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At least 775 records · Page 43Linked to original sources
PubMed2003

Analysis of O,S-dimethyl hydrogen phosphorothioate in urine, a specific biomarker for methamidophos.

A rugged and sensitive method was developed to monitor urinary concentrations of O,S-dimethyl hydrogen phosphorothioate (O,S-DMPT), a specific biomarker of exposure to the organophosphate insecticide methamidophos. After pH adjustment and C18 solid phase extraction column cleanup, the urine was lyophilized at a low temperature to prevent loss of possibly highly volatile and unstable O,S-DMPT metabolite. The dried residue was derivatized using N-methyl-N-(tert-butyldimethylsilyl)trifluoroacetamide and 1% tert-butyldimethylchlorosilane (MTBSTFA + 1% TBDMCS) in acetonitrile. After it was filtered, the derivatized product was analyzed and quantified by gas chromatography using a pulse flame photometric detector specific for phosphorus compounds. The limit of detection for this method was 0.004 ppm with a limit of quantitation of 0.02 ppm of urine. The mean recovery value for O,S-DMPT from 17 urine samples fortified at varying concentrations was 108% with a standard deviation of 12%.

Biomarkers↗
PubMed1984

Phosphorus analogues of gamma-aminobutyric acid, a new class of anticonvulsants.

A series of phosphorus compounds, designed as analogues of gamma-aminobutyric acid (GABA) in that they possess a P = O moiety separated by three atoms from an amino or acetamido group, was synthesized and tested by using in vitro GABAA and GABAB receptor binding, GABA uptake assays, and was examined for anticonvulsant activity. Weak GABAB receptor affinity was noted for one agent, whereas six compounds displayed moderate to high potencies as inhibitors of electroshock- and pentylenetetrazol-induced seizures. The best anticonvulsant effect was found with the (m-aminophenyl) phosphinic acid compounds, with members of this class selected for further study.

Animals↗
PubMed1996

Ryanodine action at calcium release channels. 1. importance of hydroxyl substituents.

Ryanodine (1) and dehydroryanodine (2) have a polar face formed by cis-hydroxyls at C-2, C-4, C-6, and C-12. The importance of the hydroxyls to the action of 1 and 2 at the ryanodine receptor (ryr) of calcium release channels is examined at [3H]-1 binding sites in brain and skeletal muscle and in heart membranes relative to cardiac contractility, a pharmacologic response which appears to be mediated by the ryr. Five types of changes are considered: blocking the 4- and 6-hydroxyls as cyclic borates and boronates; blocking the 10- and 12-hydroxyls as cyclic phosphates, phosphonates, and phosphoramidates; methylation at nitrogen or hydroxyls at C-4 and C-10; dehydration of the C-2 hydroxyl; additional data for a 4,12-oxygen-bridged series. The first change has little effect on potency possibly due to the lability of the boron protective groups whereas the cyclic phosphorus compounds have reduced activity. Methylation reduces potency the least at nitrogen and the C-4 hydroxyl. Dehydration of 1 to 2-deoxy-2(13)-dehydro-1 allows the restoration of oxygen at C-2 by conversion to epoxides or a diol. One of the epoxides and 2-deoxy-2(13)-dehydro-2 retain 8-31% of ryanodine's potency in the ryr assays and 81% in the cardiac contractility system. In the 4,12-oxygen-bridged series, high potency at the receptor and cardiac muscle is retained in the 4-hydroxy ketal.

Animals↗
PubMed1998

Novel peptidyl phosphorus derivatives as inhibitors of human calpain I.

Dipeptidyl phosphorus compounds were synthesized as potential bioisosteric mimics of peptide alpha-ketoesters and alpha-ketoacids. alpha-Ketophosphonate Cbz-Leu-Leu-P(O)(OCH3)2 (1b), containing an alpha-ketoester bioisostere, inhibits human calpain I with an IC50 = 0.43 microM. The potency of 1b compares very favorably with that of alpha-ketoester Cbz-Leu-Leu-CO2Et (IC50 = 0.60 microM). Monomethyl ketophosphonate Cbz-Leu-Leu-P(O)(OH)(OCH3) (1a, IC50 = 5.2 microM), an alpha-ketoacid mimic, is less potent. Dibutyl and dibenzyl alpha-ketophosphonates 1c,e,f are much less potent calpain inhibitors than dimethyl alpha-ketophosphonate 1b. alpha-Ketophosphinate 1g (IC50 = 0.37 microM) and alpha-ketophosphine oxide 1h (IC50 = 0.35 microM) are also potent calpain inhibitors.

Calpain↗
PubMed2000

Preparation of 1,5-disubstituted pyrrolidin-2-ones.

1,5-Disubstituted pyrrolidin-2-ones 18a-g, 19a-h, and 20a-f were synthesized in good to excellent yields via the nucleophilic substitution of 5-(benzotriazol-1-yl)-1-substituted-pyrrolidin-2-ones 9 with allylsilanes, organozinc reagents, and phosphorus compounds. Compounds 9 and 5-(benzotriazol-2-yl)-1-substituted-pyrrolidin-2-one isomers 10 are readily prepared in total 70-84% yields from 2, 5-dimethoxy-2,5-dihydrofuran (7), primary amines 8, and benzotriazole; 9 and 10 react identically with nucleophiles.

Drug Design↗
PubMed2006

An electrochemical study of PCl3 and POCl3 in the room temperature ionic liquid [C4mpyrr][N(Tf)2].

Voltammetric studies of PCl3 and POCl3 have not been reported in the literature to date, probably due to the instability of these molecules in conventional aprotic solvents giving unstable and irreproducible results. From a previous study [Amigues et al. Chem. Commun. 2005, 1-4], it was found that ionic liquids have the ability to offer a uniquely stable solution phase environment for the study of these phosphorus compounds. Consequently, the electrochemistry of PCl3 and POCl3 has been studied by cyclic voltammetry on a gold microelectrode in the ionic liquid [C4mpyrr][N(Tf)2] (1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide). For both compounds, reduction and oxidation waves were observed and a tentative assignment of the waves is given. For PCl3, the reduction was thought to proceed via the following mechanism: PCl3 + e- <=> PCl3-, PCl3- <=> Cl- + P*Cl2, and Cl- + PCl3 <=> PCl4-. For POCl3, the suggested reduction mechanism was analogous to that of PCl3: POCl3 + e- <=> POCl3-, POCl3- <=> Cl- + P*OCl2, and Cl- + POCl3 <=> POCl4-. In both cases P*Cl2 and P*OCl2 are likely to engage in further reactions. Potential step microdisk chronoamperometry was carried out on the reductive waves of PCl3 and POCl3 to measure diffusion coefficients and number of electrons transferred. It was found that the diffusion of PCl3 was unusually slow (3.1 x 10(-12) m2 s(-1)): approximately 1 order of magnitude less than that for POCl3 (2.2 x 10(-11) m2 s(-1)). For both PCl3 and POCl3, a "split wave" was observed, with an overall electron count of 1. This observation is shown to be consistent with and to "fingerprint" the mechanisms proposed above.

Journal Article↗
PubMed2003

Effect of inhibitors on polyphosphate metabolism in the yeast Saccharomyces cerevisiae under hypercompensation conditions.

After re-inoculation of the yeast Saccharomyces cerevisiae from phosphate-deficient to complete medium, the total content of polyphosphates increased tenfold during 2 h (hypercompensation), but the content of certain fractions increased differently. The content of acid-soluble polyphosphate increased to the maximal extent. The ratio of the activities of two exopolyphosphatases also changed in the cytosol. Activity of a low molecular weight exopolyphosphatase (40 kD) decreased almost twice, whereas activity of a high molecular weight exopolyphosphatase (830 kD) increased tenfold. Cycloheximide blocks the increase in activity of high molecular weight exopolyphosphatase and hence, under these conditions the latter is synthesized de novo. Inhibitors of energy metabolism and cycloheximide, an inhibitor of protein synthesis, differently influence accumulation of certain polyphosphate fractions under hypercompensation conditions. The effect of iodoacetamide, an inhibitor of glycolysis, on any fraction is negligible, while cycloheximide suppresses accumulation of only polyP4 fraction associated with the cell envelope and bafilomycin A1, an inhibitor of vacuolar H+-ATPase, suppresses accumulation of polyP3 fraction. The protonophore carbonyl cyanide p-(trifluoromethoxy)phenylhydrazone (FCCP) to variable extent inhibits accumulation of all the fractions. Analysis of the effect of inhibitors on accumulation of polyphosphates under hypercompensation conditions confirms various localization, heterogeneity, and multiplicity of the routes of biosynthesis of certain fractions of these macroergic phosphorus compounds and also suggests interrelation between their biosynthesis and the gradient of H+ electrochemical potential.

Acid Anhydride Hydrolases↗
PubMed2003

Synthesis of 18pi annulenic fluorofullerenes from tertiary carbanions: size matters!

A range of tertiary carbanions XCH(CO2Et)2 of differing sizes have been reacted with C60F18 to assess the steric effect of X on the position of nucleophilic substitution. For X = CO2Et, NO2, P(O)(OMe)2, SO2CH2Ph, the all trans annulenes (trannulenes) were obtained as a result of extended S(N)2' (i.e. S(N)2'') substitution; in the case of the phosphorus compound, with reduced amounts of base (DBU) dephosphonylation of one or more P(O)(OMe)2 groups by hydrogen occurred. Trannulene formation did not occur for X = F, CN due to the smaller size of the nucleophile, and in the latter case substitution was shown to take place by an S(N)2' mechanism, resulting in the addend being adjacent to a fluorine addend. Trannulenes (X = CO2Et, Br, Cl) exhibited reversible one-electron reductions at potentials (-0.02 to -0.09 V) significantly more positive than for [60]fullerene. Trannulene (X = NO2) exhibited an irreversible one-electron reduction (0.08 V); the irreversibility may be associated with fluorine loss. Conformational isomerism at temperatures below 298 K was observed for all trannulene derivatives as a result of eclipsing addend-addend interactions. Minimum energy conformations with a rotational energy barrier of 12-15 kcal mol(-1) were observed when these interactions are calculated using molecular mechanics.

Journal Article↗
PubMed1981

Alkaline O leads to N-transacylation. A new method for the quantitative deacylation of phospholipids.

1. Quantitative O-deacylation of phospholipids has been achieved by incubation with a reagent containing monomethylamine, methanol and water. The reaction is primarily an O leads to N-transacylation with N-methyl fatty acid amides being formed. 2. The reagent can be removed easily by volatilization and under defined conditions no secondary decomposition of the phosphorus-containing deacylation products occurs. 3. The water-soluble phosphorus compounds derived by deacylation of mammalian tissue O-diacylated phospholipids have been completely separated by a single-dimensional paper ionophoresis with a volatile pH9 buffer. 4. The O-deacylated alkyl and alkenyl phospholipids have been examined by t.l.c. before and after catalytic hydrolysis with Hg2+. 5. A complete analysis of rat brain phospholipids by the above methods agrees closely with that obtained by other procedures.

Acylation↗
PubMed2006

Development of microalgae communities in the Phytotelmata of allochthonous populations of Sarracenia purpurea (Sarraceniaceae).

The phytotelmata of the North American pitcher plant Sarracenia purpurea are colonised by a great variety of aquatic organisms and, thus, provide an ideal model to study trophic interactions in small freshwater ecosystems. Although algae are discussed as a potential food source for predators, little is known about the structure of algae coenoses in pitchers of S. purpurea. This study aims to elucidate temporal shifts in the algae community structure in pitchers of an allochthonous population of S. purpurea in Saxony, Germany. A total of 78 algae taxa was found in the pitchers. Mean algae abundances in new and old pitchers were similar (2.6 x 10(5) and 2.3 x 10(5) algae ml(-1), respectively). Taxa from the orders Chlamydomonadales, Chlorococcales, and Ochromonadales were the primary colonisers. With increasing age of the pitchers the filamentous green algae from the order Klebsormidiales became more abundant. In contrast, pennate diatoms dominated the algae coenoses in the fen. Algae community structure in vase-shaped 50 ml Greiner tubes was similar to those of natural pitchers. Differences in the temporal patterns of algae coenoses in individual pitchers suggested a colonisation of the pitchers by algae via trapped insects, air and rain water rather than via the surrounding fen. Biomass of algae approximated 0.3 mg C ml(-1), which corresponds to 82.8 % of the living biomass (bacteria, heterotrophic nanoflagellates, algae, protozoans and rotifers). Rotifers were abundant in new pitchers; nematodes and mites were seldom found in all pitchers. A similar qualitative and quantitative composition of the aquatic biocoenoses was observed in pitchers of another allochthonous S. purpurea population growing in Blekinge, Sweden. Biomass of algae represented nearly one quarter of the total organic matter content in the pitchers. Thus, nitrogen and phosphorus compounds present in the algae biomass might be used by the carnivorous S. purpurea plant as additional food source in allochthonous populations in Europe lacking top predators.

Animals↗
PubMed1991

Age dependence of steady state mitochondrial oxidative metabolism in the in vivo hypoxic dog brain.

Mitochondrial bioenergetics were investigated in newborn, neonatal and adult dog brains during normoxia and hypoxia. The ratio of the rate of ATP synthesis to the maximum synthesis rate (V/Vmax), phosphorylation potential, [ADP] and PCr/Pi, were used to evaluate age related mitochondrial hypoxic tolerance. These indicators were calculated from the phosphorus compounds measured by in vivo 31P MRS quantitatively using ATP as an internal reference. Indicators and substrates of mitochondrial function, V/Vmax, ADP, and Pi reached a peak value during the neonatal (3-21 days) period of development, suggesting that the oxidative metabolism of the neonate is more vulnerable to stress when compared to newborns and adults. Distinction among newborns and neonates became apparent during hypoxia. Newborns (0-2 days old) showed substantial tolerance by maintaining V/Vmax until exposure to severe hypoxia. Older neonates (3-21 days old) showed increases in V/Vmax, [Pi] and [ADP] under less than severe conditions of hypoxia. Adults exhibited low V/Vmax values even during exposure to severe hypoxia, further indicating that mitochondrial oxidative processes are more stable in adults than in newborns and neonates. This study provides evidence that newborns and adults are more capable of maintaining mitochondrial function under conditions of minimal to moderate hypoxia than 3-21 day old neonates.

Adenosine Triphosphate↗
PubMed1977

Some enzymatic properties of peptidyl dipeptide hydrolase (angiotensin I-converting enzyme).

Peptidyldipeptide hydrolase [angiotensin I-converting enzyme, EC 3.4.15.1] was inhibited by inorganic and organic phosphorus compounds tested, except for beta-glycerophosphate, 5'-AMP, and 5'-ADP, at the reagent concentrations used. Orthophosphate and pyrophosphate nonspecifically inhibited the enzyme activity. The enzyme was also inhibited specifically by carboxylates. The degree of inhibition by aliphatic monocarboxylates increased in proportion to their chain length up to C14. Aromatic and omega-phenylalkylcarboxylates also inhibited the enzyme activity. The enzyme was noncompetitively inhibited by acetate, 3-phenylpropionate and laurate. The Ki's for acetate, 3-phenylpropionate, and laurate were 60, 3.3, and 2.5 mM, respectively.

Acetates↗
PubMed1999

Organophosphorus-induced neurotoxicity in the absence of neuropathy target esterase inhibition: the effects of triphenyl phosphine in the European ferret.

Abou-Donia et al. (in Toxicologist, Vol. 30, 1996) have reported that repeated oral administration of the organo-phosphorus compound triphenyl phosphine (TPPn) to the domestic chicken results in neuropathological changes in the spinal cord and peripheral nerves, accompanied by ataxia and paralysis. This study also noted that single doses of TPPn resulted in no inhibition of the enzymes neuropathy target esterase (NTE) and acetylcholinesterase (AChE). We undertook the present study to determine the biochemical, neuropathological, and clinical effects of single doses of TPPn in the European ferret, a mammalian species shown to be susceptible to organophosphorus-induced neurotoxicity. Eight 12-week-old ferrets were each injected subcutaneously with either 250 mg TPPn/kg bw or 500 mg TPPn/kg bw, or with the peanut oil/ethyl ether vehicle. Twenty-four h after dosing, the brains of 5 animals from each dose group were examined for NTE and AChE activities. The remaining 3 animals in each group were observed for 6 days for the development of clinical signs, after which their brains were processed for the presence of axonal degeneration using the Fink-Heimer silver impregnation method. Single injections of TPPn had no effect on the activities of whole-brain NTE or AChE 24 h after injection. The animals observed for clinical signs showed increasing trunk and hindlimb ataxia beginning 4 days after injection, culminating in fore-and hindlimb paralysis 6 days after injection. All brains exposed to either dose of TPPn showed widespread axonal degeneration extending from the brainstem and cerebellum into midbrain and forebrain areas. The results of this study support the hypothesis that TPPn-induced neurotoxicity is a separate and distinct form of organophosphorus-induced neurotoxicity not dependent on NTE inhibition, and therefore not a variant of organophosphorus-induced delayed neurotoxicity (OPIDN).

Acetylcholinesterase↗
PubMed2000

Synthesis and antitumor activity of cyclotriphosphazene-(diamine)platinum(II) conjugates.

A new class of water-soluble cyclotriphosphazene-(diamine)platinum(II) conjugate drugs [NP(Am-Li2)(Am.PtA2)]3 (Am: dicarboxylic amino acid; A2: diamine) has been synthesized and characterized by means of elemental analysis, multinuclear (1H, 31P, 13C, 195Pt) NMR and IR spectroscopies. All the title compounds were subjected to both in vitro and in vivo assays against the murine leukemia L1210 cell line and selected human tumor cells. Most of the title compounds have shown higher in vivo antitumor activity than cisplatin and carboplatin, and, in particular, [NP(L-Glu-Li2)(L-Glu.Pt(-dach)]3 (Glu=glutamate, dach=trans(+/-)-1,2-diaminocyclohexane) showed extraordinary high activity (ILS>500%) equally against both parent and cisplatin-resistant leukemia L1210 cell lines. Furthermore, this candidate compound (KI 60606) exhibited a wider spectrum of in vitro activity by showing higher cytotoxicity against all the selected human tumor cells than cisplatin and, therefore, was subjected to preclinical studies which are now near completion.

Animals↗
PubMed2000

Prochlorococcus marinus Chisholm et al. 1992 subsp. pastoris subsp. nov. strain PCC 9511, the first axenic chlorophyll a2/b2-containing cyanobacterium (Oxyphotobacteria).

The formal description of Prochlorococcus marinus Chisholm et al. 1992, 299 was based on the non-axenic nomenclatural type, strain CCMP 1375T. The purification and properties of the axenic strain PCC 9511, derived from the same primary culture (SARG) as the type species, are reported here. Prochlorococcus PCC 9511 differs from the latter in possessing horseshoe-shaped thylakoids, exhibiting a low chlorophyll b2 content and lacking phycoerythrin, but shares these phenotypic properties with Prochlorococcus strain CCMP 1378. This relationship was confirmed by 16S rRNA sequence analyses, which clearly demonstrated that the axenic isolate is not co-identic with the nomenclatural type. Strain PCC 9511 has a low mean DNA base composition (32 mol% G+C) and harbours the smallest genome of all known oxyphotobacteria (genome complexity 1.3 GDa = 2 Mbp). Urea and ammonia are the preferred sources of nitrogen for growth, whereas nitrate is not utilized. Several different organic phosphorus compounds efficiently replace phosphate in the culture medium, indicative of ecto-phosphohydrolase activity. In order to distinguish strain PCC 9511 from the nomenclatural type, a new subspecies is proposed, Prochlorococcus marinus Chisholm et al. 1992 subsp. pastoris subsp. nov.

Bacterial Typing Techniques↗
PubMed2001

Optimization of aquatic-terrestrial ecosystem in relation to soil nitrogen status for the cultivation of fish and aquatic food crops of the Indian subtropics.

A case study was undertaken during wet and postwet seasons to improve the perennial and alternate submerged saucer-shaped ponded lands (tal and semi-tal lands) in the coasts and northeastern plains of the Indian subtropics through pisciculture and cultivation of starch- and protein-rich aquatic food crops like water chestnut (Trapa bispinosa Roxb.) and makhana or fox nut (Euryale ferox Salisb.). The study revealed that the physico-chemical properties of soils (pH, organic C, organic matter, available N, P, and K) as well as quality of water (pH, EC, BOD, COD, CO3 +, HCO3-, NO3-N, SO4-S-, and Cl-), growing fish, makhana, and water chestnut was remarkably influenced by different moisture regimes and exhibited a significant improvement of soil health. The amount of organic C, available N, P, and K content were found significantly highest in the treatment where makhana was grown under alternate flooding and drying situation with a depth >2 m as compared to other treatments. Such enrichment of soil fertility, particularly in available N and P content, might be due to the accumulation of considerable amounts of biomass and fish excreta and their subsequent decomposition in situ in the soils. Therefore, the present study suggests that the N-enriched soil may effectively be utilized further for growing subsequent arable crops surroundings during summer season, which not only saves the amount of applied N fertilizer but also increases the apparent N efficiency with simultaneous increase in yield, and would benefit the farmers in this region.

Animals↗