Search PubMed⌕ Search

SEARCH · Search PubMed

Results for “Oxamic Acid”

Search indexed PubMed citations on genomics, clinical trials, systematic reviews and public health. Explore titles, authors and supplied subject terms, then open the PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 199 records · Page 11Linked to original sources
PubMed2002

Determination of oxanilic and sulfonic acid metabolites of acetochlor in soils by liquid chromatography-electrospray ionisation mass spectrometry.

An analytical method is presented that describes the extraction and quantification of oxanilic and sulfonic acid metabolites of the herbicide acetochlor in soil samples. Experiments were performed on 50 g of soil using a solvent extraction technique with an acetonitrile-water (60:40) mixture in an acidic medium. Analysis was carried out by reversed-phase liquid chromatography and detection by electrospray ionisation mass spectrometry in single ion monitoring and negative modes. Four different soil matrices were spiked in triplicate with standards of each degradation compound at three concentration levels between 2 and 80 microg/kg. The average recoveries range from 90 to 120% for both the metabolites, with relative standard deviations lower than 15%. The limits of quantification are about 1 and 2 microg/kg for the ethanesulfonic acid and the oxanilic acid metabolites, respectively. The method has been applied to soils and solids recovered from the deeper unsaturated zone of a small French catchment closely monitored as part of the European project "Pesticides in European Groundwaters: detailed study of Aquifers and Simulation of possible Evolution scenarios (PEGASE)".

Chromatography, Liquid↗
PubMedDate not supplied

Lodoxamide versus spaglumic acid: a comparative double-blind trial on patients suffering from seasonal allergic conjunctivitis induced by Parietaria pollen.

In order to evaluate the efficacy and tolerability of lodoxamide in the treatment of allergic conjunctivitis, the authors conducted a double-blind trial with intrapatient comparison on 32 patients, using lodoxamide versus spaglumic acid in the course of two conjunctival provocation tests performed with specific allergens. The patients received one drop of lodoxamide in one eye and one drop of spaglumic acid in the other; 15 minutes later, 25 microliters of allergen extract at a pre-established concentration was instilled. After 10 minutes, the signs and symptoms of the allergic response were evaluated and recorded. Six hours later, the instillation of the allergen extract in both eyes was repeated following the same procedure, to establish the duration of the effect of the two drugs. The results, obtained by evaluating the main clinical signs and symptoms (itching, lacrimation, hyperaemia, palpebral oedema and chemosis), demonstrate with statistically significant differences that lodoxamide inhibits the conjunctival response to exposure to the allergen with greater efficacy than spaglumic acid, and for a longer duration. The two drugs provided similar and satisfactory tolerability. In view of these results, lodoxamide can definitely be considered and effective drug in the treatment of allergic conjunctivitis.

Adult↗
PubMed1980

A comparison of potato and vertebrate lactate dehydrogenases.

A 2000-fold purification of L(+)-lactate dehydrogenase from potatoes is reported. Five isoenzymes of lactate dehydrogenase can be detected in crude extracts of potato, and three of these are present in the purified preparation. The enzyme (mol.wt. 150 000), which is composed of four subunits (mol.wt. 37 500), is active with the same oxo acids and hydroxy acids that have been reported as substrates with the same oxo acids and hydroxy acids that have been reported as substrates for vertebrate lactate dehydrogenases. These similarities between potato and vertebrate lactate dehydrogenases contrast sharply with some other reports on potato lactate dehydrogenase. These discrepancies are discussed in relation to the proposition that vertebrate and potato lactate dehydrogenases share a common evolutionary origin.

Adenosine Triphosphate↗
PubMed2005

Synthesis and evaluation of thiazole carboxamides as vanilloid receptor 1 (TRPV1) antagonists.

A thiazole derivative, 2-(2,6-dichlorobenzyl)-N-(4-isopropylphenyl) thiazole-4-carboxamide (1), was identified as a TRPV1 antagonist. We synthesized various thiazole analogs and evaluated them for their ability to block capsaicin- or acid-induced calcium influx in TRPV1-expressing CHO cells. The IC(50) values of the most potent antagonists were ca. 0.050microM in these assays.

Amides↗
PubMed1975

L-asparagine uptake in Escherichia coli.

The uptake of L-asparagine by Escherichia coli K-12 is characterized by two kinetic components with apparent Km values of 3.5 muM and 80 muM. The 3.5 muM Km system displays a maximum velocity of 1.1 nmol/min per mg of protein, which is a low value when compared with derepressed levels of other amino acid transport systems but is relatively specific for L-asparagine. Compounds providing effective competition for L-asparagine uptake were 4-carbon analogues of the L-isomer with alterations at the beta-amide position, i.e., 5-diazo-4-oxo-L-norvaline (Ki = 4.6 muM), beta-hydroxyamyl-L-aspartic acid (Ki = 10 muM), and L-aspartic acid (Ki = 50 muM). Asparagine uptake is energy dependent and is inhibited by a number of metabolic inhibitors. In a derived strain of E. coli deficient in cytoplasmic asparaginase activity asparagine can be accumulated several-fold above the apparent biosynthetic pool of the amino acid and 100-fold above the external medium. The high affinity system is repressed by culture of cells with L-asparagine supplements in excess of 1 mM and is suggested to be necessary for growth of E. coli asparagine auxotrophs with lower supplement concentrations.

Asparagine↗
PubMed2005

Are neutral chloroacetamide herbicide degradates of potential environmental concern? Analysis and occurrence in the upper Chesapeake Bay.

Although laboratory studies have revealed that many different neutral degradates of chloroacetamide herbicides can form during thermochemical, biological, and photochemical transformations, relatively few have been sought in the environment, despite their likely generation in appreciable amounts, relative persistence, and known or potential toxicity. The present paper describes a GC/ MS method for the analysis of 20 neutral chloroacetamide degradates, along with the four parent compounds, three triazine herbicides, and two neutral triazine degradates. Using large volume injections and 300:1 concentration via solid phase extraction, detection limits for most neutral chloroacetamide degradates were in the hundreds of pg/L range (low ng/L range for degradates possessing a hydroxy group). In a depth profile taken in midsummer from the upper Chesapeake Bay, 19 of the 20 neutral chloroacetamide degradates of interest were detected, along with three ionic oxanilic acid derivatives. Of those degradates encountered, eight do not appear to have been previously reported in natural or affected environmental samples. Concentrations of most neutral chloroacetamide degradates exceeded those of the parent compounds, while the total concentration of the neutral chloroacetamide degradates was 20-30 times that of the parents. These micropollutants therefore merit more detailed attention as contaminants of potential environmental concern.

Acetamides↗
PubMed1996

A novel automated assay for malate dehydrogenase isoenzymes.

We have developed a new automated method for the determination of malate dehydrogenase (MDH) isoenzymes in serum employing guanidine hydrochloride. Our proposed method showed good reproducibility; within-run precision coefficient of variations (CVs) were less than 2.5 (mean 13.6-42.9 U/L) for total MDH (T-MDH) and less than 6.7% (mean 6.3-23.5 U/L) for mitochondrial MDH (m-MDH) (n = 10). The upper detection limit of the proposed method exhibited good linearity up to 1,000 U/L for both T-MDH and m-MDH. In the proposed m-MDH reagent, the presence of up to 2,000 U/L of cytosolic MDH(c-MDH) activity had no effect on the outcome of m-MDH assay. Results of our proposed method (y) correlated well with those of the electrophoretic method (x) giving the regression equation: y = 1.46 x + 6.87 (N = 30); r = 0.99. Normal concentrations of various anticoagulants and bilirubin did not affect the assay results. Both ascorbic acid and glucose exhibited a slight positive interference with the proposed assay. Clinically, we found that m-MDH activity in serum had greater diagnostic predictive value than T-MDH activity for judging successful outcome of reperfusion therapy; the prognosis was poor when the m-MDH/T-MDH ratio was greater than 20%.

Adult↗
PubMed2002

Structure-metabolism relationships of substituted anilines: prediction of N-acetylation and N-oxanilic acid formation using computational chemistry.

1. The relationship between the in vivo metabolism of substituted anilines, in particular N-acetylation and subsequent formation of oxanilic acids, and their molecular physico-chemical properties has been investigated using computational chemistry and pattern-recognition methods. The methods revealed that the physico-chemical properties most important for N-acetylation and subsequent oxanilic acid formation were electronic descriptors based on partial atomic charges and the susceptibility of the molecules to nucleophilic attack at certain ring positions. 2. The calculated partial atom charge on the amine nitrogen was the parameter most important for predicting that an aniline would be N-acetylated. The calculated nucleophilic susceptibility of the aromatic carbon para to the amino group (NS4) was the most significant parameter for determining oxanilic acid formation following N-acetylation. Thus, highly electron-withdrawing groups substituted at this position gave higher nucleophilic susceptibilities that were related to the presence of an oxanilic acid metabolite. 3. If the parameters relating to N-acetylation were modified by other electron-withdrawing groups in the ring (particularly at the position ortho to the amino group), then acetylation and subsequent oxanilic acid formation did not occur. The introduction of groups that allow the possibility of competing oxidative metabolic pathways elsewhere in the molecule (e.g. CH(3)) also affected the production of oxanilic acids. 4. Using chemometric analysis of the computed physico-chemical properties, the result has been the generation of a model that classifies the metabolism of a number of anilines. This could be used to predict the acetylation and oxanilic formation propensity of a number of substituted anilines whose metabolism was unknown to the system, demonstrating that such techniques may be of use for predicting metabolism and hence could provide support for rational drug design.

Acetylation↗
PubMedDate not supplied

Development of EPA method 535 for the determination of chloroacetanilide and other acetamide herbicide degradates in drinking water by solid-phase extraction and liquid chromatography/tandem mass spectrometry.

U.S. Environmental Protection Agency (EPA) Method 535 has been developed in order to provide a method for the analysis of "Alachlor ESA and other acetanilide degradation products," which are listed on EPA's 1998 Drinking Water Contaminant Candidate List. Method 535 uses solid-phase extraction with a nonporous graphitized carbon sorbent to extract the ethane sulfonic acid (ESA) and oxanilic acid degradates of propachlor, flufenacet, dimethenamid, alachlor, acetochlor, and metolachlor from finished drinking water matrixes. Separation and quantitation of the target analytes are achieved with liquid chromatography/tandem mass spectrometry. Dimethachlor ESA and butachlor ESA were chosen during the method development as the surrogate and internal standard. Drinking water samples were dechlorinated with ammonium chloride without adversely affecting the analyte recoveries. Typical mean recoveries of 92-116% in deionized water and 89-116% in ground water were observed with relative standard deviations of <5%.

Acetamides↗
PubMed1993

Effect of lodoxamide on in vitro and in vivo conjunctival immediate hypersensitivity responses in rats.

The antiallergic compound, lodoxamide, was evaluated for its abilities to attenuate a local allergic reaction in rat conjunctiva in vivo and to inhibit rat conjunctival mast cell mediator release in vitro. Topically applied lodoxamide (0.01, 0.10 and 1.0%, w/v) dose-dependently reduced the allergic response (23, 43 and 72%, respectively) in vivo. Lodoxamide was more effective than cromolyn sodium, N-acetyl aspartyl glutamic acid (Naaxia) and levocabastine, and 25 (7-200) times more potent than nedocromil sodium in direct comparisons. Addition of lodoxamide (10 micrograms/ml) to sensitized conjunctival tissue in vitro immediately prior to antigen challenge significantly reduced the amount of histamine released by the tissue. These data suggest that lodoxamide's in vivo anti-allergic activity in the conjunctiva is associated with its ability to prevent allergic mediator release from mast cells contained in this same tissue.

Administration, Topical↗
PubMed2000

Preparation of N'-[2-(5,6-dimethylbenzothiazolyl)]-N-furfuryloxamide with plant growth regulatory activity.

The reaction of the N-furfuryloxamic acid sodium salt (12) with 1,1'-oxalyldiimidazole (ODI) yielded the imidazolide (13) as an intermediate, and this directly reacted with 2-aminothiazole derivatives (14) or 2-aminobenzothiazole derivatives (15) under essentially neutral conditions to afford the N'-12-(substituted thiazolyl)]- or N'-[2-(substituted benzothiazolyl)]-N'-furfuryloxamides (6 or 7). The prepared compounds (6 and 7) were examined for plant growth regulatory activity in a seed germination assay. The examination resulted in the discovery of some new revelations that N'-[2-(5,6-dimethylbenzothiazlyl)]-N-furfuryloxamide (7c) at the concentration of 1.0 x 10(-3) M completely inhibited the radicle growth of both rape and leek seedlings.

Allium↗
PubMedDate not supplied

Blood acidification in the swimbladder: mechanisms and metabolic pathways.

The metabolism of gas gland cells of the swimbladder epithelium is specialized for the production of acidic metabolites that are released into the blood stream and provoke an increase in gas partial pressure by reducing the effective gas-carrying capacity of the blood. In a subsequent step this initial increase in gas partial pressure is multiplied by back-diffusion of gas molecules from the venous to the arterial side in the countercurrent system, the rete mirabile. Thus, gas partial pressures of up to several hundred atmospheres can be generated in the swimbladder. Measurements of metabolic end products and analysis of the formation of 14CO2 from [1-14C]glucose and [6-14C]glucose revealed that the acidic metabolites are lactic acid, produced in the glycolytic pathway, and also CO2, formed in the pentose phosphate shunt. CO2 easily enters the blood stream by diffusion. The release of protons from isolated gas gland cells, however, is highly dependent on the extracellular sodium concentration. This sodium dependence can in part be blocked by addition of amiloride, indicating that a Na+/H+ exchanger is involved in the release of protons. A significant decrease in the rate of proton secretion in the presence of the carbonic anhydrase inhibitor ethoxzolamide indicates that the second major route for the release of protons includes carbonic anhydrase activity and the diffusion of CO2.

Air Sacs↗
PubMed2006

Cisplatin-induced toxicity is associated with platinum deposition in mouse kidney mitochondria in vivo and with selective inactivation of the alpha-ketoglutarate dehydrogenase complex in LLC-PK1 cells.

The anticancer drug cisplatin is nephrotoxic and neurotoxic. Previous data support the hypothesis that cisplatin is bioactivated to a nephrotoxicant. The final step in the proposed bioactivation is the formation of a platinum-cysteine S-conjugate followed by a pyridoxal 5'-phosphate (PLP)-dependent cysteine S-conjugate beta-lyase reaction. This reaction would generate pyruvate, ammonium, and a highly reactive platinum (Pt)-thiol compound in vivo that would bind to proteins. In this work, the cellular location and identity of the PLP-dependent cysteine S-conjugate beta-lyase were investigated. Pt was shown to bind to proteins in kidneys of cisplatin-treated mice. The concentration of Pt-bound proteins was higher in the mitochondrial fraction than in the cytosolic fraction. Treatment of the mice with aminooxyacetic acid (AOAA, a PLP enzyme inhibitor), which had previously been shown to block the nephrotoxicity of cisplatin, decreased the binding of Pt to mitochondrial proteins but had no effect on the amount of Pt bound to proteins in the cytosolic fraction. These data indicate that a mitochondrial enzyme catalyzes the PLP-dependent cysteine S-conjugate beta-lyase reaction. PLP-dependent mitochondrial aspartate aminotransferase (mitAspAT) is a mitochondrial enzyme that catalyzes beta-elimination reactions with cysteine S-conjugates of halogenated alkenes. We reasoned that the enzyme might also catalyze a beta-lyase reaction with the cisplatin-cysteine S-conjugate. In this study, mitAspAT was stably overexpressed in LLC-PK(1) cells. Cisplatin was significantly more toxic in confluent monolayers of LLC-PK(1) cells that overexpressed mitAspAT than in control cells containing vector alone. AOAA completely blocked the cisplatin toxicity in confluent mitAspAT-transfected cells. The Pt-thiol compound could rapidly bind proteins and inactivate enzymes in close proximity of the PLP-dependent cysteine S-conjugate beta-lyase. Treatment with 50 or 100 microM cisplatin for 3 h, followed by removal of cisplatin from the medium for 24 h, resulted in a pronounced loss of alpha-ketoglutarate dehydrogenase complex (KGDHC) activity in both mitAspAT-transfected cells and control cells. Exposure to 100 microM cisplatin resulted in a significantly greater loss of KGDHC activity in the cells overexpressing mitAspAT than in control cells. Aconitase activity was diminished in both cell types, but only at the higher level of exposure to cisplatin. AspAT activity was also significantly decreased by cisplatin treatment. By contrast, several other enzymes (both cytosolic and mitochondrial) involved in energy/amino acid metabolism were not significantly affected by cisplatin treatment in the LLC-PK(1) cells, whether or not mitAspAT was overexpressed. The susceptibility of KGDHC and aconitase to inactivation in kidney cells exposed to cisplatin metabolites may be due to the proximity of mitAspAT to KGDHC and aconitase in mitochondria. These findings support the hypothesis that a mitochondrial cysteine S-conjugate beta-lyase converts the cisplatin-cysteine S-conjugate to a toxicant, and the data are consistent with the hypothesis that mitAspAT plays a role in the bioactivation of cisplatin.

Animals↗
PubMed2000

Roles of the Dal82p domains in allophanate/oxalurate-dependent gene expression in Saccharomyces cerevisiae.

Allophanate/oxalurate-induced gene expression in Saccharomyces cerevisiae requires at least five transcription factors, four of which act positively (Gln3p, Gat1p, Dal81p, and Dal82p) and one negatively (Dal80p). Gln3p binds to and Gat1p is proposed to bind to single GATA sequences; Dal80p binds to pairs of specifically oriented and spaced GATA sequences, and Dal82p binds to a pathway-specific element, UIS(ALL). Dal82p consists of at least three domains as follows: (i) UIS(ALL) DNA-binding, (ii) transcriptional activation, and (iii) coiled-coil(DAL82). Here we show that the coiled-coil(DAL82) domain possesses two demonstrable functions. (i) It prevents Dal82p-mediated transcription when inducer is absent. (ii) It is a major, although not exclusive, domain through which the inducer signal is received. Supporting the latter conclusion, a 38-amino acid fragment, containing little more than the coiled-coil(DAL82) domain, supports oxalurate-inducible, Dal81p-dependent, reporter gene transcription. Dal81p is required for inducer responsiveness of LexAp-Dal82p and LexAp coiled-coil(DAL82)-mediated transcription but isn't needed for inducer-dependent activation mediated by a Dal82p containing deletions in both the coiled-coil(DAL82), UIS(ALL)-binding domains. There may be an interaction between Dal81p and the coiled-coil(DAL82) domain since (i) Dal81p is required for transcription mediated by LexA-coiled-coil(DAL82)p and (ii) a Dal81p-Dal82p complex is detected by two-hybrid assay.

Bacterial Proteins↗
PubMed2004

Degradation of metolachlor in bare and vegetated soils and in simulated water-sediment systems.

A study was conducted to determine the half-life (t1/2), degradation rate, and metabolites of metolachlor in a water-sediment system and in soil with and without switchgrass. Metolachlor degradation in a laboratory was determined in sediment from Bojac sandy loam soil incubated at 24 degrees C. The study also was conducted in a greenhouse on tilted beds filled with Bojac soil and planted with switchgrass. In both experiments, samples were collected at days 0, 7, 14, 28, 42, 56, and 112 and analyzed for metolachlor and its major metabolites. The water-sediment oxidation-reduction potential took 28 d to reach -371 mV and the pH increased from 5.6 to 6.5 by the last sampling day (day 112). The average soil temperature of the tilted beds with or without switchgrass during the study was 21degrees C and the soil moisture content was 23% by volume. The t1/2 of metolachlor was 34 d in sediment and 8 d in the water phase. The t1/2 of metolachlor in soil from the switchgrass filter strip (6 d) was not different from that in soil without grass (9.6 d). The metolachlor metabolites ethanesulfonic acid (ESA) and oxanilic acid (OA) were detected in the water-sediment system and in soil from tilted beds. In both sediment and soil from tilted beds, the two metabolites peaked by day 56 of incubation and declined after that, indicating transformation to other products. In the water-sediment system, greater quantities of OA and ESA were detected in sediment than in the aqueous phase. The production of OA and ESA in the watersediment system occurred in the first 28 d, when the system was at an aerobic redox state. Metolachlor can degrade in sediment and the relatively high soil temperature and moisture level accelerated its breakdown in beds with and without switchgrass. Under warm and moist soil conditions, the presence of switchgrass has no effect on the degradation of metolachlor.

Acetamides↗
PubMedDate not supplied

Novel chromatographic separation and carbon solid-phase extraction of acetanilide herbicide degradation products.

One acetamide and 5 acetanilide herbicides are currently registered for use in the United States. Over the past several years, ethanesulfonic acid (ESA) and oxanilic acid (OA) degradation products of these acetanilide/acetamide herbicides have been found in U.S. ground waters and surface waters. Alachlor ESA and other acetanilide degradation products are listed on the U.S. Environmental Protection Agency's (EPA) 1998 Drinking Water Contaminant Candidate List. Consequently, EPA is interested in obtaining national occurrence data for these contaminants in drinking water. EPA currently does not have a method for determining these acetanilide degradation products in drinking water; therefore, a research method is being developed using liquid chromatography/negative ion electrospray/mass spectrometry with solid-phase extraction (SPE). A novel chromatographic separation of the acetochlor/alachlor ESA and OA structural isomers was developed which uses an ammonium acetate-methanol gradient combined with heating the analytical column to 70 degrees C. Twelve acetanilide degradates were extracted by SPE from 100 mL water samples using carbon cartridges with mean recoveries >90% and relative standard deviations < or =16%.

Acetanilides↗
PubMed1986

[The effect of selected preparations for the protection of draft horses against dipterous blood-sucking insects].

Dipterous blood-sucking insects (horseflies, black flies, gnats, midges) have negative impacts on the performance of draught horses in forest enterprises. For the protection of these animals, the following preparations were applied at the interval of 24 hours: diethyltoluamide, Oxamat (N,N-diethyloxamine acid, USSR) and Stomoxin (synthetic pyrethroid, product of the firm Wellcome, England). In the course of 66 working days, the performance of test animals treated with 10% water emulsion of diethyltoluamide increased by 49.25 cu. m. of skidded wood, i.e. by 0.74 cu. m. wood per horse/day (21.65%), as compared with the control group. The daily savings of prime costs per test horse/day made 16.99 Kcs (Czechoslovak crowns). In comparison with the control group, the performance of horses treated with 5% water emulsion of Oxamat increased by 85.50 cu. m. wood, i.e. by 1.29 cu. m. wood per horse/day (38.00%). Stomoxin at the concentration of 0.05% acted as a good insecticide but had no marked repellent effect. The results of this study document that the production of effective repellents should be introduced in the Czechoslovak Socialist Republic.

Animals↗
PubMed2000

Determination of chloroacetanilide herbicide metabolites in water using high-performance liquid chromatography-diode array detection and high-performance liquid chromatography/mass spectrometry.

Analytical methods using high-performance liquid chromatography-diode array detection (HPLC-DAD) and high-performance liquid chromatography/mass spectrometry (HPLC/MS) were developed for the analysis of the following chloroacetanilide herbicide metabolites in water: alachlor ethanesulfonic acid (ESA); alachlor oxanilic acid; acetochlor ESA; acetochlor oxanilic acid; metolachlor ESA; and metolachlor oxanilic acid. Good precision and accuracy were demonstrated for both the HPLC-DAD and HPLC/MS methods in reagent water, surface water, and ground water. The average HPLC-DAD recoveries of the chloroacetanilide herbicide metabolites from water samples spiked at 0.25, 0.5 and 2.0 microg/l ranged from 84 to 112%, with relative standard deviations of 18% or less. The average HPLC/MS recoveries of the metabolites from water samples spiked at 0.05, 0.2 and 2.0 microg/l ranged from 81 to 118%, with relative standard deviations of 20% or less. The limit of quantitation (LOQ) for all metabolites using the HPLC-DAD method was 0.20 microg/l, whereas the LOQ using the HPLC/MS method was at 0.05 microg/l. These metabolite-determination methods are valuable for acquiring information about water quality and the fate and transport of the parent chloroacetanilide herbicides in water.

Acetamides↗