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PubMed1983

pH Dependence of the inhibition of yeast glyoxalase I by porphyrins.

A number of porphyrin derivatives have been found to inhibit yeast glyoxalase I (EC 4.4.1.5) at 25 degrees C, including haemin, protoporphyrin IX, coproporphyrin III, haematoporphyrin, deuteroporphyrin as well as meso-(tetrasubstituted) porphines. Bilirubin and chlorophyllin were also inhibitory, but not cobalamin, adipic, pimelic or suberic acids. Whilst the Ki value for linear competitive inhibition by meso-tetra(4-methylpyridyl)porphine was pH-dependent, analogous Ki values for meso-tetra(4-carboxyphenyl)- and meso-tetra(4-sulphonatophenyl)porphines followed the Henderson-Hasselbalch equation with pKapp values of 7.10 and 6.50, respectively. Protoporphyrin showed similar behaviour (pKapp 7.06) with a deviation at lower pH. The haemin pH profile for Ki showed a maximum at approx. pH 6.5. The redox reaction between haemin and glutathione did not interfere in the inhibition studies. The Ki value for S-(p-bromobenzyl)glutathione was pH-independent. A detailed analysis of porphyrin binding modes was undertaken.

Glutathione↗
PubMed1994

Isolation and properties of mitochondrial aspartate aminotransferase from red muscle of grey mullet, Mugil auratus Risso.

Following the chromatographic separation of the grey mullet (Mugil auratus Risso) red muscle extract, two fractions with aspartate aminotransferase activity were detected. One of the anticipated enzymes was purified to homogeneity. The isolated enzyme was a dimeric protein composed of identical subunits with the overall M(r) of about 65,000. It consisted of three electrophoretically distinct subforms with isoelectric points at pH 8.50, 8.70 and 8.85, respectively. The Michaelis-Menten constants of the substrates L-aspartate and 2-oxoglutarate were estimated to be 0.29 +/- 0.012 mM and 0.45 +/- 0.016 mM, respectively. For the reverse reaction, the Km for L-glutamate was 8.57 +/- 2.1 mM and for oxaloacetate it was 0.13 +/- 0.035 mM. The inhibition of the isolated enzyme by hydroxylamine was of a mixed linear noncompetitive type for L-aspartate as a substrate, whereas with 2-oxoglutarate hyperbolic uncompetitive inhibition was observed. The inhibition by aminooxyacetic acid and D,L-glyceraldehyde 3-phosphate was of a mixed linear noncompetitive type with respect to L-aspartate and 2-oxoglutarate. The isolated enzyme was slightly affected by maleate and succinate and no effects were produced by adipate. According to its subcellular distribution, susceptibility to inhibitors molecular and catalytic properties the isolated enzyme belonged to the mitochondrial form of aspartate aminotransferase.

Animals↗
PubMed1992

Influence of medium composition on the cephalosporin C production with a highly productive strain Cephalosporium acremonium.

Cephalosporin production by a highly productive Cephalosporium acremonium strain was carried out and optimized by fed-batch operation in a 40 l stirred tank reactor using a complex medium containing 30-120 g l-1 peanut flour. The concentrations of cephalosporin C (CPC) and its precursors: penicillin N (PEN N), deacetoxy cephalosporin C (DAOC), and deacetyl cephalosporin C (DAC) were monitored with an on-line HPLC. The concentrations of amino acids valine (VAL), cysteine (CYS), alpha-amino adipic acid (alpha-AAA), the dipeptide alpha-amino-adipyl-cysteine (AC), and the tripeptide alpha-amino-adipyl-cysteinyl-valine (ACV), were determined off-line by HPLC. The RNA content and dry weight of the sediment as well as the oxygen transfer rate (OTR) and the CO2 production rate (CPR) were used to calculate the cell mass concentration (X). The influences of peanut flour (PF) and the on-line monitored and controlled medium components: glucose (GLU), phosphate, methionine (MET) as well as the dissolved oxygen (DOC) on the cell growth, the product formation, and the pathway of cephalosporin C biosynthesis were investigated and evaluated. When the glucose fed-batch cycle was optimized and oxygen transfer limitation was avoided (DOC greater than 20% of the saturation value), high process performance (103.5 g l-1 X, 11.84 g l-1 CPC, a maximum CPC productivity of 118 mg l-1 h-1, and the whole concentration of the beta-lactam antibiotics CPC, DAC, DAOC, PEN N 17.34 g l-1) was achieved by using 100 g l-1 PF in the medium with the optimum concentration of phosphate (260-270 mg l-1) and a low glucose concentration (less than 0.5 g l-1). The cultivations with different medium concentrations demonstrated that the product formation was directly proportional to the cell mass concentration. On the average, the cell mass-based yield coefficient of CPC: YCPC/X amounted to 0.115 g CPC per g cell mass.

Acremonium↗
PubMed1991

Escherichia hermannii (ATCC 33651) polysaccharide-protein conjugates: comparison of two conjugation methods for the induction of humoral responses in mice.

Escherichia hermannii (ATCC 33651) LPS O-polysaccharide was covalently linked to a carrier (bovine serum albumin) to form conjugates either directly or with a spacer arm (adipic acid dihydrazide). The immunogenicity of both conjugates at three different doses was tested in mice. Antibodies to the conjugate were produced and were shown to react with free lipopolysaccharide. The directly-coupled conjugate was found to be more immunogenic than the indirect one (i.e. lower dose necessary for a similar response). The antibody response elicited by the directly coupled conjugate (1 microgram/animal) began at 21 days and was sustained for at least 4 months. The mouse model described here may be applicable to the testing of other conjugates composed of bacterial cell wall polysaccharides and LPS O-chains.

Animals↗
PubMed1995

Synthesis and characterization of a polyvalent Escherichia coli O-polysaccharide-toxin A conjugate vaccine.

A 12-valent Escherichia coli O-polysaccharide (O-PS)-toxin A conjugate vaccine was formulated. Nonpyrogenic, low-molecular-weight O-PS was derived from lipopolysaccharides (LPS) of the following serotypes: O1,O2,O4,O6,O7,O8,O12, O15,O16,O18,O25, and O75. Individual O-PS were covalently coupled to Pseudomonas aeruginosa toxin A using adipic acid dihydrazide as a spacer molecule and carbodiimide as a coupling agent. On a weight basis, the final multivalent vaccine was composed of 43% O-PS and 57% toxin A. The vaccine was nontoxic nad nonpyrogenic in anti-LPS immunoglobulin G (IgG) antibody titers. When passively transferred to mice, immune rabbit IgG conferred statistically significant (p < 0.05) protection against a challenge with 9 of the 12 vaccine serotypes. For two serotypes, although the mortality rate declined by > or 50% in the passively immunized versus the control group, the difference did not reach statistical significance. The degree of protection provided by passively transferred IgG was influenced by both the anti-LPS antibody levels in the IgG preparation and the virulence of the challenge strain. Active immunization of mice with either conjugate vaccine or killed E. coli whole cells did not confer protection. This was most probably due to the fact that these antigens induced a meagre anti-LPS IgG antibody response.

ADP Ribose Transferases↗
PubMed1995

Effect of conjugation methodology, carrier protein, and adjuvants on the immune response to Staphylococcus aureus capsular polysaccharides.

Conjugate vaccines were prepared with S. aureus type 8 capsular polysaccharide (CP) using three carrier proteins: Pseudomonas aeruginosa exotoxin A (ETA), a non-toxic recombinant ETA (rEPA), and diphtheria toxoid (DTd). Adipic acid dihydrazide (ADH) or N-succinimidyl 3-(2-pyridyldithio) propionate (SPDP) was used as a spacer to link the CP to carrier protein. All conjugates gave a high immune response with a boost after the second immunization. Conjugates prepared with ADH gave higher antibody titers than conjugates prepared with SPDP. IgG1 was the primary subclass elicited by all conjugates regardless of the carrier protein or the conjugation method used to prepare the vaccines. The non-immunogenic CP and the conjugates were formulated with either monophosphoryl lipid A (MPL), QS21, or in Novasomes and evaluated in mice. While the adjuvants failed to improve the immunogenicity of the nonconjugated CP, a more than fivefold increase in the antibody levels was observed when these adjuvants were used with the conjugates. Significant rises in IgG2b and IgG3 were observed with all formulations. The enhancement of the immunogenicity and the IgG subclass shift, as seen with some adjuvants, may prove to be important in immunocompromised patients.

ADP Ribose Transferases↗
PubMed1996

A simple, quantitative, reproducible avidin-biotin ELISA for the evaluation of group B streptococcus type-specific antibodies in humans.

Type-specific antibodies to the capsular polysaccharides (CP) of group B Streptococcus (GBS) are protective. Historically, the radioactive antigen-binding assay (RABA) has been used to determine GBS antibody levels. This method measures total immunoglobulin and employs the use of radioactive materials. We have developed an avidin-biotin ELISA that is less hazardous and is able to measure GBS Ia, Ib, II or III CP specific IgG. To avoid inconsistent binding to the plate, the CPs from GBS Ia, Ib, II and III were derivatized using adipic acid dihydrazide (ADH) and subsequently biotinylated without altering their antigenic epitopes and bound to avidin coated plates. Plasma from three different human subjects immunized with a tetravalent CP vaccine were used to prepare IgG references for Ia, II and III, respectively, thus rendering the assay quantitative for those types. The assay is able to detect nanograms per milliliter of GBS Ia, Ib, II or III specific antibody. This method is reproducible, sensitive and correlates with RABA by 76%.

Antibodies, Bacterial↗
PubMed1982

Toxicity of 29 plasticizers to HeLa cells in the MIT-24 system.

The toxicity to HeLa cells of 29 plasticizers was determined in the MIT-24 test system. The 7-day IC50 for HeLa cells varied from 260 to 1.5 g/l. Phthalates, adipates, sebacates, azelates and phosphates with long carbon chain alcohols were very non-toxic to the cells, probably due to insolubility in water of the compounds, while the citrates, some phosphates and the 2 polymer plasticizers had a higher toxicity to the cells. A comparison of the HeLa cytotoxicity with the toxicity in vitro to other cells for 7 plasticizers showed a similarity of the cytotoxicity to all cell types. A comparison of the HeLa cytotoxicity for 20 plasticizers with i.p. lethal dosage in rodents demonstrated a rough similarity of values, suggesting a toxicity in rodents of the compounds by toxic interference of the agents with basal functions and structures of tissues (basal cytotoxicity). Tissue culture studies of the cytotoxic mechanisms of the plasticizers therefore could reveal modes of toxic action in vivo.

Animals↗
PubMed1985

Bacterial mutagenicity testing of urine from rats dosed with 2-ethylhexanol derived plasticizers.

Di-(2-ethylhexyl)phthalate (DEHP) produced hepatocellular carcinomas in rodents at high doses in a NTP/NCI bioassay. DEHP has not shown evidence of genotoxic activity in in vitro mutagenicity tests. We extended these studies by examining the mutagenicity of urine from rats dosed with DEHP, 2-ethylhexanol (2-EH), and several other 2-EH derived plasticizers, i.e. di-(2-ethylhexyl)adipate (DEHA), di-(2-ethylhexyl)terephthalate (DEHT) and tri-(2-ethylhexyl)trimellitate (TEHT). A modified Ames Salmonella/microsome assay was used to determine mutagenicity. Urine was pooled from male Sprague--Dawley rats dosed daily for 15 days with 2000 mg/kg of each test substance with the exception of 2-EH which was given at 1000 mg/kg. Direct plating procedures were used to determine the presence of mutagens in urine. Urine from rats dosed with 8-hydroxyquinoline was used as a positive control. There was no evidence that mutagenic substances were excreted in the urine by rats dosed with either DEHP, DEHA, DEHT, TEHT or 2-EH as determined in the presence or absence of rat liver microsomes, and with or without treatment with beta-glucuronidase/aryl sulfatase. Our findings indicate that the above test compounds were not converted to urinary metabolites that were mutagenic. These observations provide no evidence for a genotoxic mechanism for DEHP carcinogenicity in rodents.

Animals↗
PubMed1987

Amino acids, including neurotransmitter candidates, in a hair cell-enriched fraction from the lateral line of Xenopus laevis.

A hair cell-enriched neuromast fraction from the lateral line of Xenopus laevis was compared with adjacent tactile organ and epidermis for content of primary amine-containing components. Of 32 components quantitated by cation-exchange HPLC with fluorescence detection of orthophthalaldehyde adducts, L-alpha-amino adipic acid, O-phosphoethanolamine, L-alpha-glycerophosphorylethanolamine, O-phospho-L-serine, and L-lysine were elevated in concentration in the neuromast relative to the tactile organ an/or epidermis. L-Aspartic acid, L-asparagine, L-glutamic acid, and taurine were present at higher levels in the tactile organ or epidermis than in the neuromast. Taurine was found in only trace amounts in the neuromast. The tactile organ and epidermis contained at least 3 unidentified primary amine components that were absent or reduced in amount in the neuromast. This study demonstrates that the epidermally-derived, hair cell-containing neuromast of the lateral line of Xenopus laevis is different in molecular composition from surrounding epidermally-derived tissue. Such differences may reflect specialized mechanoreceptive function.

2-Aminoadipic Acid↗
PubMed1994

Studies on the control of Toxocara canis in breeding kennels.

The control of Toxocara canis was investigated in naturally infected unweaned puppies. Anthelmintic treatments were administered to three litters of pups at 2, 4 and 6 weeks of age. When either a new combination anthelmintic containing febantel, pyrantel embonate and praziquantel or fenbendazole was used, the faecal egg output over the first 7 weeks of life was reduced by more than 80% and worm burdens by over 90%. In contrast, piperazine adipate had no appreciable effect on T. canis egg output, even though worm burdens were reduced by 86% by 7 weeks of age. In a further trial using three litters, the worm burden of pups treated with the combination anthelmintic was profiled before and after the 2 week dose and after the 4 week dose. Although worm numbers were substantially reduced by treatment, there was evidence of significant reinfection taking place throughout the control programme. It is concluded that more potent anthelmintics can provide longer term benefits by reducing the numbers of T. canis eggs shed into the environment, but that multiple dosing remains essential for this purpose.

Aging↗
PubMed1976

The derivatization of oxidized polysaccharides for protein immobilization and affinity chromatography.

The present report describes the preparation of modified polysaccharides matrices useful for the synthesis of affinity adsorbents and immobilized proteins. Hydrazido-matrices were synthesized by condensing an excess of the bifunctional reagent, adipic acid dihydrazide, with periodate oxidized cellulose paper, Sephadex, or Sepharose matrices. Ribonucleotide dialdehyde cofactors, glyceraldehyde 3-phosphate, pyridoxal 5'-phosphate and oxidized DNAase B were separately bound to the hydrazido-polymers. Azido-matrices obtained by modification of the hydrazido-derivatives were coupled to specific amino ligands such as amino acids and proteins. Several adsorbents were prepared and used as models for affinity chromatography.

Aldehydes↗
PubMed1996

NAD-glutamate dehydrogenase from Halobacterium halobium: inhibition and activation by TCA intermediates and amino acids.

A variety of metabolites have been found to elicit a form of inhibition or activation on an NAD-specific glutamate dehydrogenase (NAD-GDH, EC 1.4.1.2) from Halobacterium halobium. The purified halophilic enzyme was tested with several compounds known to be allosteric modifiers of mammalian glutamate dehydrogenases to determine their effects on enzyme activity. GTP, ATP, ADP and AMP did not affect the enzyme, so these effectors of bovine glutamate dehydrogenase do not play a role in the regulation of the halophilic enzyme. However, the halophilic enzyme was subject to strong inhibition by TCA intermediates. When measuring the initial rate of the reaction, the oxidative deamination of L-glutamate was inhibited by TCA metabolites such as: fumarate, oxalacetate, succinate and malate; by substrate analogues such as: NADP+, D-glutamate and glutarate; and by dicarboxylic compounds such as adipate. On the other hand, all the amino acids tested were activators of this enzyme, except the D-isomer of the substrate L-glutamate that acted as an inhibitor. The relative effectiveness of each inhibitor or activator (Ki or Ka values) was correlated with the dipole moment (mu), HOMO and LUMO molecular orbital energies, optimal distance between two carboxyl groups, and hydrophobicity. Compounds with high dipole moment acted as good activators while compounds with low dipole moment were inhibitors. We have also found that the best activators were amino acids with no polar lateral chain.

Amino Acids↗
PubMed1990

Autoradiographic characterization of putative excitatory amino acid transport sites.

Removal of excitatory amino acids from the extracellular space is now postulated to occur through at least two distinct transport systems that are distinguished by their ionic dependency. Thus, both sodium-dependent and chloride-dependent systems have been described in the mammalian central nervous system. In this report we attempt to characterize these sites by autoradiography, using D-[3H]aspartate and L-[3H]glutamate as ligands. Previous studies have shown that sequestration of radioligand into membrane vesicles can be a potential artifact when examining transport sites. We have found that sequestration can be alleviated by incubation of tissue sections in xylenes prior to incubation with radioligand. Using in vitro autoradiography we have characterized the two binding sites with respect to their distribution, kinetics and pharmacology. Both appeared to have a single, saturable binding site with Kds in the low micromolar range. Sodium-dependent D-aspartate binding predominated, having a Bmax that was five times greater than chloride-dependent L-glutamate binding in whole brain. The levels of binding to the two sites varied between brain regions. Sodium-dependent D-aspartate binding was highest in the cerebellar molecular layer greater than dentate gyrus molecular layer greater than entorhinal cortex. Chloride-dependent L-glutamate binding was highest in the outer layers of cerebral cortex greater than dentate gyrus molecular layer greater than entorhinal cortex greater than striatum. Pharmacological characterization of these sites also showed major differences. Sodium-dependent D-aspartate binding was most potently inhibited by L-aspartate greater than threo-beta-hydroxyaspartate greater than L-cysteine sulfinic acid greater than L-cysteic acid. Chloride-dependent glutamate binding was most potently inhibited by L-glutamate greater than L-alpha-amino adipic acid greater than quisqualate greater than L-serine-o-sulfate. The differences in distribution, ligand binding properties and pharmacology of these sites suggest that a significant variable in excitatory amino acid circuitry may include heterogeneity in transporters associated with excitatory pathways.

Amino Acids↗
PubMed1988

A glial toxin reduces effects of gold thioglucose on the hypothalamus and area postrema.

To see if DL-alpha amino adipate (DL-AA) an agent known to cause transient swelling and dysfunction of hypothalamic glia, would affect the ability of goldthioglucose (GTG) to cause hypothalamic lesions, groups of male, 100 g rats were given saline, 0.5 mg/g of DL-AA, or 0.75 mg/g of DL-AA 30 min before injection of 0.4 mg/g of GTG. The incidence of GTG lesions was significantly less in the DL-AA treated groups than in the saline treated group. Histochemical staining of brain tissue revealed the existence of a population of specialized iron-containing glia with an anatomical distribution similar to the specific areas in the hypothalamus area postrema most sensitive to GTG. The results suggest that GTG lesion formation may result from an effect of GTG on glia.

2-Aminoadipic Acid↗
PubMed1995

Isolation and characterization of a bacterium which utilizes polyester polyurethane as a sole carbon and nitrogen source.

Various soil samples were screened for the presence of microorganisms which have the ability to degrade polyurethane compounds. Two strains with good polyurethane degrading activity were isolated. The more active strain was tentatively identified as Comamonas acidovorans. This strain could utilize polyester-type polyurethanes but not the polyether-type polyurethanes as sole carbon and nitrogen sources. Adipic acid and diethylene glycol were probably the main degradation products when polyurethane was supplied as a sole carbon and nitrogen source. When ammonium nitrate was used as nitrogen source, only diethylene glycol was detected after growth on polyurethane.

Biodegradation, Environmental↗
PubMed1982

Serum triglyceride and cholesterol contents in male rats receiving diets containing plasticizers and analogues of the ester 2-ethylhexanol.

Male rats were administered diets containing the plasticizers di-(2-ethylhexyl) adipate and di-(ethyl)phthalate,, 2-ethylhexanol, hexanol, 2-ethylhexanoic acid, hexanoic acid, 2-ethylhexyl aldehyde, and hexyl aldehyde for 3 weeks, and serum triglyceride and cholesterol values were determined. Only those compounds which had been found to produce a proliferation of hepatic peroxisomes produced a decrease in both serum lipids.

Animals↗
PubMed1994

Ethylmalonic aciduria: an organic acidemia with CNS involvement and vasculopathy.

Five infants from 3 families, one Egyptian, two Yemeni, are described with a progressive encephalopathy, four of whom have been studied in detail. All patients showed vascular lesions of the skin, characterized by waxing and waning petechiae and ecchymoses. Acrocyanosis was present in three patients. All patients showed retinal lesions characterized by tortuous veins. Protracted diarrhea was not a consistent finding, although they had metabolic crisis in association with diarrhea. They did not show failure to thrive. The neurologic symptoms were indicative of a progressive pyramidal tract disease. Three patients died following sudden emergence of severe basal ganglia, putaminal and head of caudate lesions. In one patient the CT changes in brain were suggestive of infarction. The patients who died manifested pulmonary congestion, or wet lung, and respiratory difficulties during the terminal stage of the disease. In all patients before and during the terminal event, mild-to-moderate hematuria, and in two RBC in CSF, was observed. In one patient there was mild hemoperitoneum at the terminal event. The urine organic acids indicated increased excretion of ethylmalonic, methylsuccinic, glutaric, and adipic acids. The patients invariably showed lactic acidosis, but no ketosis, during and in between the acidotic attacks of the disease. The acylcarnitine profile in blood of two patients showed a pronounced increase in C4 and C5 carnitine esters. In three patients, biopsies from petechiae indicated absence of an immune event, showing only fresh hemorrhage. An immunologic study in one patient was normal for the suppressor:cytotoxic lymphocyte ratio and concentration of interleukin-2 receptor during and in between hemorrhagic attacks. The cytochrome c oxidase activity in fibroblasts was normal. The rate of oxidation of glucose, leucine, isoleucine, valine, propionate and butyrate by fibroblasts was normal. The disease is not responsive to treatment with riboflavin, ascorbic acid, vitamin E, glycine, or carnitine. One patient remained stable on prolonged large doses of methylprednisolone. The biochemical defect leading to ethylmalonic aciduria in this disease remains unknown.

Acidosis↗