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PubMed1989

Identification of isomeric unsaturated medium-chain dicarboxylic acids in human urine.

Dicarboxylic aciduria caused by enhanced or inhibited fatty acid metabolism is usually described as increased urinary excretion of saturated medium-chain dicarboxylic acids, such as adipic, suberic, and sebacic acids. Besides these saturated acids, increased excretion of unsaturated dicarboxylic acids is also observed. However, the structural identities of these unsaturated dicarboxylic acids are largely unknown. Using synthetic authentic samples, dual capillary column gas-liquid chromatography, and capillary column gas-liquid chromatography-mass spectrometry, we have identified these acids as trans-2-hexenedioic, trans-3-hexenedioic, cis-3-octenedioic, cis-4-octenedioic, and trans-3-octenedioic acids. The mass fragmentation pathways of these compounds (as trimethylsilyl derivative) are described. We speculate that the metabolic origin of cis-3-octenedioic acid is oleic acid through the intermediate cis-5-decenedioic acid. We also propose that cis-4-octenedioic acid is derived from linoleic acid. The metabolic origin of trans-3-octenedioic acid is less certain. Since no corresponding cis-hexenedioic acid could be detected in urine, the metabolic degradation of unsaturated dicarboxylic acids appears to terminate at octenedioic acid. Trans-2-hexenedioic acid is probably derived from dehydrogenation of adipic acid.

Acidosis↗
PubMedDate not supplied

Glutamic-oxaloacetic transaminase isozymes in human seminal plasma and sperm extracts.

Leakage of glutamic-oxaloacetic transaminase (GOT) can be used as an indicator of cryo-damage for mammalian spermatozoa. However, two GOT isozymes exist: mitochondrial (m-GOT) and cytosolic or soluble (s-GOT), with acid and alkaline pH optima, respectively. The levels of these GOT isozymes were determined in samples of cell-free human seminal plasma and sperm extracts over a pH range of 3.8 to 9.6. Optimum GOT activities were found at pH 5.2 using cacodylate-HCl buffer (m-GOT) and pH 8.4 using barbital buffer (s-GOT). Differential inhibition studies with adipate (which inhibits s-GOT) were misleading because of the presence of another NADH-linked enzyme able to use adipate as a substrate. Only relatively low levels of m-GOT could be extracted from human spermatozoa (21.4 +/- 31.5 [SD] mU/10(8) cells vs. 202.3 +/- 49.4 mU/mL seminal plasma; n = 20). Consequently, future studies on GOT leakage should be carried out at the alkaline pH optimum, and will therefore measure s-GOT, making this a marker for plasma membrane integrity rather than a measure of mitochondrial damage.

Aspartate Aminotransferases↗
PubMed1987

Acute bronchopulmonary infections: treatment with i.v. spiramycin.

This paper reports the results of an open study to assess the efficacy (433 patients) and tolerance (453 patients) of spiramycin adipate given by slow intravenous infusion to treat severe acute bronchopulmonary infections in adults. Efficacy was good in 80.4% of patients. More specifically, high efficacy was obtained in 76.5% of 85 pneumococcal respiratory infections, 72% of 50 Haemophilus influenzae and H. parainfluenzae infections, 100% of 18 Mycoplasma infections, 100% of 16 Chlamydia infections and 93% of 14 Legionella infections. Tolerance was good in 83.5% of patients, moderate in 15.4% and poor in 6%. Venous irritation was the most frequent complication, observed in 16.3% of patients. No serious complication or sequel was observed. The authors conclude that spiramycin adipate constitutes an appropriate first-line treatment of acute bronchial and/or pulmonary infections in adults. While inferior to benzylpenicillin against Mycoplasma, Chlamydia and Legionella, spiramycin is as active as, and better tolerated than, erythromycin.

Adolescent↗
PubMed1986

Concentrations of penicillin, streptomycin, and spiramycin in bovine udder tissue liquids.

Concentrations of benzylpenicillin and spiramycin adipate were determined in bovine plasma and milk and in lymph draining the udder tissue after IM or IV administration. Combined benzylpenicillin and dihydrostreptomycin sulfate concentrations were also determined in the same fluids after intramammary injection. A superficial parenchymal lymph vessel, afferent to the supramammary lymph gland of the left quarters, was cannulated with a polythene catheter from which the lymph was allowed to drain freely. After injections of 9.5 mg of benzylpenicillin/kg of body weight IM, a mean peak concentration (PC) in lymph (3.7 micrograms/ml), constituting 77% of the PC in plasma (4.8 micrograms/ml), was obtained 0.5 to 1 hour after PC in the plasma. The benzylpenicillin lymph concentration was close to that in plasma for about 7 hours after injection. Thereafter, the benzylpenicillin lymph concentration continued to exceed that in plasma, but not that in milk. After IV administration of spiramycin adipate, the lymph concentration was almost identical to that in plasma. After intramammary injection of procaine benzylpenicillin (400 mg), in combination with the same amount of dihydrostreptomycin sulfate, into 2 udder quarters each, mean PC in the lymph of 3.5 micrograms/ml and 8.4 micrograms/ml, respectively, were obtained 6 hours after injection. In plasma, the mean PC of benzylpenicillin (0.07 micrograms/ml) and of dihydrostreptomycin sulfate (0.85 micrograms/ml) were obtained after 4 and 6 hours, respectively. In milk from the nontreated quarters, a mean concentration of 5 ng of benzylpenicillin/ml was obtained, whereas dihydrostreptomycin sulfate (greater than or equal to 0.3 microgram/ml) was not detected.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1983

Effects of alpha-aminoadipate isomers on the morphology of the isolated chick embryo retina.

The glutamate analogue, alpha-aminoadipate (alpha AA), was administered in the DL-, D-, and L-forms to chick embryo retinas in vitro. Two-hour incubation of retinas, with each form of alpha AA, resulted in glial swelling of progressive severity as the concentration of the adipate increased. Damage was most severe with the L-isomer, which produced a mixed glial-neuronal lesion that affected inner neuronal structures. The effect of the D,L racemic mixture was limited to glia and was less severe than damage seen with the L-isomer. The D-isomer produced effects similar to, but less severe than, those seen with the D,L mixture. Neuronal damage was seen subsequent to extensive Müller cell swelling in longterm cultures (24 hours) with the L- and DL-isomers. In contrast, the D-isomer did not produce discernible neurotoxicity even after a 24-hour treatment with 2.4 mM. Morphologic changes resulting from 2-hour adipate treatment were, to a large extent, reversible.

2-Aminoadipic Acid↗
PubMed1978

A water-soluble cholesterol derivative for use in augmenting serum control materials.

Cholesterol determination has been hampered by the lack of suitable means to prepare lyophilized serum control materials with an appropriate range of values. We prepared a water-soluble cholesterol derivative by first esterifying cholesterol with adipic acid and then reacting the cholesterol hemiadipate with Polyethylene Glycol 600 to form polyethoxyethanyl-cholesteryl adipate. The compound reacts quantitatively in several commonly used methods, including enzymic, extraction, and direct-assay procedures. When the additive is directly mixed with human serum that has been depleted of beta- and pre-beta-lipoproteins, an optically clear solution results for which cholesterol values are stable. The clarity is retained upon lyophilization and reconstitution. Addition of this cholesterol compound to partially delipidized serum appeared to have no significant effect on results of assay of 18 other commonly measured serum constituents.

Cholesterol↗
PubMed1981

[Modification of blood serum mineral levels and aspartate aminotransferase, leucine aminopeptidase and alkaline phosphatase activity and plasma in glucose levels in healthy cattle by Ca-Mg-containing solutions].

Three high-performance cows in lactation were tested each for the effects of two kinds of infusion each, 500 ml of Tetamag-2 solution (60 g of calcium gluconate and 60 g of magnesium adipate) and 500 ml of Calcimag (100 g of calcium gluconate and 20 g of magnesium adipate), upon the levels of calcium, magnesium, Pa, potassium, and sodium as well as upon the activities of aspartate-aminotransferase, leucine-aminopeptidase, and alkaline phosphatase in blood serum and upon glucose levels in blood plasma. Migration of calcium out of blood plasma was found to take place at much higher rate than that of magnesium. Infusion of Pa and glucose was followed soon by some temporary drop of values. No directional effects were recordable from potassium and sodium. Aspartate-aminotransferase activity did not change in response to transfusion. Intravenous infusion of Tetamag-2 solution caused strong temporary rise in magnesium concentration and, consequently, activation of leucine-aminopeptidase.

Alkaline Phosphatase↗
PubMed1996

The mitochondrial permeability transition: a new pathophysiological mechanism for Reye's syndrome and toxic liver injury.

Aspirin, Neem oil, valproic, adipic, benzoic, isovaleric, 3-mercaptopropionic and 4-pentenoic acids are implicated in the pathogenesis of Reye's syndrome, Jamaican vomiting sickness, and related chemical toxicities. These disorders are characterized by hyperammonemia, hypoglycemia, microvesicular steatosis and encephalopathy. The goal of this study was to determine whether chemicals implicated in Reye's-related disorders induce the mitochondrial permeability translation (MPT). The MPT is induced by opening of a high-conductance, cyclosporin-sensitive pore in the mitochondrial inner membrane, causing swelling, depolarization and uncoupling of oxidative phosphorylation. In freshly isolated rat liver mitochondria, unhydrolyzed aspirin (300 microM) did not induce the MPT in the presence of 50 microM CaCl2. Salicylate, the hydrolysis product of aspirin and its active metabolite, was much more potent causing dose-dependent onset of the MPT in a therapeutic range of concentrations (37.5-300 microM). Similarly, Neem oil and valproic, adipic, benzoic, isovaleric, 3-mercaptopropionic and 4-pentenoic acids induced onset of the MPT. In all cases, cyclosporin A (200 nM), a specific inhibitor of the permeability transition pore, blocked the MPT caused by these inducers. Induction of the MPT by these agents was not caused by mitochondrial depolarization because concentrations of valproic acid and salicylate inducing the MPT had little effect on mitochondrial delta psi. Moreover, equivalent uncoupling caused by 5 nM carbonyl cyanide p-trifluoromethoxyphenylhydrazone did not induce an MPT. These data suggest that induction of the MPT is a common pathophysiological mechanism causing mitochondrial injury in Reye's syndrome and Reye's-related drug toxicities.

Animals↗
PubMed1999

Crosslinking of glucoamylases via carbohydrates hardly affects catalysis but impairs stability.

Mild oxidation of glucoamylases from Aspergillus niger (E.C.3.2.1.3. ) with periodate, followed by incubation with adipic acid dihydrazide, covalently linked enzyme molecules via their glycosyl groups. Size exclusion chromatography demonstrated and electron microscopy confirmed the formation of tetramers and octamers. Heat inactivation studies in the range of 60 degrees to 80 degrees C indicated that, in contrast to a priori expectations, crosslinking via the carbohydrates decreased rather than increased thermostability. The covalently linked species, even the octamers, displayed similar activity as the native forms toward maltose and soluble starch, but activity toward raw starch was completely lost.

Adipates↗
PubMed2000

Equilibrium position, kinetics, and reactor concepts for the adipyl-7-ADCA-hydrolysis process.

One of the building blocks of cephalosporin antibiotics is 7-amino-deacetoxycephalosporanic acid (7-ADCA). It is currently produced from penicillin G using an elaborate chemical ring-expansion step followed by an enzyme-catalyzed hydrolysis. However, 7-ADCA-like components can also be produced by direct fermentation. This is of scientific and economic interest because the elaborate ring-expansion step is performed within the microorganism. In this article, the hydrolysis of the fermentation product adipyl-7-ADCA is studied. Adipyl-7-ADCA can be hydrolyzed in an equilibrium reaction to adipic acid and 7-ADCA using glutaryl-acylase. The equilibrium reaction yield is described as a function of pH, temperature, and initial adipyl-7-ADCA concentration. Reaction rate equations were derived for adipyl-7-ADCA-hydrolysis using three (pH-independent) reaction rate constants and the apparent equilibrium constant. The reaction rate constants were calculated from experimental data. Based on the equilibrium position and reaction rate equations the hydrolysis reaction was optimized and standard reactor configurations were evaluated. It was found that equilibrium yields are high at high pH, high temperature and low-initial adipyl-7-ADCA concentration. The course of the reaction could be described well as a function of pH (7-9), temperature (20-40 degrees C) and concentration using the reaction rate equations. It was shown that a series of CSTR's is the best alternative for the process.

Adipates↗
PubMed1984

Capillary gas chromatographic/mass spectrometric analysis of abnormal metabolites in hypoglycin-treated rat urine.

Numerous abnormal metabolites were identified in large amounts in the urine of hypoglycin-treated rats using capillary gas chromatography/mass spectrometry-computer analysis. These metabolites are not detectable in significant amounts in normal rats' urine. Ten of them have not been previously associated with hypoglycin administration: these are several hydroxy compounds, including those from the valine and isoleucine pathways, 2-oxo-adipic acid, n-butyrylglycine and isovaleryl glucuronide. These results indicate that the pathways of isoleucine and valine metabolism are inhibited at their respective acyl-CoA dehydrogenation steps, as is the case for fatty acid, leucine and lysine metabolism, as previously shown. The mass spectra of the trimethylsilyl derivatives of cis, cis-4,7-decadiene-1,10-dioic, cis-4-decene-1,10-dioic, cis-4-octene-1,8-dioic acids, and (methylenecyclopropyl)acetylglycine, which were previously identified using nuclear magnetic resonance and oxidative cleavage or acid hydrolysis, are presented for the first time.

Adipates↗
PubMed2004

Mutational analysis of a key residue in the substrate specificity of a cephalosporin acylase.

beta-Lactam acylases are crucial for the synthesis of semisynthetic cephalosporins and penicillins. Unfortunately, there are no cephalosporin acylases known that can efficiently hydrolyse the amino-adipic side chain of Cephalosporin C. In a previous directed evolution experiment, residue Asn266 of the glutaryl acylase from Pseudomonas SY-77 was identified as being important for substrate specificity. In order to explore the function of this residue in substrate specificity, we performed a complete mutational analysis of position 266. Codons for all amino acids were introduced in the gene, 16 proteins that could be functionally expressed in Escherichia coli were purified to homogeneity and their catalytic parameters were determined. The mutant enzymes displayed a broad spectrum of affinities and activities, pointing to the flexibility of the enzyme at this position. Mutants in which Asn266 was changed into Phe, Gln, Trp and Tyr displayed up to twofold better catalytic efficiency (k(cat)/K(m))than the wild-type enzyme when adipyl-7-aminodesacetoxycephalosporanic acid (adipyl-7-ADCA) was used as substrate, due to a decreased K(m). Only mutants SY-77(N266H) and SY-77(N266M) showed an improvement of both catalytic parameters, resulting in 10- and 15-times higher catalytic efficiency with adipyl-7-ADCA, respectively. Remarkably, the catalytic activity (k(cat)) of SY-77(N266M) when using adipyl-7-ADCA as substrate was as high as when glutaryl-7-aminocephalosporanic acid (glutaryl-7-ACA) was used, and approaches commercially interesting activity. SY-77(N266Q), SY-77(N266H) and SY-77(N266M) mutants showed a modest improvement in hydrolysing Cephalosporin C. Since these mutants also have a good catalytic efficiency when adipyl-7-ADCA is used and are still active towards glutaryl-7-ACA, they can be regarded as broad substrate acylases. These results demonstrate that the combination of directed evolution for the identification of important positions, together with saturation mutagenesis for finding the optimal amino acid, is a very effective method for finding improved biocatalysts.

Adipates↗
PubMed1990

Modeling the uniaxial compaction of pharmaceutical powders using the mechanical properties of single crystals. II: Brittle materials.

A model is presented which uses the hardness and elastic moduli of brittle crystals, determined using the Vickers microindentation test, to predict the uniaxial compaction behavior of compacts. A general approach first developed in the materials science field to predict the densification of particulate matter under hydrostatic loading was followed. Modifications to account for the effects of particle geometry and the closed-die loading conditions were considered. The model predicted the densification behavior of sucrose and adipic acid. It did not predict the densification of acetaminophen as well; however, the discrepancy between the experimental and predicted values may arise either from error associated with the evaluation of the elastic modulus using the microindentation test or from error in calculating the relative density of compacts which were observed to have partially laminated. The effects of error both in the hardness value and in the ratio of punch to die-wall stress on the predictive capability of the model were also discussed briefly.

Acetaminophen↗
PubMed1998

Immobilization of saccharides and peptides on 96-well microtiter plates coated with methyl vinyl ether-maleic anhydride copolymer.

We have previously reported a method to immobilize protein ligands on microtiter plates coated with methyl vinyl ether-maleic anhydride copolymer (MMAC) [Isosaki, K., et al. (1992) J. Chromatogr. 597, 123-128]. In this study, we improved the MMAC method to efficiently immobilize not only small ligands such as peptides and oligosaccharides, which could not be efficiently immobilized previously, but also heparin via its reducing end. Amino and hydrazino groups were introduced to MMAC-coated microtiter plate wells by coupling to acid anhydride groups of MMAC with 1,6-hexamethylenediamine and adipic acid dihydrazide, respectively. The amino groups introduced were allowed to react with peptides by use of divalent cross-linkers. Hydrazino groups were allowed to react with formyl groups of saccharides by reductive amination. Peptides and oligosaccharides were immobilized in a dose-dependent manner by these methods. In the case of the angiotensin peptide thus immobilized, the detection limit by monoclonal antibodies was as low as 0.1-1 fmol peptide per well. Application of 20-200 nmol oligosaccharides to the well was sufficient to immobilize and subsequently detect lectins. Furthermore, heparin immobilized on the hydrazinocoated wells was successfully used for the binding assay of annexin IV.

Adipates↗
PubMed1992

Azelaic and pimelic acids: metabolic intermediates or artefacts?

Azelaic and pimelic acids are excreted in elevated amounts in urine in disorders of mitochondrial beta-oxidation and disorders of peroxisomal beta-oxidation, for which they are of significant diagnostic value. We have detected the presence of azelaic, pimelic and even-chain-length dicarboxylic acids (adipic, suberic and sebacic acids) arising artefactually as a result of storage of small sample volumes in plastic containers. Storage of samples for organic acid analysis in glass containers is recommended.

Adipates↗
PubMed1991

Organic acids in aqueous humour and plasma: post mortem study in infants and diagnosis of enzymopathies.

Organic acids have been determined in aqueous humour and plasma by gas chromatography-mass spectrometry in 38 cases of infant death and 4 cases of inherited metabolic disease: one had a complex fatty-acid oxidation disorder with a large urinary excretion of adipic acid, the others had a disorder of propionate catabolism with a large urinary excretion of methylmalonic acid. In each case we found in aqueous humour the abnormal metabolite present in urine. Thus aqueous humour could be a suitable material for retrospective diagnosis of inherited metabolic diseases at autopsy in sudden infant death syndrome.

Adipates↗
PubMed1987

Urinary organic acids in succinic semialdehyde dehydrogenase deficiency: evidence of alpha-oxidation of 4-hydroxybutyric acid, interaction of succinic semialdehyde with pyruvate dehydrogenase and possible secondary inhibition of mitochondrial beta-oxidation.

In addition to the previously reported abnormalities, urine extracts from three cases of succinic semialdehyde dehydrogenase deficiency have shown consistently increased amounts of 2,4-dihydroxybutyric acid, and its lactone, and 3-hydroxypropionic acid, metabolites related to the alpha-oxidation of 4-hydroxybutyric acid. Threo- and erythro-4,5-dihydroxyhexanoic acids have also been identified for the first time and probably arise from the reaction of succinic semialdehyde with an intermediate in the pyruvate dehydrogenase pathway. Adipic acid excretion is also consistently raised, suggesting secondary interference with mitochondrial beta-oxidation. The presence of these metabolites could be a source of diagnostic confusion.

Adipates↗
PubMed1990

Oriented immobilization of periodate-oxidized monoclonal antibodies on amino and hydrazide derivatives of Eupergit C.

Amino and hydrazyno derivatives of Eupergit C were prepared by reaction of the beads with hexamethylene diamine (HMD) and adipic acid dihydrazide (ADH), respectively. Monoclonal antibodies (mAbs) against carboxypeptidase A (CPA) and horse radish peroxidase (HRP) were prepared, and those that did not inhibit the respective enzymatic activities were selected. The carbohydrate moieties of these antibodies were oxidized by reaction with sodium periodate and then coupled onto the modified beads. The oxidation and coupling reactions were optimized to achieve highly active matrix-conjugated antibodies. Thus, antibody-matrix conjugates that possessed antigen-binding activities close to the theoretical value of 2 mol antigen bound/mol immobilized antibody were obtained.

Acrylic Resins↗