1-adamantyl Methyl Ketone Research Articles

A sensitive lateral flow immunoassay for the multiple residues of five adamantanes

ABSTRACTAdamantanes (ADAs) are tricyclic decane saturated derivatives, which are used in the protection against the influenza virus. However, their abuse in animal husbandry has affected human health. To help prevent drug resistance and protect food safety, a rapid, portable, sensitive, and reliable method for onsite detection of ADAs was developed. Herein, we have produced a broad-specificity anti-ADAs monoclonal antibody (mAb), the subclass of which is IgG2b, and its affinity constant is 7.25 × 109 L/mol. From this, an antibody-based lateral flow immunoassay (LFIA) was developed for the rapid detection of five ADAs in food samples. When viewed with the naked eye, the LFIA had a visual detection limit of 0.1, 0.1, 1, 5, and 10 μg/kg and a cut-off value of 2.5, 2.5, 10, 100, and 100 μg/kg for somantadine, rimantadine, amantadine, 1-adamantanemethanol, 1-adamantyl methyl ketone respectively in chicken samples. The test results for the LFIA were very similar to that seen when using an enzyme linked immunosorbent assay (ELISA). Therefore, this paper-based LFIA provides a useful tool for rapid, onsite detection of ADAs in biological samples.

Alcohol/water-soluble porphyrins as cathode interlayers in high-performance polymer solar cells

Three alcohol/water-soluble porphyrins, Zn-TPyPMeI: zinc(II) meso -tetra( N -methyl-4-pyridyl) porphyrin tetra-iodide, Zn- TPyPAdBr: zinc(II) meso -tetra[1-(1-adamantylmethyl ketone)-4-pyridyl] porphyrin tetra-bromide and MnCl-TPyPAdBr: man- ganese(III) meso -tetra[1-(1-adamantylmethyl ketone)-4-pyridyl] porphyrin tetra-bromide were employed as cathode interlayers to fabricate polymer solar cells (PSCs). The PC71BM ([6,6]-phenyl C71 butyric acid methyl ester) and PCDTBT (poly[ N -9"- hepta-decanyl-2,7-carbazole- alt -5,5-(4,7-di-2-thienyl-2,1,3-benzothiadiazole)])-blend films were used as active layers in polymer solar cells (PSCs). The PSCs with alcohol/water-soluble porphyrins interlayer showed obviously higher power conversion efficiency (PCE) than those without interlayers. The highest PCE, 6.86%, was achieved for the device with MnCl- TPyPAdBr as an interlayer. Ultraviolet photoemission spectroscopic (UPS), carrier mobility, atomic force microscopy (AFM) and contact angle ( θ ) characterizations demonstrated that the porphyrin molecules can result in the formation of interfacial dipole layer between active layer and cathode. The interfacial dipole layer can obviously improve the open-circuit voltage ( V oc) and charge extraction, and sequentially lead to the increase of PCE.

A supramolecular bifunctional artificial enzyme with superoxide dismutase and glutathione peroxidase activities

For constructing a bifunctional antioxidative enzyme with both superoxide dismutase (SOD) and glutathione peroxidase (GPx) activities, a supramolecular artificial enzyme was successfully constructed by the self-assembly of the Mn(III)meso-tetra[1-(1-adamantyl methyl ketone)-4-pyridyl] porphyrin (MnTPyP-M-Ad) and cyclodextrin-based telluronic acid (2-CD-TeO 3H) through host–guest interaction in aqueous solution. The self-assembly of the adamantyl moieties of Mn(III) porphyrin and the β-CD cavities of 2-CD-TeO 3H was demonstrated by the NMR spectra. In this supramolecular enzyme model, the Mn(III) porphyrin center acted as an efficient active site of SOD and tellurol moiety endowed GPx activity. The SOD-like activity (IC 50) of the new catalyst was found to be 0.116 μM and equals to 2.56% of the activity of the native SOD. Besides this, supramolecular enzyme model also showed a high GPx activity, and a remarkable rate enhancement of 27-fold compared to the well-known GPx mimic ebselen was observed. More importantly, the supramolecular artificial enzyme showed good thermal stability.

A modulatory bifunctional artificial enzyme with both SOD and GPx activities based on a smart star-shaped pseudo-block copolymer

An artificial smart bifunctional enzyme with both superoxide dismutase (SOD) and glutathione peroxidase (GPx) activities was successfully constructed by the self-assembly of a porphyrin core with four suspensory adamantyl moieties and β-cyclodextrin-terminated temperature-sensitive copolymer through host–guest interaction in aqueous solution. The Mn(III) porphyrin, Mn(III)meso-tetra[1-(1-adamantyl methyl ketone)-4-pyridyl] porphyrin (MnTPyP-M-Ad), was designed as both a “supramolecular linker” and an efficient active site of SOD and the temperature-responsive block copolymer (β-CD-PEG-b-PNIPAAm-Te) with incorporated tellurium moieties in the PNIPAAm chain as GPx active sites was synthesized by ATRP. As a new type of artificial bifunctional enzymes, it exhibited stable SOD-like activity of 0.137 μM (IC50) at 37 °C, and high GPx catalytic efficiency with temperature-responsive dependence characteristic, and the new artificial enzyme was found to exhibit the highest GPx catalytic efficiency (v0 = 8.11 μM min−1) in close to physical temperature.

One‐Pot Synthesis of 3‐Substituted Isoquinolin‐1‐(2H)‐ones and Fused Isoquinolin‐1‐(2H)‐ones by SRN1 Reactions in DMSO.

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Stereoselective ketone reduction by a carbonyl reductase from Sporobolomyces salmonicolor. Substrate specificity, enantioselectivity and enzyme-substrate docking studies

In our effort to search for effective carbonyl reductases, the activity and enantioselectivity of a carbonyl reductase from Sporobolomyces salmonicolor have been evaluated toward the reduction of a variety of ketones. This carbonyl reductase (SSCR) reduces a broad spectrum of ketones including aliphatic and aromatic ketones, as well as alpha- and beta-ketoesters. Among these substrates, SSCR shows highest activity for the reduction of alpha-ketoesters. Aromatic alpha-ketoesters are reduced to (S)-alpha-hydroxy esters, while (R)-enantiomers are obtained from the reduction of aliphatic counterparts. This interesting observation is consistent with enzyme-substrate docking studies, which show that hydride transfer occurs at the different faces of carbonyl group for aromatic and aliphatic alpha-ketoesters. It is worthy to note that sterically bulky ketone substrates, such as 2'-methoxyacetophenone, 1-adamantyl methyl ketone, ethyl 4,4-dimethyl-3-oxopentanoate and ethyl 3,3-dimethyl-2-oxobutanoate, are reduced to the corresponding alcohols with excellent optical purity. Thus, SSCR possesses an unusually broad substrate specificity and is especially useful for the reduction of ketones with sterically bulky substituents.

Iffland's Reaction with Methyl Ketone Oximes of Adamantane Series

Along Iffland's reactions from 1-adamantyl methyl ketone, (1-adamantyl)acetone, 3-hydroxy-1-adamantyl methyl ketone and N-bromosuccinimide were obtained the corresponding bromonitro derivatives that on reduction with sodium borohydride afforded 1-(1-adamantyl)-1-nitroethane, 1-(1-adamantyl)-2-nitropropane, and 1-(3-hydroxy-1-adamantyl)-1-nitroethane.

Synthesis and structural studies of symmetric and unsymmetric adamantylmethyleneazines

The synthesis and spectroscopic properties (1H, 13C and 15N NMR, in solution and in the solid state) of six new 1-adamantylmethylene azines are reported. The crystal and molecular structures of 1-adamantylcarbaldehyde azine and 1-adamantyl methyl ketone azine, which exist in the solid state in the E,E-configuration, were determined by x-ray analysis. The geometric characteristics of the azine central bridge and the preferred configuration with regard to it (E,E, E,Z or Z,Z) were investigated by means of the crystallographic data retrieved from the Cambridge Structural Database and ab initio quantum chemical calculations. Copyright © 1999 John Wiley & Sons, Ltd.

Titanium(IV) mediated reductive aminations of 1-adamantyl methyl ketone: facile preparation of potential antiviral agents rimantadine and its analogues

A preparatively efficient, mild method for the synthesis of rimantadine and its analogues via novel reductive aminations of 1-adamantyl methyl ketone using titanium(IV) isopropoxide and sodium borohydride is reported.

Structural effects on the thermochemical properties of carbonyl compounds II. enthalpies of combustion, vapour pressures and enthalpies of sublimation, and standard enthalpies of formation in the gaseous phase, of 1-adamantyl methyl ketone and of 1,1′-diadamantyl ketone

The energies of combustion of 1-adamantyl methyl ketone, and 1,1'-diadamantyl ketone have been determined using a static bomb calorimeter. The vapour pressures have been measured over a temperature range of about 17K by the Knudsen-effusion technique. From the experimental results the following quantities for the two compounds, at T = 298.15K, have been derived:

Adamantyl-containing heterocycles Communication 1. 3-(1-adamantyl)-3-chloropropenal in the synthesis of 2-(1-adamantyl)thiophene and 5-(1-adamantyl)isoxazole

1. By the action of POCl3 and DMF on (1-adamantyl)methylketone, we obtain the trans Z isomer of 3-(l-adamantyl)-3-chloropropenal, which is a convenient synthon for synthesis of heteryl adamantanes. 2. By the reaction of 3-(1-adamantyl)-3-chloropropenal with thioglycolic acid, we obtain 2-(1-adamantyl)-thiophene and the corresponding 5-carboxylic acid; with hydroxyl amine we obtain 5-(1-adamantyl)isoxazole.

The reaction of carbonium ions in sulphuric acid with acetylene and substituted acetylenes

Treatment of adamantan-1-ol in sulphuric acid with acetylene leads to 1-adamantylacetaldehyde or 1-adamantyl methyl ketone as major product (together with 1-methylhomoadamantan-2-one), depending on the experimental conditions (acid concentration and reaction time). The reactions of the adamantyl, diphenylmethyl, and norbornyl cations with acetylene and substituted acetylenes have been examined.