corresponding

Hydroxy-functionalized hyper-cross-linked ultra-microporous organic polymers for selective CO₂ capture at room temperature

• Partha Samanta,
• Priyanshu Chandra and
• Sujit K. Ghosh

Beilstein J. Org. Chem. 2016, 12, 1981–1986, doi:10.3762/bjoc.12.185

• for hyper-cross-linked polymers (HCPs) and b) synthesis schemes for HCP-91 and HCP-94. a) Infra-red spectra of HCP-91 (dark yellow) and HCP-94 (purple); b) N2 adsorption isotherms for HCP-91 (wine red) and HCP-94 (green) at 77 K; c) SEM image of HCP-91 and d) SEM image of HCP-94. a) CO2 adsorption

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• when assembling SNPs from CD-PEI and Fc8-PAMAM in the absence of stabilizer. SNPs were formed by adding Fc8-PAMAM (dissolved in DMSO) to an aqueous solution of CD-PEI ([CD] = 100 µM) in aqueous NaCl solution. To confirm particle formation, SNPs were characterized using DLS and SEM (Figure 3). DLS

• was achieved by changing the stoichiometry of the multivalent guest and the monovalent stabilizer while keeping the overall host–guest ratio constant and equimolar. SNPs were observed by SEM and DLS for all samples as shown in Figure 7. The particle sizes determined by SEM (see Figure 7a–c) with sizes

• ). Equipment Dynamic light scattering (DLS) Hydrodynamic diameters and zeta potentials were measured on a Zetasizer NanoZS (Malvern Instrument Ltd, Malvern, United Kingdom) at 20 °C, with a laser wavelength of 633 nm and a scattering angle of 173°. High resolution scanning electron microscopy (HR-SEM) All SEM

Preparation of Pickering emulsions through interfacial adsorption by soft cyclodextrin nanogels

• Shintaro Kawano,
• Toshiyuki Kida,
• Mitsuru Akashi,
• Hirofumi Sato,
• Motohiro Shizuma and
• Daisuke Ono

Beilstein J. Org. Chem. 2015, 11, 2355–2364, doi:10.3762/bjoc.11.257

• particle size of the primary CD nanogel and the appearance of a new peak at a larger diameter (120 nm) may be due to the self-assembly of the primary CD nanogels at 0.1 wt % concentration in water. The scanning electron microscopy (SEM) measurement was carried out in order to observe the self-assembled

• shell (whose thickness corresponds to the particle diameter) of self-assembled CD nanogels and not a multilayer structure. The outermost layer of the CD nanogel assembly was observed using SEM. A number of “deflated balloon” structures appear under low magnification (Figure 8A), while a flattened layer

• solutions, which were ultrafiltered through a 0.8 μm membrane to remove dust. Electron microscopy Scanning electron microscopy (SEM) studies were performed using a field emission gun scanning electron microscope (JSM-6700F, JEOL Ltd., Japan) with a beam current of 10 μA at a typical operating voltage of 15

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

• Xiang Sun,
• Guoqiao Lai,
• Zhifang Li,
• Yuwen Ma,
• Xiao Yuan,
• Yongjia Shen and
• Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

• microscopy (SEM) and X-ray diffraction (XRD), which showed that the self-assembly ability of T1 was better than that of T2. The results revealed that more urethane groups in a molecule did not necessarily instigate self-assembly. UV–vis and FTIR spectra were measured to explore noncovalent interactions. The

• by 1H NMR, 13C NMR, and EIMS. Self-assembly and SEM investigation of T1 and T2 The studies showed that T1 and T2 gels were not formed in several common solvents such as hexane, chloroform, dichloromethane, tetrahydrofuran, toluene, diethyl ether, acetone, dimethylformamide, ethanol, methanol and

• recorded with SEM images (Figure 2). The samples were prepared by different methods (drop-coating, spin-coating). The experiments were performed as follows: the solid compounds were completely dissolved in ethyl acetate while heating, then cooled to room temperature. The studies showed that drop-coating

Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship

• Mohamed Yacine Ameur Messaoud,
• Ghenia Bentabed-Ababsa,
• Madani Hedidi,
• Aïcha Derdour,
• Floris Chevallier,
• Yury S. Halauko,
• Oleg A. Ivashkevich,
• Vadim E. Matulis,
• Laurent Picot,
• Valérie Thiéry,
• Thierry Roisnel,
• Vincent Dorcet and
• Florence Mongin

Beilstein J. Org. Chem. 2015, 11, 1475–1485, doi:10.3762/bjoc.11.160

• % DMSO. The data are expressed as GI (%) + sem (%) from 3 independent assays. Substrates involved in deproto-metallation reaction. ORTEP diagram (30% probability) of 2e. ORTEP diagrams (30% probability) of 4c, 3d and 3e. ORTEP diagram (30% probability) of 5d. Calculated values of pKa(THF) of the

Synthesis of photoresponsive cholesterol-based azobenzene organogels: dependence on different spacer lengths

• Yuchun Ren,
• Bin Wang and
• Xiuqing Zhang

Beilstein J. Org. Chem. 2015, 11, 1089–1095, doi:10.3762/bjoc.11.122

• role in the gelation. Compound M6 is the only one that can gelate in ethanol, isopropanol and 1-butanol and the reversible gel–sol transitions are also investigated. To obtain visual insight into the microstructure of the gels, the typical structures of the xerogels were studied by SEM. Morphologies of

• in different solvents were studied by SEM (Figure 4). With the reference to the images, it can be clearly seen that the structures of the three gelators are significantly different from each other. The morphologies of the aggregates change from flower-like to network and rod with different sizes

• spectroscopy (IR) was measured on a Nicolet 6700 spectrometer from 4000 to 500 cm−1 at room temperature. The samples were prepared as KBr pellets. The morphology of the gel samples were examined by scanning electron microscopy (SEM, S5200, FEI Company) under an acceleration voltage of 30 kV. UV–vis absorption

Carboxylated dithiafulvenes and tetrathiafulvalene vinylogues: synthesis, electronic properties, and complexation with zinc ions

• Yunfei Wang and
• Yuming Zhao

Beilstein J. Org. Chem. 2015, 11, 957–965, doi:10.3762/bjoc.11.107

• gave a BET surface area of 148.2 m2 g−1 and an adsorption average pore diameter of 10.2 nm. The pore size distribution analysis data revealed that Zn-TTFV coordination polymer 8 carried microporosity primarily in the range of tens of nanometers. Scanning electron microscopic (SEM) imaging was performed

• equipped with a copper X-ray source with a wavelength of 1.54 nm. Scanning electron microscopy (SEM) was performed on an FEI MLA 650 FEG microscope. BET surface area and pore size analyses were performed on a Micromeritics TriStar II Plus instrument. The degassing was done on a Flow Prep 060 instrument

• ) in comparison with the diffraction data of zincite ZnO (blue bars). (A) Nitrogen adsorption isotherm of coordination polymer 8 measured at 77 K. Inset: pore size distributions. (B) SEM image of the powder of 8. DSC traces of compounds 6–9 measured under a nitrogen atmosphere. Scan range: 25–400 °C

Multivalent dendritic polyglycerolamine with arginine and histidine end groups for efficient siRNA transfection

• Fatemeh Sheikhi Mehrabadi,
• Hanxiang Zeng,
• Mark Johnson,
• Cathleen Schlesener,
• Zhibin Guan and
• Rainer Haag

Beilstein J. Org. Chem. 2015, 11, 763–772, doi:10.3762/bjoc.11.86

• through the middle of the cellular height was selected to present the intracellular siRNA localization. Statistical analysis All transfection studies were performed in triplicates; data were expressed as mean ± SEM. Agarose gel electrophoresis retardation assay of AAdPGs/siRNA polyplexes. (A) dPG

Potential of acylated peptides to target the influenza A virus

• Daniel Lauster,
• Damian Pawolski,
• Julian Storm,
• Kai Ludwig,
• Rudolf Volkmer,
• Henry Memczak,
• Andreas Herrmann and
• Sumati Bhatia

Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65

• in relation to the total signal before centrifugation. Error bars represent the standard error of the mean (SEM) of at least three independent experiments. Inhibition constants KiHAI of C18-PeBGF, C18-s2s, C18-rs2s and EB against Aichi H3N2 and Rostock H7N1 virus. The KiHAI reflects the lowest

• concentration needed for full hemagglutination inhibition. Error bars indicate the standard error of the mean (SEM) of at least three independent experiments. C18-PeBGF mediated protection from infection of MDCK cells by Rostock H7N1 and Aichi H3N2. MDCK II cells were incubated with viruses at an MOI of 0.05

• SEM of three titration experiments. Peptide sequences and modifications. Inhibition constants for inhibition of virus mediated hemagglutination (KiHAI) and for inhibitor caused agglutination (KiA). Supporting Information Supporting Information File 118: Experimental part. Acknowledgements The

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

• permeability. The CD nanocapsules were imaged by scanning electron microscopy (SEM). The concentration of CPT entrapped in nanocapsules was determined by reversed phase HPLC. The in vitro release study of CPT was performed with a dialysis bag method under sink conditions mimicking the gastric and intestinal pH

• Information File 1 for full experimental data). As it can be clearly seen from the results (Table 4) both anionic and cationic CPT loaded nanocapsules were in the range of 150 to 250 nm with a narrow size distribution. Figure 1 shows SEM photographs of NCs with spherical shapes having smooth surfaces. SEM

• imaging is also a tool for justifying the results obtained from Zetasizer based on DLS measurements and it can be clearly seen that SEM photographs confirm the particle size are in nanometer range. The results of zeta potential analysis, also shown in Table 4, confirm that the anionic CD nanocapsules have

Cyclodextrin–polysaccharide-based, in situ-gelled system for ocular antifungal delivery

• Anxo Fernández-Ferreiro,
• Noelia Fernández Bargiela,
• María Santiago Varela,
• Maria Gil Martínez,
• Maria Pardo,
• Antonio Piñeiro Ces,
• José Blanco Méndez,
• Miguel González Barcia,
• Maria Jesus Lamas and
• Francisco.J. Otero-Espinar

Beilstein J. Org. Chem. 2014, 10, 2903–2911, doi:10.3762/bjoc.10.308

• polysaccharides (mean ± SEM, n = 3). Values for K1:1, CE and the D:CD ratio obtained from the fluconazole–cyclodextrin complex in water at 25 °C. Fitting results yielding the quantity of fluconazole release up to 120 min using the Higuchi release kinetics.a Acknowledgements This work was supported by Fundación

Thermal and oxidative stability of the Ocimum basilicum L. essential oil/β-cyclodextrin supramolecular system

• Daniel I. Hădărugă,
• Nicoleta G. Hădărugă,
• Corina I. Costescu,
• Ioan David and
• Alexandra T. Gruia

Beilstein J. Org. Chem. 2014, 10, 2809–2820, doi:10.3762/bjoc.10.298

• microscopy, SEM (Inspect S, voltage of 25 kV, magnification of 3000–12000×, focus of 10–14.1 mm; see Supporting Information File 1). Rhombohedral prisms with dimensions up to ten micrometers for O. basilicum L. essential oil/β-CD complex were obtained. The relative concentration of the main compounds of the

Detonation nanodiamonds biofunctionalization and immobilization to titanium alloy surfaces as first steps towards medical application

• Juliana P. L. Gonçalves,
• Afnan Q. Shaikh,
• Manuela Reitzig,
• Daria A. Kovalenko,
• Jan Michael,
• René Beutner,
• Gianaurelio Cuniberti,
• Dieter Scharnweber and
• Jörg Opitz

Beilstein J. Org. Chem. 2014, 10, 2765–2773, doi:10.3762/bjoc.10.293

• -PEA. Immobilization of DND Scanning electron microscopy (SEM) was used to characterize the surface morphology of titanium samples coated with previously functionalized nanodiamonds. DND before and after functionalization were used to evaluate the improvement on the interaction of DND with the titanium

• Ti6Al7Nb followed by anodic polarization. The titanium based alloy substrate at the bottom is covered on top with an anodic oxide layer (thickness approx. 120 nm). An immobilization of 6 on titanium anodic oxide layer can clearly be seen, which was already indicated in the SEM images in Figure 4 for 6. At

• by hydrogen bridging and electrostatic affinity to positively charged amino groups. SEM results Figure 4 from unfunctionalized DND demonstrate a better interaction with the titanium oxide layer than carboxylated DND with O-PEA 3 and silanized DND 5. This may be explained by the presence of several

Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier

• Kayoko Hayashida,
• Taishi Higashi,
• Daichi Kono,
• Keiichi Motoyama,
• Koki Wada and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292

• obvious difference was not observed. These results suggest that the presence of DOX in PEG-LP scarcely alters the physicochemical properties of the PPRX. Additional studies by means of SEM or TEM may permit a more precise analysis and might confirm whether the LP structure is retained. Structure of CD

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• /polyacrylonitrile/copper nanorods composite fibers by adsorption and reduction. The composite fibers were fully characterized by FTIR, SEM, TEM, energy dispersive spectroscopy and X-ray photoelectron spectroscopy. The results indicated that the copper nanorods were not only successfully synthesized on the surface