Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines

• Eric Buchy,
• Branko Vukosavljevic,
• Maike Windbergs,
• Dunja Sobot,
• Camille Dejean,
• Simona Mura,
• Patrick Couvreur and
• Didier Desmaële

Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109

• fulfill this task, radioactive labeling or fluorescent probes have been thoroughly used. For example, the subcellular localization of the 3H-radiolabeled GemSQ conjugate has been evaluated by micro-autoradiography coupled to confocal imaging of fluorescently labeled cellular structures [21]. A dual

• , its coupling with gemcitabine and the Raman spectra of the deuterated GemSQ nanoassemblies, opening the way to perform intracellular imaging of squalenoyl nanomedicine (Figure 1). Results and Discussion Chemical synthesis of squalenic acid-d6 and GemSQ-d6 conjugate In a first approach we decided to

Creating molecular macrocycles for anion recognition

• Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

• microscopy (STM) imaging. Their shape persistence makes them ideal for the study of structure–property relationships to enable deep understanding of anion recognition phenomena. The identification of 1,2,3-triazoles as linkers, ligands and building blocks. The synthetic creation of macrocycles sets the scene

• self-assembly and anion binding (Figure 17a) using STM and were surprised by what we saw. Clear in the imaging (Figure 17b) were their shapes, looking like lumpy donuts; a shape similar to the one offered by Japan’s Mister Donut. Interestingly, these macrocycles displayed a reliable propensity for

Self and directed assembly: people and molecules

• Tony D. James

Beilstein J. Org. Chem. 2016, 12, 391–405, doi:10.3762/bjoc.12.42

• will develop as a direct result of the increased importance of animal, tissue and cellular imaging techniques using boronic acid receptors [124]. “Education is the passport to the future, for tomorrow belongs to those who prepare for it today.” – Malcolm X (1925–1965) Author biography Tony D. James is

Art, auto-mechanics, and supramolecular chemistry. A merging of hobbies and career

• Eric V. Anslyn

Beilstein J. Org. Chem. 2016, 12, 362–376, doi:10.3762/bjoc.12.40

• -based differential sensing is likewise struggling for a solid foothold in the economy. In contrast, imaging agents are clearly a frontier. These are the kinds of sensors that Tony Czarnik originally envisioned [72], and commercial success has been achieved with the company Life Technologies, formally

Diastereoselective synthesis of new O-alkylated and C-branched inositols and their corresponding fluoro analogues

• Charlotte Collet,
• Françoise Chrétien,
• Yves Chapleur and
• Sandrine Lamandé-Langle

Beilstein J. Org. Chem. 2016, 12, 353–361, doi:10.3762/bjoc.12.39

• derivatives, bearing an arm terminated either with a hydroxy group or a fluorine atom, could be interesting candidates for diastereoisomeric intermediates and biological evaluations, especially for PET imaging experiments. Keywords: C-branched; diastereoselective; fluoroinositols; inositols; O-alkylated

• this compound crosses the blood brain barrier (BBB) with difficulty [32]. The same PET imaging studies using the diastereoisomeric compound of myo configuration (2-[18F]fluoro-2-deoxy-myo-inositol), did not get better results [33]. On the other hand, these radiotracers have shown interesting features

• in the diagnosis of breast cancer with this imaging technique [33][34]. Considering the synthetic and biological importance of inositol analogues, the design of new inositol derivatives to study their biological properties and to understand their binding mechanisms with molecular targets, for

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

• identified as piericidin derivatives (e.g., piericidin A1 (1), Figure 3) and the chlorinated indole derivative streptochlorin (2). Imaging analysis based on a combination of laser desorption/ionization (LDI)–time of flight (TOF) mass spectrometry imaging visualized the spatial distribution of the antibiotics

• pathways. This in turn can lead to the discovery of new metabolic pathways that would otherwise be silent or undetected under typical laboratory cultivation conditions. In recent years many successful analytical methods including UHPLC–DAD and UHPLC–MS-based techniques, imaging mass spectrometry (IMS) [138

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• -soluble cyanine/β-CD derivatives have been efficiently prepared via CuAAC under simultaneous US/MW irradiation at 75 °C for 2 h (MW 15 W and US 20 W) in good yields (23% and 33%). These dyes were used as versatile carriers for drug delivery and optical imaging. Preparation of CD-grafted materials and CD

Bright molecules for sensing, computing and imaging: a tale of two once-troubled cities

• A. Prasanna de Silva

Beilstein J. Org. Chem. 2015, 11, 2774–2784, doi:10.3762/bjoc.11.298

Synthesis of cyclic N¹-pentylinosine phosphate, a new structurally reduced cADPR analogue with calcium-mobilizing activity on PC12 cells

• Ahmed Mahal,
• Stefano D’Errico,
• Nicola Borbone,
• Brunella Pinto,
• Agnese Secondo,
• Valeria Costantino,
• Valentina Tedeschi,
• Giorgia Oliviero,
• Vincenzo Piccialli and
• Gennaro Piccialli

Beilstein J. Org. Chem. 2015, 11, 2689–2695, doi:10.3762/bjoc.11.289

• ) equipped with a FLUAR 40X oil objective lens. The experiments employed a digital imaging system composed of a MicroMax 512BFT cooled CCD camera (Princeton Instruments, Trenton, NJ, USA), LAMBDA 10-2 filter wheeler (Sutter Instruments, Novato, CA, USA), and Meta-Morph/MetaFluor Imaging System software

• (Universal Imaging, West Chester, PA, USA). After loading, the cells were illuminated alternately at 340 and 380 nm by a Xenon lamp. The emitted light was passed through a 512 nm barrier filter. Fura-2AM fluorescence intensity was measured every 3 s. Forty to sixty-five individual cells were selected and

Carbon–carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations

• Tsuyuka Sugiishi,
• Hideki Amii,
• Kohsuke Aikawa and
• Koichi Mikami

Beilstein J. Org. Chem. 2015, 11, 2661–2670, doi:10.3762/bjoc.11.286

• PET imaging. The reason is that the [18F] isotope has a longer half-life (110 min) than 13N (10 min) or 15O (2 min); however, the incorporation of [18F] must be rapid and the use of the products containing [18F] must be immediate. Many of the reported strategies have a limited scope of starting

• materials or require expensive reagents and a multistep synthesis. The [18F]trifluoromethylation performed with commercially available reagents by using [18F]fluoride demands no complex such as [18F]CF2Cu, and thus the method should contribute to efficient PET imaging [42] (Scheme 8). Synthesis of

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

• Nikon SMZ-10 stereoscopic microscope. The Soft Imaging system, analySIS [31] was used to process the images. For TGA a Mettler Toledo TGA/SDTA851e instrument was employed with a nitrogen gas purge (flow rate 30 cm3/min). Indium (mp 156.6 °C) and aluminium (mp 660.3 °C) were used for all calibrations

Smart molecules for imaging, sensing and health (SMITH)

• Bradley D. Smith

Beilstein J. Org. Chem. 2015, 11, 2540–2548, doi:10.3762/bjoc.11.274

• imaging, ion-pair receptors, rotaxane synthesis, squaraine rotaxanes, and synthtavidin technology. The article concludes with a short perspective of likely future directions in biomedical supramolecular chemistry. Keywords: fluorescence; ion-pair receptors; membrane transport; molecular imaging; rotaxane

• phosphatidylserine appear on the surface of cells and induce subsequent secondary biological signaling processes such as blood clotting and cell clearance by macrophages [8]. Molecular imaging Our work on synthetic phospholipid scramblases required us to develop methods for quantifying phospholipid levels on the

• on the cell surface during the process of apoptosis or programmed cell death. Thus, phosphatidylserine is an excellent biomarker of cell death and an attractive target for molecular imaging. We reasoned that synthetic anion receptors such as zinc dipicolylamine (ZnDPA) coordination complexes would

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

• applications owing to control over their size, their assembly/disassembly, and the modular character for the versatile incorporation of agents aiming for imaging [3], photothermal therapy [4], drug delivery [5][6][7] and gene delivery [8][9][10] applications. Different approaches have been used to form SNPs

• fruitful discussions and Mark A. Smithers for HR-SEM imaging.

Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) – precursors for dyes and drugs

• Enas M. Malik,
• Younis Baqi and
• Christa E. Müller

Beilstein J. Org. Chem. 2015, 11, 2326–2333, doi:10.3762/bjoc.11.253

• synthetic AQs, are utilized for a wide range of applications, e.g., in textile industry [7][8], paints, foods, cosmetics, pharmaceuticals, and imaging devices [3][9][10][11][12][13], and there is a continuous interest in optimizing this class of compounds as documented in recent literature [14][15][16][17

Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition

• Nicolas Desbois,
• Sandrine Pacquelet,
• Adrien Dubois,
• Clément Michelin and
• Claude P. Gros

Beilstein J. Org. Chem. 2015, 11, 2202–2208, doi:10.3762/bjoc.11.239

• easily prepared as potential MRI/PET (SPECT) bimodal contrast agents incorporating one metal (Mn, Gd) for the enhancement of contrast for MRI applications and one “cold” metal (Cu, Ga, In) for future radionuclear imaging applications. Preliminary relaxivity measurements showed that the reported complexes

• are promising contrast agents (CA) in MRI. Keywords: click chemistry; corrole; DOTA; microwave; NOTA; porphyrin; Introduction Magnetic resonance imaging (MRI), positron emission tomography (PET) or single photon emission computed tomography (SPECT) are actually the most commonly used imaging

• modalities. MRI provides high-resolution (at the submillimeter level), but is limited by its low sensitivity. Conversely, PET and SPECT imaging are more sensitive methods but they both suffer from low anatomical resolution. As one single modality is usually not sufficient to obtain all the necessary

Hexacoordinate Ru-based olefin metathesis catalysts with pH-responsive N-heterocyclic carbene (NHC) and N-donor ligands for ROMP reactions in non-aqueous, aqueous and emulsion conditions

• Shawna L. Balof,
• K. Owen Nix,
• Matthew S. Olliff,
• Sarah E. Roessler,
• Arpita Saha,
• Kevin B. Müller,
• Ulrich Behrens,
• Edward J. Valente and
• Hans-Jörg Schanz

Beilstein J. Org. Chem. 2015, 11, 1960–1972, doi:10.3762/bjoc.11.212

• contains a molecule of cocrystallized water. The hydrogen atoms of the water molecule were omitted from the structure due to thermal uncertainty. AFM image produced from COE/DCPD latex film. Measurement: AFM tapping at room temperature, material contrast using Phase Imaging. Synthesis of 2nd Grubbs-type

Polythiophene and oligothiophene systems modified by TTF electroactive units for organic electronics

• Alexander L. Kanibolotsky,
• Neil J. Findlay and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1749–1766, doi:10.3762/bjoc.11.191

• -type semiconductor in OFETs using two solvents for spin-coating – chloroform and chlorobenzene [93]. A bottom contact, bottom gate device configuration was used with an n-doped silicon gate and a SiO2 dielectric layer. After annealing at 120 °C, AFM imaging indicated a closely packed grain-like surface

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

Terminal lipophilization of a unique DNA dodecamer by various nucleolipid headgroups: Their incorporation into artificial lipid bilayers and hydrodynamic properties

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2015, 11, 913–929, doi:10.3762/bjoc.11.103

• perfusion step using the Ionovation perfusion unit was followed by an incubation step. This procedure was repeated until the brightness of the bilayer stabilized. All confocal imaging and lifetime measurements were performed on a confocal laser scanning microscope (Insight Cell 3D, Evotec Technologies GmbH

• . A) Logarithmic imaging of fluorescence intensity–time decay of LONs 10–15 and the corresponding fitting curves (–). B) The residuals show some minor systematic errors (the color legend is the same as in A and C). C) Normalized logarithmic fluorescence intensity of the fitting curves. Diffusion times

Glycodendrimers: tools to explore multivalent galectin-1 interactions

• Jonathan M. Cousin and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2015, 11, 739–747, doi:10.3762/bjoc.11.84

• acknowledge Dr. Linda Baum and Mabel Pang for providing the galectin-1, the Imaging and Chemical Analysis Laboratory at MSU for guidance with the fluorescent microscope, Dr. Candace Goodman for assistance with DLS and fluorescence microscopy, and Dr. Anna Michel for assistance with the cell-based assays. This

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

• Franziska Klitsche,
• Julian Ramcke,
• Julia Migenda,
• Andreas Hensel,
• Tobias Vossmeyer,
• Horst Weller,
• Silvia Gross and
• Wolfgang Maison

Beilstein J. Org. Chem. 2015, 11, 678–686, doi:10.3762/bjoc.11.77

• their pharmacokinetic properties [38][39]. The resulting particles show a reduced tendency towards plasma protein and tissue binding, both important factors influencing elimination and tissue distribution of biological imaging reagents. Based on our good experiences with the immobilization of tripodal

Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

• Mathieu L. Lepage,
• Antoine Mirloup,
• Manon Ripoll,
• Fabien Stauffert,
• Anne Bodlenner,
• Raymond Ziessel and
• Philippe Compain

Beilstein J. Org. Chem. 2015, 11, 659–667, doi:10.3762/bjoc.11.74

• adequate tailoring, including fluorescence amplification [50], and ratiometric pH reporter for imaging protein–dye conjugates in living cells [51], or display physiological binding of D-glucose [52]. The pyrene nucleus was also selected as an alternative fluorophore since it may be easily

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

• 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

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• ethidium bromide–ruthenium(II) complex also proved to be an imaging probe whose fluorescence intensity and lifetime changes substantially in the presence of RNA [85], thus supporting a strategy of phenanthridinium incorporation into the heterogenic two-chromophore system. Phenanthridines are rarely

Mono- and multilayers of molecular spoked carbazole wheels on graphite

• Stefan-S. Jester,
• A. Vikas Aggarwal,
• Daniel Kalle and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 2783–2788, doi:10.3762/bjoc.10.295

• ) supramolecular adlayers at the liquid/solid interface of TCB and HOPG. When using 1-phenyloctane, another commonly used solvent for STM measurements, we could acquire some images of the MSWs, but imaging was less stable (Supporting Information File 1). However, much better images of 2 were obtained using a third

• solvent, octanoic acid (OA), which has also previously been used for imaging MSWs [2][4]. We compared the so-obtained images of MSW 2 with its precursor 1 under similar conditions. In all images, regions covered with conjugated backbones and alkoxy side chains are observed in bright and dark colors

• conditions. Typically, 0.5 µL of a 10−5–10−6 M solution of the respective substance in OA was dropped onto a piece of freshly cleaved HOPG at elevated temperature (70–80 °C), and the sample was allowed to cool to rt prior to STM imaging. All STM measurements were performed in situ (with the tip immersed into