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PubMed2006

Effect of acrylamide on the cytoskeleton and apoptosis of bovine lens epithelial cells.

Acrylamide, a known disrupter of intermediate filaments, has been used to produce the collapse of vimentin filaments in bovine lens epithelial (BEL) cells, and its potential modulation of staurosporine-induced apoptosis has been investigated. In BEL cells, short treatments with acrylamide caused the collapse of vimentin filaments and microtubules and the almost complete disappearance of stress fibers, with thick f-actin bundles remaining in the cell periphery. Actin organization was less affected in cells pretreated with colchicine and in spreading cells, suggesting that extended microtubules and vimentin filaments are required for acrylamide to produce its maximal effects. Acrylamide alone slightly increased apoptosis compared to controls. However, simultaneous exposure to acrylamide and staurosporine for 8h produced significantly less apoptosis than staurosporine alone, and preincubation with acrylamide followed by staurosporine markedly reduced apoptosis at 8 and 24h of treatment. Acrylamide seems therefore to have a dual effect on BEL cell survival.

Acrylamide↗

PubMed2005

Bis-(acrylamide)s as new cross-linkers for resin-based composite restoratives.

OBJECTIVES: The objective of this study was to investigate the use of three new bis-(acrylamide)s as cross-linker in resin-based composite restoratives. Selected mechanical properties such as flexural strength and flexural modulus of model composites containing bis-(acrylamide)s were investigated and compared to the properties of composites that are based on only conventional dimethacrylates. In addition, the hydrolytic stability of composites containing an acidic monomer was examined. METHODS: The flexural strength and flexural modulus of elasticity were determined according to ISO 4049:2000. For this purpose, test specimens (2 mm x 2 mm x 25 mm) of the composites investigated were prepared in stainless steel moulds and light-cured (150 mW/cm2, 2 x 180 s). The flexural strength and flexural modulus were measured after the samples had been stored in dry conditions or in water for 24 h at 37 degrees C as well as after they had been stored in water for 7 days at 37 degrees C, and in certain cases, after they had been boiled for 24 h in water. RESULTS: Visible light cured mixtures of dimethacrylates with bis-(acrylamide)s and composites based on these mixtures show a similar reactivity, flexural strength and flexural modulus of elasticity compared to materials that contain only dimethacrylate. The composites did not show any deterioration of the mechanical properties after water storage. Only when strongly acidic monomers were added to the composites containing dimethacrylates or bis-(acrylamide)s did the flexural strength and flexural modulus of the samples decrease after they were stored in water. SIGNIFICANCE: Bis-(acrylamide)s were similarly reactive than dimethacrylates and therefore can be used as diluents to substitute dimethacrylate diluents in composites. Although the bis-(acrylamide)s are entirely soluble in water, non-ionic materials based on bis-(acrylamide)s did not strongly change their mechanical properties during storage in water.

Acrylamides↗

PubMed2005

Micellar copolymerization of associative polymers: study of the effect of acrylamide on sodium dodecyl sulfate-poly(propylene oxide) methacrylate mixed micelles.

Mixed micelles of sodium dodecyl sulfate (SDS) and poly(propylene oxide) methacrylate (PPOMA) have been studied in the presence of acrylamide using conductimetry, fluorescence spectroscopy, and small-angle neutron scattering (SANS) under the following conditions: (i) the SDS-acrylamide binary system in water; (ii) the SDS-acrylamide-PPOMA ternary system in water. The addition of acrylamide in SDS solutions perturbs the micellization of the surfactant by decreasing the aggregation number of the micelles and increasing their ionization degree. The variations of the various micellar parameters versus the weight ratio R=PPOMA/SDS are different in the presence of acrylamide or in pure water. These differences are much more pronounced for the lower than for the higher PPOMA concentrations. There is competition between acrylamide and PPOMA and at higher PPOMA concentration, acrylamide tends to be released from SDS micelles and is completely replaced by PPOMA.

Acrylamide↗

PubMed2006

Acrylamide, an in vivo thyroid carcinogenic agent, induces DNA damage in rat thyroid cell lines and primary cultures.

Chronic treatment of rats with acrylamide induces various tumors among which thyroid tumors are the most frequent. The aim of the present study was to develop an in vitro model of acrylamide action on thyroid cells to allow the investigation of the mechanism of this tumorigenic action. The first part of the study considered as targets, characteristics of thyroid metabolism, which could explain the thyroid specificity of acrylamide action: the cAMP mitogenic effect and the important H2O2 generation by thyroid cells. However, acrylamide did not modulate H2O2 or cAMP generation in the thyroid cell models studied. No effect on thyroid cell proliferation was observed in the rat thyroid cell line FRTL5. On the other hand, as shown by the comet assay, acrylamide induced DNA damage, as the positive control H2O2 in the PC Cl3 and FRTL5 rat thyroid cell lines, as well as in thyroid cell primary cultures. The absence of effect of acrylamide on H2AX histone phosphorylation suggests that this effect does not reflect the induction of DNA double strand breaks. DNA damage leads to the generation of mutations. It is proposed that such mutations could play a role in the carcinogenic effect of acrylamide. The mechanism of this effect can now be studied in this in vitro model.

Acrylamide↗

PubMed2005

Acrylamide-induced oxidative stress and biochemical perturbations in rats.

Acrylamide is neurotoxic to experimental animals and humans. Also, it has mutagenic and carcinogenic effects. The present study was carried out to investigate the effects of different doses of acrylamide on some enzyme activities and lipid peroxidation in male rats. Animals were assigned at random to one of the following treatments: group 1 served as control, while groups 2, 3, 4, 5, 6 and 7 were treated with 0.5, 5, 25, 50, 250 and 500 microg/kg body weight of acrylamide, respectively in drinking water for 10 weeks. Acrylamide significantly decreased plasma protein levels and the activity of creatine kinase, while increased plasma phosphatases. The activities of transaminases and phosphatases were significantly decreased in liver and testes, while lactate dehydrogenase did not change compared to control group. Plasma and brain acetylcholinesterase activity was significantly decreased. The concentration of thiobarbituric acid reactive substances, and the activities of glutathione S-transferase and superoxide dismutase in plasma, liver, testes, brain, and kidney were increased in acrylamide-treated rats. On the other hand, results obtained showed that acrylamide significantly reduced the content of sulfhydryl groups and protein in different tissues. The present results showed that different doses of acrylamide exerted deterioration effects on enzyme activities and lipid peroxidation in a dose-dependent manner.

Acrylamide↗

PubMed2001

Denitrification with acrylamide by pure culture of bacteria isolated from acrylonitrile-butadiene-styrene resin manufactured wastewater treatment system.

Acrylamide is widely used in industrial applications as cement binder and solidification agent. Due to its carcinogenicity and toxicity, discharge of acrylamide to the natural water and soil systems may lead to an adverse environmental impact on water quality and thus endanger public health and welfare. This study attempts to isolate and identify the denitrifying bacteria, which utilize acrylamide as the substrate from the acrylonitrile-butadiene-styrene resin manufactured wastewater treatment system. The performance of the denitrifying bacteria for treating different initial acrylamide concentrations was also investigated under aerobic and anaerobic conditions. The test results indicated that the Pseudomonas stutzeri could remove acrylamide at concentrations below 440 mg/l under aerobic conditions. The acrylic acid and ammonia intermediates were used as carbon and nitrogen sources, respectively. However, P. stutzeri did not show the capability of metabolizing acrylonitrile under aerobic conditions. Furthermore, the P. stutzeri could utilize both acrylamide and acrylic acid in the presence of nitrate (denitrification) and acrylamide could be removed completely from the wastewater.

Acrylamide↗

PubMed2004

In-depth mechanistic study on the formation of acrylamide and other vinylogous compounds by the maillard reaction.

The formation of acrylamide was studied in low-moisture Maillard model systems (180 degrees C, 5 min) based on asparagine, reducing sugars, Maillard intermediates, and sugar degradation products. We show evidence that certain glycoconjugates play a major role in acrylamide formation. The N-glycosyl of asparagine generated about 2.4 mmol/mol acrylamide, compared to 0.1-0.2 mmol/mol obtained with alpha-dicarbonyls and the Amadori compound of asparagine. 3-Hydroxypropanamide, the Strecker alcohol of asparagine, generated only low amounts of acrylamide ( approximately 0.23 mmol/mol), while hydroxyacetone increased the acrylamide yields to more than 4 mmol/mol, indicating that alpha-hydroxy carbonyls are much more efficient than alpha-dicarbonyls in converting asparagine into acrylamide. The experimental results are consistent with the reaction mechanism based on (i) a Strecker type degradation of the Schiff base leading to azomethine ylides, followed by (ii) a beta-elimination reaction of the decarboxylated Amadori compound to afford acrylamide. The beta-position on both sides of the nitrogen atom is crucial. Rearrangement of the azomethine ylide to the decarboxylated Amadori compound is the key step, which is favored if the carbonyl moiety contains a hydroxyl group in beta-position to the nitrogen atom. The beta-elimination step in the amino acid moiety was demonstrated by reacting under low moisture conditions decarboxylated model Amadori compounds obtained by synthesis. The corresponding vinylogous compounds were only generated if a beta-proton was available, for example, styrene from the decarboxylated Amadori compound of phenylalanine. Therefore, it is suggested that this thermal pathway may be common to other amino acids, resulting under certain conditions in their respective vinylogous reaction products.

Acetone↗

PubMed2005

Acrylamide formation from asparagine under low moisture Maillard reaction conditions. 2. Crystalline vs amorphous model systems.

The formation of acrylamide was investigated in model systems based on asparagine and glucose under low moisture Maillard reaction conditions as a function of reaction temperature, time, physical state, water activity, and glass transition temperature. Equimolar amorphous glucose/asparagine systems with different water activities were prepared by freeze drying and were shown to quickly move to the rubbery state already at room temperature and a water activity of above 0.15. The acrylamide amounts were correlated with physical changes occurring during the reaction. Pyrolysis and kinetics of acrylamide release in amorphous and crystalline glucose/asparagine models indicated the importance of the physical state in acrylamide formation. In amorphous systems, acrylamide was generated in higher concentrations and at lower temperatures as compared to the crystalline samples. Time and temperature are covariant parameters in both systems affecting the acrylamide formation by thermal processes. On the other side, the water activity and glass transition temperature do not seem to be critical parameters for acrylamide formation in the systems studied.

Acrylamide↗

PubMed2005

Influence of storage practices on acrylamide formation during potato frying.

A number of parameters linked to storage of potatoes were evaluated with regard to their potential to influence the acrylamide formation in French fries. Acrylamide, which is a potential human carcinogen, is reported to be formed during the frying of potatoes as a result of the reactions between asparagine and reducing sugars. This study was conducted using three potato varieties (Bintje, Ramos, and Saturna) typically used in Belgium, The Netherlands, and the northern part of France for French fry and crisp production. Saturna, mainly used in crisp production, appeared to be the least susceptible for acrylamide formation during frying. Especially storage at low temperatures (4 degrees C) compared to storage at 8 degrees C seemed to enhance acrylamide formation due to a strong increase in reducing sugars caused by low-temperature storage. Because of the reversible nature of this physiological reaction, it was possible to achieve a significant reduction of the reducing sugars after a reconditioning of the cold-stored potatoes for 3 weeks at 15 degrees C. All changes in acrylamide concentrations could mainly be explained by the reducing sugar content of the potato (R2 = 0.84, n = 160). This means that, by ensuring a low reducing sugar content of the potato tuber, the risk for acrylamide formation will largely be reduced. Finally the use of a sprout inhibitor did not influence the composition of the potato, and thus acrylamide formation was not susceptible to this treatment.

Acrylamides↗

PubMed2005

Acrylamide in roasted almonds and hazelnuts.

The influences of composition and roasting conditions on acrylamide formation in almonds and hazelnuts were investigated. Eighteen samples of almonds originating from the U.S. and Europe were analyzed for sugars and free amino acids, and acrylamide formed during roasting was determined. Asparagine was the main free amino acid in raw almonds and correlated with the acrylamide content of dark roasted almonds. Roasting temperature was another key factor and had a very strong influence on acrylamide formation. Almonds of European origin contained significantly less free asparagine and formed significantly less acrylamide during roasting as compared to the almonds from the U.S. Roasted hazelnuts contained very little acrylamide because of the low content of free asparagine in the raw nut. Reducing sugars, although being consumed much faster than free amino acids in both types of nuts, were not decisive for the extent of acrylamide formation during roasting.

Acrylamide↗

PubMed2005

On-line MS/MS monitoring of acrylamide generation in potato- and cereal-based systems.

An on-line MS/MS technique was used to study the generation of acrylamide in rye-, wheat-, and potato-based systems during cooking. Acrylamide release to the gas phase was monitored continuously and was correlated with the acrylamide content of samples using a calibration based upon the partition of [1,2,3-(13C3)]acrylamide. On-line results at 180 degrees C were compared with data relating to the same systems obtained through GC-MS analysis. Agreement between the two techniques was notable, both in terms of the temporal profiles of acrylamide generation and when comparing the relative magnitudes of results for potato, wheat, and rye determined by each method. The effects of pH (citric acid) and added amino acids (soy protein hydrolysate) on the generation of acrylamide in hydrated potato flake were modeled at 180 degrees C. It was concluded that a combined treatment of low levels of each additive could result in significant reductions in acrylamide, although the effects of such treatments on sensory properties such as color and flavor remain to be evaluated.

Acrylamide↗

PubMed2006

Influence of thermal processing conditions on acrylamide generation and browning in a potato model system.

Fried potato products such as French fries and chips may contain substantial amounts of acrylamide. Numerous efforts are undertaken to minimize the acrylamide content of these products while sensory properties such as color and flavor have to be respected as well. An optimization of the frying process can be achieved if the basic kinetic data of the browning and acrylamide formation are known. Therefore, heating experiments with potato powder were performed under controlled conditions (moisture, temperature, and time). Browning and acrylamide content both increased with heating time at all temperatures and moisture contents tested. The moisture content had a strong influence on the activation energy of browning and acrylamide formation. The activation energy strongly increased at moisture contents below 20%. At higher moisture contents, it was very similar for both parameters. At low moisture contents, the activation energy of acrylamide formation was larger as compared to the one for browning. This explains why the end of the frying process is very critical. Therefore, a lower temperature toward the end of frying reduces the acrylamide content of the product while color development is still good.

Acrylamide↗

PubMed2006

Analysis of acrylamide in green tea by gas chromatography-mass spectrometry.

Optimization of the solid-phase extraction cleanup procedure enabled the GC-MS analysis of acrylamide in tea samples without the interference of bromination by tea catechins. Although polyvinylpolypyrrolidone (PVPP) is available for removing tea catechins from tea extract, the peaks derived from PVPP had the same retention time as brominated acrylamide in mass chromatograms obtained by GC-MS. A considerable amount of acrylamide was formed at roasting temperatures of > or =120 degrees C; the highest acrylamide level was observed when tea samples were roasted at 180 degrees C for 10 min. Higher temperatures and longer processing times caused a decrease in the acrylamide content. Furthermore, an analysis of 82 tea samples showed that rather than the reducing sugar content, the asparagine content in tea leaves was a significant factor related to acrylamide formation in roasted products. The acrylamide level in roasted tea products was controlled by asparagine in the presence of reducing sugars.

Acrylamide↗

PubMed2006

Influence of agronomic factors and extraction rate on the acrylamide contents in yeast-leavened breads.

Because the impact of agronomical factors on bakery products quality is still an insufficiently studied field, acrylamide contents of breads produced from flours of nine wheat, two rye, and two spelt varieties harvested in 2003 and 2004 were investigated. It could be demonstrated that acrylamide content in bread strongly depends on the cultivar, with extremes differing by a factor of 5.4 due to marked differences in free asparagine and crude protein contents. Nitrogen fertilization also resulted in elevated amino acid and protein contents, thus increasing acrylamide levels from 10.6 to 55.6 mug/kg. Independent of fertilization, harvest year turned out to be another factor influencing acrylamide formation. Breads produced from 2003 flours showed significantly higher acrylamide contents than those of 2004, which was ascribed to favorable light and temperature conditions during the cultivation period, thus enhancing amino acid and protein contents. Sprouting of the grain also resulted in significantly higher acrylamide levels, which was attributed to elevated enzyme activities and the formation of precursors from protein and starch. Furthermore, bakery products made from flours with higher extraction rates were shown to contain higher acrylamide levels resulting from extracted free asparagine and protein from the aleuron layers of the cereal grain.

Acrylamide↗

PubMedDate not supplied

Characterization and quantitation of urinary metabolites of [1,2,3-13C]acrylamide in rats and mice using 13C nuclear magnetic resonance spectroscopy.

Acrylamide, widely used for the production of polymers and as a grouting agent, causes neurotoxic effects in humans and neurotoxic, genotoxic, reproductive, and carcinogenic effects in laboratory animals. In this study, 13C NMR spectroscopy was used to detect metabolites of acrylamide directly in the urine of rats and mice following administration of [1,2,3-13C]acrylamide (50 mg/kg po). Two-dimensional NMR experiments were used to correlate carbon signals for each metabolite in the urine samples and to determine the number of hydrogens attached to each carbon. Metabolite structures were identified from the NMR data together with calculated values of shift for biochemically feasible metabolites and by comparison with standards. The metabolites assigned in rat and mouse urine are N-acetyl-S-(3-amino-3-oxopropyl)cysteine, N-acetyl-S-(3-amino-2-hydroxy-3-oxopropyl)cysteine, N-acetyl-S-(1-carbamoyl-2-hydroxy-ethyl)cysteine, glycidamide, and 2,3-dihydroxypropionamide. These metabolites arise from direct conjugation of acrylamide with glutathione or from oxidation to the epoxide, glycidamide, and further metabolism. Acrylamide was also detected in the urine. Quantitation was carried out by integrating the metabolite carbon signals with respect to that of dioxane added at a known concentration. The major metabolite for both the rat (70% of total metabolites excreted) and the mouse (40%) was formed from direct conjugation of acrylamide with glutathione. The remaining metabolites for the rat (30%) and mouse (60%) are derived from glycidamide. The species differences in extent of metabolism through glycidamide may have important consequences for the toxic and carcinogenic effects of acrylamide.

Acetylcysteine↗

PubMed2003

A sensitive gas chromatographic-tandem mass spectrometric method for detection of alkylating agents in water: application to acrylamide in drinking water, coffee and snuff.

A sensitive analytical method for the analysis of acrylamide and other electrophilic agents in water has been developed. The amino acid L-valine served as a nucleophilic trapping agent. The method was applied to the analysis of acrylamide in 0.2-1 mL samples of drinking water or Millipore-filtered water, brewed coffee, or water extracts of snuff. The reaction product, N-(2-carbamoylethyl)valine, was incubated with pentafluorophenyl isothiocyanate to give a pentafluorophenylthiohydantoin (PFPTH) derivative. This derivative was extracted with diethyl ether, separated from excess reagent and impurities by a simple extraction procedure, and analyzed by gas chromatography-tandem mass spectrometry. (2H3)Acrylamide, added before the reaction with L-valine, was used as internal standard. Acrylamide and the related compound, N-methylolacrylamide, gave the same PFPTH derivative. The concentrations of acrylamides were < or = 0.4 nmol L(-1) (< or = 0.03 microg acrylamide L(-1)) in water, 200 to 350 nmol L(-1) in brewed coffee, and 10 to 34 nmol g(-1) snuff in portion bags, respectively. The precision (the coefficient of variation was 5%) and accuracy of the method were good. The detection limit was considerably lower than that of previously published methods for the analysis of acrylamide.

Acrylamide↗

PubMed2002

Verification of the findings of acrylamide in heated foods.

We report here the first confirmation of the recent Swedish findings of acrylamide in heated foods. The verification exercise used an LC-MS/MS method developed for the purpose as well as an established GCMS method for acrylamide analysis. LC-MS/MS was suitable for the direct determination of acrylamide in aqueous extracts of foods by isotope dilution mass spectrometry (IDMS) using triply deuterated acrylamide. Some food matrices were not suited to the new method and mixed-mode solid-phase extraction (SPE) was used to clean these extracts. The foods tested included UK versions of some of the key food groups analysed in Sweden. Also tested were some foods heated under home-cooking conditions. There was good agreement between the LC-MS/MS results and the GC-MS results and the levels of acrylamide found here were similar to those reported for the corresponding foods analysed in the Swedish study. The analyses confirmed that acrylamide is absent from the raw or boiled foods but present at significant levels in fried, grilled, baked and toasted foods. The highest result was 12000 microg kg(-1) acrylamide in overcooked oil-fried chips.

Acrylamide↗

PubMed2005

An occupational hygiene investigation of exposure to acrylamide and the role for urinary S-carboxyethyl-cysteine (CEC) as a biological marker.

Acrylamide has a range of toxicological hazards including neurotoxicity and reproductive toxicity; however, occupational risk management is driven by its genotoxic and carcinogenic potential (it is classified within the EU as a Category 2 carcinogen, R45 and Category 2 mutagen, R46). Since there is the potential for skin absorption and systemic toxicity, biological monitoring may be a useful aid for the assessment of exposure via inhalation, ingestion and dermal absorption. However, there are currently no biological monitoring guidance values (BMGVs). This study describes an extensive survey of potential workplace exposure to acrylamide at the Ciba (Bradford) site to gather data suitable for a BMGV. This manufacturing site is typical within the industry as a whole and includes a cross section of activities and tasks representative of acrylamide exposure. Acrylamide is used in the manufacture of polyacrylamide based products for applications in water treatment; oil and mineral extraction; paper, paint and textile processes. Workers (62 plus 6 controls) with varying potential exposures provided a total of 275 pre shift and 247 post-shift urine samples along with 260 personal air samples. A small non-exposed control group was similarly monitored. Urine samples were analysed for S-carboxyethyl-cysteine (CEC). Airborne, surface and glove samples were analysed for acrylamide. Inhalation exposures were well controlled with values consistently below one-tenth of the UK Workplace Exposure Limit. Engineering controls, personal protective equipment and work practice, all contributed to good control of occupational exposure. CEC was found in urine samples from both exposed workers and non-occupationally exposed controls. At the low levels of exposure found, smoking made a significant contribution to urinary CEC levels. Nevertheless a correlation between urinary CEC and airborne acrylamide was found. A mixed effects model incorporating inhalation concentrations of acrylamide and smoking habits could predict some of the variation in observed post-shift urine results but could be improved through the use of additional surface contamination data. However, the data does not suggest that dermal absorption was a major contributor to the systemic dose. Based on the 90th percentile of the data, inclusive of the effects of smoking and environmental factors, a value of 4 mmol mol(-1) creatinine is proposed as a pragmatic BMGV associated with good occupational hygiene practice and control of workplace exposure. CEC in urine analysis has the utility for routine use as a means to estimate biological uptake where there is a potential for significant exposure or loss of workplace control.

Acrylamide↗