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PubMed1981

[Effect of lithium preparations on the toxic effects of adrenaline].

Experiments on rats have shown that intravenous injection of adrenaline in a dose of 0.3-0.4 mg/kg causes cardiac arrhythmia. In this case the primary arrhythmia developing immediately after adrenaline injection is followed by the recovery of sinusal rhythm which was replaced by the secondary arrhythmia. Apart from arrhythmias, there developed pulmonary edema. The animals died 2--3 minutes after adrenaline injections. Lithium chloride and lithium hydroxybutyrate removed the secondary arrhythmia and pulmonary edema. Lithium hydroxybutyrate has proved to be more effective.

Animals↗
PubMed1984

[Effects of lithium salts on experimental neurogenic lesions of the stomach and heart].

It has been demonstrated in experiments on noninbred rats that lithium chloride and lithium hydroxybutyrate exert a prophylactic therapeutic effect in respect to neurogenic gastric lesions and reduction in the content of creatine phosphate in gastric and cardiac tissues, induced by stressful exposures (3-hour immobilization and electric stimulation of hungry animals). The effects of lithium hydroxybutyrate were more demonstrable than those of lithium chloride.

Animals↗
PubMed1993

Isolation of RNA from cells in culture using Catrimox-14 cationic surfactant.

Traditional RNA isolation methods use chaotropic agents and anionic detergents to lyse cells and solubilize nucleic acids. In contrast, the cationic surfactant, Catrimox-14, lyses cells and simultaneously precipitates RNA, thereby protecting it from RNases. We describe and compare four methods for extracting RNA from cultured cells that differ in the technique used to extract the RNA from the precipitate. The first uses a high-salt solution (guanidinium isothiocyanate). In the second, the RNA is extracted with a polar solvent (formamide). The third involves conversion of the RNA to the sodium salt by treatment of the precipitate in situ with sodium acetate in ethanol. The fourth uses 2 M lithium chloride to convert the RNA in the pellet to the lithium salt in situ. We applied these methods to human leukemia cells growing in culture and each method resulted in excellent yields of RNA (typically 23 micrograms/million K562 cells, 13 micrograms/million HL-60 cells) over a wide range of cell concentrations (1 x 10(5) - 3 x 10(7)/ml) and of good to excellent quality as judged by agarose electrophoresis and UV absorbance data (OD260/280 1.90-2.05). The advantages and limitations of each method are discussed.

Acetates↗
PubMed2006

Diastereoselective multicomponent cyclizations of Fischer carbene complexes, lithium enolates, and allylmagnesium bromide leading to highly substituted five- and six-membered carbocycles.

The one-pot sequential reaction of a chromium alkoxycarbene complex, a ketone or ester lithium enolate, and allylmagnesium bromide enabled the selective synthesis of novel diastereomerically pure pentasubstituted cyclopentanols or tetrasubstituted 1,4-cyclohexanediols, depending on the degree of substitution at the Cbeta position of the enolate anion. A few exceptions have been encountered in which tetrasubstituted cyclopentanols or pentasubstituted 1,4-cyclohexanediols were selectively formed. The use of 2-iodoethoxycarbene complexes gave access to 1,2,4-cyclohexanetriols. These multicomponent-coupling reactions involved the formation of lithium alkylpentacarbonylchromates as key intermediates, which further evolved through intramolecular processes, such as insertion of an alkene, CO insertion or addition to a carbonyl group, and, moreover, could be trapped in intermolecular reactions with different electrophiles and styrene. The substitution pattern of the alkylchromate carbon chain has been proposed to control the nature of the annulation process.

Alcohols↗
PubMedDate not supplied

Prenatal adverse effects of various drugs and chemicals. A review of substances of frequent concern to mothers in the community.

Using the number of calls to the Canadian Motherisk Program as an indicator of the drugs and chemicals frequently of concern to mothers during pregnancy, the risks to the fetus of exposure to these compounds have been reviewed. The drugs which were of concern, and have been proven to be teratogenic, included alcohol, alkylating and antimetabolite agents, stilboestrol, disulfiram, heparin, lithium carbonate, phenytoin, tretinoin (retinoic acid), troxidone and valproic acid. For other compounds studied, there was either no data in the literature or no clear evidence of teratogenicity. The combination of doxylamine and pyridoxine, for example, has been associated with limb reduction defects in isolated case reports: cohort and case-control studies have failed to show a higher-than-baseline risk of malformations. In some cases of exposure to compounds with no known teratogenic potential, other adverse effects to the fetus are possible, and these effects are discussed in detail. In conclusion, when advising a pregnant woman about the potential teratogenic effect of a particular drug or chemical exposure, the health professional should also discuss other factors such as age, obstetric and medical history and the history of other exposures (including alcohol and smoking). In every pregnancy there is a 1 to 5% risk of mayor malformations, and even if the exposure does not appear to increase the teratogenic risk, such a risk still exists.

Adult↗
PubMed1998

[Synthesis and bioaction of 2-alkyl-4(1H)-quinolone].

Five quinolone alkaloids (IVa, Va, c, d, g) including two new compounds (IVa, Vc) from Evodia rutaecarpa and nine analogs are synthesized in good yield by using acid-catalyzed condensation of a series of 3-oxoalkkanoic acid esters with aniline and further methylized with methyl iodide. The other analogue Vh is prepared through the reaction of lithium enolate methyl ketone with N-methylisatoic anhydride. Eight compounds (IVa, d, f; Vb, c, d, f, h) were synthesized for the first time. Pharmacological studies showed that these compounds have vasoconstriction inhibiting and antiulcer effects. Compound IVb also has cytotoxic effect.

Alkaloids↗
PubMed2005

Chloride-bridged oxovanadium(V) complexes with alkoxyalkoxide ligands. Synthesis, structure, electrochemistry and reactivities.

A series of mixed alkoxyalkoxo chloro complexes of vanadium(V), [VOCl2(OCH2CH2OR)]2 (R = Me, Et, iPr, Bz), [VOCl2(OCMe2CH2OMe)]2 and [VOCl2(OCH2(cyclo-C4H7O)]2, were synthesised and characterised. The title compounds can be obtained either from VOCl3 and the alkoxyalcohols by HCl elimination or from the corresponding lithium alkoxides and VOCl3 by salt metathesis reaction. X-Ray diffraction studies revealed the title compounds to be dimers with chloride bridging ligands and intramolecular ether coordination. Electrochemical results obtained by cyclic voltammetry indicate irreversible, reductive behaviour. The interactions of the title compounds with oxygen, nitrogen and phosphorus donor ligands were examined. Phosphorus and nitrogen donors lead to reduction products whereas tetrahydrofuran coordinates to the vanadium(V) centre by breaking the chloride bridge. All tetrahydrofuran complexes, [VOCl2(OCH2CH2OR)(thf)] (R = Me, Et, iPr) and [VOCl2(OCMe2CH2OMe)(thf)], have been characterised by single-crystal X-ray diffraction. The solid-state structures of these complexes show that they consist of six-coordinate monomers. Reaction of [VOCl2(OCH2CH(2)OMe)]2 with Me3SiCH2MgCl gave [VO(CH2SiMe3)3], which has been structurally characterised. The compounds were tested as catalysts for epoxidation and polymerisation reactions. They convert unfunctionalised olefins into the corresponding epoxides with moderate activity. They are good pre-catalysts for the polymerisation of ethene and oligomerise 1-hexene.

Catalysis↗
PubMed1992

[Is the lithium chloride-coated heat and moisture exchanger a danger for patients?].

Such hygroscopic compounds as LiCl, CaCl2, and MgCl2 are used to improve water retention capacity and, as a consequence, the effectiveness of heat and moisture exchangers (HME). Resorption of these substances via the bronchopulmonary tract and a resulting systemic action cannot be excluded, especially if additional active moisturizing devices are used. The narrow therapeutic range of lithium is known, as are its unwanted side effects, such as nausea, vomiting, somnolence and even cardiac arrhythmia. These are symptoms that also frequently occur during anaesthesia and intensive care, so that differentiation against effects of lithium is nearly impossible. We investigated whether, in theory and in practice, LiCl-coated HME could result in effective Li plasma concentrations. We measured (1) total LiCl content of HMEs, (2) release of this content, simulating the worst-case situation with a breathing model, and (3) lithium plasma concentrations of adult patients being ventilated during anaesthesia with a rebreathing circuit and LiCl-coated HME, but with no additional active moisturizing system incorporated. RESULTS. The results show striking differences with LiCl content ranging from 3 to 251 mg varying not only between different types of HME but also within the same lots. After 20 min of ventilation more than 90% of the LiCl coating was rinsed into the test lung of the breathing model. In practical use, we observed an increase in lithium plasma concentration in 3 of 20 investigated patients. The plasma values of maximum 49.5 micrograms/l (= 0.007 mmol/l) do not amount to potentially toxic concentrations. Nevertheless, clinically relevant concentrations might occur in patients with small distribution volumes, e.g. newborns or infants with frequent exposition within short intervals such as in intensive care units. The differences in lithium content also indicate qualitative differences in water retention capacity. Because of the potential side effects of lithium, we prefer qualitatively equivalent HMEs, e.g., with MgCl2 or CaCl2 as hygroscopic substance.

Adult↗
PubMed1971

The mechanism of acetylcholine release from parasympathetic nerves.

1. The output of acetylcholine from the plexus of the guinea-pig ileum longitudinal strip has been used to study the mechanism of acetylcholine release. From the effects of hexamethonium and tetrodotoxin, it was inferred that 60% of the normal resting output is due to propagated activity in the plexus, and 40% to spontaneous release. Tetrodotoxin virtually abolishes the increase in output in response to electrical stimulation.2. Resting acetylcholine output is increased when the bathing medium is changed in the following ways:(a) sodium replacement by sucrose, trometamol or lithium;(b) addition of ouabain or p-hydroxymercuribenzoate (PHMB), or withdrawal of potassium;(c) the combination of PHMB and partial sodium replacement;(d) addition of potassium; this increase in output becomes greater in the absence of sodium.3. The resting output is virtually abolished by calcium withdrawal, and is restored by barium substitution for calcium. It is also reduced by raising the magnesium concentration.4. The enhanced resting output in response to sodium withdrawal also occurs in the absence of calcium.5. Cooling to 5 degrees C greatly reduces both the resting output and the output in response to raised potassium concentration or to electrical stimulation.6. The increase in resting output due to potassium excess is slight up to 25 mM [K(+)](o), but increases thereafter with about the fourth power of the potassium concentration; it is resistant to tetrodotoxin.7. Synthesis of acetylcholine by the longitudinal strip is increased when output is enhanced by electrical stimulation, by potassium excess or by addition of barium, so that the acetylcholine content of the strip is maintained approximately normal. Synthesis is reduced, in relation to output, by potassium lack or by treatment with ouabain, and is virtually abolished by sodium withdrawal.8. The theory is discussed that acetylcholine release depends on inhibition of the activity of a (Na(+) + K(+) + Mg(2+))-activated ATPase at the axonal membrane.

Acetylcholine↗
PubMed2003

A DFT-derived model predicts solvation-dependent configurational stability of organolithium compounds: a case study of a chiral alpha-thioallyllithium compound.

Density functional theory calculations (B3LYP/6-31+G*) were performed to evaluate a model previously published by us which suggests that aggregation and solvation of organolithium compounds can be of large importance for their configurational stability. In this study, we demonstrate how THF solvation of the monomer of a chiral alpha-thioallyllithium compound impedes the racemization, while upon dimerization the inversion process accelerates. These findings agree with experiments performed by Hoppe and co-workers. These findings may be used to further develop organolithium compounds which should be designed to resist aggregation and efficient transition-state solvation.

Lithium↗
PubMed2001

Theoretical studies to understand surface chemistry on carbon anodes for lithium-ion batteries: reduction mechanisms of ethylene carbonate.

Reductive decomposition mechanisms for ethylene carbonate (EC) molecule in electrolyte solutions for lithium-ion batteries are comprehensively investigated using density functional theory. In gas phase the reduction of EC is thermodynamically forbidden, whereas in bulk solvent it is likely to undergo one- as well as two-electron reduction processes. The presence of Li cation considerably stabilizes the EC reduction intermediates. The adiabatic electron affinities of the supermolecule Li(+)(EC)n (n = 1-4) successively decrease with the number of EC molecules, independently of EC or Li(+) being reduced. Regarding the reductive decomposition mechanism, Li(+)(EC)n is initially reduced to an ion-pair intermediate that will undergo homolytic C-O bond cleavage via an approximately 11.0 kcal/mol barrier, bringing up a radical anion coordinated with Li(+). Among the possible termination pathways of the radical anion, thermodynamically the most favorable is the formation of lithium butylene dicarbonate, (CH2CH2OCO2Li)2, followed by the formation of one O-Li bond compound containing an ester group, LiO(CH2)2CO2(CH2)2OCO2Li, then two very competitive reactions of the further reduction of the radical anion and the formation of lithium ethylene dicarbonate, (CH2OCO2Li)2, and the least favorable is the formation of a C-Li bond compound (Li carbides), Li(CH2)2OCO2Li. The products show a weak EC concentration dependence as has also been revealed for the reactions of LiCO3(-) with Li(+)(EC)n; that is, the formation of Li2CO3 is slightly more favorable at low EC concentrations, whereas (CH2OCO2Li)2 is favored at high EC concentrations. On the basis of the results presented here, in line with some experimental findings, we find that a two-electron reduction process indeed takes place by a stepwise path. Regarding the composition of the surface films resulting from solvent reduction, for which experiments usually indicate that (CH2OCO2Li)2 is a dominant component, we conclude that they comprise two leading lithium alkyl bicarbonates, (CH2CH2OCO2Li)2 and (CH2OCO2Li)2, together with LiO(CH2)2CO2(CH2)2OCO2Li, Li(CH2)2OCO2Li and Li2CO3.

Journal Article↗
PubMed2000

Alkali salts of C3-symmetric, linked aryloxides: selective binding of substrates with metal aggregates.

The lithium, sodium, and potassium salts of tris(3,5-dialkyl-2-hydroxyphenyl)methanes (tert-butyl, tert-pentyl, methyl) have been prepared by reaction of the triarylmethane with n-butyllithium, sodium hydride, and potassium hydride, respectively. These compounds are all hexanuclear aggregates composed of two triarylmethane units. Whereas the lithium salt is compact and cannot bind oxygen-donor solvent molecules, the sodium and potassium systems have vacant coordination sites that can interact with solvents. For the sodium compounds, the solvent can be subsequently removed, and the resulting coordinatively unsaturated compounds have been shown to selectively bind oxygen-donor substrates (ethers, aldehydes, and ketones) of suitable size and shape. The paper reports the synthesis and characterization of these novel compounds, including thirteen crystal structures of the salts and their adducts.

Journal Article↗
PubMed1989

2-(Fluoromethyl)-3-phytyl-1,4-naphthoquinone and its 2,3-epoxide. Inhibition of vitamin K epoxide reductase.

2-(Fluoromethyl)-3-phytyl-1,4-naphthoquinone (7) was synthesized from the known compound 2-bromo-3-methyl-1,4-dimethoxynaphthalene by N-bromosuccinimide bromination of the 3-methyl group, conversion to the corresponding 3-fluoromethyl compound with silver fluoride, attachment of the 3-phytyl substitutent via the lithium diaryl cuprate and phytyl bromide, and then silver oxide oxidation to 7. Epoxidation with basic hydrogen peroxide gave the corresponding 2,3-oxide (1) in a very low yield. Compound 1 was not a time-dependent inhibitor of beef liver microsomal vitamin K epoxide reductase, but it was a competitive, reversible inhibitor. It was not possible to determine if 1 was a substrate for the enzyme because the expected product of reduction, namely 7, rapidly decomposed under the assay conditions.

Animals↗
PubMed2004

Novel hypervalent complexes of main-group metals by intramolecular ligand-->metal electron transfer.

New fascinating electronic features of the simple diketoamine chelate ligand HN[CH2C(tBu)=O]2 (1) are described. Unexpectedly, the corresponding trianionic amido-dienolate form of 1 is capable of reducing main-group metal atoms M after initial coordination and intramolecular L-->M two-electron transfer and of stabilizing main-group elements in unusual low oxidation states. This is impressively shown by the synthesis and structural characterization of the novel Ge and Sn complexes 4-6 by redox reactions of lithiated 1 with the corresponding metal halides GeCl4 and MCl2 (M=Ge, Sn). Surprisingly, conversion of tris-lithiated 1 with GeCl4 readily consumes two molar equivalents of GeCl4 and results in the formation of the neutral GeCl3 complex 4 and GeCl2. The former represents the second example of a structurally characterized neutral octahedrally coordinated germanium compound. Reaction of dilithiated 1 with GeCl2 does not lead to the expected ClGe(+2) complex but affords the novel dimeric germylene 5, whereas similar reaction using SnCl2 furnishes the monomeric stannylene (ClSn(+2) complex) 2 and elemental tin due to the higher oxidation potential of Sn(+2). Unexpectedly, a similar redox reaction of dilithiated 1 with PbCl2 furnishes the first air- and water-stable lithium 1,2-diketoimine-enolate 7 and elemental lead. Compound 7 is tetrameric in the solid state and consists of a strongly distorted Li4O4 cubic core with trigonal-bipyramidal coordinated Li+ ions.

Journal Article↗