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Investigating Structural Requirements for the Antiproliferative Activity of Biphenyl Nicotinamides

Articles from Wiley - 3 agosto, 2017 - 00:00

Investigating Structural Requirements for the Antiproliferative Activity of Biphenyl Nicotinamides

Stopping the cell cycle: The screening of a small library of trimethoxybenzoic and nicotinic acid anilides, previously studied as P-gp modulators, allowed us to identify some N-biphenyl nicotinoyl anilides that show very interesting antiproliferative activities. The next hit refinement by a bioisosteric approach led us to observe potent antiproliferative activity of the cyano derivative 36 against MCF-7 and MDA-MB-231 cell lines.

[Full Paper]
Maria Majellaro, Angela Stefanachi, Piero Tardia, Chiara Vicenti, Angelina Boccarelli, Alessandra Pannunzio, Federica Campanella, Mauro Coluccia, Nunzio Denora, Francesco Leonetti, Modesto de Candia, Cosimo Damiano Altomare, Saverio Cellamare
ChemMedChem, August 03, 2017, https://doi.org/10.1002/cmdc.201700365 Read article

Bridging Pharmaceutical Chemistry with Drug and Nanoparticle Targeting to Investigate the Role of the 18-kDa Translocator Protein TSPO

Articles from Wiley - 3 agosto, 2017 - 00:00

Bridging Pharmaceutical Chemistry with Drug and Nanoparticle Targeting to Investigate the Role of the 18‐kDa Translocator Protein TSPO

Ligand logistics: Compounds with high affinity and selectivity for the 18-kDa mitochondrial translocator protein (TSPO) are useful for intracellular drug and nanoparticle targeting. The number of identified structurally distinct TSPO ligands has increased in recent years, highlighting our growing understanding of the roles of TSPO in normal and pathological conditions. This review summarizes some examples of drug delivery systems characterized by TSPO-targeting compounds.

[Minireview]
Rosa Maria Iacobazzi, Antonio Lopalco, Annalisa Cutrignelli, Valentino Laquintana, Angela Lopedota, Massimo Franco, Nunzio Denora
ChemMedChem, August 03, 2017, https://doi.org/10.1002/cmdc.201700322 Read article

CuAAC in a Distal Pocket: Metal Active-Template Synthesis of Strapped-Porphyrin [2]Rotaxanes

Articles from Wiley - 3 agosto, 2017 - 00:00

 Metal Active‐Template Synthesis of Strapped‐Porphyrin [2]Rotaxanes

The friendship is illustrated by the convivial atmosphere that surrounds the science on our plates.” Read more about the story behind the cover in the Cover Profile and about the research itself on page ▪▪ ff. (DOI: 10.1002/chem.201702553).

[Cover Profile]
Yuta Miyazaki, Christophe Kahlfuss, Ayumu Ogawa, Takashi Matsumoto, Jennifer A. Wytko, Koji Oohora, Takashi Hayashi, Jean Weiss
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201703337 Read article

Dinaphthotetrathiafulvalene Bisimides: A New Member of the Family of π-Extended TTF Stable p-Type Semiconductors

Articles from Wiley - 3 agosto, 2017 - 00:00

 A New Member of the Family of π‐Extended TTF Stable p‐Type Semiconductors

A new member of the π-expanded TTF family, dinaphthotetrathiafulvalene bisimide, is proven to be an air-stable p-type semiconductor. The hole-carrier mobility of the organic field-effect transistor of the film was improved from 3.7×10−3 cm2 V−1 s−1 to 0.30 cm2 V−1 s−1 under ambient conditions by raising the substrate temperature from 25 to 200 °C during sublimation, because of the acceleration of end-on packing from a mixture of face-on, edge-on and end-on packing. More information can be found in the Communication by H. Yamada et al. (DOI: 10.1002/chem.201702657).

[Cover Picture]
Masataka Yamashita, Koki Kawano, Akinobu Matsumoto, Naoki Aratani, Hironobu Hayashi, Mitsuharu Suzuki, Lei Zhang, Alejandro L. Briseno, Hiroko Yamada
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201703243 Read article

A Lithium Ion Highway by Surface Coordination Polymerization: In Situ Growth of Metal–Organic Framework Thin Layers on Metal Oxides for Exceptional Rate and Cycling Performance

Articles from Wiley - 3 agosto, 2017 - 00:00

 In Situ Growth of Metal–Organic Framework Thin Layers on Metal Oxides for Exceptional Rate and Cycling Performance

It does get in: A thin layer of a highly porous metal–organic framework material, ZIF-8, is fabricated uniformly on the surface of nanostructured ZnO nanoflakes and MnO2 nanorods to boost the transfer of lithium ions.

[Communication]
Yuzhen Han, Danni Yu, Junwen Zhou, Peiyu Xu, Pengfei Qi, Qianyou Wang, Siwu Li, Xiaotao Fu, Xing Gao, Chenghao Jiang, Xiao Feng, Bo Wang
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201703016 Read article

Catalytic Functionalization of Styrenyl Epoxides via 2-Nickela(II)oxetanes

Articles from Wiley - 3 agosto, 2017 - 00:00

Catalytic Functionalization of Styrenyl Epoxides via 2‐Nickela(II)oxetanes

Nickel squares up: Low-valent nickel(0) is shown to isomerize styrenyl epoxides to aldehydes in high yields. Mechanistic studies indicate that these isomerizations occur via 2-nickelaoxetane intermediates. Catalytic hydroboration of styrene oxide with HBpin was also demonstrated to be facile.

[Communication]
Addison N. Desnoyer, Jialing Geng, Marcus W. Drover, Brian O. Patrick, Jennifer A. Love
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201702824 Read article

Cooperative Activation of Cobalt–Salen Complexes for Epoxide Hydration Promoted on Flexible Porous Organic Frameworks

Articles from Wiley - 3 agosto, 2017 - 00:00

Cooperative Activation of Cobalt–Salen Complexes for Epoxide Hydration Promoted on Flexible Porous Organic Frameworks

Porous organic frameworks are synthesized with a high concentration of Co(salen) in the network and having high flexibility. This system efficiently promotes the cooperation between the nearby Co(salen) moieties in the epoxide hydration reaction.

[Communication]
Mingmei Zhong, He Li, Jian Chen, Lin Tao, Can Li, Qihua Yang
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201702810 Read article

Facilitating Active Species Generation by Amorphous NiFe-B<sub>i</sub> Layer Formation on NiFe-LDH Nanoarray for Efficient Electrocatalytic Oxygen Evolution at Alkaline pH

Articles from Wiley - 3 agosto, 2017 - 00:00

Facilitating Active Species Generation by Amorphous NiFe‐Bi Layer Formation on NiFe‐LDH Nanoarray for Efficient Electrocatalytic Oxygen Evolution at Alkaline pH

Amorphous layer: A core-shell NiFe-LDH@NiFe-Bi nanoarray on carbon cloth (NiFe-LDH@NiFe-Bi/CC) behaves as a superior OER electrocatalyst with strong durability in alkaline media. It only requires an overpotential of 294 mV to drive 50 mA cm−2; 116 mV less than that needed by NiFe-LDH/CC.

[Communication]
Ling Zhang, Rong Zhang, Ruixiang Ge, Xiang Ren, Shuai Hao, Fengyu Xie, Fengli Qu, Zhiang Liu, Gu Du, Abdullah M. Asiri, Baozhan Zheng, Xuping Sun
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201702745 Read article

Visible-Light-Mediated Excited State Relaxation in Semi-Synthetic Genetic Alphabet: d5SICS and dNaM

Articles from Wiley - 3 agosto, 2017 - 00:00

 d5SICS and dNaM

Let there be light: Excited state relaxation in the sub-picosecond timescales of unnatural nucleobases—d5SICS and dNaM—arise from the strong spin-orbit couplings between the singlet and triplet states (see figure).

[Communication]
Kalishankar Bhattacharyya, Ayan Datta
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201702583 Read article

Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino-Staudinger Synthesis

Articles from Wiley - 3 agosto, 2017 - 00:00

 Direct Access to Azetidinimines by an Imino‐Staudinger Synthesis

Base Jump: Under strongly basic conditions ynamides gave highly reactive ketenimines that could be trapped with imines in a [2+2] cycloaddition. This imino-Staudinger synthesis led to a variety of imino analogues of &#x3B2;-lactams, namely azetidinimines (20 examples), that could be further functionalized through a broad range of transformations.

[Communication]
Eugénie Romero, Corinne Minard, Mohamed Benchekroun, Sandrine Ventre, Pascal Retailleau, Robert H. Dodd, Kevin Cariou
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201702545 Read article

In vivo Evaluation of an Engineered Cyclotide as Specific CXCR4 Imaging Reagent

Articles from Wiley - 3 agosto, 2017 - 00:00

In vivo Evaluation of an Engineered Cyclotide as Specific CXCR4 Imaging Reagent

A 64Cu-labeled cyclotide with high specificity for receptor CXCR4 was used for in vivo PET imaging of tumors with high CXCR4 expression level, showing the potential of this microprotein molecular scaffold for in vivo bio-imaging applications.

[Full Paper]
Wojciech G. Lesniak, Teshome Aboye, Samit Chatterjee, Julio A. Camarero, Sridhar Nimmagadda
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201702540 Read article

Structural Study of a New HIV-1 Entry Inhibitor and Interaction with the HIV-1 Fusion Peptide in Dodecylphosphocholine Micelles

Articles from Wiley - 3 agosto, 2017 - 00:00

Structural Study of a New HIV‐1 Entry Inhibitor and Interaction with the HIV‐1 Fusion Peptide in Dodecylphosphocholine Micelles

No admittance! The peptide E1P47 forms a helix–turn–helix motif in zwitterionic dodecylphosphocholine (DPC) micelles, a structure, which is relevant for its inhibitory activity. E1P47 interacts with the HIV-1 fusion peptide at the membrane level by interfering with those domains in the HIV-1, which are critical for stabilizing the six-helix bundle formation in a membranous environment (see figure).

[Full Paper]
Yolanda Pérez, Maria José Gómara, Eloísa Yuste, Patricia Gómez-Gutierrez, Juan Jesús Pérez, Isabel Haro
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201702531 Read article

Double-Arm Lanthanide Tags Deliver Narrow Gd<sup>3+</sup>–Gd<sup>3+</sup> Distance Distributions in Double Electron–Electron Resonance (DEER) Measurements

Articles from Wiley - 3 agosto, 2017 - 00:00

Double‐Arm Lanthanide Tags Deliver Narrow Gd3+–Gd3+ Distance Distributions in Double Electron–Electron Resonance (DEER) Measurements

Metal on a tether: Double-arm cyclen-based Gd3+ tags confine the space accessible to the metal ion (see figure) and produce accurate nanometer scale Gd3+–Gd3+ distance measurements by double electron-electron resonance (DEER) experiments, which show excellent agreement with predictions both for the maximum and width of the measured distance distributions. This research opens new opportunities to study the conformational landscape of proteins in solution.

[Full Paper]
Adarshi P. Welegedara, Yin Yang, Michael D. Lee, James D. Swarbrick, Thomas Huber, Bim Graham, Daniella Goldfarb, Gottfried Otting
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201702521 Read article

Silver(I) Clusters with Carba-<i>closo</i>-dodecaboranylethynyl Ligands: Synthesis, Structure, and Phosphorescence

Articles from Wiley - 3 agosto, 2017 - 00:00

 Synthesis, Structure, and Phosphorescence

The silver lining: Neutral, monoanionic, and dianionic silver(I) clusters stabilized by carba-closo-dodecaboranylethynyl and pyridine ligands were obtained with organic cations (see figure). Selected clusters were studied by photoluminescence spectroscopy and found to be room-temperature phosphorescent. The quantum yields were strongly influenced by the pyridine ligands.

[Full Paper]
Michael Hailmann, Natalia Wolf, Rebecca Renner, Benjamin Hupp, Andreas Steffen, Maik Finze
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201702515 Read article

Cancer Stem Cell and Bulk Cancer Cell Active Copper(II) Complexes with Vanillin Schiff Base Derivatives and Naproxen

Articles from Wiley - 3 agosto, 2017 - 00:00

Cancer Stem Cell and Bulk Cancer Cell Active Copper(II) Complexes with Vanillin Schiff Base Derivatives and Naproxen

Two birds with one copper stone: We present a series of copper(II) complexes containing vanillin Schiff base derivatives and the nonsteroidal anti-inflammatory drug, naproxen. Three of the complexes kill bulk cancer cells and cancer stem cells with similar doses. The most effective complex evokes cell death by inducing DNA damage and inhibiting cyclooxygenase-2.

[Full Paper]
Chunxin Lu, Arvin Eskandari, Paul B. Cressey, Kogularamanan Suntharalingam
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201701939 Read article

Synthesis of Copper Oxide/Graphite Composite for High-Performance Rechargeable Battery Anode

Articles from Wiley - 3 agosto, 2017 - 00:00

Synthesis of Copper Oxide/Graphite Composite for High‐Performance Rechargeable Battery Anode

Graphite composite anode: A one-step synthesis of advanced graphite/Cu oxide composites (GCuO) is developed. Thermal treatment of a Cu ion complex and graphite induces graphite interlayer expansion and Cu oxide formation. The resulting GCuO cell shows a high capacity of 532 mAh g−1 and a good stability of 83 % after 250 cycles (see figure).

[Full Paper]
Sanghun Cho, Yong-keon Ahn, Zhenxing Yin, Duck-Jae You, Hyunjin Kim, Yuanzhe Piao, Jeeyoung Yoo, Youn Sang Kim
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201701931 Read article

Glycodendrimers as Chondroitin Sulfate Mimetics: Synthesis and Binding to Growth Factor Midkine

Articles from Wiley - 3 agosto, 2017 - 00:00

 Synthesis and Binding to Growth Factor Midkine

Click for chondroitin sulfates: Dendrimers displaying CS disaccharides were efficiently synthesized. These multivalent systems showed high protein binding affinities, mimicking the activity of this biologically relevant polysaccharide.

[Full Paper]
Pedro Domínguez-Rodríguez, José J. Reina, Sergio Gil-Caballero, Pedro M. Nieto, José L. de Paz, Javier Rojo
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201701890 Read article

Ambient Water-Stable Dianionic Electron Donors: Intramolecular Noncovalent Conduits Assist Charge Delocalization

Articles from Wiley - 3 agosto, 2017 - 00:00

 Intramolecular Noncovalent Conduits Assist Charge Delocalization

Moving charges: We report the first example of an exceptionally stable naphthalenediimide-based dianion in ambient and hot water. The dianionic state was confirmed by X-ray crystallography. The noncovalent electronic conduits introduced for the first time in dianions aid in delocalizing the dianionic charge. The dianions harness strong NIR absorption and electron donor ability to organic acceptors and metal ions.

[Full Paper]
Sudhir Kumar Keshri, Sharvan Kumar, Kalyanashis Mandal, Pritam Mukhopadhyay
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201701868 Read article

A Secondary Structural Element in a Wide Range of Fucosylated Glycoepitopes

Articles from Wiley - 3 agosto, 2017 - 00:00

A Secondary Structural Element in a Wide Range of Fucosylated Glycoepitopes

Rigid sugars: NMR structure determination revealed a common 3D scaffold in 25 % of all fucose-containing carbohydrates. The central feature is a C−H⋅⋅⋅O hydrogen bond, indicated by a characteristic chemical shift. This work suggests that fucosylation of certain glycans leads to a rigidification in addition to generating glyco-epitopes for recognition events.

[Full Paper]
Thomas Aeschbacher, Mirko Zierke, Martin Smie&#x161;ko, Mayeul Collot, Jean-Maurice Mallet, Beat Ernst, Frédéric H.-T. Allain, Mario Schubert
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201701866 Read article

DFT Studies of Dimerization Reactions of Boroles

Articles from Wiley - 3 agosto, 2017 - 00:00

DFT Studies of Dimerization Reactions of Boroles

Boroles undergo dimerization reactions to give Diels–Alder (DA) dimers, bridged-bicyclic (BB) dimers or spiro dimers (SD) depending on the substituents on the borole. DFT calculations were performed to investigate how different substituents at the carbon atoms of the butadiene backbone as well as at the boron atom influence the dimerization reaction pathways.

[Full Paper]
Zheng Wang, Yu Zhou, Ka-Ho Lee, Wai Han Lam, Rian D. Dewhurst, Holger Braunschweig, Todd B. Marder, Zhenyang Lin
Chem. Eur. J., August 03, 2017, https://doi.org/10.1002/chem.201701737 Read article

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