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PubMed2003

The first conjugate addition reaction of terminal alkynes catalytic in copper: conjugate addition of alkynes in water.

We document that alkynyl copper reagents generated under aqueous conditions from terminal acetylenes, catalytic Cu(OAc)2, and sodium ascorbate undergo additions to Meldrum's acid-derived Michael acceptors at room temperature (Scheme 1). The additions are not only novel, but also constitute the first example of the conjugate addition reaction of an acetylide catalytic in copper.

Journal Article↗
PubMed2002

Lewis acid-promoted Kharasch-Curran additions: a competition kinetics study of bromine atom transfer addition of N-alpha-bromoacetyl-oxazolidinone to 1-hexene.

Lewis acids can efficiently promote free radical atom transfer reactions of an oxazolidinone imide substrate, 1, derived from alpha-bromo acetic acid. Thus, 1 undergoes a radical chain addition to 1-hexene giving the atom transfer addition compound, 6, in the presence of scandium or ytterbium triflate in 1,2-dichloroethane or a cosolvent mixture of 1/9 THF/dichloromethane. In 1,2-dichloroethane the solution is heterogeneous, while the cosolvent mixture gives a homogeneous solution, even at temperatures of -78 degrees C. Competition experiments were carried out in both solvent systems with added carbon tetrachloride to study how Lewis acid affected the product distribution. In the presence of carbon tetrachloride, chloride 7 is formed in addition to 6 and the ratio of these two products depends on the amount of Lewis acid present. In the presence of ytterbium triflate, in the cosolvent system, the reaction rate of bromine atom transfer was enhanced up to 400-fold compared to the reaction without added Lewis acid. Significant rate enhancements were also obtained in the solvent 1,2-dichloroethane, although the analysis of the system is complicated by the heterogeneous nature of the medium. Computation of C-Br bond dissociation energies (BDE) of the complexed and uncomplexed oxazolidinone bromide suggest that complexation lowers the BDE due to the effect of the strong electron-withdrawing group on the C-Br bond dipole.

Alkenes↗
PubMed2004

A silicon tether approach for addition of functionalized radicals to chiral alpha-hydroxyhydrazones: diastereoselective additions of hydroxymethyl and vinyl synthons.

Stereocontrolled additions of hydroxymethyl and vinyl groups to chiral alpha-hydroxyhydrazones can be achieved by radical cyclizations using bromomethyl or vinyl radical precursors tethered via a temporary silicon connection. Tin-mediated 5-exo radical cyclization of alpha-hydroxyhydrazones using a silicon-tethered bromomethyl group, followed by oxidative removal of the tether, provides anti-2-hydrazino 1,3-diols in good yield. Tandem thiyl radical addition-cyclization of alpha-hydroxyhydrazones using a silicon-tethered vinyl group, followed by treatment with potassium fluoride, affords acyclic allylic anti-hydrazino alcohols in good yield. The thiyl addition-cyclization method has been successfully extended to the use of alpha,beta-dihydroxyhydrazones without prior protection or hydroxyl differentiation. Diastereoselection in both reaction types increases with increasing A values of the appended groups, consistent with prediction by the Beckwith-Houk model for stereocontrol in 5-hexenyl radical cyclizations.

Journal Article↗
PubMed2005

Theoretical analysis of fluorine addition to single-walled carbon nanotubes: functionalization routes and addition patterns.

We present a theoretical investigation on the chemical addition patterns governing the fluorination of single wall carbon nanotubes. Monte Carlo calculations based on a Hückel model suggest that fluorination is stabilized in a bandlike pattern due to electronic confinement effects on the tube bond network topology. Ab initio analysis of the fluorination of small nanotubes show that fluorine addition along the nanotube axis direction is favored by a mechanism of carbon framework distortion. The experimentally observed formation of fluorine bands may be thus explained in terms of multiple axial C(2)F rows expanding by contiguous axial addition.

Journal Article↗
PubMed2006

Radical addition to 1,4-benzoquinones: addition at O- versus C-atom.

Addition of alkyl radicals generated from B-alkylcatecholboranes onto 1,4-benzoquinones leads to substituted hydroquinones in good overall yields. Formation of aryl ethers via a unique radical addition to the oxygen atom of the enone system is the main reaction when bulky secondary and tertiary alkyl radicals are used. Less hindered secondary and primary radicals give the expected 1,4-conjugate addition products. [reaction: see text]

Journal Article↗
PubMed2006

Self-administered heroin and cocaine combinations in the rat: additive reinforcing effects-supra-additive effects on nucleus accumbens extracellular dopamine.

The concurrent use of cocaine and opiate combinations (speedball) has increased since the 1970s and now represents a growing subset of intravenous drug abusers. An isobolographic analysis was applied to the ascending limb of the dose-effect curves for rat self-administration of cocaine, heroin, and their combination to determine the nature of the interaction. The addition of heroin to cocaine shifted the dose-effect curve for self-administration to the left, and the modulation in reinforcing efficacy of the combination of cocaine and heroin was found to be additive. A second experiment used microdialysis to determine the effects of this drug combination on nucleus accumbens (NAc) extracellular levels of dopamine ([DA](e)) in rats self-administering low doses of cocaine, heroin, or cocaine/heroin combinations. These doses of cocaine and cocaine/heroin combinations significantly increased NAc [DA](e), while heroin alone did not. The ratio of the % baseline of [DA](e) (or the dialysate concentrations of DA) to cocaine in the dialysate was higher during self-administration of cocaine/heroin combinations than with cocaine alone. These data indicate that although the interaction between cocaine and heroin in maintaining self-administration is additive, a potentiation of NAc dopaminergic neurotransmission is present, suggesting that NAc [DA](e) may not be a direct measure of reinforcing efficacy and/or it is not central to the mediation of the self-administration of this drug combination.

Animals↗
PubMed1981

Additive and non-additive effects of mixtures of short-acting intravenous anaesthetic agents and their significance for theories of anaesthesia.

1 The potency of a series of short-acting anaesthetics was established by measuring the duration of the loss of righting reflex following a single bolus injection into the tail vein of male Wistar rats. The agents were, in order of potency, etomidate, alphaxalone, methohexitone, alphadalone acetate and propanidid.2 The potency of binary mixtures of these agents was also assessed to see whether the anaesthetic effects of different agents were additive as classical theories of anaesthesia suggest. Mixtures of alphaxalone and alphadalone acetate, alphaxalone and propanidid and methohexitone and propanidid all showed simple additive effects. Mixtures of alphaxalone and etomidate and of alphaxalone and methohexitone showed a greater potency than would be expected if their effects were simply additive. Mixtures of etomidate and methohexitone were not examined.3 Mixtures of alphaxalone and either methohexitone or pentobarbitone produced a greater depression of synaptic transmission in in vitro preparations of guinea-pig olfactory cortex than would have been expected from the sum of the activities of the individual anaesthetics. Other combinations of anaesthetics did not show similar effects although the interaction between alphaxalone and etomidate was not examined.4 Neither alphaxalone nor pentobarbitone affected the membrane: buffer partition coefficient of the other for a model membrane system.5 These results are interpreted as evidence against the classical unitary hypotheses of anaesthetic action based on correlations of anaesthetic potency with lipid solubility and as supporting the view that different anaesthetics act on different structures in the neuronal membranes to produce anaesthesia.

Anesthesia, Intravenous↗
PubMed2002

Survey of residual solvents in natural food additives by standard addition head-space GC.

Residual levels of 12 solvents in 87 natural food additives (66 samples of food colours, 19 samples of natural antioxidants and two natural preservatives) collected between 1997 and 1999 were determined by automated head-space GC using FID, with a porous-polymer (PLOT) column. Calibration curves were prepared by the method of standard addition. Confirmation was by manually injected head-space GC using mass spectrometric detection. 1,2-Dichloroethane was found in turmeric colour (natural food colour) collected in 1997 at the concentrations of 8.6 microg g(-1), but was not found in samples collected in 1998 and 1999. Hexane was found in three samples of dunaliella carotene (11, 72 and 75 microg g(-1)), and in chlorophyll at 93 microg g(-1) (both natural food colours). Acetone was found in turmeric colour, annatto colour, dunaliella carotene, kaoliang colour, cacao colour at a concentration between 8.7 and 42 microg g(-1) (all natural food colours).

Antioxidants↗
PubMed1996

Improved blood compatibility of segmented polyurethanes by polymeric additives having phospholipid polar groups. I. Molecular design of polymeric additives and their functions.

To improve the blood compatibility of a segmented polyurethane (SPU), 2-methacryloyloxyethyl phosphorylcholine (MPC) polymer was blended with the SPU. The MPC was copolymerized with cyclohexyl methacrylate (CHMA) or 2-ethylhexyl methacrylate (EHMA), and the MPC polymers obtained could be dissolved in the same solvent as the SPU (Tecoflex 60). The blended membranes composed of SPU and MPC polymers were prepared by a solvent evaporation method. A small amount of MPC polymer in the blended membrane leached out after immersion in water for 10 days. The X-ray photo electron spectra indicated that the MPC moieties were located at the surface of the SPU membrane blended with poly(MPC-co-CHMA). On the other hand, the poly-(MPC-co-EHMA) was located homogeneously in the SPU membrane. The mechanical properties of the SPU membrane, as determined by tensile stress-strain measurements, changed very little even after addition of the MPC polymers. Blood compatibility of the blended membrane was evaluated by blood-cell adhesion on the surface when the membranes were placed in contact with rabbit whole blood or platelet-rich plasma. The addition of MPC polymer in the SPU membrane dramatically reduced cell adhesion. It is concluded that the blending of the MPC polymer in the SPU membrane is an effective method for imparting nonthrombogenicity.

Animals↗
PubMed1994

Combination treatments of Chinese hamster ovary cells with various restriction endonucleases result in chromosomal aberrations whose frequencies are additive or less than additive.

Chinese hamster ovary cells were treated with combinations of different restriction endonucleases (RE). The frequencies of chromosomal aberrations after combination treatments were additive or less than additive when compared with the effects of the single RE. These data indicate that DNA double-strand breaks (DSB) induced by different types of RE in combination treatments lead to chromosomal aberrations in the same way as DSB induced by single RE.

Animals↗
PubMed2005

Oxathiolene oxide synthesis via chelation-controlled addition of organometallic reagents to alkynols followed by addition of sulfur electrophiles and evaluation of oxathiolene oxides as anticarcinogenic enzyme inducers.

A number of alkynols have been prepared by Sonogashira coupling of propargyl alcohol to aromatic halides. Chelation-controlled addition of organometallic nucleophiles to these alkynols was then effected followed by the addition of the sulfur electrophiles, sulfur dioxide or thionyl chloride. This methodology was used to prepare a number of oxathiolene oxides, which have been screened as NQO1 (quinone oxidoreductase) inducers.

Alcohols↗
PubMed2003

Bioaccumulation and critical body residue of PAHs in the amphipod, Diporeia spp: additional evidence to support toxicity additivity for PAH mixtures.

Polycyclic aromatic hydrocarbons (PAHs) are considered to act additively when exposed as congener mixtures. Additive internal concentrations at the site of toxic action is the basis for recent efforts to establish a sum PAH guideline for sediment-associated PAH toxicity. This study determined the toxicity of several PAH congeners on a body residue basis in Diporeia spp. These values were compared to the previously established LR(50) value for a PAH mixture based on the molar sum of PAH congeners and demonstrated similar LR(50) values for individual PAH. These results support the contention that the PAH act at the same molar concentration whether present as individual compounds or in mixture. Aqueous exposures were conducted for 28 d, and the water was exchanged daily to maintain the exposure concentration. The concentration in the exposures declined by an average of 22% between water exchanges across all compounds, and ranged from 11% to 32%. The toxicokinetics were determined using both time-weighted-average (TWA) and time-variable water concentrations and were not statistically different between the two source functions. Toxicity was determined for both mortality and immobility (failure to swim on prodding) and on both a TWA water concentration and a body residue basis. The LC(50) values ranged from 1757 microg l(-1) for naphthalene after 10 d exposure to 79.1 microg l(-1) for pyrene after 28 d exposure, and the EC(50) ranged from 1587 microg l(-1) for naphthalene after 10 d exposure to 38.2 microg l(-1) for pyrene after 28 d exposure. The LR(50) values for all congeners at all lengths of exposure were essentially constant and averaged 7.5+/-2.6 micromol g(-1), while the ER(50) for immobility averaged 2.6+/-0.6 micromol g(-1). The bioconcentration factor declined with increasing exposure concentration and was driven primarily by a lower uptake rate with increasing dose, while the elimination remained essentially constant for each compound.

Amphipoda↗
PubMed2003

A human homolog of Additional sex combs, ADDITIONAL SEX COMBS-LIKE 1, maps to chromosome 20q11.

The Additional sex combs (Asx) gene of Drosophila is an Enhancer of trithorax and Polycomb (ETP), and is required to maintain activation and silencing of homeotic loci. The molecular basis of this dual function is not understood. Here, we identify a human homolog of Asx, termed ADDITIONAL SEX COMBS-LIKE 1 (ASXL1). Overall, the amino acid sequence of ASXL1 has 21% identity and 41% similarity to Drosophila ASX. The ASXL1 protein contains a 118 amino acid conserved amino terminal region of unknown function that we term the ASX homology domain (ASXH) that contains two LXXLL consensus sequences for nuclear receptor binding. ASXL1 also contains a conserved C-terminal cysteine cluster that is a variant of the PHD domain. Three ASXL1 transcripts of differing size are detected, which are widely expressed in adult tissues. ASXL1 maps to chromosome 20q11, a region frequently amplified in human tumors. Interestingly, ASXL1 is overexpressed in cell lines derived from carcinomas.

Amino Acid Sequence↗
PubMed1999

Evaluation of the H-point standard additions method (HPSAM) and the generalized H-point standard additions method (GHPSAM) for the UV-analysis of two-component mixtures.

The H-point standard additions method (HPSAM) and two versions of the generalized H-point standard additions method (GHPSAM) are evaluated for the UV-analysis of two-component mixtures. Synthetic mixtures of anhydrous caffeine and phenazone as well as of atovaquone and proguanil hydrochloride were used. Furthermore, the method was applied to pharmaceutical formulations that contain these compounds as active drug substances. This paper shows both the difficulties that are related to the methods and the conditions by which acceptable results can be obtained.

Anti-Inflammatory Agents, Non-Steroidal↗
PubMed2004

Elimination-addition mechanism for nucleophilic substitution reaction of cyclohexenyl iodonium salts and regioselectivity of nucleophilic addition to the cyclohexyne intermediate.

The reaction of 4-substituted cyclohex-1-enyl(phenyl)iodonium tetrafluoroborate with tetrabutylammonium acetate gives both the ipso and cine acetate-substitution products in aprotic solvents. The isomeric 5-substituted iodonium salt also gives the same mixture of the isomeric acetate products. The reaction is best explained by an elimination-addition mechanism with 4-substituted cyclohexyne as a common intermediate. The cyclohexyne formation was confirmed by deuterium labeling and trapping to lead to [4 + 2] cycloadducts and a platinum-cyclohexyne complex. Cyclohexyne can also be generated in the presence of some other mild bases such as fluoride ion, alkoxides, and amines, though amines are less effective bases for the elimination. Kinetic deuterium isotope effects show that the anionic bases induce the E2 elimination (k(H)/k(D) > 2), while the amines allow formation of a cyclohexenyl cation in chloroform to lead to E1 as well as S(N)1 reactions (k(H)/k(D) approximately 1). Bases are much less effective in methanol, and methoxide was the only base to efficiently afford the cyclohexyne intermediate. Nucleophiles react with the cyclohexyne to give regioisomeric products in the ratio dependent on the ring substituent. The observed regioselectivity of nucleophilic addition to substituted cyclohexynes is rationalized from calculated LUMO populations, which are governed by the bond angles at the acetylenic carbons: The less deformed carbon has a higher LUMO population and is preferentially attacked by the nucleophile.

Acetates↗
PubMed2005

Site-specific binding of quinones to proteins through thiol addition and addition-elimination reactions.

Ubiquinone-0, menaquinone-0, and 2,3,5-trimethyl-1,4-benzoquinone were site-specifically bound to free cysteine of proteins (yeast iso-1 cytochrome c as a model protein) through thioether bond formation. Model thioether quinone conjugates showed unexpected reactivity to cysteine of proteins as their parent quinones by thiol addition-elimination reaction. Cyclic voltammetry studies of the model compounds showed only minor differences in their redox potentials as compared to their parent quinones. Thioether ligation provides a general, simple, and fast method to construct model quinone protein systems. In addition, these studies also contribute to the understanding of biological activities, toxicity, and anti-cancer mechanism of quinones and thioether quinone adducts.

Amino Acid Sequence↗