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PubMedDate not supplied

PD fluids contain high concentrations of cytotoxic GDPs directly after sterilization.

OBJECTIVE: Glucose degradation products (GDPs) in peritoneal dialysis (PD) fluids are cytotoxic and affect the survival of the peritoneal membrane. One of the most reactive GDPs in PD fluids is 3,4-dideoxyglucosone-3-ene (3,4-DGE). 3,4-DGE has been reported as an intermediate between 3-deoxyglucosone (3-DG) and 5-hydroxymethyl furaldehyde (5-HMF) during degradation of glucose. In PD fluids, 3,4-DGE exists in a temperature-dependent equilibrium with a pool of unidentified substances. The aim of this study was to explore this equilibrium and its temperature dependence during the first months of storage after the sterilization procedure. METHODS: GDPs and inhibition of cell growth (ICG) were measured directly after sterilization of the PD fluid and during storage at different temperatures for 60 days. The following GDPs were analyzed: 3-DG, 3,4-DGE, 5-HMF, formaldehyde, acetaldehyde, glyoxal, and methylglyoxal. RESULTS: Immediately after sterilization, the concentration of 3,4-DGE was 125 micromol/L. During the first weeks of storage, it decreased by about 80%. At the same time, the 3-DG concentration increased. None of the other GDPs were significantly affected. Cytotoxicity correlated well with the concentration of 3,4-DGE. When pure 3,4-DGE was substituted for the lost amount of 3,4-DGE after 30 days of storage, the initial ICG was almost completely regained. CONCLUSIONS: Heat sterilization of PD fluids promotes the formation of large quantities of 3,4-DGE, rendering the fluid highly cytotoxic. During storage, the main part of 3,4-DGE is reversibly converted in a temperature-dependent manner to a less cytotoxic pool, consisting mainly of 3-DG. Cytotoxicity seems to be dependent exclusively on 3,4-DGE. In order to avoid higher levels of 3,4-DGE concentrations, PD fluids should not be used too soon after sterilization and should not be stored at temperatures above room temperature.

Aldehydes↗
PubMedDate not supplied

Take care in how you store your PD fluids: actual temperature determines the balance between reactive and non-reactive GDPs.

OBJECTIVE: During heat sterilization and during prolonged storage, glucose in peritoneal dialysis fluids (PDF) degrades to carbonyl compounds commonly known as glucose degradation products (GDPs). Of these, 3,4-dideoxyglucosone-3-ene (3,4-DGE) is the most cytotoxic. It is an intermediate in degradation between 3-deoxyglucosone (3-DG) and 5-hydroxymethyl-2-furaldehyde (5-HMF). We have earlier reported that there seems to be equilibrium between these GDPs in PDF. The aim of the present study was to investigate details of this equilibrium. METHODS: Aqueous solutions of pure 3-DG, 3,4-DGE, and 5-HMF were incubated at 40 degrees C for 40 days. Conventional and low-GDP fluids were incubated at various temperatures for up to 3 weeks. Formaldehyde, acetaldehyde, glyoxal, methylglyoxal, 3-DG, 3,4-DGE, and 5-HMF were analyzed using high performance liquid chromatography. RESULTS: Incubation of 100 micromol/L 3,4-DGE resulted in the production of 36 micromol/L 3-DG, 4 micromol/L 5-HMF, and 40 micromol/L unidentified substances. With the same incubation, 200 micromol/L 3-DG was converted to 9 micromol/L 3,4-DGE, 6 micromol/L 5-HMF, and 14 micromol/L unidentified substances. By contrast, 100 micromol/L 5-HMF was uninfLuenced byincubation. In a conventional PDF incubated at 60 degrees C for 1 day, the 3,4-DGE concentration increased from 14 to a maximum of 49 micromol/L. When the fluids were returned to room temperature, the concentration decreased but did not reach original values until after 40 days. In a low GDP fluid, 3,4-DGE increased and decreased in the same manner as in the conventional fluid but reached a maximum of only 0.8 micromol/L. CONCLUSIONS: Considerable amounts of 3,4-DGE may be recruited by increases in temperature in conventional PDFs. Lowering the temperature will again reduce the concentration but much more time will be needed. Precursors for 3,4-DGE recruitment are most probably 3-DG and the enol 3-deoxyaldose-2-ene, but not 5-HMF. Considering the ease at which 3,4-DGE is recruited from its pool of precursors and the difficulty of getting rid of it again, one should be extremely careful with the temperatures conventional PDFs are exposed to.

Animals↗
PubMed1989

[Studies on the chemical constituents of Excoecaria cochinchinensis Lour. var. viridis Merr].

Eight compounds have been obtained from the root and stem of Excoecaria cochinchinensis var. viridis growing in Tonghai county of Yunnan province. According to their spectroscopic analyses and physicochemical constants, they have been identified as: shikimic acid, 1-cyclohexene-1-carboxylic acid-5-hydroxy-3,4-isopropylidene-dioxy, oxy-bis(5-methylene-2-furaldehyde), beta-sitosterol, tetracosanoic acid, palmic acid, steric acid and hentriacontane.

Cyclohexanes↗
PubMed1995

In vitro biocompatibility of a heat-sterilized, low-toxic, and less acidic fluid for peritoneal dialysis.

OBJECTIVE: The aim of this study was to investigate a peritoneal dialysis (PD) fluid (PD-Bio), produced with the intention of reducing the amount of glucose degradation products and to increase the final pH. The heat sterilization of the fluid was performed with the glucose separated from the electrolytes. After sterilization the two solutions were combined. METHODS: The in vitro biocompatibility of PD-Bio was measured as the inhibition of cell growth of a cultured fibroblast cell line and as the stimulated release of interleukin-1 beta from cultured human mononuclear cells. The glucose degradation products were measured as UV absorbance at 228 nm or 284 nm and the concentration of aldehydes was estimated with high-performance liquid chromatography and gas chromatography. RESULTS: Our results demonstrate that in comparison to conventional PD fluids the pH of PD-Bio was increased, to about 6.5. Due to less contaminating glucose degradation products in PD-Bio, basal cytotoxicity was significantly decreased for both 1.5% and 4% glucose-containing fluids, and the stimulated release of interleukin-1 beta was normalized compared to sterile filtered controls with the same pH. UV absorbance measured at 228 nm was decreased, whereas the absorbance at 284 nm was equal to that of a conventional fluid. In PD-Bio the concentrations of formaldehyde, acetaldehyde, methylglyoxal, and 2-furaldehyde were found to be below the detection limit, whereas glyoxal was present in the same and 5-hydroxymethylfurfural (5-HMF) in higher concentrations than in conventionally produced PD fluid. CONCLUSIONS: The results demonstrate that it is possible to improve biocompatibility of PD fluids by simply changing the way the fluid is produced.

Acetaldehyde↗
PubMed2000

Effect of alcohol compounds found in hemicellulose hydrolysate on the growth and fermentation of ethanologenic Escherichia coli.

Lignocellulose can be readily hydrolyzed into a mixture of sugars using dilute mineral acids. During hydrolysis, a variety of inhibitors are also produced which include aromatic alcohols from lignin and furfuryl alcohol from pentose destruction. Seven compounds were investigated individually and in binary combinations (catechol, coniferyl alcohol, furfuryl alcohol, guaiacol, hydroquinone, methylcatechol, and vanillyl alcohol). Aromatic alcohols and furfuryl alcohol inhibited ethanol production from xylose in batch fermentations primarily by inhibiting the growth of Escherichia coli LY01, the biocatalyst. The toxicities of these compounds were directly related to their hydrophobicity. Methylcatechol was the most toxic compound tested (MIC = 1.5 g/L). In binary combination, the extent of growth inhibition was roughly additive for most compounds tested. However, combinations with furfuryl alcohol and furfural (furaldehyde) appear synergistic in toxicity. When compared individually, alcohol components which are formed during hemicellulose hydrolysis are less toxic for growth than the aldehydes and organic acids either on a weight basis or a molar basis.

Alcohols↗
PubMed1982

Stability of phenylpropanolamine hydrochloride in liquid formulations containing sugars.

Stability studies with a decongestant syrup formulation containing phenylpropanolamine hydrochloride in a sugar vehicle indicated a loss of phenylpropanolamine hydrochloride. To ascertain the biological significance of this indicated chemical loss, the degraded formulation was administered to human volunteers and the urinary excretion of phenylpropanolamine hydrochloride was determined. The excretion and chemical assay patterns were in good agreement, indicating that the sugar vehicle was both chemically and biologically incompatible with phenlypropanolamine hydrochloride. A control formulation made with phenylpropanolamine hydrochloride in a sorbitol vehicle showed good chemical stability and urinary excretion patterns. Further studies showed chemical losses with phenylpropanolamine hydrochloride in the presence of fructose, dextrose, and 5-(hydroxymethyl)-2-furaldehyde but not with levulinic acid. Possible mechanisms for the sugar-phenylpropanolamine hydrochloride interaction are discussed.

Carbohydrates↗
PubMed1989

Kinetic evidence for human liver and stomach aldehyde dehydrogenase-3 representing an unique class of isozymes.

Substrate and coenzyme specificities of human liver and stomach aldehyde dehydrogenase (ALDH) isozymes were compared by staining with various aldehydes including propionaldehyde, heptaldehyde, decaldehyde, 2-furaldehyde, succinic semialdehyde, and glutamic gamma-semialdehyde and with NAD+ or NADP+ on agarose isoelectric focusing gels. ALDH3 isozyme was isolated from a liver via carboxymethyl-Sephadex and blue Sepharose chromatographies and its kinetic constants for various substrates and coenzymes were determined. Consistent with the previously proposed genetic model for human ALDH3 isozymes (Yin et al., Biochem. Genet. 26:343, 1988), a single liver form and multiple stomach forms exhibited similar kinetic properties, which were strikingly distinct from those of ALDH1, ALDH2, and ALDH4 (glutamic gamma-semialdehyde dehydrogenase). A set of activity assays using various substrates, coenzymes, and an inhibitor to distinguish ALDH1, ALDH2, ALDH3, and ALDH4 is presented. As previously reported in ALDH1 and ALDH2, a higher catalytic efficiency (Vmax/Km) for oxidation of long-chain aliphatic aldehydes was found in ALDH3, suggesting that these enzymes have a hydrophobic barrel-shape substrate binding pocket. Since the Km value for acetaldehyde for liver ALDH3, 83 mM, is very much higher than those of ALDH1 and ALDH2, ALDH3 thus represents an unique class of human ALDH isozymes and it appears not to be involved in ethanol metabolism.

Aldehyde Dehydrogenase↗
PubMed1994

Oxazole, pyrazole and piperidine derivatives having an o-hydroxyaryl moiety with anticipated molluscicidal activity.

The condensation reactions of hippuric acid and its furyl derivative with salicylaldehydes or that of salicylhippuric acid analogues with furaldehyde led to the corresponding oxazoles. These were subsequently treated with hydrazine hydrate, hydroxylamine or subjected to alkaline hydrolysis to yield new o-hydroxyaryl or salicyl containing derivatives. 5-Substituted salicylanilides were treated with piperidine and formaldehyde in a Mannich type reaction affording the corresponding 3-(N-piperidinomethyl) salicylanilides. It was noticed that the presence of an electron donating group in position 3 in the salicylanilide moiety decreases the molluscicidal activity.

Animals↗
PubMed2004

A sphingolipid and tyrosinase inhibitors from the fruiting body of Phellinus linteus.

This paper for the first time reports the isolation of 5 compounds from Phellinus linteus. A sphingolipid (1) and two tyrosinase inhibitory compounds (2, 3) along with two carboxylic acids (4, 5), were isolated from the fruiting body of Phellinus linteus (Berk & Curt) Aoshima. The structure of compound 1 was identified as 1-omicron-beta-D-glucopyranosyl-(2S, 3R, 4E, 8E)-2-[(2R)-2-hydroxyhexadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol, known as cerebroside B, based on spectroscopic methods such as 1 D and 2D NMR as well as by acid hydrolysis. Compounds 2 -5 were identified as protocatechualdehyde (2), 5-hydroxymethyl-2-furaldehyde (HMF) (3), succinic acid (4), and fumaric acid (5) based on the spectroscopic evidence. Compounds 2 and 3 inhibited the oxidation of L-tyrosine catalyzed by mushroom tyrosinase with an IC50 of 0.40 and 90.8 microg/mL, respectively. The inhibitory kinetics, which were analyzed by the Lineweaver-Burk plots, were found to be competitive and noncompetitive inhibitors with a Ki of 1.1 microM and 1.4 mM, respectively.

Acetylation↗
PubMed1989

Glutathione conjugation of nitro compounds by monkey glutathione S-transferases.

The distribution in Japanese monkey tissues of glutathione S-transferase activity toward some aromatic nitro compounds was examined by measuring the release of the nitro group as nitrite ion. The activity was especially high in liver, kidney and small intestine when compounds such as 4-nitroquinoline N-oxide, 5-nitrofurfural diacetal and o-dinitrobenzene were used as substrates. The nitrite-releasing activity of the major enzyme purified from rhesus monkey liver was also tested on fifty-two nitro compounds including nineteen nitrofuran derivatives. Among the thirty-three nitro compounds other than the nitrofuran derivatives tested as substrates, the purified enzyme showed activity only toward o-dinitrobenzene, 4-nitroquinoline N-oxide, 3,4-dinitrobenzoic acid, p-dinitrobenzene, 2,5-dinitrobenzoic acid, 2,5-dinitrophenol, tetra-chloronitrobenzene and 2,4-dinitrobenzoic acid. The crude supernatant fraction of rhesus monkey liver showed activity in substrate specificity roughly similar to that of the purified enzyme. On the other hand, among at least ten carcinogenic 2-substituted 5-nitrofran derivatives tested, 4,6-diamino-2-(5-nitro-2-furyl)-s-triazine, 5-nitro-2-furaldehyde semicarbazone, N-[[3-(5-nitro-2-furyl)-1,2,4-oxadiazol-5-yl]methyl] acetamide, and N-[5-(5-nitro-2-furyl)-1-3,4-thiadiazol-2-yl)acetamide were shown to be enzymatically conjugated with reduced glutathione. Among the other nine 2-substituted 5-nitrofuran derivatives tested, six compounds could be the substrates of the enzyme, and 5-nitrofurfural and 5-nitrofurfural diacetal were especially good substrates. There was, however, little apparent correlation between their carcinogenicity and susceptibility to glutathione S-transferase. The bulky substituents at position 2 appeared to decrease the susceptibility of these nitrofuran derivatives to the enzyme. Both Vmax and Km values of the purified enzyme varied greatly among the substrates, and the optimum pH fell between 7.5 and 9.0 in most cases.

Animals↗
PubMed1980

Formation and excision of nitrofuran-DNA adducts in Escherichia coli.

When Escherichia coli were incubated with the strong mutagen 2[14C]2-amino-4-(5-nitro-2 furyl)-thiazole (ANFT) radioactivity became tightly and presumably covalently bound to DNA. Hydrolysis of the DNA with nucleases yielded low molecular weight radioactive material. The bound radioactivity was associated with at least two functionally and chemically distinct adducts. One of these was rapidly removed in uvr+ E. coli while the other was more persistent. Analysis of enzymatic hydrolysates on a Dowex AG 50W-X4 column showed that the 'excisable adducts' were chromatographically different from most of the persistent ones. ANFT caused daughter-strand gaps when the DNA of treated cells was replicated, provided this DNA contained excisable adducts. In situations where removal of these adducts was complete no gaps were found in newly synthesized DNA. 3-[14C]2-(2-furyl)-3-(5-nitro-2-furyl) acrylamide (AF2) (another strongly mutagenic nitrofuran) became bound to the DNA of E. coli WP2 uvrA to a slightly greater extent than did [14C]ANFT. In contrast, [14C]nitrofurazone (the semicarbazide of 5-nitro-2-furaldehyde) a much weaker mutagen, gave considerably less binding. With AF2 and ANFT there was roughly the same relation between the amount of adduct formed and the subsequent yield of daughter strand gaps when the DNA replicated while with nitrofurazone the yield of gaps per adduct was somewhat lower. Incubation in vitro of [14C]ANFT with DNA in the presence of an E. coli nitrofuran reductase preparation also resulted in the binding of 14C to DNA.

DNA, Bacterial↗
PubMed1993

Diet, aberrant crypt foci and colorectal cancer.

We have used the aberrant crypt focus (ACF) assay to test and develop hypotheses linking diet and colon cancer. The hypotheses were suggested by epidemiological studies that identified possible dietary factors associated with colorectal cancer risk. The ACF assay was used to quantitate the effect of the dietary factors on the initiation and growth of these putative precursors of colon cancers in experimental animals. Using this approach we have developed 3 new hypotheses for the role of diet in colorectal cancer. These are (1) a risk associated with 5-hydroxymethyl-2-furaldehyde in caramelized sugar, (2) a risk associated with some factor in thermolyzed casein, and (3) a risk associated with single nutrient boluses of sucrose and fructose. The importance of these hypotheses has still to be tested in long term carcinogenesis experiments, in analytic epidemiology studies and then, perhaps, in intervention trials.

Animals↗
PubMed1996

Dermatolactone, a cytotoxic fungal sesquiterpene with a novel skeleton.

The nematicidal 5-pentyl-2-furaldehyde and the cytotoxic sesquiterpene dermatolactone were isolated from the extracts of an Ascomycete belonging to the Dermateaceae. The furan has previously been reported from the Basidiomycete Irpex lacteus, while dermatolactone is a new compound the structure of which was determined by spectrosocpic methods.

Animals↗
PubMed1992

On the induction of umu gene expression in Salmonella typhimurium strain TA1535/pSK1002 by some nitrofurans.

Several nitrofurans were found to induce umu gene expression in Salmonella typhimurium TA1535/pSK1002 as defined on the basis of at least a 2-fold increase of beta-galactosidase activity over the background level. beta-Galactosidase activity increased with increasing concentrations of the chemical, attained a maximum at a concentration which was different for different nitrofurans used, and then gradually decreased with a further increase of the nitrofuran concentration. The umu gene expression test revealed that the genotoxic activity was highest for furazolidone and lowest for 5-nitro-2-furaldehyde.

Azides↗
PubMed1987

Genotoxicity of a variety of nitroarenes and other nitro compounds in DNA-repair tests with rat and mouse hepatocytes.

Genotoxicity of a variety of nitroarenes and other compounds was examined in DNA-repair tests with rat or mouse hepatocytes. Out of 15 nitroarenes tested, 9 compounds, i.e., 1-nitropyrene, 1,3-dinitropyrene, 1,6-dinitropyrene, 1,8-dinitropyrene, 1-nitro-3-acetoxypyrene, 3-nitrofluoranthene, 2-nitrofluorene, 2,7-di-nitrofluorene and 5-nitroacenaphthene elicited positive response of DNA repair in the tests with rat and mouse hepatocytes. Among the positive chemicals, the DNA-repair level of the 3 dinitropyrene isomers was much higher than other nitroarenes. The results indicate that a number of nitroarenes are metabolically activated in the primary culture of rodent hepatocytes, and suggest potential carcinogenicity of 1-nitropyrene and 1-nitro-3-acetoxypyrene the carcinogenicity of which is either not clear or unknown. Of the other nitro compounds, 2-(2-furyl)-3-(5-nitro-2-furyl)acrylamide as well as 4-nitroquinoline 1-oxide were clearly genotoxic in the assays with hepatocytes of both species. However, 5-nitro-2-furaldehyde semicarbazone was negative in both assays with hepatocytes of 2 species.

Animals↗
PubMed1989

The popliteal lymph node assay in mice to screen for the immune disregulating potential of chemicals--a preliminary study.

Low mol. wt compounds were tested in the popliteal lymph node (PLN) assay to study whether PLN reactivity could be related to the ability of the compounds to induce autoimmune disorders in man. PLN reactions were measured 7 days after a single subcutaneous (s.c.) injection of dissolved compounds in amounts of 0.3-2.0 mg into one hind footpad of mice and assessed as the weight increase of the draining PLN relative to the PLN weight of the untreated contralateral paw. Hydralazine, chlorpromazine, diphenylhydantoin, carbamazepine, phenylbutazone and nitrofurantoin, all being drugs with a documented potential to induce systemic immunological disorders in man, caused marked PLN reactions. False negative PLN responses were observed following injection of procainamide and isoniazid. Among systemic drugs without known potential to induce autoimmune reactions in humans, quinacrine, denzimol and niridazole significantly increased PLN weights, while phenobarbital, levamisole and disulfiram had no effect. Chemicals with a well-known capacity to induce contact dermatitis in man like 2,4-dinitro-1-chlorobenzene, alpha-methylene-gamma-butyrolactone, p-phenylenediamine, 5-nitro-2-furaldehyde semicarbazone, 2-mercapto-benzothiazol and 1,3-dibutyl-2-thiourea caused marked PLN reactions, while the non-sensitizer 2,4-dichloro-1-nitrobenzene failed to do so. It is concluded that the PLN assay as applied in this study may give a rapid first indication of immunomodulating potential of low mol. wt compounds, but it does not discriminate as to the kind of immunomodulation.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1988

Effect of pyridoxal isonicotinoyl hydrazone and other hydrazones on iron release from macrophages, reticulocytes and hepatocytes.

A model consisting of 59Fe-labelled macrophages was developed for screening potential iron-chelating drugs. Mouse peritoneal macrophages, induced by previous intraperitoneal injections of 3% thioglycollate, were labelled in vitro by their exposure to immune complexes of 59Fe-transferrin-antitransferrin antibody. Optimal conditions for macrophage labelling and subsequent 59Fe release were established. Sixty-two aromatic hydrazones, the majority of which had iron binding structures similar to pyridoxal isonicotinoyl hydrazone, were synthesized by condensation of aromatic aldehydes (pyridoxal, salicylaldehyde, 2-hydroxy-1-naphthylaldehyde and 2-furaldehyde) with various acid hydrazides prepared by systematic substitutions on the benzene ring. These compounds were examined for their potential to stimulate 59Fe release from 59Fe-labelled macrophages and also from reticulocytes and hepatocytes loaded with non-heme 59Fe. The majority of hydrazones derived from pyridoxal, salicylaldehyde and 2-hydroxy-1-naphthylaldehyde seemed to be equally effective in both the macrophage and reticulocyte testing systems. However, the pyridoxal hydrazones were much more active in hepatocytes than the other groups of hydrazones. Several compounds proved to be very potent in mobilizing 59Fe. These included hydrazones derived from 2-hydroxy-1-naphthylaldehyde and benzoic acid hydrazide, p-hydroxybenzoic acid hydrazide, 2-thiophenecarboxylic acid hydrazide, and also pyridoxal benzoyl hydrazone, pyridoxal m-fluorobenzoyl hydrazone and pyridoxal 2-thiophenecarboxyl hydrazone.

Animals↗
PubMed2006

Noncatalytic hydrolysis of guar gum under hydrothermal conditions.

Guar gum, a naturally occurring heteropolysaccharide made of mannose and galactose, was hydrolytically degraded without a catalyst in a batch reactor to produce water-soluble (WS) saccharides including mono- and oligosaccharides. The degradation was carried out under hydrothermal conditions over ranges of temperature from 180 to 240 degrees C and of reaction time from 3 to 60min. Guar gum was readily dissolved and hydrolyzed, and the major products identified in the WS components were oligosaccharides with degrees of polymerization up to about 20, monosaccharides containing mannose and galactose, and 5-hydroxymethyl-2-furaldehyde (5-HMF). At 200 degrees C, the oligosaccharide yield, obtained from the difference between the yields of the total WS saccharides and monosaccharides, showed the highest value of 94.4% at 7min among all conditions studied, on the basis of the saccharide content in the initial sample. The oligosaccharide yield decreased with reaction time, and the yield of monosaccharides correspondingly increased, and reached the highest value of 34.5% (mannose 22.8%, galactose 11.7%) at 60min. The monosaccharides produced were further decomposed to secondary products such as 5-HMF. The maximum yield of 5-HMF obtained was 26.3% at 220 degrees C and 30min. The production and the decomposition of galactose somewhat preceded those of mannose.

Bioreactors↗