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At least 19 recordsLinked to original sources
PubMed2004

Denitrification with epsilon-caprolactam by acclimated mixed culture and by pure culture of bacteria isolated from polyacrylonitrile fibre manufactured wastewater treatment system.

The aim of this study is to isolate denitrifying bacteria utilizing epsilon-caprolactam as the substrate, from a polyacrylonitrile fibre manufactured wastewater treatment system. The aim is also to compare the performance of PAN (polyacrylonitrile) mixed bacteria cultures acclimated to epsilon-caprolactam and isolated pure strain for treating different initial epsilon-caprolactam concentrations from synthetic wastewater under anoxic conditions. The result showed that the PAN mixed bacteria cultures acclimated to epsilon-caprolactam could utilize 1538.5 mg/l of epsilon-caprolactam as a substrate for denitrification. Sufficient time and about 2200 mg/l of nitrate were necessary for the complete epsilon-caprolactam removal. Paracoccus thiophilus was isolated from the polyacrylonitrile fibre manufactured wastewater treatment system and it could utilize 1722.5 mg/l of epsilon-caprolactam as a substrate for denitrification. About 3500 mg/l of nitrate was necessary for the complete removal of epsilon-caprolactam. When the initial epsilon-caprolactam concentration was below 784.3 mg/l, the removal efficiency of epsilon-caprolactam by Paracoccus thiophilus was better than that for the PAN mixed bacteria cultures. The growth of Paracoccus thiophilus was better. However, when the initial epsilon-caprolactam concentration was as high as 1445.8 mg/l, both the epsilon-caprolactam removal efficiency by Paracoccus thiophilus and Paracoccus thiophilus specific growth rate were similar to the PAN mixed bacteria cultures.

Acrylic Resins↗
PubMed1985

Differential modulation of gamma-aminobutyric acid receptors by caprolactam derivatives with central nervous system depressant or convulsant activity.

The effects of a series of caprolactam derivatives with central depressant, convulsant or muscle relaxant activity were investigated upon gamma-aminobutyric acid (GABA) receptor-ionophore binding to rat brain membranes using [3H]GABA, [3H]GABA, [3H]muscimol and [35S]-tert.-butylbicyclophophorothionate ([35S]TBPS) as ligands, and GABA responses in mouse spinal cord neurones in dissociated cell culture. Some caprolactams produced a picrotoxin-like chloride-dependent partial inhibition of muscimol binding and were potent inhibitors of TBPS binding. One compound that was further investigated (4,4,6,6-tetramethylhexahydro-2H-azepin-2-one), inhibited GABA responses and increased the frequency of paroxysmal depolarizations in cultured neurones. Other caprolactams enhanced muscimol binding and were relatively weak inhibitors of TBPS binding, and one (3,3-diallyl-6,6-dimethylhexahydro-2H-azepin-2,4-dione) was shown to enhance GABA responses and produced quiescence of activity in cultured neurones. There was a direct correlation between caprolactam effects on muscimol binding in the presence of chloride ions and their effects on TBPS binding suggesting a similar site of action for the caprolactams influencing the binding of these two ligands. For the two classes of caprolactams, with respect to inhibition or enhancement of muscimol binding, there appeared to be a relationship between in vitro effects and their convulsant or depressant activity in mice. Caprolactams may be useful low molecular weight probes for the study of GABA receptor-ionophore complexes.

Animals↗
PubMed1987

Developmental toxicity studies of caprolactam in the rat and rabbit.

Caprolactam was evaluated for developmental toxicity potential in both rats and rabbits by the oral route. In rats dosed on days 6-15 of gestation with 100, 500 or 1000 mg/kg/day of caprolactam, the maternal survival rate was significantly lower in the high-dose group and implantation efficiencies were slightly lower in the 100 and 1000 mg/groups (but not the 500 mg/kg) than in the control. The incidence of fetal death was comparable for all groups, and the incidence of fetal viability was considerably lower in the high-dose group (but not the mid or low) than in the control group. Visceral anomalies and one visceral variant were observed in one 100 mg/kg and one 500 mg/kg pup, respectively. The anomalies included exencephaly, an incomplete left eyelid, microphthalmia (right), and a protruding tongue. No skeletal anomalies were observed. It was concluded that caprolactam at levels up to at least 500 mg/kg of body weight produced no teratogenic effects in the Fischer 344 rats. In rabbits receiving 50, 150 or 250 mg/kg caprolactam on days 6-28 of gestation, the pregnancy rate in all groups was at least 80%. The numbers of corpora lutea, live and dead fetuses, resorptions, the sex ratio and the pre- and post-implantation losses were not significantly different among the test and control groups. The incidence of major malformations and of minor skeletal anomalies was unaffected by treatment with caprolactam. Maternal weights were depressed in the group receiving 250 mg/kg. Treatment of a separate group with a positive control substance (6-aminonicotinamide) resulted in significantly (P less than 0.001) increased incidences of major malformations, minor visceral anomalies and minor skeletal anomalies. Maternal toxicity in terms of mortality was observed in pregnant rabbits treated with caprolactam at a dose of 250 mg/kg/day. Fetotoxicity was evidenced by lower fetal weights at the 150 and 250 mg/kg/day levels, and an increased incidence of thirteenth ribs was observed at the 250 mg/kg/day dose level. Neither embryotoxicity nor teratogenicity occurred at any dose level.

Animals↗
PubMed1998

Bioremediation of epsilon-caprolactam from nylon-6 waste water by use of Pseudomonas aeruginosa MCM B-407.

Nylon-6, a man-made polymer that finds its application in the manufacture of car tires, ropes, fabrics, automobile parts etc., is manufactured with epsilon-caprolactam. Waste water generated during production of nylon-6 contains the unreacted monomer. Owing to the polluting and toxic nature of epsilon-caprolactam, its removal from waste streams is necessary. Pseudomonas aeruginosa MCM B-407 was isolated from activated sludge used to treat waste from a factory producing nylon-6. This organism was able to remove epsilon-caprolactam with simultaneous reduction in chemical oxygen demand (COD). The degradation of epsilon-caprolactam in waste water was found to be optimal over a wide range of pH from 5.0 to 9.0, temperature of 30 degrees C, and under shake or aerated conditions, with an inoculum density of 10(5) cells/ml and with an incubation period of 24 - 48 h. Thus, Pseudomonas aeruginosa MCM B-407 isolated from the activated sludge exposed to epsilon-caprolactam may play an important role in the bioremediation of epsilon-caprolactam from the waste waters of industries manufacturing nylon-6.

Caprolactam↗
PubMed1998

Subchronic inhalation toxicity study of caprolactam (with a 4-week recovery) in the rat via whole-body exposures.

This study was designed to assess the potential subchronic inhalation toxicity of caprolactam when administered as a 3-micron aerosol from an aqueous solution to Sprague-Dawley CD rats (10/sex/group) via whole-body exposure. The study was enhanced with the inclusion of motor activity measurements and a functional observational battery to assess the neurotoxic potential of caprolactam. The rats were exposed at least 65 times over a 13-week period for 6 h per day, 5 days per week, to target concentrations (3 microns, mass median aerodynamic diameter) of 0, 25, 75, and 250 milligrams per cubic meter (mg/m3). An additional 10 animals/sex/group were similarly exposed and then held for a 4-week recovery period. Exposure levels were determined gravimetrically six times daily; one daily sample was analyzed by high-pressure liquid chromatography. No deaths were observed in the study during the exposure or recovery periods. Treatment-related responses such as labored breathing and nasal discharge were seen during many of the exposures. Similar responses as well as moist rales were seen during the nonexposure periods during the 13 weeks of exposure. However, these responses abated during the 4-week recovery period. There were no clearly treatment-related responses observed with ophthalmoscopic examinations, body weight measurements, food consumption measurements, neurobehavioral evaluations, clinical pathology evaluations, organ weight measurements, or macroscopic pathology examinations. Microscopic findings that were considered related to exposure to the test material were seen in the nasoturbinal tissues (hypertrophy/hyperplasia of goblet cells in the respiratory mucosa and intracytoplasmic eosinophilic material in epithelial cells of the olfactory mucosa) of the two higher-exposure group animals and in the laryngeal tissues (squamous/squamoid metaplasia/hyperplasia of the pseudostratified columnar epithelium covering the ventral seromucous gland) of all three exposure group animals. These changes were considered to be adaptive responses to an irritant (caprolactam). The keratinization of the metaplastic epithelium in the larynx was considered to be an adverse effect. By the end of the 4-week recovery period, there was complete regression of the keratinization in the larynx, but recovery of the adaptive nasoturbinal effects had not completely resolved. In conclusion, the whole-body exposure of Sprague-Dawley rats to caprolactam as a respirable aerosol for 6 h/day, 5 days/week, for 13 weeks at gravimetrically determined levels of 24, 70, and 243 mg/m3 resulted in respiratory tract effects (laryngeal) at the highest exposure level with complete recovery within 4 weeks postexposure. The results indicate that the no-observed-adverse-effect level for caprolactam is 70 mg/m3, based on upper respiratory effects, with 243 mg/m3 representing a no-observed-effect level for systemic toxicity, neurotoxicity, and lower respiratory tract effects.

Administration, Inhalation↗
PubMed2006

Isolation of the epsilon-caprolactam denitrifying bacteria from a wastewater treatment system manufactured with acrylonitrile-butadiene-styrene resin.

epsilon-Caprolactam has high COD and toxicity, so its discharge to natural water and soil systems may lead to an adverse environmental effect on water quality, endangering public health and welfare. This investigation attempts to isolate epsilon-caprolactam denitrifying bacteria from a wastewater treatment system manufactured with acrylonitrile-butadiene-styrene (ABS) resin. The goal is to elucidate the effectiveness of isolated pure strain and ABS mixed strains in treating epsilon-caprolactam from synthetic wastewater. The results reveal that Paracoccus versutus MDC-3 was isolated from the wastewater treatment system manufactured with ABS resin. The ABS mixed strains and P. versutus MDC-3 can consume up to 1539mg/l epsilon-caprolactam to denitrify from synthetic wastewater. Complete epsilon-caprolactam removal depended on the supply of sufficient electron acceptors (nitrate). Strain P. versutus MDC-3, Hyphomicrobium sp. HM, Methylosinus pucelana and Magnetospirillum sp. CC-26 are related closely, according to the phylogenetic analyses of 16S rDNA sequences.

Acrylic Resins↗
PubMed2004

Method of test and survey of caprolactam migration into foods packaged in nylon-6.

An analytical method for the determination of the nylon-6 monomer caprolactam in foods is described. The foodstuff was extracted with ethanol: water (1:2) containing capryllactam as internal standard and the extract was defatted using hexane. The extract was analysed by liquid chromatography coupled with mass spectrometry. The test method was calibrated down to 0.7 mg kg(-1). The repeatability of the method was good, with a relative standard deviation of 9% at the 15 mg kg(-1) level. The method was demonstrated to be accurate in an independent external check sample exercise. The new method was applied to the analysis of 50 retail foodstuffs packaged in nylon-6. Caprolactam was detected and confirmed in nine of the 50 food samples, in the range 2.8-13 mg kg(-1). The presence of caprolactam was indicated in a further 15 samples, in the range 0.8-11 mg kg(-1), but these samples did not meet all of the five confirmation criteria applied. All migration levels (both confirmed and unconfirmed) were below the European specific migration limit for caprolactam, which is 15 mg kg(-1). The average migration for all 50 samples, setting non-detectables at half the limit of detection, was 2.6 mg kg(-1) with a standard deviation of 3.1 mg kg(-1) (n = 50). All samples found to contain detectable levels of caprolactam migration were for applications involving heating the food in the packaging. They were packs of, for example, sausage meat for which the food would have been heat processed in the nylon casing, or they were nylon pouches for heating foods by boiling, microwaving or roasting.

Caprolactam↗
PubMed1986

Mechanism of alpha-amino-epsilon-caprolactam racemase reaction.

alpha-Amino-epsilon-caprolactam racemase catalyzes the exchange of the alpha-hydrogen of the substrate with deuterium during racemization in deuterium oxide. The rate of the hydrogen exchange measured by 1H NMR is lower than that of racemization in deuterium oxide for both the enantiomers. Both the enantiomers of alpha-amino-epsilon-caprolactam show an overshoot of the optical rotation during the enzymatic racemization in deuterium oxide (but not in water). This phenomenon may be attributable to a primary deuterium isotope effect at the alpha-position: alpha-deuterium isotope effects of 3.6 and 2.0 were observed for the racemization of the D and L enantiomers of alpha-amino-epsilon-caprolactam, respectively. Results of tritium-labeling experiments showed that the enzyme catalyzes both retention and inversion of configuration of the substrate with a similar probability in each turnover. Conversion of [alpha-2H]-D-alpha-amino-epsilon-caprolactam in water and unlabeled D-alpha-amino-epsilon-caprolactam in deuterium oxide into the L isomer under nearly single turnover conditions with the enzyme showed significant internal return of the alpha-hydrogen. These results support a single base mechanism for the racemization reaction catalyzed by the enzyme.

Alcaligenes↗
PubMedDate not supplied

[Plasmids controlling biodegradation of epsilon-caprolactam].

Bacterial strains (190) capable of growth on epsilon-caprolactam as a sole source of carbon and nitrogen were isolated from epsilon-caprolactam industrial sewage. Most of the strains (90%) were found to contain plasmids. Some of the strains (36.8%) assigned provisionally to the genus Pseudomonas contained plasmids controlling epsilon-caprolactam catabolism. The plasmids had a molecular mass from 50 to 300 MDa. Certain plasmids differed in the frequency of conjugation transfer and in the presence of other genetic determinants (resistance against heavy metal ions) and also determined the different character of bacterial growth on epsilon-caprolactam and on its intermediate catabolites.

Bacteria↗
PubMed1981

Seizures and dermatitis after exposure to caprolactam.

A 22-year-old man was initially seen with dermatitis, fever, and seizures after three days of occupational exposure to caprolactam, a nylon fiber precursor. A comprehensive neurological investigation showed no organic CNS abnormalities. Although caprolactam has been shown to induce convulsive disorders in experimental animals, to our knowledge, there are no reports of caprolactam-induced seizures in man. The coincidence of typical skin lesions with otherwise unexplained grand mal seizures in this strongly suggests that caprolactam was the cause.

Adult↗
PubMedDate not supplied

[Influence of clay minerals on the oxidative activity of the caprolactam destructors Bacillus subtilis 6 and 21].

By the Warburg manometric method the respiratory activity of the caprolactam destructors--Bacillus subtilis strains 6 and 21 was measured. The bacteria grown on the synthetic nutrient medium with caprolactam as the sole source of carbon and nitrogen oxidized that substrate more intensively than the cells grown on meat-peptone agar. The activity of caprolactam oxidation by the cultures showed strain differences. Clay minerals--montmorillonit, palygorskit, bentonit and vermiculit--stimulated the glucose and caprolactam oxidation by the above bacteria. The highest stimulating effect was produced by montmorillonit.

Bacillus subtilis↗
PubMed1989

A spectrophotometric assay for meso-diaminopimelate decarboxylase and L-alpha-amino-epsilon-caprolactam hydrolase.

A spectrophotometric assay for the activities of mesodiaminopimelate decarboxylase and L-alpha-amino-epsilon-caprolactam hydrolase is described. With the commercially available enzyme saccharopine dehydrogenase lysine formed either by decarboxylation of meso-diaminopimelate or by hydrolysis of L-alpha-amino-epsilon-caprolactam is converted to saccharopine with the concomitant oxidation of NADH, which is monitored by the decrease in absorbance at 340 nm. For meso-diaminopimelate decarboxylase this assay can be performed either as an endpoint determination, when working with crude extracts, or as a continuous spectrophotometric assay of partially purified enzyme preparations. The activity of L-alpha-amino-epsilon-caprolactam hydrolase can only be assayed by the endpoint method because of the great differences in the pH optima of the hydrolase and the saccharopine dehydrogenase.

Azepines↗
PubMed1989

Abnormal sperm assay tests on benzoin and caprolactam.

Benzoin and caprolactam, two noncarcinogenic chemicals found in association with consumer products, were tested in the mammalian in vivo abnormal spermhead assay. Each chemical was dissolved in a pharmaceutical grade corn oil and administered by gavage. Toxic effects were observed only with caprolactam-treated mice. Neither benzoin nor caprolactam induced a significant increase in the frequency of abnormal sperm as compared to that for animals treated only with the corn oil.

Animals↗
PubMed1987

Identification of ninhydrin-positive caprolactam metabolites in the rat.

Caprolactam (2-oxohexamethylenimine) is metabolized in the rat partly to 4-hydroxycaprolactam or the corresponding free acid. The 4-hydroxy metabolite rearranges spontaneously in acidic aqueous medium to an equilibrium mixture of which 6-amino-gamma-caprolactone is the major component and 6-amino-4-hydroxyhexanoic acid is a minor component. Approximately 16% of the caprolactam ingested daily by rats fed a diet containing 3% caprolactam was excreted as the 4-hydroxy metabolite and a small amount was excreted as the non-hydroxylated acid, 6-aminohexanoic acid. The metabolites were isolated by ion-exchange chromatography and identified by gas chromatography-mass spectroscopy and infra-red and nuclear magnetic resonance spectroscopy.

Amino Acids↗
PubMed2005

Leukemia risk in caprolactam workers exposed to benzene.

PURPOSE: To investigate the leukemia risk in a group of benzene exposed workers. METHODS: We conducted a retrospective cohort mortality study on 311 men who worked between January 1, 1951 and December 31, 1968 in a Caprolactam plant in the Netherlands. In the production of Caprolactam (the Nylon 6 monomer) pure benzene is used as an extracting agent and the workers at this plant have been exposed to substantial concentrations of benzene. The cohort was followed for mortality until January 1, 2001. The total mortality was below the expected number, which was mainly caused by a deficit of cardiovascular disease mortality. RESULTS: In the total group, there was one death from leukemia, compared with an expected number of 1.17. Despite the substantial exposures to benzene (on average 159 ppm-years per person) there was no indication for increased leukemia mortality within the cohort. We have applied earlier quantitative risk assessments to our cohort and conclude that some of these assessments overestimate the risk observed in our cohort of Caprolactam workers.

Algorithms↗
PubMed1997

Synthesis and anticonvulsant activities of 3,3-dialkyl- and 3-alkyl-3-benzyl-2-piperidinones (delta-valerolactams) and hexahydro-2H-azepin-2-ones (epsilon-caprolactams).

A series of 3-substituted 2-piperidinone (delta-valerolactam) and hexahydro-2H-azepin-2-one (epsilon-caprolactam) derivatives were prepared and evaluated as anticonvulsants in mice. In the 2-piperidinone series, 3,3-diethyl compound 7b is the most effective anticonvulsant against pentylenetetrazole-induced seizures (ED50, 37 mg/kg; PI (TD50/ED50), 4.46), and 3-benzyl compound 4c (ED50, 41 mg/kg; PI, 7.05) is the most effective anticonvulsant against seizures induced by maximal electroshock. By contrast, none of the epsilon-caprolactams tested had anticonvulsant effects below doses causing rotorod toxicity. log P values were correlated with neurotoxicity and [35S]TBPS displacement, but not with anticonvulsant activity. Electrophysiological evaluations of selected compounds from each series indicated that both the delta-valero-lactams and epsilon-caprolactams potentiated GABA-mediated chloride currents in rat hippocampal neurons.

Animals↗
PubMedDate not supplied

[Regulation of the expression of plasmid determination responsible for caprolactam degradation by bacteria of the genus Pseudomonas].

On the basis of the study of some Tn5 induced mutants in Pseudomonas putida strain BS836 containing the plasmid pBS268 coding caprolactam degradation, growth on caprolactam and its intermediates, and the data on the induction of oxidative activities in plasmid containing P. putida strain BS831 it was shown that plasmid and chromosome genes regulated the expression of CAP-determinants. The regulation has some elements of the negative control mechanism. Caprolactam is the inducer of the synthesis of key enzymes cleaving it and its intermediates (aminocaproic and adipic acids). At the same time each of its intermediates induced the synthesis of enzymes responsible for its cleavage.

Caprolactam↗
PubMed1977

[Methods for the sampling and tracing of caprolactam monomer dispersed in the air].

The problem of hygiene in the production of epsilon-caprolactam is very important; pollution of work room air is possible when the substance is stored, transported or packed in bags. In this work toxic and irritant properties of epsilon-caprolactam are described. Infrared spectroscopic, gas chromatrographic and spectrophotometric methods used by us, for the determination of epsilon-caprolactam traces, are also described.

Air Pollutants↗