Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• ) solutions in ethanol with a Horiba Jobin Yvon Fluorolog 3 steady-state fluorescence spectrometer. For decay time measurements a PicoQuant LDH-P-C-375 pulsed diode laser (λexc = 372 nm, pulse width 100 ps) was applied as the excitation source. The emission signal was detected with a cooled photomultiplier

• the dye for 15 minutes. The imaging was performed using a LSM 780 confocal system (Zeiss), equipped with an AxioObserver Z1 inverted microscope, a 63× oil immersion objective (NA 1.4), a 355 nm DPSS laser (50 mW), a 561 nm DPSS laser (20 mW), and a multi-anode PMT (32 elements). The luminescence

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• ) BlueBox laser source (excitation wavelength 785 nm) equipped with B&W-Tek fiber optic Raman BAC102 probe, and coupled with Maya2000Pro (OceanOptics) spectrometer. The probe was positioned under the milling vessel using a movable stand, so to place a focus of the laser ≈1 mm inside of the vessel. ESR

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• –vis spectrum, do not aggregate in solution. These dyes are expected to be developed into medical imaging probes. Phthalocyanine is expected to be used not only as a biological imaging agent but also in cancer treatment. Photodynamic therapy (PDT) is a laser cancer therapy that introduces organic dyes

• laser only to the target tumor cells. The features of ideal PDT agents include, among others: i) strong absorption in the red wavelength region; ii) non-aggregation property; iii) high biocompatibility; iv) good selectivity to cancer cells; v) high quantum yield of singlet oxygen [96]. Since the PDT

• . Solubility of phthalocyanines in liquid CO2 and supercritical CO2. Comparison of IC50 values with laser PDT among phthalocyanine conjugated with cyclodextrin against B16-F10. Characteristics of phthalocyanine/P3HT heterojunction organic thin-film solar cells. Comparison of axial ligand substitution

Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

• Magdalena Ceborska,
• Magdalena Zimnicka,
• Aneta Aniela Kowalska,
• Kajetan Dąbrowa and
• Barbara Repeć

Beilstein J. Org. Chem. 2017, 13, 2252–2263, doi:10.3762/bjoc.13.222

• resolution of 5 cm−1 and with a 300 mW diode laser emitting a 785 nm line, used as an excitation source. The Raman scattering signal was recorded by a 1024 × 256 pixel RenCam CCD detector. Typically, the spectra were acquired for 60 s, with 10% of the laser power. Molecular structures with atom numbering of

The effect of milling frequency on a mechanochemical organic reaction monitored by in situ Raman spectroscopy

• Patrick A. Julien,
• Ivani Malvestiti and
• Tomislav Friščić

Beilstein J. Org. Chem. 2017, 13, 2160–2168, doi:10.3762/bjoc.13.216

• poly(methyl methacrylate) (PMMA) optically transparent milling jar, using a Retsch® MM400 mixer mill. For all real-time reaction monitoring, reactions were monitored using a RamanRxn1™ analyzer by Kaiser Optical Systems Inc. every 5 seconds using a 785 nm laser. Spectra were dark and intensity

• on a 300 MHz Varian Mercury spectrometer. The ambient temperature was measured using a digital thermometer by VWR and the internal jar temperature was acquired immediately after milling finished using a Mastercraft Temperature Reader with Digital Display and Laser Pointer (accuracy ±2 °C). Time

Mechanochemical Knoevenagel condensation investigated in situ

• Sebastian Haferkamp,
• Franziska Fischer,
• Werner Kraus and
• Franziska Emmerling

Beilstein J. Org. Chem. 2017, 13, 2010–2014, doi:10.3762/bjoc.13.197

• of the reactants reveal a complete and quantitative reaction (see Figure 1). For the in situ investigations, time-resolved X-ray diffraction patterns and Raman spectra were recorded during the milling reaction. The Raman laser and the X-ray beam were focused on the same spot at the inner wall of a

Ni nanoparticles on RGO as reusable heterogeneous catalyst: effect of Ni particle size and intermediate composite structures in C–S cross-coupling reaction

• Debasish Sengupta,
• Koushik Bhowmik,
• Goutam De and
• Basudeb Basu

Beilstein J. Org. Chem. 2017, 13, 1796–1806, doi:10.3762/bjoc.13.174

• ) lasers. The laser power was kept sufficiently low to avoid heating of the samples and spectra were collected with a resolution of 1 cm−1. X-ray diffraction (XRD) studies of the powder samples were performed with Rigaku Smartlab X-ray diffractometer operating at 9 kW (200 mA; 45 kV) using Cu Kα radiation

Block copolymers from ionic liquids for the preparation of thin carbonaceous shells

• Sadaf Hanif,
• Bernd Oschmann,
• Dmitri Spetter,
• Muhammad Nawaz Tahir,
• Wolfgang Tremel and
• Rudolf Zentel

Beilstein J. Org. Chem. 2017, 13, 1693–1701, doi:10.3762/bjoc.13.163

• aluminum garnet (Nd:YAG) laser. X-ray diffraction was performed on a Siemens D 5000 diffractometer equipped with Cu Kα radiation source (wavelength of 1.54056 Å) for both as synthesized as well as carbon coated TiO2 nanoparticles. TEM samples were prepared by dispersing the sample in ethanol and drop

Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions

• Manuel Anselmo,
• Lisa Moni,
• Hossny Ismail,
• Davide Comoretto,
• Renata Riva and
• Andrea Basso

Beilstein J. Org. Chem. 2017, 13, 1456–1462, doi:10.3762/bjoc.13.143

• with various alkenes [5], which prompted us to disclose our results in this communication. Results and Discussion When we reacted diazonium salt 2a with methyl methacrylate (3a) in acetonitrile in the presence of a catalytic amount of Ru(bpy)3Cl2 under blue laser irradiation, we could isolate

• loading of photocatalyst (0.5% vs 2%) and excess of alkene (2 equiv vs 3 equiv) employed; moreover, the use of an inert atmosphere did not lead to significant improvements. No differences were observed when the 440 nm laser was replaced by blue LEDs (maximum wavelength 455 nm). Diazonium salts were

Mechanochemistry-assisted synthesis of hierarchical porous carbons applied as supercapacitors

• Desirée Leistenschneider,
• Nicolas Jäckel,
• Felix Hippauf,
• Volker Presser and
• Lars Borchardt

Beilstein J. Org. Chem. 2017, 13, 1332–1341, doi:10.3762/bjoc.13.130

• −1 indicates complexation [51]. The sample Polymer-SF-3 was investigated by matrix-assisted laser desorption/ionization with a time-of-flight mass spectrometer (MALDI–TOF) revealing a weight-averaged molar mass (Mw) of 2015.6 g mol−1, which is equivalent to 6 monomeric units. Synthesis of the

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

• experienced increased attention in chemistry [6][7][8][9][10] and life science applications [11][12][13]. On the grounds of high fluorescence quantum yield, narrow spectral characteristics, and sufficient chemical stability, BODIPYs have been utilized for example as laser dyes, tags of small organic molecules

Kinetic analysis of mechanoradical formation during the mechanolysis of dextran and glycogen

• Naoki Doi,
• Yasushi Sasai,
• Yukinori Yamauchi,
• Tetsuo Adachi,
• Masayuki Kuzuya and
• Shin-ichi Kondo

Beilstein J. Org. Chem. 2017, 13, 1174–1183, doi:10.3762/bjoc.13.116

• ) equipped with a He/Ne laser. A scattering angle of 90° was used in this study. The hydrodynamic diameter and the polydispersity factor of the polymers, represented as μ2/Γ2, were calculated using the Stokes–Einstein equation and the cumulant method. The number-average particle diameter and weight-average

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• biology and the investigation of macromolecular structure and function relationships. Major contributions also came from considerable advances in high resolution NMR spectrometry and electron microscopy along with the continuous evolution of synchrotron radiation and free electron laser light sources

• that had been synthesized. They all included a substrate donor, either UDP-Gal or UDP-GalNAc with an additional group on the sugar or on the uracil. Photolysis at 100 K was monitored by UV–vis absorption, both in solution and in crystals in order to assess the efficiency of the laser ablation in the

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

• containing mannose-binding receptors) [46] and thyroglobulin in serum [47] and to study the internalization pathway in dendritic cells, employing confocal laser microscopy (CLSM) and flow cytometry [48]. Moreover, even techniques based on light scattering, like dark field microscopy (DFM), resulted

Expression, purification and structural analysis of functional GABA transporter 1 using the baculovirus expression system

• Jing Hu,
• Chris Weise,
• Christoph Böttcher,
• Hua Fan and
• Jian Yin

Beilstein J. Org. Chem. 2017, 13, 874–882, doi:10.3762/bjoc.13.88

• , and tryptic peptides were analyzed either directly by matrix-assisted laser desorption/ionization-time-of-flight mass spectrometry (MALDI–TOF MS) or guanidinated and then analyzed by MALDI. The labeled peptide peaks (Figure 2B) in the mass spectrum were identified as either GAT or GFP by matching the

• mass fingerprinting was performed by Dr. Chris Weise (Free University Berlin, Germany) with a Bruker-Biflex Reflex Mass spectrometer (Bruker Daltonics) in the reflector-mode with alpha-cyano-4-hydroxycinnamic acid as matrix. Ionization was enhanced with the 337 nm-ray of a nitrogen laser. The peptide

Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

• Cristian Peptu,
• Mihaela Balan-Porcarasu,
• Alena Šišková,
• Ľudovít Škultéty and
• Jaroslav Mosnáček

Beilstein J. Org. Chem. 2017, 13, 779–792, doi:10.3762/bjoc.13.77

• ionization like matrix-assisted laser desorption ionization (MALDI) and electrospray ionization (ESI). Liquid chromatography (LC) separation with evaporative light scattering detection (ELSD) and NMR analysis were employed in order to elucidate the structural profiles of the obtained mixtures. The results

• not asses their products whether these were CD-VL, CD-LA or CD-VL/LA covalent conjugates [19][20]. The results presented by the Harada group generally evaluated the CD-oligoester samples by matrix-assisted laser desorption ionization mass spectrometry (MALDI–MS) and nuclear magnetic resonance (NMR

• ELS-1000 from PL-Agilent Technologies, Stretton, UK. Mass spectra of polymers were measured on an UltrafleXtreme TOF instrument (Bruker), equipped with a 355 nm smartbeam-2 laser, capable of a pulsing frequency of 1 kHz. The mass spectrometer was operated by FlexControl 3.3 software (Bruker). The

Membrane properties of hydroxycholesterols related to the brain cholesterol metabolism

• Malte Hilsch,
• Ivan Haralampiev,
• Peter Müller,
• Daniel Huster and
• Holger A. Scheidt

Beilstein J. Org. Chem. 2017, 13, 720–727, doi:10.3762/bjoc.13.71

• dithionite across the bilayer) were determined. The latter ones were used as the parameter for membrane permeability. Confocal laser scanning microscopy For microscopy, a Visitron VisiScope scanning disk confocal laser microscope (Visitron Systems, Puchheim, Germany) with a 60× oil objective and an Andor

• iXon 888 EMCCD camera (1024 × 1024 pixels, Andor, Belfast, Northern Ireland) were used. N-Rh-DOPE was excited by a 561 nm diode laser. Fife µL GUVs were mixed with 15 µL 250 mM glucose buffer (5.8 mM NaH2PO4, 5.8 mM Na2HPO4, osmolarity of 300 mOsm/kg, pH 7.2) in tissue culture treated microscopy

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• : top-down or bottom-up syntheses. Top-down methods are characterised by using a bulk carbon substrate as the starting material; using conditions that remove nanoparticles from the bulk substrate such as electrochemistry, chemical oxidation, arc discharge or laser ablation, carbon-based nanoparticles

• internalisation studies with HepG2 cells [29]. The green CDs were non-toxic to cells at concentrations of up to 625 μg/mL and exposures of 72 h. Laser scanning confocal microscopy (LSCM) demonstrated cell internalization, making these materials a good candidate as a bioimaging agent. In 2011 Qu et al. developed a

• the CDs, while significant toxicity was seen at concentrations at and above 400 μg/mL. CDs (100 μg/mL) were also incubated with HepG2 for 24 h and laser scanner confocal microscopy (LCSM) was used to image the internalization of the CDs within the cells using the green, yellow and red channels

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

• ], biofunctionalization [23][24] and fabrication of 3D structures via direct laser writing (DLW) [25]. Results and Discussion Synthesis of CMP thin films We prepared the CMP nanomembranes in a LbL approach using the thiol–yne coupling (TYC) reaction. In order to perform the reaction on surfaces, we first functionalized

Total synthesis of a Streptococcus pneumoniae serotype 12F CPS repeating unit hexasaccharide

• Peter H. Seeberger,
• Claney L. Pereira and
• Subramanian Govindan

Beilstein J. Org. Chem. 2017, 13, 164–173, doi:10.3762/bjoc.13.19

• -dimethylformamide; EtOAc: ethyl acetate; GlcA: glucouronic acid; HPLC: high-performance liquid chromatography; Lev: levulinoyl; MALDI–TOF MS: matrix-assisted laser desorption/ionization–time of flight mass spectrometry; NAP: 2-naphthylmethyl; TBS: tert-butyldimethylsilyl; THF: tetrahydrofuran; TMSOTf

A postsynthetically 2’-“clickable” uridine with arabino configuration and its application for fluorescent labeling and imaging of DNA

• Heidi-Kristin Walter,
• Bettina Olshausen,
• Ute Schepers and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2017, 13, 127–137, doi:10.3762/bjoc.13.16

• to the cells. The cells were incubated for 24 h with the respective transfection mixture at 37 °C in a 5% CO2 atmosphere. The visualization of the DNA duplexes was performed by confocal laser scanning microscopy using a Leica TCS SPE (DMi8) inverted microscope with an ACS APO 63×/1.30 oil objective

• . Fluorophores were excited using an UV laser (405 nm) for duplexes DNA2aD1–DNA3rD5 and DNA2rD1–DNA3aD8 and an argon ion laser (488 nm) for duplexes DNA2aD2–DNA3aD8 and DNA2rD4–DNA2aD8. The emission detection bandwidths were at 435–470 nm (blue) and 575–750 nm (yellow) for DNA2aD1–DNA3rD5, 415–550 nm (blue) and

• DNA2aD1–DNA3rD5 λexc = 405 nm (UV laser), λem = 435–470 nm (blue) and 575–750 nm (yellow), for DNA2rD1–DNA3aD8 λexc = 405 nm (UV laser), λem = 415–550 nm (blue) and 575–750 nm (red), for DNA2aD2–DNA3aD8 λexc = 488 nm (argon ion laser), λem = 490–550 nm (green) and 550–675 nm (red), for DNA2rD4–DNA3aD8

3D printed fluidics with embedded analytic functionality for automated reaction optimisation

• Andrew J. Capel,
• Andrew Wright,
• Matthew J. Harding,
• George W. Weaver,
• Yuqi Li,
• Russell A. Harris,
• Steve Edmondson,
• Ruth D. Goodridge and
• Steven D. R. Christie

Beilstein J. Org. Chem. 2017, 13, 111–119, doi:10.3762/bjoc.13.14

• micro- and milliscale fluidic devices. When coupled with online monitoring and optimisation software, this offers an advanced, customised method for performing automated chemical synthesis. This paper reports the use of two additive manufacturing processes, stereolithography and selective laser melting

• , to create multifunctional fluidic devices with embedded reaction monitoring capability. The selectively laser melted parts are the first published examples of multifunctional 3D printed metal fluidic devices. These devices allow high temperature and pressure chemistry to be performed in solvent

• reaction analysis; reaction optimisation; selective laser melting; stereolithography; Introduction Additive manufacturing (AM), or as it is widely known ‘3D printing’, is the internationally recognised term used to describe a wide range of manufacturing processes that can generate complex three

Synthesis of multi-lactose-appended β-cyclodextrin and its cholesterol-lowering effects in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2017, 13, 10–18, doi:10.3762/bjoc.13.2

• of multi-Lac-β-CD (DSL5.6) The intracellular distribution of TRITC-multi-Lac-β-CD (DS5.6) in NPC-like HepG2 cells was assayed by confocal laser scanning microscopy, as reported previously [14]. Intracellular cholesterol levels post treatment with multi-Lac-β-CD (DSL5.6) The intracellular cholesterol

• . Cells were incubated in medium [FBS (−)] with or without 100 μM TRITC-CDs for 24 h. (B) The fluorescence intensities of TRITC-CDs were determined in ten randomly selected cells per image by confocal laser scanning microscopy and BZ-II analyzer. Data represents mean ± S.E.M. of three experiments. *p

Versatile synthesis of end-reactive polyrotaxanes applicable to fabrication of supramolecular biomaterials

• Atsushi Tamura,
• Asato Tonegawa,
• Yoshinori Arisaka and
• Nobuhiko Yui

Beilstein J. Org. Chem. 2016, 12, 2883–2892, doi:10.3762/bjoc.12.287

• 7 could be utilized for monitoring the intracellular internalization of the PRXs, the intracellular uptake of 7 was investigated. HeLa cells were treated with 7 for 26 h, before observation by confocal laser scanning microscopy (CLSM) (Figure 5). The punctate 7 is clearly observed at the perinuclear

• , followed by staining with Hoechst 33342 (Dojindo Laboratories, Kumamoto, Japan) (1 μg/mL) for 10 min at 37 °C. CLSM images were acquired with a FluoView FV10i (Olympus, Tokyo, Japan) equipped with a 60x water-immersion objective lens (N/A 1.2) and a diode laser. SEC charts for crude products of reaction 1

Stabilization of nanosized titanium dioxide by cyclodextrin polymers and its photocatalytic effect on the degradation of wastewater pollutants

• Tamás Zoltán Agócs,
• István Puskás,
• Erzsébet Varga,
• Mónika Molnár and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2016, 12, 2873–2882, doi:10.3762/bjoc.12.286

• by dynamic light scattering: Determination of the particle size distribution of the nanoTiO2 particles and aggregates was performed by dynamic light scattering method (also known as photon correlation spectroscopy) using a Malvern Zetasizer Nano ZS instrument using a He-Ne laser of 4 mW power and 633