bluuebunny/crossref_metadata_2025 huggingface dataset:
Glycoside hydrolase inventory drives plant polysaccharide deconstruction by the extremely thermophilic bacterium Caldicellulosiruptor saccharolyticus
Authors: VanFossen Amy L. , Ozdemir Inci , Zelin Samantha L. , Kelly Robert M.
Published: February 2011

The genome of Caldicellulosiruptor saccharolyticus encodes a range of glycoside hydrolases (GHs) that mediate plant biomass deconstruction by this bacterium. Two GH‐based genomic loci that appear to be central to the hydrolysis of hemicellulosic and cellulosic substrates were examined. XynB‐XynF (Csac_2404‐Csac_2411) encodes intracellular and extracellular GHs that are active towards xylan and xylan side‐chains, as well as carboxymethyl cellulose (CMC). XynD (Csac_2409) and XynE (Csac_2410) were produced recombinantly and confirmed to be xylanases. XynF (Csac_2411) was produced in two separate polypeptides, each with one GH43 catalytic domain displaying α‐L‐arabinofuranosidase activity. CelA‐ManB (Csac_1076‐Csac_1080) encodes four multi‐domain, extracellular GHs, including CelB (Csac_1078), a 118 kDa extracellular enzyme not present in the other genome‐sequenced member of this genus, Caldicellulosiruptor bescii (formerly Anaerocellum thermophilum). CelB contains both GH10 and GH5 domains, separated by a family 3 carbohydrate‐binding module (CBM3). CelB encoded in Csac_1078 differed from the version originally reported (Saul et al., 1990, Appl Environ Microbiol 56:3117–3124) with respect to linker regions. CelB hydrolyzed xylan and CMC, as well as barley β‐glucan, glucomannan, and arabinoxylan. For all substrates tested, intact CelB was significantly more active than either the individual GH5 and GH10 domains or the two discrete domains together, indicating that the multi‐domain architecture is essential for complex carbohydrate hydrolysis. Transcriptomes for C. saccharolyticus grown at 70°C on glucose, xylose, xyloglucan, switchgrass, and poplar revealed that certain GHs were particularly responsive to growth on switchgrass and poplar and that CelB was in the top decile of all transcripts during growth on the plant biomass. Biotechnol. Bioeng. 2011; 108:1559–1569. © 2011 Wiley Periodicals, Inc.
Model‐based analysis of the role of biological, hydrological and geochemical factors affecting uranium bioremediation
Authors: Zhao Jiao , Scheibe Timothy D. , Mahadevan R.
Published: February 2011

Uranium contamination is a serious concern at several sites motivating the development of novel treatment strategies such as the Geobacter‐mediated reductive immobilization of uranium. However, this bioremediation strategy has not yet been optimized for the sustained uranium removal. While several reactive‐transport models have been developed to represent Geobacter‐mediated bioremediation of uranium, these models often lack the detailed quantitative description of the microbial process (e.g., biomass buildup in both groundwater and sediments, electron transport system, etc.) and the interaction between biogeochemical and hydrological process. In this study, a novel multi‐scale model was developed by integrating our recent model on electron capacitance of Geobacter (Zhao et al., 2010) with a comprehensive simulator of coupled fluid flow, hydrologic transport, heat transfer, and biogeochemical reactions. This mechanistic reactive‐transport model accurately reproduces the experimental data for the bioremediation of uranium with acetate amendment. We subsequently performed global sensitivity analysis with the reactive‐transport model in order to identify the main sources of prediction uncertainty caused by synergistic effects of biological, geochemical, and hydrological processes. The proposed approach successfully captured significant contributing factors across time and space, thereby improving the structure and parameterization of the comprehensive reactive‐transport model. The global sensitivity analysis also provides a potentially useful tool to evaluate uranium bioremediation strategy. The simulations suggest that under difficult environments (e.g., highly contaminated with U(VI) at a high migration rate of solutes), the efficiency of uranium removal can be improved by adding Geobacter species to the contaminated site (bioaugmentation) in conjunction with the addition of electron donor (biostimulation). The simulations also highlight the interactive effect of initial cell concentration and flow rate on U(VI) reduction. Biotechnol. Bioeng. 2011; 108:1537–1548. © 2011 Wiley Periodicals, Inc.
Effects of bacteriophage on the surface properties of chalcopyrite (CuFeS2), and phage‐induced flocculation of chalcopyrite, glacial till, and oil sands tailings
Authors: Curtis Susan B. , MacGillivray Ross T.A. , Dunbar W. Scott
Published: February 2011

The binding of mineral‐specific phage to the surface of chalcopyrite (CuFeS2) was investigated by using X‐ray photoelectron spectroscopy and scanning Auger microscopy. These studies confirmed the elemental composition of the minerals and confirmed that bacteriophage were bound to the mineral surface. These techniques also revealed that the phage were not forming a continuous film over the entire surface of the CuFeS2 particles, but selectively bound to the slimes coating the particles. In addition, the effect of mineral‐specific phage binding to the surface of CuFeS2 was investigated using induction time and zeta potential measurements. Bacteriophage (1012/mL) increased the induction time (contact time resulting in 50% particle attachment to a bubble) from ∼7.5 to ∼17 ms and reversed the zeta potential from negative to positive. In the course of performing the zeta potential measurements on particles <45 µm in diameter, phage‐induced aggregation was observed. The mechanism of aggregation was explored using a range of pH (3–11) and cation concentrations. Aggregation was observed across the tested pH range and with all cations. Phage also mediated aggregation of glacial till and oil sands tailings in a dose‐dependent and particle size‐dependent manner. We conclude that binding of bacteriophage to the surface of CuFeS2 does alter its surface properties. Biotechnol. Bioeng. 2011; 108:1579–1590. © 2011 Wiley Periodicals, Inc.
Carbohydrate nanoparticle‐mediated colloidal assembly for prolonged efficacy of bacteriocin against food pathogen
Authors: Bi Lin , Yang Lei , Bhunia Arun K. , Yao Yuan
Published: February 2011

The goal of this study was to demonstrate the ability of carbohydrate nanoparticle‐stabilized emulsion to prolong the efficacy of bacteriocin against food pathogens. An amphiphilic, negatively charged carbohydrate nanoparticle, phytoglycogen octenyl succinate (PG‐OS), was used to form oil‐in‐water emulsion for delivering bacteriocin nisin against the food pathogen Listeria monocytogenes. Dynamic light scattering test showed that in emulsion all PG‐OS nanoparticles were adsorbed at the surface of oil droplets. Zeta‐potential analysis indicated an effective adsorption of positively charged nisin molecules at the surface of PG‐OS interfacial layer. Nisin depletion model showed that, during 50 days of storage, the anti‐listerial activity of nisin‐containing PG‐OS‐stabilized emulsion was substantially greater than that of nisin solution. In contrast, the emulsion stabilized with a neutral, small‐molecule surfactant (Tween 20) or negatively charged, hyperbranched carbohydrate polymer (modified starch) was either ineffective or less effective than the nanoparticle‐stabilized emulsion to retain nisin activity during storage. Biotechnol. Bioeng. 2011; 108:1529–1536. © 2011 Wiley Periodicals, Inc.
Improvement of HepG2/C3a cell functions in a microfluidic biochip
Authors: Prot Jean Matthieu , Aninat Caroline , Griscom Laurent , Razan Florence , Brochot Céline , Guillouzo Christiane Guguen , Legallais Cécile , Corlu Anne , Leclerc Eric
Published: February 2011

Current developments in tissue engineering and microtechnology fields allow the use of microfluidic biochip as microtools for in vitro investigations. In the present study, we describe the behavior of HepG2/C3a cells cultivated in a poly(dimethylsiloxane) (PDMS) microfluidic biochip coupled to a perfusion system. Cell culture in the microfluidic biochip for 96 h including 72 h of perfusion provoked a 24 h delay in cell growth compared to plate cultures. Inside the microfluidic biochip, few apoptosis, and necrosis were detected along the culture and 3D cell organization was observed. Regarding the hepatic metabolism, glucose and glutamine consumptions as well as albumin synthesis were maintained. A transcriptomic analysis performed at 96 h of culture using Affymetrix GeneChip demonstrated that 1,025 genes with a fold change above 1.8 were statistically differentially expressed in the microfluidic biochip cultures compared to plate cultures. Among those genes, phase I enzymes involved in the xenobiotic's metabolism such as the cytochromes P450 (CYP) 1A1/2, 2B6, 3A4, 3A5, and 3A7 were up‐regulated. The CYP1A1/2 up‐regulation was associated with the appearance of CYP1A1/2's activity evidenced by using EROD biotransformation assay. Several phase II enzymes such as sulfotransferases (SULT1A1 and SULT1A2), UDP‐glucuronyltransferase (UGT1A1, UGT2B7) and phase III transporters (such as MDR1, MRP2) were also up‐regulated. In conclusion, microfluidic biochip could and provide an important insight to exploring the xenobiotic's metabolism. Altogether, these results suggest that this kind of biochip could be considered as a new pertinent tool for predicting cell toxicity and clearance of xenobiotics in vitro. Biotechnol. Bioeng. 2011; 108:1704–1715. © 2011 Wiley Periodicals, Inc.
Combining Aminocyanine Dyes with Polyamide Dendrons: A Promising Strategy for Imaging in the Near‐Infrared Region
Authors: Ornelas Cátia , Lodescar Rachelle , Durandin Alexander , Canary James W. , Pennell Ryan , Liebes Leonard F. , Weck Marcus
Published: February 2011

Cyanine dyes are known for their fluorescence in the near‐IR (NIR) region, which is desirable for biological applications. We report the synthesis of a series of aminocyanine dyes containing terminal functional groups such as acid, azide, and cyclooctyne groups for further functionalization through, for example, click chemistry. These aminocyanine dyes can be attached to polyfunctional dendrons by copper‐catalyzed azide alkyne cycloaddition (CuAAC), strain‐promoted azide alkyne cycloaddition (SPAAC), peptide coupling, or direct SNR1 reactions. The resulting dendron–dye conjugates were obtained in high yields and displayed high chemical stability and photostability. The optical properties of the new compounds were studied by UV/Vis and fluorescence spectroscopy. All compounds show large Stokes shifts and strong fluorescence in the NIR region with high quantum yields, which are optimal properties for in vivo optical imaging.
Amine Exchange in Formamidines: An Experimental and Theoretical Study
Authors: Capela Marinha dF. , Mosey Nicholas J. , Xing Liyan , Wang Ruiyao , Petitjean Anne
Published: February 2011

NH‐containing formamidines combine a reasonably strong association to carboxylic acids to form complexes of well‐defined geometries with a simultaneous proton‐induced electrophilicity enhancement that allows for the exchange of their amine portion. The NC(H)NH fragment, therefore, undergoes “imine‐like” exchange with N‐containing nucleophiles. Because of the prototropic equilibrium, the NC(H)NH fragment may behave as a “bisimine” centred on the same carbon, in which both N‐containing fragments can be exchanged. Considering the proton‐induced sensitisation of both CN units and the well‐defined formamidine–carboxylic acid complex geometry, it should be possible to use carboxylic acids as templates for the synthesis of defined architectures by dynamic amine exchange within formamidines. This study highlights three exchange regimes based on the nature of the incoming amine (aliphatic amines, aromatic amines and alkoxyamines), as well as exchange rules based on the amine leaving groups. Following this analysis, a proof of concept for carboxylic acid templated macrocycle formation through dynamic exchange is provided.
Highly Crystalline and Conductive Nitrogen‐Doped Mesoporous Carbon with Graphitic Walls and Its Electrochemical Performance
Authors: Datta Kasibhatta K. R. , Balasubramanian Veerappan V. , Ariga Katsuhiko , Mori Toshiyuki , Vinu Ajayan
Published: February 2011

We present a rational and simple methodology to fabricate highly conductive nitrogen‐doped ordered mesoporous carbon with a graphitic wall structure by the simple adjustment of the carbonization temperature of mesoporous carbon nitride without the addition of any external nitrogen sources. By simply controlling the heat‐treatment temperature, the structural order and intrinsic properties such as surface area, conductivity, and pore volume, and the nitrogen content of ordered graphitic mesoporous carbon can be controlled. Among the materials studied, the sample heat‐treated at 1000 °C shows the highest conductivity, which is 32 times higher than that for the samples treated at 800 °C and retains the well‐ordered mesoporous structure of the parent mesoporous carbon nitride and a reasonable amount of nitrogen in the graphitic framework. Since these materials exhibit high conductivity with the nitrogen atoms in the graphitic framework, we further demonstrate their use as a support for nanoparticle fabrication without the addition of any external stabilizing or size‐controlling agent, as well as the anode electrode catalysts. Highly dispersed platinum nanoparticles with a size similar to that of the pore diameter of the support can be fabricated since the nitrogen atoms and the well‐ordered porous structure in the mesoporous graphitic carbon framework act as a stabilizing and size‐controlling agent, respectively. Furthermore the Pt‐loaded, nitrogen‐doped mesoporous graphitic carbon sample with a high conductivity shows much higher anodic electrocatalytic activity than the other materials used in the study.
Unusual Inversion Phenomenon of β‐Cyclodextrin Dimers in Water
Authors: Menuel Stéphane , Azaroual Nathalie , Landy David , Six Natacha , Hapiot Frédéric , Monflier Eric
Published: February 2011

A conformational analysis of three triazole‐containing bridged bis‐β‐ cyclodextrins (CD) has been carried out to evaluate their recognition ability. NMR spectroscopy and ITC measurements clearly demonstrate that one of the CD glucopyranose units undergoes a 360° rotation in water so that the spacer linking the two CDs is deeply included into one of the CD cavities. The amplitude of this inversion phenomenon depends on the nature of the spacer and results in a limited accessibility to the CD cavities in line with previous catalytic results.
ChemInform Abstract: Site Specific X‐Ray Anomalous Dispersion of the Geometrically Frustrated Kagome Magnet, Herbertsmithite, ZnCu3(OH)6Cl2.
Authors: Freedman Danna E. , Han Tianheng H. , Prodi Andrea , Mueller Peter , Huang Qing‐Zhen , Chen Yu‐Sheng , Webb Samuel M. , Lee Young S. , McQueen Tyrel M. , Nocera Daniel G.
Published: February 2011

A single crystal of (Zn0.85Cu0.15)Cu3 (OH)6Cl2 is obtained from a mixture of CuO, ZnCl2, and H2O (185 °C, 2 d) followed by recrystallization of the microcrystalline product.
ChemInform Abstract: Local and Permeating Disorder of Copper(I) Cations in Cu3BiS2Br2 and Cu4Bi3S5Br3‐xClx (x = 1.19)
Authors: Heerwig Andreas , Nitsche Fabian , Ruck Michael
Published: February 2011

Cu3BiS2Br2 (I) and Cu4Bi3S5Br1.81Cl1.19 (II) are synthesized from stoichiometric mixtures of Cu, Bi2S3, S, CuCl, NaCl, and CuBr (silica ampules, 570 °C, 14 d) and characterized by powder and single crystal XRD.
ChemInform Abstract: Hydrogen Insertion Effect on the Magnetic Properties of Ce2Pd2In.
Authors: Iwasieczko Waclaw , Kaczorowski Dariusz
Published: February 2011

The effect of hydrogen insertion into the crystal lattice of the ferromagnetic title compound is investigated by powder XRD and magnetic measurements.
ChemInform Abstract: Experimental Study of the Isothermal Section of the Ho—Fe—Cr System at 873 K.
Authors: Yao Q. R. , Zhou H. Y. , Pan S. K. , Wang Z. M.
Published: February 2011

Phase equilibria of the title system at 873 K are characterized by powder XRD, metallography, and SEM/EDS.
ChemInform Abstract: Beryllosilicate Frameworks and Zeolites.
Authors: Armstrong Jennifer A. , Weller Mark T.
Published: February 2011

The new compounds with zeolite topologies (IV) (new zeolite topology, orthorhombic, Pnma), (V) (new zeolite topology, pseudo‐tetragonal, P1/P42), the layered compound K6[Si7Be3]O18(OH)4 (monoclinic, Cc), and the potassium and sodium nabesites K8 [Be4Si16O40]·12H2O (orthorhombic, C2221), and Na5.28 [Be2.64Si17.36O40] ·12.5H2O (orthorhombic, P21212) are hydrothermally synthesized from aqueous solutions containing Be(OH)2, SiO2, Et4NOH, and an alkali metal hydroxide (autoclave, 130—240 °C, 48 h).
ChemInform Abstract: Synthesis, Crystal Structure and Characterization of a New Protonated Magnesium Borophosphate: (H3O)Mg(H2O)2 [BP2O8]·H2O.
Authors: Yang Yang , Wu Jian , Wang Yu , Zhu Jiang , Liu Ruibin , Meng Changgong
Published: February 2011

The title compound is hydrothermally synthesized from a mixture of MgCl2, B2O3, H3PO4, pyridine, HCl, and H2O (autoclave, 170 °C, 3 d, 10% yield).
ChemInform Abstract: Synthesis and Anticancer Properties of Rare Earth Substituted tungstophosphoric Polyoxometalate Containing 5‐Fluorouracil.
Authors: Liu Xia , Wang Shuaishuai , Feng Changgen
Published: February 2011

The new compounds (III) containing Keggin‐type heteropolyanions and 5‐fluorouracil are characterized by powder XRD, IR, and 183W NMR spectroscopy.
ChemInform Abstract: Synthesis and Structure of Technetium Trichloride.
Authors: Poineau Frederic , Johnstone Erik V. , Weck Philippe F. , Kim Eunja , Forster Paul M. , Scott Brian L. , Sattelberger Alfred P. , Czerwinski Kenneth R.
Published: February 2011

Compound (II), an intermediate in the formation of TcCl3 from (I), crystallizes in the triclinic space group P$\bar 1$ with Z = 1 (single crystal XRD).
ChemInform Abstract: Synthesis of Novel Carbazolyl‐Oxazolone Derivatives and Their Spectroscopic Properties.
Authors: Guendogdu Cevher , Topkaya Derya , Oeztuerk Guelsiye , Alp Serap , Erguen Yavuz
Published: February 2011

Compounds (I) are prepared by an Erlenmeyer reaction and show promising photochemical properties.
ChemInform Abstract: Chiral N‐Phosphino Sulfinamide Ligands in Rhodium(I)‐Catalyzed [2 + 2 + 2] Cycloaddition Reactions.
Authors: Brun Sandra , Parera Magda , Pla‐Quintana Anna , Roglans Anna , Leon Thierry , Achard Thierry , Sola Jordi , Verdaguer Xavier , Riera Antoni
Published: February 2011

Cationic Rh—chiral N‐phosphinosulfinamide complex is successfully applied in [2 + 2 + 2] cycloaddition reactions.
ChemInform Abstract: Novel Application of Electrooxidative Method for the Cyclization of N‐Benzyl‐2‐(hydroxymethyl)‐ and N‐Benzyl‐2‐(2‐hydroxyethyl)piperidines.
Authors: Okimoto Mitsuhiro , Yoshida Takashi , Hoshi Masayuki , Ohashi Kousuke
Published: February 2011

The electrochemical oxidation of title compounds (I) is conducted under mild conditions without the use of hazardous oxidants.
ChemInform Abstract: Mild Oxidation of Alcohols Using Soluble Polymer‐Supported Tempo in Combination with Oxone: Effect of a Basic Matrix of Tempo Derivatives.
Authors: Matsumoto Kazutsugu , Iwata Toshiaki , Suenaga Masahiro , Okudomi Masayuki , Nogawa Masaki , Nakano Mariko , Sugahara Ai , Bannai Yuta , Baba Kenji
Published: February 2011

Two types of PEG‐supported TEMPO derivatives are synthesized by means of esterification or click chemistry and applied in the oxidation of primary and secondary alcohols in combination with Oxone as the co‐oxidant.
ChemInform Abstract: Allylic C—H Acetoxylation with a 4,5‐Diazafluorenone‐Ligated Palladium Catalyst: A Ligand‐Based Strategy to Achieve Aerobic Catalytic Turnover.
Authors: Campbell Alison N. , White Paul B. , Guzei Ilia A. , Stahl Shannon S.
Published: February 2011

The method affords linear allylic acetoxylation products in high yields under oxygen atmosphere.
ChemInform Abstract: Different Reactivity of Hydroxylamine with Carbamoyl Azides and Carbamoyl Cyanides: Synthesis of Hydroxyureas and Carbamoyl Amidoximes.
Authors: Paz Jairo , Perez‐Balado Carlos , Iglesias Beatriz , Munoz Luis
Published: February 2011

Treatment of carbamoyl azides with hyrdroxylamine allows a new and convenient access to hydroxyureas.
ChemInform Abstract: Thermally Induced Electrocyclic Reaction of Methylenecyclopropane Methylene Diketone Derivatives: A Facile Method for the Synthesis of Spiro[2.5]octa‐3,5‐dienes.
Authors: Tang Xiang‐Ying , Wei Yin , Shi Min
Published: February 2011

The substrates undergo thermal rearrangement to give the target compounds in moderate to good yields.
ChemInform Abstract: Vicinal‐Diamine‐Based Chiral Chain Dienes as Ligands for Rhodium(I)‐Catalyzed Highly Enantioselective Conjugated Additions.
Authors: Wang Yazhou , Hu Xichao , Du Haifeng
Published: February 2011

The novel diene DAH effectively catalyzes the reaction of a variety of cyclic ketones and boronic acids in combination with KOH.
ChemInform Abstract: Conversion of 1,4‐Diketones into para‐Disubstituted Benzenes.
Authors: Ziffle Vincent E. , Cheng Ping , Clive Derrick L. J.
Published: February 2011

A practical and widely applicable method to prepare para‐disubstituted benzenes including sugar‐substituted ones and the macrocyclic analogue (XI) is reported.
ChemInform Abstract: Recyclable Catalysts for Palladium‐Catalyzed C—O Coupling Reactions, Buchwald—Hartwig Aminations, and Sonogashira Reactions.
Authors: Dumrath Andreas , Wu Xiao‐Feng , Neumann Helfried , Spannenberg Anke , Jackstell Ralf , Beller Matthias
Published: February 2011

Novel cationic imidazolium‐based phosphanes are developed as agents which are very stable towards water and air.
ChemInform Abstract: Binary 1,4‐Asymmetric Induction Toward Imines from a Single Allyltin Reagent with a Chiral Oxygen Functional Group.
Authors: Nishigaichi Yutaka , Fujimoto Takahiro , Takuwa Akio , Iwamoto Hidetoshi
Published: February 2011

The stereochemical outcome of the reaction can be controlled by the Lewis acid.
ChemInform Abstract: Titanium‐Mediated Synthesis of 1,4‐Diketones from Grignard Reagents and Acyl Cyanohydrins.
Authors: Setzer Paul , Beauseigneur Alice , Pearson‐Long Morwenna S. M. , Bertus Philippe
Published: February 2011

The cyanohydrin substrates react with titanacyclopropanes, obtained in situ from Grignard reagents and Ti(OiPr)4, to produce 1,4‐diketones.
ChemInform Abstract: Active‐Sodium‐Promoted Reductive Cleavage of Halogenated Benzoic Acids.
Authors: Azzena Ugo , Dettori Giovanna , Mocci Sarah , Pisano Luisa , Cerioni Ciovanni , Mocci Francesca
Published: February 2011

The effect of the increasing reducing power of disodioethanes from (Ia) to (Id) is studied on F‐, Cl‐, Br‐, and I‐benzoic acids.
ChemInform Abstract: Solvent‐Dependent Enantiodivergent Mannich‐Type Reaction: Utilizing a Conformationally Flexible Guanidine/Bisthiourea Organocatalyst.
Authors: Sohtome Yoshihiro , Tanaka Shinji , Takada Keisuke , Yamaguchi Takahisa , Nagasawa Kazuo
Published: February 2011

A simple methodology is presented for the reaction of aromatic N‐Boc imines with dialkyl malonate which allows access to both enantiomers of adduct (III) using a single chiral catalyst in different solvents.
ChemInform Abstract: Ammonia in Ugi—Smiles and Ugi Couplings.
Authors: Barthelon Anaelle , El Kaim Laurent , Gizzi Marion , Grimaud Laurence
Published: February 2011

Novel reaction conditions allow Ugi—Smiles and Ugi couplings to be performed with ammonia as amine component.
ChemInform Abstract: A Mild and Efficient Palladium‐Catalyzed Cyanation of Aryl Mesylates in Water or tBuOH/Water.
Authors: Yeung Pui Yee , So Chau Ming , Lau Chak Po , Kwong Fuk Yee
Published: February 2011

Optimized reaction conditions allow the cyanation of aryl mesylates and tosylates.
ChemInform Abstract: Synthesis of 2‐Arylacrylates from Pyruvate by Tosylhydrazide‐Promoted Pd‐Catalyzed Coupling with Aryl Halides.
Authors: Barluenga Jose , Tomas‐Gamasa Maria , Aznar Fernando , Valdes Carlos
Published: February 2011

The products can be prepared by in situ generation of the tosylhydrazone followed by aryl bromides or directly from tosylhydrazones.
ChemInform Abstract: Decarboxylative Homocoupling of (Hetero)aromatic Carboxylic Acids.
Authors: Cornella Josep , Lahlali Hicham , Larrosa Igor
Published: February 2011

Pd(II)‐catalyzed decarboxylative homocoupling of aromatic carboxylic acids is achieved in the presence of stoichiometric amounts of silver carbonate furnishing biaryls in good to excellent yields.
ChemInform Abstract: Chemoselective Hydrazine Addition to Diethyl 2‐(2,3‐Dioxo‐1,3‐diarylpropyl)malonates and a Tandem Deesterification.
Authors: Saravanan Sivaperuman , Purushothaman Santhanagopalan , Muthusubramanian Shanmugam
Published: February 2011

Only one of the two keto groups of the title compound (I) reacts with hydrazine.
ChemInform Abstract: Carbonates: Eco‐Friendly Solvents for Palladium‐Catalyzed Direct Arylation of Heteroaromatics.
Authors: Dong Jia Jia , Roger Julien , Verrier Cecile , Martin Thibaut , Le Goff Ronan , Hoarau Christophe , Doucet Henri
Published: February 2011

Diethyl carbonate and propylene carbonate are good solvents for Pd‐catalyzed arylation of a variety of heterocyclic compounds, e.g. benzoxazole, oxazoles, thiazoles, furans, thiophenes, and pyrroles.
ChemInform Abstract: A New Synthesis of Spiropyrrolidine—Tetralones via an Unexpected Formal Ring‐Contraction of 4‐Disubstituted Piperidine to 3‐Disubstituted Pyrrolidine.
Authors: Bandarage Upul K. , Davies Robert J.
Published: February 2011

With a view to preparing the biologically interesting target compound (XI), mesylate (II) is treated with NaCN to obtain the corrresponding nitrile.
ChemInform Abstract: Controlled Diastereo‐ and Enantioselection in a Catalytic Asymmetric Aziridination.
Authors: Desai Aman A. , Wulff William D.
Published: February 2011

In connection with previously published results this protocol provides selective access to both trans and cis aziridines, respectively, using the same catalyst.
ChemInform Abstract: Synthesis of 4‐Aryl‐azetidinones via Intramolecular Alkylation of Nucleophilic Arenes Using Acyliminium Cations.
Authors: Zambron Bartosz , Masnyk Marek , Furman Bartlomiej , Kalicki Przemyslaw , Chmielewski Marek
Published: February 2011

Vinyloxy‐ or formyloxyazetidinones bearing N‐(arylthiomethyl) or N‐(aryloxymethyl) substituents (I) and (IX) undergo Lewis acid‐mediated intramolecular arylation of the azetidinone ring to give azetidine‐fused thiazine (II) or oxazine derivatives (X).
ChemInform Abstract: Gold(I)‐Catalyzed Cycloisomerization of 2‐Fluoroalk‐3‐yn‐1‐ones: Synthesis of 2,5‐Substituted 3‐Fluorofurans.
Authors: Li Yan , Wheeler Kraig A. , Dembinski Roman
Published: February 2011

Fluorination of substrates (I) with Selectfluor gives 2‐mono‐fluorobutynones (II) which undergo subsequent 5‐endo‐dig cyclization in the presence of a gold(I)‐catalyst and silver triflate providing 2,5‐diaryl‐substituted 3‐fluorofurans in high yields.
ChemInform Abstract: One‐Pot Synthesis of Chiral α‐Methylene‐γ‐lactams with Excellent Diastereoselectivities and Enantioselectivities.
Authors: Shen An , Liu Min , Jia Zhen‐Shan , Xu Ming‐Hua , Lin Guo‐Qiang
Published: February 2011

The Zn‐promoted aza‐Barbier‐type allylation of sulfinyl imines with allyl bromides affords substituted α‐methylene γ‐lactams.
ChemInform Abstract: Intramolecular Hydroamination of Dithioketene Acetals: An Easy Route to Cyclic Amino Acid Derivatives.
Authors: Xu Hai‐Chao , Moeller Kevin D.
Published: February 2011

The reaction is efficiently achieved in the presence of catalytic BuLi to give proline and pipecolic acid derivatives in good yields.
ChemInform Abstract: One‐Step Continuous Flow Synthesis of Highly Substituted Pyrrole‐3‐carboxylic Acid Derivatives via in situ Hydrolysis of tert‐Butyl Esters.
Authors: Herath Ananda , Cosford Nicholas D. P.
Published: February 2011

The target compounds are synthesized from β‐keto esters, primary amines and phenacyl bromides.
ChemInform Abstract: Fast, Efficient, Mild and Metal‐Free Synthesis of Pyrroles by Domino Reactions in Water.
Authors: Rueping Magnus , Parra Alejandro
Published: February 2011

Reaction of both regioisomers (I) and (IV) of N‐substituted enaminones with β‐bromostyrenes offers novel approaches to trisubstituted pyrroles.
ChemInform Abstract: Iron(III)‐Catalyzed Consecutive Aza‐Cope—Mannich Cyclization: Synthesis of trans‐3,5‐Dialkyl Pyrrolidines and 3,5‐Dialkyl‐2,5‐dihydro‐1H‐pyrroles.
Authors: Carballo Ruben M. , Purino Martin , Ramirez Miguel A. , Martin Victor S. , Padron Juan I.
Published: February 2011

The cyclization of substrates (I) with aldehydes is promoted by Fe(III)‐salts to yield pyrrolidines (III) after reductive work‐up.
ChemInform Abstract: meso‐Alkylidene (m‐Benzi)pentaphyrin: A Modified Pentaphyrin Bearing Exocyclic Double Bonds at meso‐Positions.
Authors: Jeong Seung‐Doo , Nowak‐Krol Agnieszka , Kim Youngmee , Kim Sung‐Jin , Gryko Daniel T. , Lee Chang‐Hee
Published: February 2011

The title pentaphyrin (IV), synthesized and characterized for the first time, displays concentration‐dependent chromogenic responses for fluoride anion in organic solvents.
ChemInform Abstract: Synthesis and Antimicrobial Activity of 5‐Substituted‐2‐phenyl‐3‐(o‐carboethoxyphenyl)iminomethyl Indoles and Their Derivatives.
Authors: Mruthyunjayaswamy B. H. M. , Shanthaveerappa B. K. , Basavarajaiah S. M.
Published: February 2011

The compounds (I) are synthesized via a condensation reaction.
ChemInform Abstract: A New Synthesis of Phthalimidines.
Authors: Ukhin L. Yu. , Suponitsky K. Yu. , Belousova L. V. , Orlova Zh. I.
Published: February 2011

Two novel routes for the synthesis of 3‐acyloxyphthalimidines [cf.
ChemInform Abstract: Enantioselective Intramolecular Aza‐Michael Additions of Indoles Catalyzed by Chiral Phosphoric Acids.
Authors: Cai Quan , Zheng Chao , You Shu‐Li
Published: February 2011

The asymmetric N‐alkylation of indoles proceeds in the absence of electron‐withdrawing groups under acidic conditions.
ChemInform Abstract: Rapid and Convenient Thermal or Microwave‐Assisted Synthesis of Substituted 2‐Phenylbenzothiazoles.
Authors: Weekes Ashley A. , Dix Matthew C. , Bagley Mark C. , Westwell Andrew D.
Published: February 2011

The microwave assisted procedure needs the same for derivatives (IIa)—(IIc) or smaller reaction times for derivatives (IId)—(IIg).
ChemInform Abstract: Efficient Synthesis of Deuterated 1,2,3‐Triazoles.
Authors: Gonda Zsombor , Loerincz Kristian , Novak Zoltan
Published: February 2011

Various triazole derivatives can be easily prepared by 1,3‐dipolar cycloaddition of aliphatic and aromatic azides with acetylene, generated in situ from CaC2 and water.
ChemInform Abstract: Convenient Route to Water‐Sensitive Sol—Gel Precursors Using Click Chemistry.
Authors: Moitra Nirmalya , Moreau Joel J. E. , Cattoen Xavier , Wong Chi Man Michel
Published: February 2011

An efficient method for the synthesis of triazoles (III), (V), and (VII) by copper‐catalyzed alkyne‐azide cycloaddition under microwave irradiation is reported.
ChemInform Abstract: New HA 14‐1 Analogues: Synthesis of 2‐Amino‐4‐cyano‐4H‐chromenes.
Authors: Moafi Leila , Ahadi Somayeh , Bazgir Ayoob
Published: February 2011

A one‐pot three‐component reaction renders possible the synthesis of title compounds (IV) via iminochromene formation and subsequent cyanation.
ChemInform Abstract: Cyclic Hydroxamic Acids Derived from α‐Amino Acids. Part 1. Regioselective Synthesis, Structure, NO‐Donor and Antimetastatic Activities of Spirobicyclic Hydroxamic Acids Derived from Glycine and DL‐Alanine.
Authors: Vystorop I. V. , Konovalova N. P. , Nelyubina Yu. V. , Varfolomeev V. N. , Fedorov B. S. , Sashenkova T. E. , Berseneva E. N. , Lyssenko K. A. , Kostyanovsky R. G.
Published: February 2011

Both spiro hydroxamic acids (III) are found to be NO donors in in vitro biological systems.
ChemInform Abstract: Synthesis of 1,2‐Annulated and 1,2‐Unsubstituted Pyrrolo[2,1,5‐de]quinolizin‐5‐ones (Cycl[3.3.2]azin‐5‐ones) via [3 + 2] Cycloadditions of 1‐Oxoquinolizinium Ylides with Cyclic Alkenes.
Authors: Liu Yun , Hu Hua‐You , Zhang Yan , Hu Hong‐Wen , Xu Jian‐Hua
Published: February 2011

One‐pot tandem reactions under conditions A) afford the title systems (III), (V) and (VII), respectively.
ChemInform Abstract: Synthesis of 2‐Pyridones and Iminoesters via Rh(III)‐Catalyzed Oxidative Coupling Between Acrylamides and Alkynes.
Authors: Su Yan , Zhao Miao , Han Keli , Song Guoyong , Li Xingwei
Published: February 2011

In most cases the reaction leads to 2‐pyridones as the oxidative coupling product.
ChemInform Abstract: A Tandem Amination/Lactamization Route to 2‐Azabicyclo[2.2.2]octanones.
Authors: Cuthbertson James D. , Godfrey Andrew A. , Taylor Richard J. K.
Published: February 2011

The reaction can be extended to the synthesis of N‐substituted derivatives.
ChemInform Abstract: New Pyridazinone Derivatives with Vasorelaxant and Platelet Antiaggregatory Activities.
Authors: Costas Tamara , Besada Pedro , Piras Alessandro , Acevedo Laura , Yanez Matilde , Orallo Francisco , Laguna Reyes , Teran Carmen
Published: February 2011

Novel pyridazinones (III), (VI), (VIIb), (IXa), and (XIb) demonstrate moderate vasorelaxant activity and moderate to potent inhibition of collagen‐induced platelet aggregation.
ChemInform Abstract: Copper‐Catalyzed Aerobic Oxidative Coupling of Aminocarbazoles and Aminoindoles: Synthesis of Diindolophenazines and Dipyrrolophenazines.
Authors: Meesala Ramu , Nagarajan Rajagopal
Published: February 2011

Simple reaction conditions are developed for the title process.
ChemInform Abstract: Synthesis and Characterization of s‐Triazine Based 1,5‐Benzothiazepines and Isoxazoles.
Authors: Solankee Anjani
Published: February 2011

The compounds (III) and (IV) are evaluated for their in vitro antibacterial activity against S.
ChemInform Abstract: A Simple and General Platform for Generating Stereochemically Complex Polyene Frameworks by Iterative Cross‐Coupling.
Authors: Lee Suk Joong , Anderson Thomas M. , Burke Martin D.
Published: February 2011

Boronates such as (IX) are employed to construct complex polyene frameworks, e.g. present in vacidin A.
ChemInform Abstract: Nickel‐Catalyzed Hydrosilylation/Cyclization of Difluoro‐Substituted 1,6‐Enynes.
Authors: Takachi Manabu , Chatani Naoto
Published: February 2011

Optimized conditions A) are developed for the title process where silane (II) is found to be the most efficient silylation agent.
ChemInform Abstract: Efficient Approach to 3,3‐Bissilyl Carbonyl and Enol Derivatives via Retro‐[1,4] Brook Rearrangement of 3‐Silyl Allyloxysilanes.
Authors: Song Zhenlei , Lei Zheng , Gao Lu , Wu Xia , Li Linjie
Published: February 2011

The reaction provides a practical route to the title compounds.The synthetic utility of product (VIa) is demonstrated by a Sakurai reaction to give the anti‐diol (VIII).
ChemInform Abstract: A New Synthesis of Triphenylhosphorane Ylide Precursors to α‐Keto Amide/Ester and Tricarbonyl Units via Horner—Wadsworth—Emmons Reaction.
Authors: Lee Kieseung
Published: February 2011

Newly developed Horner—Wadsworth—Emmons reagents (III) readily condense with various carbonyl compounds to afford the corresponding β,γ‐unsaturated α‐keto triphenylphosphoran ylides of type (V) or (VIII) which can easily be reduced to the corresponding β,γ‐saturated α‐keto triphenylphosphoran ylides of type (VI) or (IX).
ChemInform Abstract: Synthesis and Spectral Characterization of 2‐(Substituted) ‐1,3,2λ5‐oxazaphosphinan‐2‐ones/‐2‐thiones.
Authors: Venkateswarlu C. , Satyanarayana P. V. V. , Rao C. V. Nageswara , Raju C. Naga
Published: February 2011

With a view to using organophosphorus compounds as antimetabolites in cancer chemotherapy the title compounds (III) and (V) are prepared.
ChemInform Abstract: Three‐Component Condensation of Trifluoromethyl‐Substituted Cyanovinylphosphonates, Arylamines, and Ketones and Cytotoxic Activity of Products Thus Obtained.
Authors: Shidlovskii A. F. , Peregudov A. S. , Averkiev B. B. , Bulychev Yu. N. , Antipin M. Yu. , Chkanikov N. D.
Published: February 2011

A variety of phosphorylpyridine and related fused pyridine derivatives are synthesized via multicomponent reactions.
ChemInform Abstract: A Convenient Synthesis of 1,3,4‐Thiadiazole and 1,3,4‐Oxadiazole Based Peptidomimetics Employing Diacylhydrazines Derived from Amino Acids.
Authors: Nagendra G. , Lamani Ravi S. , Narendra N. , Sureshbabu Vommina V.
Published: February 2011

The products are obtained in good to excellent yields with high purity and without detectable racemization.
ChemInform Abstract: A New Monoterpenoid Glycoside from Myrica esculenta and the Inhibition of Angiotensin I‐Converting Enzyme.
Authors: Kim Young Ho , et al. et al.
Published: February 2011

The new monoterpenoid glycoside myresculoside (I) is isolated along with eleven known compounds from the methanol extract of Myrica esculenta leaves by repeated column chromatography.
ChemInform Abstract: A Novel Versatile Strategy for Synthesis of New Series of 4(3H)‐Quinazolinone N‐Nucleosides.
Authors: Siddiqui I. R. , Singh Pravin K. , Srivastava Vishal , Yadav Sanjay , Singh J.
Published: February 2011

An environmentally benign one‐step process is presented.
ChemInform Abstract: Inorganic Nanoparticles for Catalysis
Authors: Toshima Naoki
Published: February 2011

Review: 88 refs.
ChemInform Abstract: Quasicrystals Dealing with Catalysis
Authors: Tsai A. P. , Kameoka S.
Published: February 2011

Review: 33 refs.
ChemInform Abstract: Computational Studies of Reactivity in Transition Metal Chemistry
Authors: Harvey Jeremy N.
Published: February 2011

Review: 54 refs.
ChemInform Abstract: Studies on the Kinetics and Mechanism of Thermal Decomposition of ZnAl‐hydrotalcite‐like Compounds
Authors: Xie Xianmei , Hu Qiuxia , Shi Xinzhen , Wu Zhenghuang
Published: February 2011

Review: 10 refs.
ChemInform Abstract: Graphene — How a Laboratory Curiosity Suddenly Became Extremely Interesting.
Authors: Boehm Hanns‐Peter
Published: February 2011

Review: 50 refs.
ChemInform Abstract: Ionic Liquids in the Organometallic Field
Authors: Torrecilla Jose S.
Published: February 2011

Review: 50 refs.
ChemInform Abstract: Copper‐Promoted C—N‐ and C—O‐type Cross‐Coupling Reactions
Authors: Das Pralay , Sharma Dharminder , Kumar Manish , Singh Bikram
Published: February 2011

Review: 142 refs.
ChemInform Abstract: Catalytic Applications of Heterogeneous Systems Based on Cyclodextrins
Authors: Senra J. D. , Malta L. F. B. , Aguiar L. C. S. , Simas A. B. C. , Antunes O. A. C.
Published: February 2011

Review: 133 refs.
ChemInform Abstract: Molecular Imprinting Technique for the Design of Cyclodextrin‐Based Materials and Their Application in Catalysis
Authors: Karakhanov E. A. , Maximov A. L.
Published: February 2011

Review: 67 refs.
ChemInform Abstract: Highly Enantioselective Cu(I)—Tol‐BINAP‐Catalyzed Asymmetric Conjugate Addition of Grignard Reagents to α,β‐Unsaturated Esters
Authors: Wang Shun‐Yi , Loh Teck‐Peng
Published: February 2011

Review: 29 refs.
ChemInform Abstract: 2‐Azetidinone — A New Profile of Various Pharmacological Activities.
Authors: Mehta Parul D. , Sengar N. P. S. , Pathak A. K.
Published: February 2011

Review: < <[103 refs.].
ChemInform Abstract: Synthesis of Dihydropyrimidinones and Thiones by Multicomponent Reactions: Strategies Beyond the Classical Biginelli Reaction
Authors: Wan Jie‐Ping , Liu Yunyun
Published: February 2011

Review: about 70 refs.
ChemInform Abstract: Diels—Alder Cycloaddition in Protein Chemistry
Authors: Palomo Jose M.
Published: February 2011

Review: 116 refs.
ChemInform Abstract: Coupling Effects in Optical Metamaterials
Authors: Liu Na , Giessen Harald
Published: February 2011

Review: 92 refs.
ChemInform Abstract: Pharmacologically Active Metabolites of Currently Marketed Drugs: Potential Resources for New Drug Discovery and Development
Authors: Kang Myug Joo , Song Woo Heon , Shim Byung Ho , Oh Seung Youn , Lee Hyun Young , Chung Eun Young , Sohn Yesung , Lee Jaehwi
Published: February 2011

Review: 148 refs.
ChemInform Abstract: C—C Coupling Reactions in Biomass Exploitation Processes
Authors: Iliopoulou Eleni F.
Published: February 2011

Review: 61 refs.
ChemInform Abstract: Towards Greener and More Efficient C—C and C—Heteroatom Couplings: Present and Future
Authors: Vargas Carolina , Balu Alina Mariana , Campelo Juan Manuel , Gonzalez‐Arellano Camino , Luque Rafael , Romero Antonio Angel
Published: February 2011

Review: 104 refs.
ChemInform Abstract: The Allylic Chalcogen Effect in Olefin Metathesis
Authors: Lin Yuya A. , Davis Benjamin G.
Published: February 2011

Review: 45 refs.
ChemInform Abstract: Electron Tomography: From 3D Statics to 4D Dynamics.
Authors: Su Dang Sheng
Published: February 2011

Review: 26 refs.
ChemInform Abstract: The Insatiable Quest for Near‐Infrared Fluorescent Probes for Molecular Imaging.
Authors: Achilefu Samuel
Published: February 2011

Review: 9 refs.
ChemInform Abstract: Generation and Control of Chirality by Crystallization: Asymmetric Synthesis Using the Crystal Chirality in Fluid Media
Authors: Sakamoto Masami , Mino Takashi , Fujita Tsutomu
Published: February 2011

Review: about 30 refs.
Flow regimes and vertical solids conveying in a spout‐fluid bed with a draft tube
Authors: Nagashima Hiroshi , Ishikura Toshifumi , Ide Mitsuharu
Published: February 2011

Pressure fluctuation data were obtained in a semi‐cylindrical spout‐fluid bed with draft tube, and statistical analyses of them were employed to recognise flow regimes. Also, the effects of spouting‐gas and auxiliary‐gas velocities, and length of entrainment zone on solids loading ratio in a draft tube were examined. As a result, five flow regimes appeared by changing spouting‐gas and auxiliary‐gas velocities and it was found that the simplest method to determine flow regime is to measure pressure fluctuations in a draft tube. Moreover, solids loading ratio could be controlled flexibly by auxiliary‐gas velocity and length of entrainment zone.
High White Blood Cell Count and Low Estimated Glomerular Filtration Rate Are Independently Associated With Serum Level of Monocyte Chemoattractant Protein‐1 in a General Population
Authors: Fukami Ako , Yamagishi Sho‐ichi , Adachi Hisashi , Matsui Takanori , Yoshikawa Kuniko , Ogata Kinuka , Kasahara Akiko , Tsukagawa Eri , Yokoi Kanako , Imaizumi Tsutomu
Published: February 2011

Background

Monocyte chemoattractant protein‐1 (MCP‐1) plays a role in cardiovascular disease (CVD) and renal injury. Recent clinical studies have suggested that circulating levels of MCP‐1 could be a biomarker of atherosclerosis and future cardiovascular events in humans. Because chronic kidney disease (CKD) is one of the risk factors of CVD, it is conceivable that elevated MCP‐1 levels may link the increased risk of CVD in CKD patients. However, as far as we know, in addition to well‐known traditional risk factors for atherosclerosis, whether renal dysfunction could be independently associated with the elevation of MCP‐1 levels in a general population remains unknown. Therefore, we examined here which anthropometric and metabolic variables, including renal function, could be independent correlates of circulating levels of MCP‐1 in a general population.

Hypothesis

We hypothesized that renal function was one of the independent correlates of serum MCP‐1 levels.

Methods

A total of 860 Japanese residents (318 males and 542 females, mean age 65.4 ± 9.8 years) in a small fishing community underwent a complete history and physical examination with determination of blood chemistries, including serum levels of MCP‐1.

Results

Mean MCP‐1 levels were 281.4 pg/mL. Multiple stepwise regression analyses revealed that male sex (P < 0.0001), age (P = 0.03), estimated glomerular filtration rate (eGFR) (P < 0.0001, inversely), and white blood cell count (P = 0.037) were independently associated with MCP‐1 levels.

Conclusions

The present study demonstrated for the first time that other than white blood cell count, eGFR was an independent correlate of serum levels of MCP‐1 in a Japanese general population. Elevated MCP‐1 levels may partly explain the increased risk of CVD in CKD patients. © 2011 Wiley Periodicals, Inc.

The authors have no funding, financial relationships, or conflicts of interest to disclose.
Bicyclic Substituted Hydroxyphenylmethanone Type Inhibitors of 17 β‐Hydroxysteroid Dehydrogenase Type 1 (17 β‐HSD1): The Role of the Bicyclic Moiety
Authors: Oster Alexander , Klein Tobias , Henn Claudia , Werth Ruth , Marchais‐Oberwinkler Sandrine , Frotscher Martin , Hartmann Rolf W.
Published: February 2011

An attractive target that has still to be explored for the treatment of estrogen‐dependent diseases, such as breast cancer and endometriosis, is the enzyme responsible for the last step in the biosynthesis of estradiol (E2): 17β‐hydroxysteroid dehydrogenase type 1 (17β‐HSD1). It catalyzes the reduction of the weakly active estrone (E1) into E2, which is the most potent estrogen in humans. Inhibition of 17β‐HSD1 lowers intracellular E2 concentrations and thus presents a therapeutic target for estrogen‐dependent pathologies. Recently, we reported a new class of highly active and selective 17β‐HSD1 inhibitors: bicyclic substituted hydroxyphenylmethanones. Here, further structural variations on the bicyclic moiety are described, especially focusing on the exchange of its hydroxy function. Twenty‐nine novel inhibitors were synthesized and evaluated for 17β‐HSD1 inhibition in a cell‐free and cellular assay, for selectivity toward 17βHSD2 and estrogen receptors (ER) alpha and beta, as well as for metabolic stability. The best compound exhibited IC50 values of 12 nM (cell‐free assay) and 78 nM (cellular assay), high selectivity for 17β‐HSD1, and reasonable metabolic stability. A molecular docking study provided insight into the protein–ligand interactions of this compound with 17β‐HSD1.
Cellular Selectivity and Biological Impact of Cytotoxic Rhodium(III) and Iridium(III) Complexes Containing Methyl‐Substituted Phenanthroline Ligands
Authors: Geldmacher Yvonne , Kitanovic Igor , Alborzinia Hamed , Bergerhoff Katharina , Rubbiani Riccardo , Wefelmeier Pascal , Prokop Aram , Gust Ronald , Ott Ingo , Wölfl Stefan , Sheldrick William S.
Published: February 2011

The antiproliferative properties and biological impact of octahedral iridium(III) complexes of the type fac‐[IrCl3(DMSO)(pp)] containing pp=phenanthroline (1) and its 4‐ and 5‐methyl (2, 3) and 4,7‐ and 5,6‐dimethyl derivatives (4, 5) were investigated for both adherent and non‐adherent cells. A series of similar rhodium(III) complexes were studied for comparison purposes. The antiproliferative activity toward MCF‐7 cancer cells increases eightfold from IC50=4.6 for 1 to IC50=0.60 μM for 5, and an even more pronounced 18‐fold improvement was established for the analogous rhodium complexes 6 and 8, the respective IC50 values for which are 1.1 and 0.06 μM. Annexin V/propidium iodide assays demonstrated that the 5,6‐dimethylphenanthroline complexes 5 and 8 both cause significant inhibition of Jurkat leukemia cell proliferation and invoke extensive apoptosis but negligible necrosis. The percentages of Jurkat cells exhibiting high levels of reactive oxygen species correlate with the percentages of cells undergoing apoptosis. The antiproliferative activity of 5 and 8 is strongly selective toward MCF‐7 and HT‐29 cancer cells over normal HFF‐1 and immortalized HEK‐293 cells. Complex 5 also exhibits high selectivity toward BJAB lymphoma cells relative to healthy leukocytes. Both 5 and 8 invoke permanent decreases in the adhesion and respiration of MCF‐7 cells.