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PubMed1997

DNA-protein cross-links produced by various chemicals in cultured human lymphoma cells.

Chemicals such as cis-platinum, formaldehyde, chromate, copper, and certain arsenic compounds have been shown to produce DNA-protein cross-links in human in vitro cell systems at high doses, such as those in the cytotoxic range. Thus far there have only been a limited number of other chemicals evaluated for their ability to produce cross-links. The purpose of the work described here was to evaluate whether select industrial chemicals can form DNA-protein cross-links in human cells in vitro. We evaluated acetaldehyde, acrolein, diepoxybutane, paraformaldehyde, 2-furaldehyde, propionaldehyde, chloroacetaldehyde, sodium arsenite, and a deodorant tablet [Mega Blue; hazardous component listed as tris(hydroxymethyl)nitromethane]. Short- and long-term cytotoxicity was evaluated and used to select appropriate doses for in vitro testing. DNA-protein cross-linking was evaluated at no fewer than three doses and two cell lysate washing temperatures (45 and 65 degrees C) in Epstein-Barr virus (EBV) human Burkitt's lymphoma cells. The two washing temperatures were used to assess the heat stability of the DNA-protein cross-link, 2-Furaldehyde, acetaldehyde, and propionaldehyde produced statistically significant increases in DNA-protein cross-links at washing temperatures of 45 degrees C, but not 65 degrees C, and at or above concentrations of 5, 17.5, and 75 mM, respectively. Acrolein, diepoxybutane, paraformaldehyde, and Mega Blue produced statistically significant increases in DNA-protein cross-links washed at 45 and 65 degrees C at or above concentrations of 0.15 mM, 12.5 mM, 0.003%, and 0.1%, respectively. Sodium arsenite and chloroacetaldehyde did not produce significantly increased DNA-protein cross-links at either temperature nor at any dose tested. Excluding paraformaldehyde and 2-furaldehyde treatments, significant increases in DNA-protein cross-links were observed only at doses that resulted in complete cell death within 4 d following dosing. This work demonstrates that DNA-protein cross-links can be formed in vitro following exposure to a variety of industrial compounds and that most cross-links are formed at cytotoxic concentrations.

Acetaldehyde↗

PubMedDate not supplied

Are aldehydes in heat-sterilized peritoneal dialysis fluids toxic in vitro?

OBJECTIVE: Chemical analysis of several brands of peritoneal dialysis fluids (PD fluids) has revealed the presence of 2-furaldehyde, 5-HMF (5-hydroxymethylfuraldehyde), acetaldehyde, formaldehyde, glyoxal, and methylglyoxal. The aim of this study was to investigate if the in vitro side effects caused by glucose degradation products, mainly formed during heat sterilization, are due to any of these recently identified aldehydes. DESIGN: Cell growth media or sterile filtered PD fluids were spiked with different concentrations of thealdehydes. MEASUREMENTS: In vitro side effects were determined as the inhibition of cell growth of cultured mouse fibroblasts or stimulated superoxide radical release from human peritoneal cells. RESULTS: Our results demonstrate that the occurrences of 2-furaldehyde, 5-HMF, acetaldehyde, formaldehyde, glyoxal, or methylglyoxal in heat-sterilized PD fluids are probably not the direct cause of in vitro side effects. In order to induce the same magnitude of cell growth inhibition as the heat-sterilized PD fluids, the concentrations of 2-furaldehyde, glyoxal, and 5-HMF had to be 50 to 350 times higher than those quantified in the PD fluids. The concentrations of acetaldehyde, formaldehyde, and methylglyoxal observed in the heat-sterilized PD fluids were closer to the cytotoxic concentrations although still 3 to 7 times lower. CONCLUSION: Since none of these aldehydes caused in vitro toxicity at the tested concentrations, the toxicity found in PD fluids is likely to be due to another glucose degradation product, not yet identified. However, it is possible that these aldehydes may still have adverse effects for patients on peritoneal dialysis.

Acetaldehyde↗

PubMed1991

Inhibition of T cell mitogenesis by nitrofurans.

A group of nitrofurans (5-nitro-2-furaldehyde, nifuroxime, nitrofurazone, nitrofurantoin, 5-nitro-2-furoic acid and 2-nitrofuran) were evaluated for inhibition of mitogenesis (DNA synthesis) in human peripheral blood T cells. T cells, either triggered by phorbol myristate acetate (PMA) or in the presence of accessory cells, were activated with a specified mitogen [phytohemagglutin (PHA), concanavalin A (ConA), or anti-CD3] and the amount of tritiated thymidine incorporated into DNA was determined. The results obtained indicate that nitrofurans inhibit mitogenesis irrespective of activator. 5-Nitro-2-furaldehyde was much more inhibitory than the other compounds, while 2-nitrofuran was less inhibitory. When the aldehyde group (5-nitro-2-furaldehyde) was replaced by a carboxyl group (5-nitro-2-furoic acid), the inhibitory activity was also reduced greatly. These results show that while the nitro group alone confers inhibitory activity to the furan ring, the group at the 2 position is crucial. In general, the mitogenic response of purified T cells (lacking accessory cells) triggered by PMA (phorbol ester) was inhibited less than that of the T cell-accessory cell system. With the latter, 50% inhibition of T cell mitogenesis was achieved by nifuroxime, nitrofurazone, and nitrofurantoin at 45-51 and 34-39 microM with PHA and ConA respectively. When purified T cells were used, the values were 71-85 and 55-60 microM respectively. For a given drug concentration, mitogenesis was more inhibited when induced by ConA or anti-CD3 than by PHA. The importance of using a single cell system (purified T cells) was emphasized by the interesting finding that only this system showed enhancement of mitogenesis, up to 35-40% at low drug levels. With the exception of the nitrofuraldehyde, the nitrofurans at strongly inhibitory levels were only moderately cytotoxic, exhibiting 62-85% cell survival after exposure to drug for 68 hr. Our results suggest that nitrofurans inhibit T cell mitogenesis by a relatively non-toxic mechanism; these results are comparable to those obtained for mammalian cells under aerobic conditions.

Adult↗

PubMed1987

Mutagenicity of nitrofurans in Salmonella typhimurium TA98, TA98NR and TA98/1,8-DNP6.

8 representative 2-substituted 5-nitrofurans were assayed for mutagenicity in Salmonella typhimurium strains TA98, TA98NR and TA98/1,8-DNP6. The tested compounds were: 5-nitro-2-furanacrylic N-(5-nitro-2-furfurylidene)hydrazide (1); furazolidone (2); 5-nitro-2-furanacrolein (3); 5-nitro-2-furaldehyde semicarbazone (4); 5-nitro-2-furaldehyde (5); nitrofurantoin (6); 5-nitro-2-furaldehyde diacetate (7); and 5-nitro-2-furoic acid (8). These compounds exhibited markedly different mutagenic activities in TA98, and these mutagenicities were similar both in the presence and the absence of rat-liver hepatic S9 activation enzymes. The mutagenic responses ranged from potent (90-300 revertants/nmole, compounds 1-3), to medium (about 10 revertants/nmole, compounds 4 and 6), to weak (0-4 revertants/nmole, compounds 5, 7 and 8). The mutagenicity of 3 was similar in all 3 tester strains, while compound 8 was essentially inactive. The mutagenicities of 1, 4, 5 and 7 were decreased 30-75% in TA98NR, while 2 and 6 showed an even greater depression of activity in this strain. Compound 6 with S9 was about equally mutagenic in TA98 and TA98/1,8-DNP6, while the activities of 6 without S9 and 2 and 7 both with and without S9 were 50-75% lower in TA98/1,8-DNP6. Compounds 1, 4 and 5 were only about 5-10% as mutagenic in TA98/1,8-DNP6 as in TA98. These results suggest that: (i) nitrofurans and their S9-mediated metabolites have similar mutagenic potencies; (ii) with the possible exception of No. 3, nitroreduction is the major route of mutagenic activation for these nitrofurans; and (iii) for compounds 2, 6 and 7, both the presumed N-hydroxy and N,O-ester derivatives of the corresponding aminofuran metabolites appear to lead to mutations.

Dose-Response Relationship, Drug↗

PubMed2002

High-performance liquid chromatographic determination of furfural compounds in infant formulas. Changes during heat treatment and storage.

Furfural contents in adapted and follow-up infant formulas were measured by RP-HPLC. The evolution of furfural compound contents during storage (a year at 20 and 37 degrees C) was studied. 2-Furylmethylketone and 5-methyl-2-furaldehyde were not detectable in analysed samples. The differences in the furfural compounds at point zero between both infant formulas has to be ascribed to the differences in protein and iron contents. An increase in free 5-hydroxymethyl-2-furfuraldehyde (HMF), 2-furaldehyde (F) and HMF+F contents was observed in all samples, although the differences were not statistically significant. The storage temperature affected the total HMF content and the storage time affected the total HMF and F contents.

Chromatography, High Pressure Liquid↗

PubMed2002

Effect of different forms of alkali treatment on specific fermentation inhibitors and on the fermentability of lignocellulose hydrolysates for production of fuel ethanol.

Treatment with alkali, particularly overliming, has been widely used as a method for the detoxification of lignocellulose hydrolysates prior to ethanolic fermentation. However, the mechanisms behind the detoxification effect and the influence of the choice of cation have not been well understood. In this study, a dilute acid hydrolysate of spruce and an inhibitor cocktail consisting of six known inhibitors were used to investigate different alkali detoxification methods. The various treatments included the addition of calcium hydroxide, sodium hydroxide, potassium hydroxide, and ammonia to pH 10.0 and subsequent adjustment of the pH to 5.5 with either sulfuric or hydrochloric acid as well as treatment with the corresponding amounts of calcium, sodium, and potassium as sulfate or chloride salts at pH 5.5. An RP-HPLC method was developed for the separation of 18 different inhibitors in the hydrolysate, including furaldehydes and phenolics. Detection and quantification were carried out by means of UV, DAD, and ESI-MS in negative mode. Treatment of the spruce hydrolysate with alkali resulted in up to approximately 40% decrease in the concentration of furaldehydes. The effects on the aromatic compounds were complex. Furthermore, SFE was performed on the precipitate formed during alkali treatment to evaluate the inhibitor content of the precipitate, and the following RP-HPLC analysis implied that potential inhibitors were removed mainly through conversion rather than through filtration of precipitate. Parallel experiments in which sulfuric acid or hydrochloric acid was used for acidification to pH 5.5 after alkali treatment indicated that the choice of anion did not affect the removal of inhibitors. Detoxification with calcium hydroxide and ammonia resulted in better fermentability using Saccharomyces cerevisiae than detoxification with sodium hydroxide. The results from the experiments with the inhibitor cocktail indicated that the positive effects of alkali treatment are difficult to explain by removal of the inhibitors only and that possible stimulatory effects on the fermenting organism warrant further attention.

Acetic Acid↗

PubMed2005

An intramolecular 1,3-dipolar cycloaddition reaction towards the synthesis of chiral azetidine nucleoside analogues: the D-gluco case.

The diastereoselective intramolecular 1,3-dipolar cycloaddition reaction of unsaturated nitrones, derived from methyl alpha-D-glucopyranoside with 2-furaldehyde and 2-(benzyloxy)acetaldehyde has been studied In our pevious studies with 2-furaldehyde, the cycloaddition resulted 3 diastereoisomers in a 3:1:1 ratio. In this article, how the number of the possible isomers generated by 1,3-cycloaddition could be reduced from 4 to 1 when 2-(benzyloxy)acetaldehyde was employed as an aldehyde is shown.

Aldehydes↗

PubMed1977

Discoloration of dental pellicle by tannic acid.

The ability of tannic acid to discolor pellicle was studied in vitro and in vivo. Freshly extracted teeth were submerget in solutions of tannic acid, and in the clinical study individuals rinsed three times daily with 0.1% or 0.2% tannic acid. It was fount that 0.2% tannic acid caused brownish discolorations within 10-12 days both in vitro and in vivo. Discolored pellicle material collected from the in vivo test group was shown to contain furaldehyde after hydrolysis. The origin of the furaldehyde is not ascertained, but could be due to the presence of dietary deposits, transformation of pellicle pentoses, or from reactions between reducing sugars and amino compounds.

Dental Enamel↗

PubMed1980

High performance liquid chromatography of furfural and hydroxymethylfurfural in spirits and honey.

Furfural (2-furaldehyde) and hydroxymethylfurfural (5-hydroxy-2-furaldehyde, HMF) are determined in brandy and honey by reverse phase high performance liquid chromatography. Brandies and other spirits are injected without sample preparation; honey is diluted with water and the solution is filtered before injection onto a reverse phase column with detection at 285 nm. The mobile phase is methanol--water (10 + 90) and the effluent flow rate is maintained at 1.0 mL/min. External standardization is used for quantitative determination. Recoveries from cognac and honey spiked at different levels ranged from 95 to 99% (furfural) and 95 to 100% (HMF). The furfural content of the brandies was also determined by the existing colorimetric method of the Bureau National Interprofessionel du Cognac. The HMF content of the honey was correlated to the results of the classic method of Winkler.

Alcoholic Beverages↗

PubMed2002

Gas chromatography/mass spectrometric characterisation of pyrolysis/silylation products of glucose and cellulose.

The mass spectra of trimethylsilyl (TMS) derivatives of possible hydroxylated pyrolysis products of glucose and cellulose were recorded by gas chromatography/mass spectrometry (GC/MS) analyses of TMS derivatives of 2-hydroxymethylfuran, 2-hydroxy-1-methyl-1-cyclopenten-3-one, 5-(hydroxymethyl)-2-furaldehyde, 5-methyl-2-furoic acid, 4-hydroxy-6-methyl-(2H)-pyran-2-one, 2-methyl-3-hydroxy-(4H)-pyran-4-one (maltol) and 1,6-anhydro-beta-D-glucopyranose (levoglucosan, LG). Also, 2-O-TMS-1,6-anhydro-beta-D-glucopyranose, 4-O-TMS-1,6-anhydro-beta-D-glucopyranose and 2,4-bis-O-TMS-1,6-anhydro-beta-D-glucopyranose were identified from the interpretation of electron impact and chemical ionisation mass spectra of products obtained from partially silylated levoglucosan solutions, together with information from the known relative reactivities of OH groups of anhydrosugars. A peak at m/z 116 was found to be characteristic of the mass spectra of partially silylated anhydrosugars, and is absent from the mass spectra of the persilylated species. Pyrolysis/GC/MS of cellulose in the presence of hexamethyldisilazane afforded principally the 2- and 4-TMS ethers and the 2,4-bis-TMS ether of LG, whereas the 5-TMS-oxymethyl-2-furaldehyde was a prominent pyrolysis/silylation product of glucose. The mass spectra of other relevant pyrolysis/silylation products are presented.

Cellulose↗

PubMed1978

The inhibitory effect of cysteine on the mutagenic activities of several carcinogens.

The Salmonella/microsome mutagenesis assay was used to determine the effect of cysteine (alpha-amino-beta-mercaptopropionic acid) on the mutagenic actions of several carcinogens: N-methyl-N'-nitro-N-nitrosoguanidine. N-acetoxy-2-acetylaminofluorene, N-hydroxy-2-acetylaminofluorene, 4-nitroquinoline-1-oxide, methyl methanesulfonate, 5-nitro-2-furaldehyde semicarbazone, 2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide, aflatoxin B1 and the nitrosation products of methylurea and methylguanidine. Cysteine, at non-toxic concentrations, significantly decreased the frequency of reversion to histidine prototrophy when it was added to treatment mixtures. The extent of the inhibition of mutagenic action by cysteine depended on the carcinogen studied as well as the doses of cysteine and carcinogen employed. Cysteine (2.5--10 mM) completely inhibited the mutagenic actions of N-methyl-N'-nitro-N-nitrosoguanidine and methylguanidine nitrosation products while only partially preventing the mutagenic effects of the other carcinogens assayed. Inhibition of 5-nitro-2-furaldehyde semicarbazone-induced mutagenesis occurred only with higher cysteine concentrations (20--200 mM).

2-Acetylaminofluorene↗

PubMed2000

Determination of aldehydes in food by high-performance liquid chromatography with biosensor coupling and micromembrane suppressors.

A high-performance liquid chromatography system for the determination of aldehydes in food was developed incorporating an Cation MicroMembrane Suppressor (CMMS) and enzyme reactors packed with VA-Epoxy on which aldehyde dehydrogenase from bakers yeast and NADH oxidase from Bacillus licheniformis were immobilized. The method was based on the principle that the separation efficiency of HPLC is combined with the sensitivity of electrochemical detection and the specificity of enzymes. Main attention was directed to the determination of 5-hydroxymethyl-2-furaldehyde and 2-furaldehyde, the occurrence of which is an indication of quality deterioration in several food products. The efficiency of the method has been shown by the analysis of honey, coffee and related beverages, refreshments, sherry, port, dry fruits and breakfast cereals.

Aldehydes↗

PubMed2005

Controlling hydrothermal reaction pathways to improve acetic acid production from carbohydrate biomass.

A two-step hydrothermal process to improve the production of acetic acid was discussed. The first step was to accelerate the formation of 5-hydroxymethyl-2-furaldehyde (HMF), 2-furaldehyde (2-FA), and lactic acid (LA), and the second step was to further convert the furans (HMF, 2-FA) and LA produced in the first step to acetic acid by oxidation with newly supplied oxygen. The acetic acid obtained by the two-step process had not only a high yield but also better purity. The contribution of two pathways via furans and LA in the two-step process to convert carbohydrates into acetic acid was roughly estimated as 85-90%, and the ratio of the contributions of furans and LA to yield acetic acid was estimated as 2:1. The fact that WO of carbohydrates is not capable of producing a large amount of acetic acid, while the two-step process can enhance the acetic acid yield, can be explained because formic acid is a basic product of direct oxidation of carbohydrate, and acetic acid in WO of carbohydrates may come from the oxidation of dehydration products of aldose.

Acetic Acid↗

PubMed2003

Racemic and enantiopure synthesis and physicochemical characterization of the novel taste enhancer N-(1-carboxyethyl)-6-(hydroxymethyl)pyridinium-3-ol inner salt.

Convenient syntheses were developed to obtain on a multigram scale the novel taste enhancer N-(1-carboxyethyl)-6-(hydroxymethyl)pyridinium-3-ol 1, called alapyridaine, as a racemic mixture and as pure (+)-(S) and (-)-(R) enantiomers, respectively. 5-(Hydroxymethyl)-2-furaldehyde was used as key intermediate and was reacted with l-alanine under alkaline conditions to obtain racemic 1. Alternatively, reductive amination of 5-(hydroxymethyl)-2-furaldehyde with Raney-Ni/hydrogen and l- or d-alanine followed by mild oxidation led to (+)-(S)-1 and (-)-(R)-1, respectively. Racemization was promoted under alkaline and boiling conditions via a carbanion, the formation of which was facilitated by the electron-withdrawing effect of the iminium cation and the resonance-stabilizing capacity of the pyridinium moiety. Under these conditions, 1 was obtained in a 1:1 mixture of the phenol (1) and phenolate (1-H) forms as shown by X-ray diffraction. Racemic 1 formed monoclinic crystals of high molecular organization in which the phenol-type (RS)-1, the phenolate-type (RS)-1-H, sodium cations, and ethanol molecules are present. The crystal structure of [Na(1)(1-H).(C(2)H(6)O)] shows one-dimensional mu(2)-bridging-oxygen polymers stabilized by a three-dimensional network of ionic, hydrogen bond, and pi-stacking interactions with channels occupied by solvent molecules.

Alanine↗

PubMed2001

Occupational exposure to harmful chemical substances while processing phenol-formaldehyde resins.

Air pollutants emitted while processing phenol-formaldehyde resins have been investigated. Gas chromatography-mass-selective detection was used to separate and identify chemical compounds. It was determined that workers were exposed to formaldehyde in all workplaces. Besides, phenol, acetaldehyde, acrylaldehyde, 2-furaldehyde, xylene, ethylbenzene, toluene, tetrachlorethene, ethyl acetate, butyl acetate were found during the production of frictional materials; and 2-furaldehyde, phenol, naphthalene, 2-furanmethanol, polycyclic aromatic hydrocarbons (PAHs) during the production of abrasive materials. Quantitative analyses were performed with gas chromatography and high performance liquid chromatography. Assessment of occupational exposure indicated that chemical compounds emitted during the investigated processes might be dangerous for human health, mainly because of suspected carcinogenic compounds: formaldehyde and PAHs.

Air Pollutants, Occupational↗

PubMed1976

Mutagenic action of nitrofurans on Euglena gracilis and Mycobacterium phlei.

There is a pronounced difference between the action of antibiotics and nitrofurans on Euglena gracilis. Those antibiotics that induce hereditary loss of chloroplasts do so only when they affect dividing cells. On the other hand, nitrofurans induce a mass mutation in both dividing and nondividing cells (under conditions of continuous illumination of cultures). It was found that a breakdown product, 5-nitro-2-furaldehyde, is liberated from furadantin and furoxone. This intermediate is responsible for the observed specific mutagenicity of 5-nitrofuran drugs. The mutagenic action of 5-nitro-2-furaldehyde is very similar to that of nitrosoguanidine. Both compounds induce bleached mutants of E. gracilis when acting on growing or resting cells, regardless of the dark or light conditions. Similarly, both compounds induce reverse mutations in auxotrophic strains of Mycobacterium phlei.

Animals↗

PubMed1996

Cytotoxicity, pH, and glucose degradation products in four different brands of PD fluid.

This study was undertaken in order to evaluate differences in pH, cytotoxicity, and concentration of glucose degradation products between different peritoneal dialysis (PD) fluids. Four brands of commercial PD fluids were selected: Gambrosol, Bieffe, Dianeal, and Lock-olys, with a glucose concentration between 3.86% and 4.25%. The cytotoxicity of unused PD fluid was measured as inhibition of cell growth after three days' exposure of a fibroblast cell line using neutral red vital stain. The concentration of 2-furaldehyde, 5-hydroxymethyl-furaldehyde (5-HMF), acetaldehyde, formaldehyde, glyoxal, and methylglyoxal was analyzed by high-performance liquid chromatography technique. All the investigated PD fluids were cytotoxic and contained noticeable amounts of aldehydes. No major differences were observed in pH, although one fluid with a slightly lower pH was found to be less cytotoxic. This fluid also contained less formaldehyde, acetaldehyde, methylglyoxal, and glyoxal but instead contained more 5-HMF. We conclude that all brands of PD fluid are cytotoxic due to glucose degradation products and that they contain noticeable concentrations of low-molecular aldehydes. Our results also demonstrate that the concentration of 5-HMF, used as a regulatory control of PD fluids, does not correlate well with cytotoxicity.

Acid-Base Equilibrium↗

PubMed1976

Volatile degradation products of l-dehydroascorbic acid.

Volatile degradation products were isolated from a solution of L-dehydroascorbic acid in phosphate buffer solution of pH 2,4,6 and 8 heated under reflux for 3 h or left at 25 degrees C for 200 h. The products were identified by comparison of their gas chromatographic retention data, infra-red and mass spectra with those of authentic compounds. Fifteen products were identified, among which 12 had not yet been reported as degradation products of L-dehydroascorbic acid. Concentrations of 5 main degradation products, i.e. 3-hydroxy-2-pyrone, 2-furancarboxylic acid, 2-furaldehyde, acetic acid and 2-acetylfuran depended on the pH values and temperature; the presence of oxygen had no pronounced effect.

Acetates↗