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PubMed2000

Characterization of iridoids by fast atom bombardment mass spectrometry followed by collision-induced dissociation of

Fast atom bombardment mass spectra of a series of naturally occurring and synthetically modified iridoid glycosides were studied using lithium cationization and collision-induced dissociation of the resulting [M+Li]+ ions. Lithium cationization leads to the unambiguous determination of the molecular masses of these compounds. Collision-induced dissociation of the lithiated molecular ions give valuable structural information regarding the nature of the substituent on both the aglycone and the sugar moieties. The characteristic fragmentation pathways identified are (1) elimination of neutral molecules comprising the substituents on either the aglycone or sugar moieties, (2) formation of lithiated aglycone and their fragment ions, (3) formation of lithiated sugar and their fragment ions, (4) fragmentation corresponding to the cleavage of the aglycone or sugar ring and (5) fragmentation characteristic of the substituents present in either the aglycone or sugar parts of the molecule. Elimination of two acyloxy radicals from the lithiated molecular ion is a characteristic fragmentation in the case of acyloxy derivatives.

Journal Article↗
PubMed2005

Deformed phthalocyanines: synthesis and characterization of zinc phthalocyanines bearing phenyl substituents at the 1-, 4-, 8-, 11-, 15-, 18-, 22-, and/or 25-positions.

The synthesis of a series of zinc phthalocyanines partially phenyl-substituted at the 1-, 4-, 8-, 11-, 15-, 18-, 22-, and/or 25-positions (the so-called alpha-positions) is reported. Macrocycle formation based on 3,6-diphenylphthalonitrile, o-phthalonitrile, and zinc acetate predominantly yielded the near-planar disubstituted complex and opposite tetrasubstituted isomer, while the lithium method yielded the sterically hindered hexasubstituted complex and adjacent tetrasubstituted isomer. All compounds have been characterized by 1H NMR, MALDI-TOF-MS, and elemental analysis methods. In addition, crystal structures have been solved for the di-, hexa-, and octasubstituted complexes and the adjacent tetrasubstituted isomer. DFT geometry optimization calculations predict more highly deformed structures than those observed in the crystals. The packing force of the crystals cannot therefore be ignored, particularly for the less phenyl-substituted derivatives. The crystal structures have revealed that overlap of the phenyl groups causes substantial deformation of the phthalocyanine (Pc) ligands within the crystals, while strong pi-pi stacking in the remainder of the Pc moiety lacking phenyl substituents can suppress the impact of the deformation. Absorption spectra show sizable red shifts of the Q-band with increasing number of phenyl groups. Analysis of the results of absorption spectra and electrochemical measurements reveals that a substantial portion of the red shift is attributable to the ring deformations. Molecular orbital calculations lend further support to this conclusion. A moderately intense absorption band emerging at around 430 nm for highly deformed octaphenyl-substituted zinc Pc can be assigned to the HOMO-->LUMO+3 transition, which is parity-forbidden for planar Pcs, but becomes allowed since the ring deformations remove the center of symmetry.

Journal Article↗
PubMed1990

The amphiphilic action of vasopressin and analogues on the plasma membrane of Amoeba proteus.

Arginine (AVP) and lysine vasopressin induce a weak but statistically significant increase in the water permeability of Amoeba proteus plasmalemma. Vasotocin and deaminovasopressin, which share the hydroosmotic properties of AVP on classical vertebrate systems, are without effects on Amoeba while SKF 101926, a synthetic AVP antagonist, is even more effective than the parent compound. Theophyllin and dibutyryl-cAMP do not affect AVP action on Amoeba. Lithium, oxytocin, and carbachol are also without effect. Thus, it is unlikely that either V2 (cAMP) or V1 (phosphatidylinositol choline) receptors are involved. A clear correlation has been found between the amphiphilic character of tested peptides and their effect on Amoeba water permeability. Classical amphiphilic peptides, melittin, mastoparan, and fragment 1-8 of alpha-neoendorphin, also increased water permeability in Amoeba. It is known that vasopressin can interact with artificial lipid membranes, increasing their permeability to water. We propose that amphiphilic members of the AVP family interact directly with the lipid phase of the Amoeba membrane. Their incorporation within the lipid bilayer may cause local disruptions or may create micellar water channels as shown for other amphiphilic proteins. Our observations provide a model for the early evolution of peptide hormone systems, preceding the appearance of specific membrane receptors and associated second messenger amplifying mechanisms.

Amoeba↗
PubMed2001

An enantioselective synthesis of insecticidal 4-alkynyloxazolines.

2-(2,6-Difluorophenyl)-4-phenylalkynyl oxazolines are potent insect growth regulators. An efficient and enantioselective synthesis to these compounds has been developed which relies on a (-)-sparteine mediated hydroxymethylation of the lithium dianion of propargylic amides.

Alkynes↗
PubMed2006

Synthesis of bulky and electron-rich MOP-type ligands and their applications in palladium-catalyzed C-N bond formation.

A series of 2-dialkylphosphino-2'-alkoxy-1,1'-binaphthyl ligands (6a-c and 8a-c) have been prepared conveniently by a lithium-initiated ring-opening reaction of dinaphthofuran, followed by selective phosphorylation. These compounds displayed a remarkable air and moisture stability, both in solid form and in solution. Application of these phosphine ligands in palladium-catalyzed C-N bond forming reactions revealed the crucial roles of the steric bulk of the substituents on the phosphorus atom governing the catalytic activity. Specifically, 2-di-tert-butylphosphino-2'-isopropoxy-1,1'-binaphthyl (8b) proved to be the most effective for the aminations of aryl halides with primary amines, while the less bulky 2-dicyclohexyl-2'-methoxy-1,1'-binaphthyl (6a) was more effective for the aminations with secondary amines. The steric and electronic effects of the ligands were analyzed to account for these observations.

Amination↗
PubMed2002

Stereoselective cycloadditions of chiral acyl-nitroso compounds; selective reactions of ring-cleaved cycloadducts leading to a new approach to polyoxamic acid.

Diesters obtained from diacids produced by oxidative ring cleavage of cycloadducts derived from acyl-nitroso compounds and cyclic 1,3-dienes undergo highly regioselective hydrolysis on reaction with lithium hydroperoxide, which allows for easy differentiation of the carboxyl groups leading to a new approach to polyoxamic acid.

Journal Article↗
PubMed2001

Phosphatidylinositol 3-kinase inhibition enhances human sperm motility.

BACKGROUND: The number of spermatozoa with forward motility after capacitation procedures represents the limiting factor for application of IVF versus intracytoplasmatic sperm injection (ICSI) procedure in cases of oligoasthenozoospermia. The possibility of increasing this number may thus be of help to the patient. A complex array of signalling pathways is involved in the regulation of sperm motility and recent data pointed out an important role for kinase/phosphatase-regulated phosphorylation of proteins. Here, we investigated the role of phosphatidylinositol 3-kinase (PI3K), a lipid and protein kinase involved in the regulation of several biological aspects of somatic cells, on human sperm motility by using the specific PI3K inhibitor LY294002. METHODS AND RESULTS: We demonstrated that in-vitro incubation of swim-up selected or unselected human spermatozoa with LY294002 determined an increase of percentage forward motility in all the treated samples. The effect was dose-dependent with an EC(50) of 1.09 +/- 0.54 micromol/l. LY294002 also increased sperm movement characteristics and hyperactivation as evaluated by computer-assisted motion analyser. The compound was also able to overcome the detrimental effect of hydrogen peroxide and lithium chloride on sperm motility. CONCLUSIONS: Our results suggest a negative role for PI3K in the development and maintenance of sperm motility and suggest a possible use of PI3K inhibitors to enhance motility in cases of asthenozoospermia.

Chromones↗
PubMed1987

Synthesis and anti-HIV activity of various 2'- and 3'-substituted 2',3'-dideoxyadenosines: a structure-activity analysis.

A systematic synthesis was undertaken of 2',3'-dideoxyadenosine analogues with either an azido, fluorine, or hydroxyl group substituted in the "up" or "down" position of C-2 or C-3 of the sugar moiety. The compounds were evaluated against the cytopathogenicity of human immunodeficiency virus (HIV) for MT-4 cells. The four azido derivatives 6, 7, 8, and 9 were synthesized by a nucleophilic displacement reaction with lithium azide on the mesylates 3, 2, 5, and 4. (Diethylamido)sulfur trifluoride was used for the synthesis of 10-12. The compound 13 was obtained by 2'-deoxygenation of 9-(3-fluoro-3-deoxy-beta-D-xylofuranosyl)adenine. Among the azido derivatives, compound 8 with the 3'-azido "down" was slightly more active than 2',3'-dideoxyadenosine (1) but considerably more toxic, and, of the fluorine series, compound 11, with the 2'-fluoro "up", was the most selective inhibitor of HIV, although it was less active than 1. Hence, none of the newly synthesized compounds proved more selective in their anti-HIV activity than the parent compound, 1.

Antiviral Agents↗
PubMed1999

Porosity control of hydroxyapatite implants.

Conformation of hydroxyapatite (HAp) bodies was carried out using a multiple slip-casting technique, in order to obtain dual-layer samples with differential sized porosities. The external layer, because of its porosity, controlled by the addition of organic compounds (polyvinyl polyacrylate, PVC), will promote bone ingrowth. The internal denser layer, due to the addition of lithium phosphate (Li3PO4) as sintering additive, will give mechanical resistance to the implant. HAp aqueous suspensions were characterized by rheological measurements. Scanning electron microscopy (SEM) and intrusion mercury porosimetry (MP) were used to characterize sintered bodies. It can be concluded that it is possible to introduce gross porosity in HAp bodies by the addition of organic compounds. The results show that a compatible shrinking of the layers during the sintering process and a good frequency of pores with an appropriate size in the external layer can be achieved with the use of organic additives.

Journal Article↗
PubMedDate not supplied

High-performance liquid chromatographic method for the separation and quantitative estimation of anti-parasitic melaminophenyl arsenical compounds.

A sensitive high-performance liquid chromatographic method has been developed for the separation and quantitative estimation of melaminophenyl arsenical drugs used in the treatment of human and veterinary trypanosomiases. Five clinically relevant compounds (melarsoprol, melarsonyl potassium, cymelarsan, melarsen oxide, and sodium melarsen) can be separated with an octadecylsilane reverse-phase column and detected down to 10 pmol per injection. The chromatographic system utilizes a propanol gradient in water, with lithium camphor sulphonate as ion modifier, and detection by ultraviolet absorbance at 280 nm. Preliminary results indicate that the arsenical compounds can be extracted and concentrated from serum using octadecylsilane solid-phase extraction cartridges. This method represents the first specific and sensitive assay system for separating and quantitatively estimating this important class of antiparasitic agents.

Arsenicals↗
PubMed2003

Structure of lithium benzilate hemihydrate solved by simulated annealing and difference Fourier synthesis from powder data.

The crystal structure of lithium benzilate hemihydrate (C(14)H(11)O(3)(-)Li(+).0.5H(2)O) was solved from synchrotron powder diffraction data. This compound crystallizes in the monoclinic space group P2(1)/a. The structure was solved via the direct space search for two benzilate fragments using the simulated-annealing program DASH, localization of the lithium ions and water molecule from a difference Fourier map, and a restrained Rietveld refinement (R(wp) = 0.0687). The structure is a coordination polymer of [Li(2)(C(14)H(11)O(3))(2).H(2)O](2) tetramers building helical fourfold one-dimensional channels parallel to [010]. Inside the channels the tetrahedral coordination spheres of the lithium ions contain hydroxyl and carbonyl groups, and water molecules. The water molecule functions as the cohesive entity forming extended hydrogen-bonded chains running along [010], and bifurcated donor hydrogen bonds with the two nearest carboxylates. At the outer edge of the channels, weaker intermolecular C-H.Ph hydrogen bonds along [100] and [001] contribute to the supramolecular aggregation of the structure.

Benzilates↗
PubMed2005

Acute effects of candesartan on rat renal haemodynamics and proximal tubular reabsorption.

1. The effects of the specific angiotensin II receptor type I (AT1) antagonist candesartan on renal proximal tubular sodium transport were studied using lithium clearance. The effects of candesartan on mean arterial blood pressure (MABP), renal plasma flow (RPF), glomerular filtration rate (GFR) and sodium and potassium excretion were also investigated. 2. Male Wistar rats were anaesthetized with Inactin (thiobutabarbital sodium; Sigma, St Louis, MO, USA). Clearance markers (8% polyfructosan, 1% para-aminohippuric acid and 4 mmol/l lithium chloride) were given into a jugular vein at the rate of 1.6 mL/h per 100 g bodyweight. Candesartan was given as bolus injection (0.01, 0.1, 0.2, 0.5 and 1.0 mg/kg) followed by 60 min continuous infusion at a rate of 0.5, 5, 10, 25 and 50 microg/min per kg, respectively. 3. The non-depressor dose of candesartan (0.01 mg/kg) did not alter RPF or GFR, whereas diuresis, natriuresis and kaliuresis were observed. The higher doses of candesartan reduced MABP, RPF and GFR, although diuresis, natriuresis and kaliuresis were still observed. 4. Renal tubular sodium and water reabsorption were inhibited after intravenous administration of candesartan independently of an alteration in arterial pressure. Lithium clearance data indicate that the site of inhibition was in the proximal nephron segment.

Angiotensin II↗
PubMed2006

Molecular oxygen dianions trapped in lithium cluster cages.

In an important recent report, Coles and Hitchcock (Chem. Commun. 2005, 3165) have synthesized a unique compound of the form Li9O2(hpp)7, with an O2 unit encapsulated in the Li cluster. The group hpp is the bicyclic guanidinate 1,3,4,6,7,8-hexahydropyrimido[1,2-a]pyrimidinate. Coles and Hitchcock raise the interesting possibility that the trapped species is the O2 dianion. We have theoretically investigated (with full geometry optimization) the structural, vibrational, and electronic properties of this fascinating system with 165 atoms. Every indication supports the qualitative conclusion that this system is best represented as an O2 dianion embedded in a Li cluster. Several smaller model systems, including replacement of the hpp ligands by Cl atoms, are also examined and provide some interesting comparisons.

Journal Article↗
PubMedDate not supplied

[Chemotherapy in the treatment of bulimic behaviors].

Bulimia has been treated with various drugs. MAOI and heterocyclic non MAOI antidepressants have proved efficacious in controlled studies. Whereas Benzodiazepines, Lithium and antiepileptic medications appear less promising or have not yet been widely assessed in methodologically valid studies. Serotoninergic compounds are particularly specific of bulimic disorders. The links of bulimia with depressive states are briefly discussed.

Anti-Anxiety Agents↗
PubMed2003

Asymmetric conjugate addition of arylthiols to enoates and its application to organic synthesis of biologically potent compounds.

As a part of our studies aimed at asymmetric catalytic reactions by using an external chiral ligand, we have developed a catalytic asymmetric addition reaction of an arylthiol to alpha,beta-unsaturated esters under the control of an external chiral ligand. The characteristic of our technology is a double activation of a thiol by lithiation and chelate formation with a chiral tridentate amino diether ligand, which simultaneously and effectively controls a stereochemistry of the reaction. One significant feature of an arylthiol is a bulky 2-substitution on aryl group, which enables the formation of a really reactive monomeric thiolate species. s-Cis conformation and capability of electron lone pair-differentiating coordination of a carbonyl oxygen to lithium are structural requirements of the substrates for high enantioselectivity. The enantioselectivity came up to 97% under the cited conditions. Asymmetric protonation of a transient enolate, generated by conjugate addition of a lithium thiolate to an enoate, was also realized. The stereochemistry of the protonation was controlled by the conformation of initially formed transient enolate in a 1,2-asymmetric induction manner. This technology enabled the asymmetric synthesis of (S)-naproxene. Stereoselective tandem C-S and C-C bond-forming reaction was developed as a logical extension by trapping the transient enolate intermediate with an aldehyde as a carbo-electrophile in the presence of phenylthiotrimethylsilane as an equilibrium-shift reagent. This tandem reaction was extended to a stereoselective cyclization of omega-oxo-alpha,beta-unsaturated esters initiated by a lithium thiolate. Stereoselectivity of both tandem inter- and intramolecular reaction is predictable by an allylic strain-controlled conformation model of the enolate, in which an approach of aldehyde takes place anti to C-S bond through coordination of an aldehyde oxygen to lithium. Total synthesis of (-)-neplanocin A was achieved by using the tandem cyclization as a key tool for the direct construction of a five-membered carbocycle where every carbon is functionalized.

Adenosine↗
PubMed2001

A novel mixed dimer of a norephedrine-derived chiral lithium amide and 2-lithium-1-methylimidazole, and catalytic enantioselective deprotonation of cyclohexene oxide.

Improved stereoselectivity has been obtained by using 2-lithium-1-methylimidazole, 2, as a replacement for lithium diisopropylamide (LDA) as a bulk base in catalytic deprotonations. The chiral lithium amide 6 of (1R,2S)-N-methyl-1-phenyl-2-pyrrolidinylpropanamine, 5, has been found to deprotonate cyclohexene oxide 3 in the presence of compound 2 to yield (S)-cyclohex-2-en-1-ol, 4, in 96% ee. Compound 2 is a carbenoid species conveniently generated from nBuLi and 1-methylimidazole, 1. The base 2 has also been found to play a more intimate role in the deprotonation. Investigations by 1H, 6Li and 13C NMR of the 6Li/15N isotopologue 8 of 6 have shown that 6 is homodimeric in THF and that, in the presence of 2, it forms a novel heterodimer 10. This heterodimer is found to be the dominant reagent in the initial state, rather than the homodimer of 6. Computational investigations with PM3 and B3LYP/6-311 + G(d,p) have shown possible structures of the heterodimers, as well as the role of THF and I in the solvation of the dimers. The results are in line with the NMR results. Favoured complexes in the equilibria between homo- and heterocomplexes are also reported.

Adrenergic alpha-Agonists↗