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

Phosphonic acid: preparation and applications

• Charlotte M. Sevrain,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2017, 13, 2186–2213, doi:10.3762/bjoc.13.219

• bone targeting, for the design of supramolecular or hybrid materials, for the functionalization of surfaces, for analytical purposes, for medical imaging or as phosphoantigen. These applications are covering a large panel of research fields including chemistry, biology and physics thus making the

• develop bone targeting which was assessed for therapy [96] and imaging [97][98]. Finally, the phosphonic acid group was also employed to immobilize organic or organometallic molecules on the surface of metal oxide [99][100] (Al2O3 [101], TiO2 [102][103], SnO2 [104], Fe3O4 [105], ZnO [106]), CdSe quantum

• dots [107] and used as anchoring group for dye-sensitized solar cells [108][109][110] or for the immobilization of organocatalyst [111][112]. Phosphonic acid was also used for coating superparamagnetic iron oxide (e.g., magnetite) assessed as contrast agent in magnetic resonance imaging [113] or to

Superstructures with cyclodextrins: Chemistry and applications IV

• Gerhard Wenz

Beilstein J. Org. Chem. 2017, 13, 2157–2159, doi:10.3762/bjoc.13.215

• magnetic resonance imaging (MRI) [22]. Well-defined fluorescent polyrotaxanes with alternating, threaded cucurbit[6]uril and CD rings were assembled by Fraser Stoddart’s group via an alkyne–azide click reaction exploiting supramolecular catalysis [23][24]. The concurrent radical copolymerization of 1,3

Direct catalytic arylation of heteroarenes with meso-bromophenyl-substituted porphyrins

• Alexei N. Kiselev,
• Olga K. Grigorova,
• Alexei D. Averin,
• Sergei A. Syrbu,
• Oskar I. Koifman and
• Irina P. Beletskaya

Beilstein J. Org. Chem. 2017, 13, 1524–1532, doi:10.3762/bjoc.13.152

• fields of modern organic chemistry due to their unique structure and electronic properties. These molecules have already proved to be powerful tools in phototherapy, radioimmunotherapy and imaging [1], for cancer treatment [2], and actually sophisticated theranostic porphyrin-based nanodevices have been

• application of such medicaments are antitumor remedies and non-invasive diagnostic imaging agents for PET, SPECT and MRI methods [5]. The combination of porphyrin and heterocyclic moieties in one molecule is perspective for the design of new compounds with potential powerful pharmaceutical properties. Up to

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

• . Based on this approach, multimodal agents delivered using a vehicle containing a drug capable of both imaging and curing were developed [4]. A meaningful information about biomolecule/drug localization and action can be gained employing fluorescence imaging, since it provides non-invasiveness

• of globular structures, that prepared liposomes were uniform in shape (high variability in shape or inhomogeneous peak structure would extensively increase the roughness value) and the cover over the surface was also homogeneous. Live-cell imaging of construct 6 and its liposomal formulation The

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

• proportional to Z4). This phenomenon produces the contrast that is used in X-ray imaging techniques. The synchrotron light spectrum is polychromatic, with a spectral bandwidth that depends on the type and configuration of the sources. Many experiments require a narrower bandwidth, or a monochromatic beam, and

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

• resulting biological processes [3][4]. The increasing ability to manipulate material at the nanosize allowed the development of many glyco nanoparticles helpful in a wide range of applications, from the drug delivery to the imaging [5][6][7]. Among the large number of nanomaterials, gold is one of the main

• demonstrated that GLUT1-targeting GAuNPs are well compatible with blood and do not significantly interact with ovine red blood cells [93]. In the last years, numerous compounds containing Gd3+ have been developed and used as magnetic resonance imaging (MRI) contrast agents. Recently, gold based nanosystems

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

• % phosphotungstic acid or 2% ammonium molybdate in the presence of 0.1% trehalose) was added, blotted again and air-dried. Imaging was performed using a Tecnai F20 FEG (FEI Company, Oregon) at an accelerating voltage of 160 kV under low-dose conditions. Micrographs were recorded according to the low-dose protocol

• and -stage (Model 626). Samples were constantly cooled by LN2 during imaging to maintain a sample temperature of T = 93 K. Imaging was performed at an accelerating voltage of 160 kV with a defocus value of 600 nm, which corresponds to the first zero of the CTF at 13 Å (Cs = 2.0 mm). Micrographs were

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

• traditional semiconductor quantum dots (QDs). Particularly in the areas of live imaging and drug delivery, due to their water solubility, low toxicity and photo- and chemical stability. Carbohydrates are readily available chiral biomolecules in nature which offer an attractive and cheap starting material from

• fluorophores, in addition to bright visible emission, have become particularly popular for their versatility as non-isotopic detection labels which are amenable to live cell imaging and immunoassay applications [7]. In particular, cadmium-based QDs (e.g., CdS, CdSe, CdSe/ZnS) are commonly used for in vitro

• fluorescent nanomaterials combined with their myriad of applications, has led to CDs being hailed as the potential non-toxic successors to traditional semiconductor QDs, particularly in the areas of live imaging and drug delivery. Synthetic approaches to access CDs can be classified into two broad categories

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

• conductivity. All specimen were imaged under high-vacuum conditions (1.0 Torr), using an acceleration voltage of 20 keV. Atomic force microscopy (AFM): AFM-imaging was performed using an Asylum Research Atomic Force Microscope, MFP-3D BIO. The AFM was operated at 25 °C in an isolated chamber in alternating

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• preservation of the photophysical properties of the dye. In fact, this molecular hybrid exhibits satisfactory fluorescence and 1O2 photogeneration quantum yields making it a suitable candidate for biomedical research studies in the field of imaging and PDT applications. The possibility to exploit the CD cavity

Investigation of the action of poly(ADP-ribose)-synthesising enzymes on NAD⁺ analogues

• Sarah Wallrodt,
• Edward L. Simpson and
• Andreas Marx

Beilstein J. Org. Chem. 2017, 13, 495–501, doi:10.3762/bjoc.13.49

• labelling approaches comprising different reporter-modified NAD+ building blocks have stimulated and enriched proteomic studies and imaging applications of ADP-ribosylation processes. Herein, we compare the substrate scope and applicability of different NAD+ analogues for the investigation of the polymer

• activity [15][16][17][18], the identification of PARylation sites and targets [15][19][20] and the real-time imaging [21] of PARylation processes. In this report, we systematically compare the substrate scope of the four poly(ADP-ribose)-synthesising enzymes ARTD1, ARTD2, ARTD5 and ARTD6. For this purpose

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

• yield. Especially mixed combinations, that means donor dyes with arabino-configured anchor with acceptor dyes with ribo-configured anchor, and vice versa, showed significantly improved fluorescence properties. Those were successfully applied for fluorescent imaging of DNA after transport into living

• traffic lights” [17][19][25] that are energy transfer-based nucleic acid probes that can be used in molecular beacons [26], especially for vesicular microRNA imaging in living cancer cells [27], and for siRNA transport imaging [28]. Donor and acceptor dyes are combined in an interstrand and diagonal

• -green contrast of 86). In order to test the functionality of the respective dyes as FRET pairs in DNA duplexes for imaging in cells, four representative duplexes, DNA2aD1–DNA3rD5, DNA2rD1–DNA3aD8, DNA2aD2–DNA3aD8 and DNA2rD4–DNA3aD8, were tested in HeLa cells. 5 × 104 HeLa cells were transiently

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

• modified with dibenzylcyclooctyne (DBCO)-conjugated fluorescent molecules via a copper-free click reaction; this fluorescently labeled PRX was utilized for intracellular fluorescence imaging. The method of synthesizing end-reactive PRXs described herein is simple and versatile for the design of diverse

• -catalyzed click reactions are performed. Additionally, fluorescence labeling of the PRX and intracellular fluorescence imaging were performed as an example application. Results and Discussion Synthesis of azide-terminated PRXs using bis(2-amino-3-phenylpropyl) poly(ethylene glycol) and 4-substituted benzoic

• fluorescence imaging Terminal reactive groups in the PRXs can be utilized in various biomaterials applications, such as the fabrication of cross-linked materials (e.g., hydrogels) [29], direct surface immobilization onto alkyne-immobilized surfaces [30], and the modification of other functional molecules for

Biochemical and structural characterisation of the second oxidative crosslinking step during the biosynthesis of the glycopeptide antibiotic A47934

• Veronika Ulrich,
• Clara Brieke and
• Max J. Cryle

Beilstein J. Org. Chem. 2016, 12, 2849–2864, doi:10.3762/bjoc.12.284

• Biochemistry and Molecular Biology and ARC Centre of Excellence in Advanced Molecular Imaging, Monash University, Clayton, Victoria 3800, Australia 10.3762/bjoc.12.284 Abstract The chemical complexity and biological activity of the glycopeptide antibiotics (GPAs) stems from their unique crosslinked structure

Chemical probes for competitive profiling of the quorum sensing signal synthase PqsD of Pseudomonas aeruginosa

• Michaela Prothiwa,
• Dávid Szamosvári,
• Sandra Glasmacher and
• Thomas Böttcher

Beilstein J. Org. Chem. 2016, 12, 2784–2792, doi:10.3762/bjoc.12.277

• selectively targeting the active site of an enzyme and a reporter group that allows in-gel imaging and/or affinity enrichment of target enzymes [22]. We thus synthesized a small library of chemical probes with electrophilic α-chloroacetamide, α,β-unsaturated amide, and α,β-unsaturated ketone moieties as

• and excess reporter tag were removed by SDS-polyacrylamide gel electrophoreses (SDS-PAGE), and labelling of the protein was visualized by fluorescence imaging. Consistency of protein levels was checked by coomassie staining (Supporting Information File 1, Figures S2 and S3). While the α,β-unsaturated

Synthesis of medronic acid monoesters and their purification by high-performance countercurrent chromatography or by hydroxyapatite

• Elina Puljula,
• Jouko Vepsäläinen and
• Petri A. Turhanen

Beilstein J. Org. Chem. 2016, 12, 2145–2149, doi:10.3762/bjoc.12.204

• : bisphosphonate; bisphosphonate monoester; high performance counter current chromatography; hydroxyapatite; medronic acid; Introduction Bisphosphonates (BPs) have been used for decades in the treatment of bone-related diseases as well as for bone imaging. Nevertheless, several recent reports have demonstrated

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

• Jacob R. Hauser,
• Hester A. Beard,
• Mary E. Bayana,
• Katherine E. Jolley,
• Stuart L. Warriner and
• Robin S. Bon

Beilstein J. Org. Chem. 2016, 12, 2019–2025, doi:10.3762/bjoc.12.189

• Laboratories, University of Leeds, Leeds LS2 9JT, UK 10.3762/bjoc.12.189 Abstract 2-Cyanobenzothiazoles (CBTs) are useful building blocks for: 1) luciferin derivatives for bioluminescent imaging; and 2) handles for bioorthogonal ligations. A particularly versatile CBT is 6-amino-2-cyanobenzothiazole (ACBT

• -cyanobenzothiazoles; DABCO; luciferins; organocatalysis; Introduction Functionalised 2-cyanobenzothiazoles (CBTs, 1) are key building blocks for the synthesis of luciferins 3 [1][2][3], substrates of natural and engineered firefly luciferases that are widely used for bioluminescence imaging (BLI) [4][5]. The typical

• bioorthogonal ligation and bioluminescent imaging. The procedure allowed the safe synthesis of 8 at multigram scale and in high purity. In addition, the sole use of filtrations and crystallisations for purification of all intermediates and products, in combination with the endothermic nature of the controlled

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• chelation [1][2][3][4]. BF2+-chelated ADP derivatives (Figure 1b) in particular have drawn interest for photodynamic therapy, bio-imaging and light harvesting applications [5][6][7][8]. We have shown that derivatives of Zn(ADP)2 are promising electron acceptors for organic photovoltaics (OPVs) [9][10]. A

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

• Maurizio Selva,
• Alvise Perosa,
• Sandro Guidi and
• Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

• therapeutics, imaging agents and packaging films and coatings [77]. Conclusion The literature survey illustrated in this review highlights three main facts. Firstly, organocatalysis by ionic liquids can be an efficient tool for base and even acid-catalyzed transesterification reactions in place of traditional

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• have been investigated for their potential applications in catalysis, photovoltaic cells and biomedical science [5]. Special attention has been paid to fluorescence responses of metal–terpyridine compounds permitting access to new sensors for bioassays and in vivo imaging purposes [6]. The

Dinuclear thiazolylidene copper complex as highly active catalyst for azid–alkyne cycloadditions

• Anne L. Schöffler,
• Ata Makarem,
• Frank Rominger and
• Bernd F. Straub

Beilstein J. Org. Chem. 2016, 12, 1566–1572, doi:10.3762/bjoc.12.151

• bioactive surfaces [8][14], imaging of biochemical processes [15], localization of bioactive compounds inside living cells [16], syntheses of small-molecule screening libraries [17], catenane and rotaxane syntheses [18], in reactions under continuous flow processing [19], polymer and surface science [20][21

Towards potential nanoparticle contrast agents: Synthesis of new functionalized PEG bisphosphonates

• Souad Kachbi-Khelfallah,
• Maelle Monteil,
• Margery Cortes-Clerget,
• Evelyne Migianu-Griffoni,
• Jean-Luc Pirat,
• Olivier Gager,
• Julia Deschamp and
• Marc Lecouvey

Beilstein J. Org. Chem. 2016, 12, 1366–1371, doi:10.3762/bjoc.12.130

• for biomedical imaging applications, the adsorption of plasmatic proteins on the surface of nanoparticles must be prevented to reduce the hepatic capture and increase the plasmatic time life. In biologic media, metal oxide nanoparticles are not stable and must be coated by biocompatible organic

• the development of superparamagnetic iron oxide nanoparticles (SPIONPs) because of their biocompatibility which allows there in vivo use both for diagnosis in magnetic resonance imaging and in therapy [1][2]. Most often, it is necessary to modify the surface of SPIONPs to increase the metabolic

Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA

• Svetlana V. Vasilyeva,
• Vyacheslav V. Filichev and
• Alexandre S. Boutorine

Beilstein J. Org. Chem. 2016, 12, 1348–1360, doi:10.3762/bjoc.12.128

• , so they were successfully used for both gene expression regulation and the synthesis of fluorescent probes for DNA imaging in fixed and live cells [1][2][3][8][9]. However, the length of the sequence recognized by the classical hairpin polyamides (5–6 base pairs) is much shorter than that for TFOs

Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

• Jarosław Lewkowski,
• Maria Rodriguez Moya,
• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Renata Kontek and
• Gabriela Gajek

Beilstein J. Org. Chem. 2016, 12, 1229–1235, doi:10.3762/bjoc.12.117

• biological imaging. Investigation of cytotoxic effects of studied compounds The cytotoxic effects of dimethyl aminophosphonates 3Aa, 3Ab, 3Ac, 3Ad, 3Ai and dimethyl [hydroxy(pyren-1-yl)methyl]phosphonate (5A) were investigated with two human colorectal carcinoma cell lines: HT29 and HCT116 and also on the