Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism

• Joscha Vollmeyer,
• Friederike Eberhagen,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2014, 10, 2774–2782, doi:10.3762/bjoc.10.294

• , interfere with the STM tip. However, the high flexibility, the low electric conductivity, and the low number of only two dangling alkyl chains per molecule allow a (rather) undisturbed STM imaging. In addition, the molecules are still fixed on the substrate by the remaining six adsorbed side chains and the

• ) was dropped onto a piece of freshly cleaved HOPG at elevated temperature (70 °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 the liquid) and typically completed within 30 min after the sample preparation. Bias

Synthesis and properties of novel star-shaped oligofluorene conjugated systems with BODIPY cores

• Clara Orofino-Pena,
• Diego Cortizo-Lacalle,
• Joseph Cameron,
• Muhammad T. Sajjad,
• Pavlos P. Manousiadis,
• Neil J. Findlay,
• Alexander L. Kanibolotsky,
• Dimali Amarasinghe,
• Peter J. Skabara,
• Tell Tuttle,
• Graham A. Turnbull and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2704–2714, doi:10.3762/bjoc.10.285

• have found numerous applications as laser dyes [5][6][7], labels for biological imaging [8][9][10] and low band-gap polymers [11][12][13]. Being efficient emitters in solution, small molecule BODIPY compounds often show signs of aggregation at high concentration and in solid films [14][15], which

Linear-g-hyperbranched and cyclodextrin-based amphiphilic block copolymer as a multifunctional nanocarrier

• Yamei Zhao,
• Wei Tian,
• Guang Yang and
• Xiaodong Fan

Beilstein J. Org. Chem. 2014, 10, 2696–2703, doi:10.3762/bjoc.10.284

• ; hyperbranched polymer; multifunctionality; polymer nanocarrier; Introduction In recent years, many nanostructured materials (such as polymeric micelles) used as pharmaceutical nanocarriers have been applied in different fields of biomedicine for controlled release, diagnostics, imaging, treatment and

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

• complementary analytical electron microscopy based on electron spectroscopy imaging in the transmission microscope. The existence of a uniform and interacting β-CD layer covering the nanoparticles (i.e., the presence of carbon and oxygen atoms was detected in the surface) was unambiguously proved. Finally, the

Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers

• Michael Kurlemann and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 2428–2440, doi:10.3762/bjoc.10.253

• toxins or viruses and for imaging and targeted drug delivery [3]. Hydrogels which are built up by multivalent host–guest interactions and vesicles of amphiphilic host molecules have been intensively studied for their ability to function as drug delivery systems as well [4][5][6][7][8][9]. Additionally

A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

• Chrysie Aggelidou,
• Theodossis A. Theodossiou,
• Antonio Ricardo Gonçalves,
• Mariza Lampropoulou and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 2414–2420, doi:10.3762/bjoc.10.251

• . MCF7 cells were incubated with the colorless conjugate solution for 4 h, to allow conversion of prodrug 1 into PpIX [5][18]. Indeed, upon confocal microscopy imaging of the treated cells (λex = 568 nm), intense red fluorescence was observed (Figure 2), demonstrating that either (i) cell internalization

• mounted on microscope slides for confocal fluorescence live-cell imaging performed as described previously [21]. Intracellular fluorescein isothiocyanate-labeled 1-adamantylamine was excited using the 488 nm line of an argon–krypton ion laser while the PpIX fluorescence was excited with the 568 nm line of

Expanding the scope of cyclopropene reporters for the detection of metabolically engineered glycoproteins by Diels–Alder reactions

• Anne-Katrin Späte,
• Verena F. Schart,
• Julia Häfner,
• Andrea Niederwieser,
• Thomas U. Mayer and
• Valentin Wittmann

Beilstein J. Org. Chem. 2014, 10, 2235–2242, doi:10.3762/bjoc.10.232

• min–1; mobile phase: gradient of acetonitrile with 0.1% formic acid (solvent A) in water with 0.1% formic acid (solvent B). Microscopy was performed using a point laser scanning confocal microscope Zeiss LSM 510 Meta equipped with a Meta detector for spectral imaging. The synthesis of 1 and 2 was

• the dark. Cells were washed twice with PBS, and DMEM was added for microscopy. A Zeiss LSM 510 Meta equipped with a 40 × 1.3 NA Plan-Neofluar oil DIC immersion objective was employed for imaging. Analysis of the obtained data was performed using Image J software version 1.45 S.2. Western blot analysis

Improving the reactivity of phenylacetylene macrocycles toward topochemical polymerization by side chains modification

• Simon Rondeau-Gagné,
• Jules Roméo Néabo,
• Maxime Daigle,
• Katy Cantin and
• Jean-François Morin

Beilstein J. Org. Chem. 2014, 10, 1613–1619, doi:10.3762/bjoc.10.167

• present any gelation properties. For SEM analysis, a gel sample was allowed to dry at room temperature on a metallic substrate to form a xerogel. Then, gold was sputtered on the sample prior to imaging. SEM images of PAM2 are shown in Figure 2. As previously observed with PAM1 and other phenylacetylene

The search for new amphiphiles: synthesis of a modular, high-throughput library

• George C. Feast,
• Thomas Lepitre,
• Xavier Mulet,
• Charlotte E. Conn,
• Oliver E. Hutt,
• G. Paul Savage and
• Calum J. Drummond

Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163

• products, to biomedical applications including MRI imaging agents [1][2][3], membrane-protein crystallisation media [4][5][6] and solubilising bioactive food additives (Figure 1) [7]. Furthermore, recent research has centred on the use of amphiphile nanoparticles for drug-delivery applications [8][9][10

Multivalent scaffolds induce galectin-3 aggregation into nanoparticles

• Candace K. Goodman,
• Mark L. Wolfenden,
• Pratima Nangia-Makker,
• Anna K. Michel,
• Avraham Raz and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2014, 10, 1570–1577, doi:10.3762/bjoc.10.162

• binding and cluster formation by a series of glycodendrimers is a central step in the development of a synthetic multivalent antagonist that can intercept and influence galectin-3-mediated cellular processes and may be of clinical value as a non-cytotoxic drug and/or be developed for cancer imaging

Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family

• Hirofumi Dohi,
• Takeru Kanazawa,
• Akihiro Saito,
• Keita Sato,
• Hirotaka Uzawa,
• Yasuo Seto and
• Yoshihiro Nishida

Beilstein J. Org. Chem. 2014, 10, 1504–1512, doi:10.3762/bjoc.10.155

• a laser excitation imaging kit. The residual ricin concentration in the bis-Lac-C60 colloidal suspension was determined by means of the calibration curve, which shows the ricin intensities at each concentration. Estimation of decontamination efficiency by using a salting-out agent: A ricin solution

An economical and safe procedure to synthesize 2-hydroxy-4-pentynoic acid: A precursor towards ‘clickable’ biodegradable polylactide

• Quanxuan Zhang,
• Hong Ren and
• Gregory L. Baker

Beilstein J. Org. Chem. 2014, 10, 1365–1371, doi:10.3762/bjoc.10.139

• Quanxuan Zhang Hong Ren Gregory L. Baker Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA Athinoula A. Martinos Center for Biomedical Imaging, Department of

Tailoring of organic dyes with oxidoreductive compounds to obtain photocyclic radical generator systems exhibiting photocatalytic behavior

• Christian Ley,
• Julien Christmann,
• Ahmad Ibrahim,
• Luciano H. Di Stefano and
• Xavier Allonas

Beilstein J. Org. Chem. 2014, 10, 936–947, doi:10.3762/bjoc.10.92

• of this research area, the development of photoradical generators (PRG) is still a lively topic that finds applications in triggering bioactivity [1], drug or fragrance release [2][3][4], microelectronics [5], water catalysis reduction [6][7][8], and laser imaging [9]. In organic chemistry, the

A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones

• Pitchaimani Prasanna,
• Pethaiah Gunasekaran,
• Subbu Perumal and
• J. Carlos Menéndez

Beilstein J. Org. Chem. 2014, 10, 459–465, doi:10.3762/bjoc.10.43

• ], antiviral [7], antihypertensive [8], anti-oxidant [9][10][11][12], HIV-inhibitory [13], anti-inflammatory [14][15], immunomodulatory [16], antithrombotic [17], and anticancer [18][19][20] activities. Furthermore, some chromone derivatives have been identified as suitable fluorophores for live cell imaging

Flow microreactor synthesis in organo-fluorine chemistry

• Hideki Amii,
• Aiichiro Nagaki and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2013, 9, 2793–2802, doi:10.3762/bjoc.9.314

• , electron-donating, and sterically hindered functional groups were obtained in good yields. This is an important feature of 'late-stage fluorination methodology' for efficient drug screening. [18F] is a fluorine radioisotope which acts as an important source of positrons. In the medical imaging modality

• production of PET agents with automation and ease of in-line purification is suitable for hospital use. To date, continuous flow microreactor technology has shown potential for synthesis of [18F]-radiolabeled molecular imaging probes such as [18F]FDG, [18F]fallypride, [18F]annexin, and so on, which were made

• [18F]-radiolabeled molecular imaging probes. Flow microreactor synthesis of dipeptides. Flow synthesis involving SNAr reactions. Flow synthesis of fluoroquinolone antibiotics. Highly controlled formation of PFPMgBr. Selective flow synthesis of photochromic diarylethenes. Flow microreactor system for

The total synthesis of D-chalcose and its C-3 epimer

• Jun Sun,
• Song Fan,
• Zhan Wang,
• Guoning Zhang,
• Kai Bao and
• Weige Zhang

Beilstein J. Org. Chem. 2013, 9, 2620–2624, doi:10.3762/bjoc.9.296

• Jun Sun Song Fan Zhan Wang Guoning Zhang Kai Bao Weige Zhang Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China Center for Molecular Imaging, Beth Israel Deaconess Medical Center, Harvard Medical School

Direct electrophilic N-trifluoromethylthiolation of amines with trifluoromethanesulfenamide

• Sébastien Alazet,
• Kevin Ollivier and
• Thierry Billard

Beilstein J. Org. Chem. 2013, 9, 2354–2357, doi:10.3762/bjoc.9.270

• Sebastien Alazet Kevin Ollivier Thierry Billard Institute of Chemistry and Biochemistry (ICBMS – UMR CNRS 5246), Université de Lyon, Université Lyon 1, CNRS, 43 Bd du 11 novembre 1918 – 69622 Lyon, France CERMEP - in vivo imaging, Groupement Hospitalier Est, 59 Bd Pinel – 69003 Lyon, France

A³-Coupling catalyzed by robust Au nanoparticles covalently bonded to HS-functionalized cellulose nanocrystalline films

• Jian-Lin Huang,
• Derek G. Gray and
• Chao-Jun Li

Beilstein J. Org. Chem. 2013, 9, 1388–1396, doi:10.3762/bjoc.9.155

• and analysis procedure. Acknowledgements The work was supported by a team grant from Fonds de recherche sur la nature et les technologies Québec. We thank Dr. X. D. Liu, of the Facility for Electron Microscopy (FEMR) for TEM imaging.

Linkage of α-cyclodextrin-terminated poly(dimethylsiloxanes) by inclusion of quasi bifunctional ferrocene

• Helmut Ritter,
• Berit Knudsen and
• Valerij Durnev

Beilstein J. Org. Chem. 2013, 9, 1278–1284, doi:10.3762/bjoc.9.144

• ). Acknowledgements The authors thank the Center of Advanced Imaging of the Heinrich-Heine-Universität Düsseldorf for support of this research. The authors also thank the Evonik Goldschmidt GmbH in Essen for financial support of this research and especially Dr. Wilfried Knott and Dr. Frauke Henning for the helpful

Simple and rapid hydrogenation of p-nitrophenol with aqueous formic acid in catalytic flow reactors

• Rahat Javaid,
• Shin-ichiro Kawasaki,
• Akira Suzuki and
• Toshishige M. Suzuki

Beilstein J. Org. Chem. 2013, 9, 1156–1163, doi:10.3762/bjoc.9.129

• chemicals remaining inside the tube. The Pd–Ag mixed layer thickness was estimated as ca. 4.2 μm. Subsequent removal of Ag by passing 4 M HNO3 (840 mL) at 25 °C with a flow rate of 0.5 mL min−1 gave the porous Pd surface as observed by SEM imaging. The remaining amounts of Pd and Ag were 48.1 mg (94%) and

Camera-enabled techniques for organic synthesis

• Steven V. Ley,
• Richard J. Ingham,
• Matthew O’Brien and
• Duncan L. Browne

Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118

• other enabling technologies [16][33][34][35] are receiving increased attention. With the continuing development of digital imaging technology, computer vision techniques and laboratory automation, some of these routine tasks may be delegated to a computer. Not only will this allow skilled researchers to

• later retrieval and processing. The solid-state nature of CCD (charge-coupled device) and CMOS (complementary metal–oxide–semiconductor) imaging chips means that digital cameras can be very robust, which is of significant benefit in a laboratory environment. Many devices are highly portable, being hand

• environment. However, the availability of powerful open-source image processing software such as the Python Imaging Library [68] (PIL, an image processing library for the Python [69] programming language) and OpenCV [70] (a C++ library for creating real-time computer vision applications with bindings for the

Amyloid-β probes: Review of structure–activity and brain-kinetics relationships

• Todd J. Eckroat,
• Abdelrahman S. Mayhoub and
• Sylvie Garneau-Tsodikova

Beilstein J. Org. Chem. 2013, 9, 1012–1044, doi:10.3762/bjoc.9.116

• relationships with regards to affinity for target and brain kinetics. Several probes discussed herein show particularly promising results and will be of immense value moving forward in the fight against AD. Keywords: Alzheimer’s disease; in vivo detection; near-infrared fluorescence probes; PET/SPECT imaging

• sensitivity and accuracy, especially in the early stages of the disease. Therefore, as Aβ plaques precede the onset of dementia and cognitive decline in AD patients, their detection by nuclear imaging techniques such as positron emission tomography (PET) or single-photon emission computed tomography (SPECT

• ) represents the presymptomatic diagnostic tool of choice for AD [3][4][5]. The presence of different binding sites in Aβ aggregates led medicinal chemists to investigate and develop a variety of chemical scaffolds as Aβ-imaging tracers [6][7][8][9]. To provide a high readable signal-to-background ratio, the

Use of 3-[¹⁸F]fluoropropanesulfonyl chloride as a prosthetic agent for the radiolabelling of amines: Investigation of precursor molecules, labelling conditions and enzymatic stability of the corresponding sulfonamides

• Reik Löser,
• Steffen Fischer,
• Achim Hiller,
• Martin Köckerling,
• Uta Funke,
• Aurélie Maisonial,
• Peter Brust and
• Jörg Steinbach

Beilstein J. Org. Chem. 2013, 9, 1002–1011, doi:10.3762/bjoc.9.115

• the application of the 18F-fluoropropansulfonyl group to the labelling of compounds relevant as imaging agents for positron emission tomography (PET), the stability of N-(4-fluorophenyl)-3-fluoropropanesulfonamide against degradation catalysed by carboxylesterase was investigated and compared to that

• of the analogous fluoroacetamide. Keywords: fluorine-18; hydrolytic metabolism; prosthetic groups; radiochemistry; sulfonamides; Introduction The importance of molecular imaging, i.e., the characterisation and measurement of biological processes in living organisms at the molecular level using

• remote imaging detectors, for both research and diagnostic purposes has considerably increased over the recent years. The success of this interdisciplinary field depends substantially on the development of molecular probes equipped with appropriate reporter groups [1]. Among the different imaging

Photoionisation of the tropyl radical

• Kathrin H. Fischer,
• Patrick Hemberger,
• Andras Bodi and
• Ingo Fischer

Beilstein J. Org. Chem. 2013, 9, 681–688, doi:10.3762/bjoc.9.77

• efficient source for tropyl radicals generated by pyrolysis. Furthermore, the ground and excited states of the ion have been investigated computationally [9][17]. In the present study we extend the previous work using imaging photoelectron–photoion coincidence (iPEPICO) techniques in combination with VUV

• of the gas mixture. A photon energy resolution of 5 meV was achieved at 15.764 eV, measured at the 11s resonance of argon. The iPEPICO (imaging photoelectron photoion coincidence) technique was employed to study the photoionisation of tropyl 1. This technique allows the mass-selective detection of

• threshold photoelectrons by detecting them in coincidence with ions. The spectrometer is a combination of a Wiley–McLaren time-of-flight (TOF) mass spectrometer [48] and a velocity map imaging setup [49]. The latter is equipped with a position sensitive detector with a delay line anode (Roentdek DLD40

Spin state switching in iron coordination compounds

• Philipp Gütlich,
• Ana B. Gaspar and
• Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39