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PubMed1990

Characterization of a cDNA Encoding Lens culinaris Glycolate Oxidase and Developmental Expression of Glycolate Oxidase mRNA in Cotyledons and Leaves.

mRNA obtained from green leaves of lentil (Lens culinaris) was used to construct a cDNA library in phage lambdagt11. The cDNA library was screened with antibodies raised against lentil glycolate oxidase and catalase. Clone CL 1 containing the full-length sequence complementary to glycolate oxidase mRNA was characterized and sequenced. In addition, a 800-base pair catalase cDNA clone was sequenced. To prove the correlation of cDNA insert in CL 1 with glycolate oxidase, the cDNA was transcribed in vitro. The mRNA was translated in vitro yielding a 43 kilodalton protein immunoprecipitable with anti-glycolate oxidase serum. Nucleotide sequences of lentil cDNA and spinach cDNA were 86% identical. Lentil glycolate oxidase was characterized by a C-terminal sequence -P-R-A-L-P-R-L. The expression of glycolate oxidase mRNA in cotyledons, leaves and roots was compared with that of catalase. In leaves, the relative amount of glycolate oxidase mRNA increased during the first 2 days of greening, but decreased later, and was hardly detectable during senescence. In cotyledons of germinating seeds, the level of glycolate oxidase mRNA was markedly lower than the catalase mRNA.

Journal Article↗
PubMedDate not supplied

Mode of action: oxalate crystal-induced renal tubule degeneration and glycolic acid-induced dysmorphogenesis--renal and developmental effects of ethylene glycol.

Ethylene glycol can cause both renal and developmental toxicity, with metabolism playing a key role in the mode of action (MOA) for each form of toxicity. Renal toxicity is ascribed to the terminal metabolite oxalic acid, which precipitates in the kidney in the form of calcium oxalate crystals and is believed to cause physical damage to the renal tubules. The human relevance of the renal toxicity of ethylene glycol is indicated by the similarity between animals and humans of metabolic pathways, the observation of renal oxalate crystals in toxicity studies in experimental animals and human poisonings, and cases of human kidney and bladder stones related to dietary oxalates and oxalate precursors. High-dose gavage exposures to ethylene glycol also cause axial skeletal defects in rodents (but not rabbits), with the intermediary metabolite, glycolic acid, identified as the causative agent. However, the mechanism by which glycolic acid perturbs development has not been investigated sufficiently to develop a plausible hypothesis of mode of action, nor have any cases of ethylene glycol-induced developmental effects been reported in humans. Given this, and the variations in sensitivity between animal species in response, the relevance to humans of ethylene glycol-induced developmental toxicity in animals is unknown at this time.

Abnormalities, Drug-Induced↗
PubMed2000

Rapid determination of ethylene glycol and glycolic acid in biological fluids.

Ethylene glycol poisoning of companion animals is a common occurrence and is sometimes involved in human intoxication. Ethylene glycol is of limited toxicity, but the metabolites including glycolic acid are responsible for poisoning. Conventional treatment has employed substances to prevent alcohol dehydrogenase from metabolizing the ethylene glycol, but to be effective, therapy must begin within hours of ethylene glycol consumption. We describe a rapid (10 min) analysis of biological fluids for ethylene glycol and glycolic acid using isocratic HPLC, a refractive index detector, and a Waters fast fruit juice analytical column.

Animals↗
PubMed1988

Identification and quantification of ethylene glycol and diethylene glycol in plasma using gas chromatography-mass spectrometry.

A method for the gas chromatographic-mass spectrometric identification and quantification of ethylene glycol and diethylene glycol in plasma is described. Such a method is necessary in clinical and forensic toxicology to diagnose probable intoxication and to control the efficacy of detoxification. For sample preparation, the glycols were isolated using acetone after the addition of 1,3-propylene glycol as internal standard. The glycols were then esterified by pivalic acid (pivalic acid anhydride, triethylamine and methanol, 70 degrees C, 15 min) to improve their gas chromatographic characteristics. The glycols were first identified by a comparison of the full mass spectra with reference spectra and then quantified. Therefore, the peak area ratio in the total ion chromatogram (ethylene glycol or diethylene glycol/1,3-propanediol) of the sample was compared with the calibration curve in which the peak area ratios of the standards (0.05, 0.1, 0.5, 1 and 2 g/l), prepared in the same way, were plotted versus their concentrations. The method was linear at least from 0.05 to 2 g/l, with a detection limit of less than 0.01 g/l. The analytical recoveries were 99.2-102.9% for the different concentrations. Precision studies show coefficients of variation of 3.0-6.3% for the different concentrations.

Ethylene Glycols↗
PubMed1986

Urinary excretion of polyethylene glycol 3350 and sulfate after gut lavage with a polyethylene glycol electrolyte lavage solution.

Ingestion of an electrolyte lavage solution containing polyethylene glycol 3350 and sulfate is an effective method of cleansing the colon for diagnostic studies. Polyethylene glycol and sulfate are considered poorly absorbed from the gastrointestinal tract. Because of the quantities administered, concern exists about potential toxicity of absorption of even a small percentage, particularly for polyethylene glycol. We measured the urinary excretion of both polyethylene glycol and sulfate in normal subjects and inflammatory bowel patients. Absorption of polyethylene glycol can be assessed by measuring recovery in urine, as 85%-96% of an intravenous load is excreted in urine. Similarly, appreciable sulfate absorption would exceed renal tubular reabsorption and result in increased urinary excretion. Mean percent polyethylene glycol load recovered in urine was minimal and similar for normal (0.06%) and inflammatory bowel (0.09%) subjects. Urinary sulfate excretion after lavage was also similar for both groups and was not different from baseline. These results do not suggest the likelihood of toxicity due to polyethylene glycol 3350 or sulfate absorption during gut lavage with this solution.

Colitis, Ulcerative↗
PubMed2000

A spectrophotometric method for the determination of glycolate in urine and plasma with glycolate oxidase.

An enzymatic assay was developed for the spectrophotometric determination of glycolate in urine and plasma. Glycolate was first converted to glyoxylate with glycolate oxidase, and the glyoxylate formed was condensed with phenylhydrazine. The glyoxylate phenylhydrazone formed was then oxidized with K(3)Fe(CN)(6) in the presence of excess phenylhydrazine, and A(515) of the resulting 1, 5-diphenylformazan was measured. Since glycolate oxidase also acts on glyoxylate and L-lactate, the incubation of samples with glycolate oxidase was carried out in 120-170 mM Tris-HCl (pH 8.3) to obtain glyoxylate as its adduct with Tris. The pyruvate formed from lactate was removed by subsequent brief incubation with alanine aminotransferase in the presence of L-glutamate, and alpha-ketoglutarate formed was converted back to L-glutamate by glutamate dehydrogenase and an NADPH generating system. Thus the specificity of the assay relies principally on the substrate specificity of glycolate oxidase, and high sensitivity is provided by the high absorbance of 1,5-diphenylformazan at 515-520 nm. Plasma was deproteinized with perchloric acid, and then neutralized with KOH. Plasma and urine samples were then incubated with approximately 5 mM phenylhydrazine, and then treated with stearate-deactivated activated charcoal to remove endogenous keto and aldehyde acids as their phenylhydrazones. The normal plasma glycolate and urinary glycolate/creatinine ratio for adults determined by this method are approximately 8 microM and approximately 0.036, respectively.

Alanine Transaminase↗
PubMed2004

NTP technical report on the toxicology and carcinogenesis studies of propylene glycol mono-t-butyl ether (CAS No. 57018-52-7) in F344/N rats and B6C3F1 mice and a toxicology study of propylene glycol mono-t-butyl ether in male NBR rats (inhalation studies).

BACKGROUND: Propylene glycol mono-t-butyl ether is used as a solvent in all-purpose cleaners, inks, and nail polish lacquers. We studied the effects of propylene glycol mono-t-butyl ether on male and female rats to identify potential toxic or cancer-related hazards to humans. METHODS: We exposed groups of male and female rats and mice to air containing vapors of propylene glycol mono-t-butyl ether at concentrations of 75, 300, or 1,200 parts per million (ppm) for 6 hours per day, 5 days a week for 2 years. Untreated control animals were housed in similar exposure chambers but without chemical exposure for comparison. Tissues from more than 40 sites were examined for every animal. RESULTS: Rats receiving 1,200 ppm propylene glycol mono-t-butyl ether weighed less on average than the control animals. Tumors were seen in the liver and kidney of a few male rats exposed to propylene glycol mono-t-butyl ether. No increases in the numbers of tumors were seen in female rats. In male and female mice there were large increases in the numbers of liver tumors compared with the control animals. CONCLUSIONS: We conclude that propylene glycol mono-t-butyl ether caused cancer in the liver of male and female mice. Propylene glycol mono-t-butyl ether did not cause cancer in female rats, and its effect on the liver and kidney of male rats was considered uncertain.

Administration, Inhalation↗
PubMed2001

Validated gas chromatographic-mass spectrometric assay for determination of the antifreezes ethylene glycol and diethylene glycol in human plasma after microwave-assisted pivalylation.

A gas chromatographic-mass spectrometric assay is described for identification and quantification of the antifreezes ethylene glycol (EG) and diethylene glycol (DEG) in plasma for early diagnosis of a glycol intoxication. After addition of 1,3-propanediol as internal standard, the plasma sample was deproteinized by acetone and an aliquot of the supernatant was evaporated followed by microwave-assisted pivalylation. After gas chromatographic separation, the glycols were first identified by comparison of the full mass spectra with reference spectra and then quantified. The quantification has been validated according to the criteria established by the Journal of Chromatography B. The assay was found to be selective. The calibration curves for EG and DEG were linear from 0.1 g/l to 1.0 g/l. The limit of detection for EG and DEG was 0.01 g/l and the limit of quantification for both was 0.1 g/l. The absolute recoveries were 50 and 65% for the low quality control samples and 51 and 73% for the high quality control samples of EG and DEG, respectively. Intra- and inter-day accuracy and precision were inside the required limits. The glycols in frozen plasma samples were stable for more than 6 months. The method was successfully applied to several authentic plasma samples from patients intoxicated with glycols. It has also been suitable for analysis of EG and DEG in urine.

Ethylene Glycol↗
PubMed2000

Simultaneous detection and quantitation of diethylene glycol, ethylene glycol, and the toxic alcohols in serum using capillary column gas chromatography.

Determination of toxic glycols and alcohols in an emergency setting requires a rapid yet accurate and reliable method. To simultaneously determine diethylene glycol (DEG) along with ethylene glycol, methanol, isopropanol, acetone, and ethanol, we modified a previously developed gas chromatographic (GC) method. The system used a Hewlett-Packard 6890 GC with EPC, a Gooseneck splitless liner, and an Rtx-200 capillary column (30 m x 0.53-mm i.d., 3 mm). After serum samples were deproteinized using ultrafiltration (Millipore Ultrafree-MC), 1 mL of the protein-free filtrate was manually injected into the GC. Internal standards for alcohols (and acetone) and glycols were n-propanol and 1,3-butanediol, respectively. All compounds eluted within 3.5 min (linear temperature gradient from 40 to 260 degrees C); total run time was 6.5 min. Limit of detection and linear range for all compounds were 1 or 2.5 mg/dL and 0-500 mg/dL, respectively. In addition, there was no interference from propionic acid, propylene glycol, and 2,3-butanediol. The modifications in the equipment and temperature program allowed increased resolution and thus, detection and reliable quantitation of DEG and other common toxic glycols and alcohols of clinical interest.

2-Propanol↗
PubMed1984

Developmental toxicity and structure/activity correlates of glycols and glycol ethers.

In recent years, the National Toxicology Program (NTP) has selected numerous glycol ethers for testing in routine laboratory mammals to ascertain the magnitude of their ability to injure the conceptus. From the lists available of ongoing and projected NTP test chemicals, a series of glycol ethers was selected for examination in vitro in the hydra assay. Also tested were additional chemicals of similar molecular configuration and/or composition. This short-term screening test placed the 14 glycols and glycol ethers tested into a rank order sequence according to their degree of hazard potential to developmental biology, i.e., their ability to interfere with the developmental events characteristic of all ontogenic systems. They were ranked according to the difference between the lowest dose or concentration overtly toxic to adults (A) and the lowest concentration interfering with development (D) of the artificial embryo of reaggregated adult hydra cells and the A/D ratio. Published data from mammalian studies were available for a few of the test chemicals, and in each instance the hydra assay was in direct agreement with the outcomes reported of the more elaborate and standard animal tests. Ethylene glycol and ethylene glycol monomethyl ether were shown by both standard evaluations in mammals, and by the hydra assay, to disrupt embryos only at or very near to their respective adult toxic doses, whereas the mono-ethyl ether perturbed development at approximately one-fifth of the lowest dose overtly toxic to adults.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed1979

Cardiovascular effects of intravenous administration of propylene glycol and of oxytetracycline in propylene glycol in calves.

Comparisons were made of the acute cardiovascular effects of oxytetracycline, oxytetracycline in propylene glycol, and propylene glycol alone given to conscious dairy calves. The calves were chronically instrumented with intravascular catheters and electromagnetic flowmeter transducers in and on the pulmonary and renal arteries. Injection (IV) of aqueous preparations of oxytetracycline produced no statistically significant (P greater than 0.05) cardiocirculatory changes in these calves. Oxytetracycline in propylene glycol and propylene glycol alone both produced transient (1 to 4 minute) periods of cardiovascular depression characterized by cardiac asystole, systemic hypotension, and decreased pulmonary and renal arterial blood flow. The two preparations, in equivalent doses and volumes, produced statistically similar hemodynamic changes in the calves. The data from this study support the conclusion that the monitored cardiovascular effects of the commercially available oxytetracycline in propylene glycol in the intact, awake calves were due to the solvent propylene glycol. This conclusion is consistent with reports of other injectable products containing the same solvent.

Animals↗
PubMed1986

Ethylene glycol poisoning. The value of glycolic acid determinations for diagnosis and treatment.

Glycolic acid is the ethylene glycol (EG) metabolite that accumulates in the highest concentrations in the blood and may be the major contributing factor to the acute toxicity of EG. Serum and urine levels of glycolic acid have been found to correlate directly with clinical symptoms and mortality in poisoning cases, making it a valuable diagnostic tool. A high pressure liquid chromatographic (HPLC) method for quantitation of glycolic acid in serum was used in several cases of EG ingestion presented to the Louisiana Regional Poison Control Center. The data collected in this study support the value of glycolic acid determination for diagnosis and evaluation of patients poisoned by EG.

Charcoal↗
PubMedDate not supplied

A gas-liquid chromatographic method for quantitation of 1,3-butylene glycol in whole blood or plasma and the separation of the short chain glycols.

A microanalytical method with direct on-column specimen injection for determination of 1,3-butylene glycol (1,3-butanediol) in whole blood or plasma using gas-liquid chromatography with flame ionization is described. Whole blood or serum (minimum of 10 microL) was mixed with an equal volume of internal standard (1,2-propanediol, 50 mg/dL) and a 2-microL aliquot was injected onto the column without prior derivatization or extraction. The other short chain (C2 to C4) alkyldiols were separated by this method and did not interfere with the quantitation of 1,3-butylene glycol. The method was linear (y = 0.0206x + [-0.0073], r = 0.9990) over the range of 25 to 100 mg/dL and the coefficient of variation varied between 0.74 and 6.03%. Minimum detectable concentration of 1,3-butylene glycol was 5.0 mg/dL. The method described is suitable for the rapid detection of potentially toxic blood or plasma levels of 1,3-butylene glycol, as well as for the detection of other short chain glycols.

Animals↗
PubMed2005

Comparison of biodegradation of poly(ethylene glycol)s and poly(propylene glycol)s.

The biodegradation of poly(ethylene glycol)s (PEGs) and poly(propylene glycol)s (PPGs), both being major by-products of non-ionic surfactants biodegradation, was studied under the conditions of the River Water Die-Away Test. PEGs were isolated from a water matrix using solid-phase extraction with graphitized carbon black sorbent, then derivatized with phenyl isocyanate and determined by HPLC with UV detection. PPGs were isolated from a water matrix by liquid-liquid extraction with chloroform, then derivatized with naphthyl isocyanate and determined by HPLC with fluorescence detection. The primary biodegradation of both PEGs and PPGs reached approximately 99% during the test. The tests show different biodegradation pathways of PEG and PPG. During PEG biodegradation, their chains are shortened leading to the formation of ethylene glycol and diethylene glycol. During PPG biodegradation, no short-chained biodegradation products were found.

Biodegradation, Environmental↗
PubMed1984

The effects on the rat testis of single inhalation exposures to ethylene glycol monoalkyl ethers, in particular ethylene glycol monomethyl ether.

The effects of a single inhalation exposure to the rat of the saturated vapours derived from four ethylene glycol monoalkyl ethers have been investigated. No effects on the testis were observed following exposure to ethylene glycol isopropyl ether (EG ISOPE) and ethylene glycol butyl ether (EGBE), but there were marked reductions in testicular weight 14 days after exposure to ethylene glycol monomethyl ether (EGME) and ethylene glycol monoethyl ether (EGEE). Further studies were designed to establish the effect of a single exposure to EGME. Mature male albino rats were exposed to various levels of EGME vapour for a single 4-h period and killed 14 days later. Following this single exposure a dose-related decrease in testis weight was observed in rats exposed to 5,000, 2,500 or 1,250 ppm EGME. Histopathological examination revealed disordered spermatogenesis and tubular atrophy in these animals. Minimal degenerative changes were seen in the testis of rats exposed to 625 ppm EGME. When rats were examined at various time intervals after exposure to EGME vapour for 4 h, testis weight was reduced in rats examined 2 days after exposure to 2,500 and 1,000 ppm EGME and remained depressed when compared with control values for up to 19 days following exposure. Histopathological examination of the testis revealed disordered spermatogenesis in exposed animals evident at 1 day following exposure to either 2,500 or 1,00 ppm EGME.

Animals↗
PubMedDate not supplied

A strategy for characterization of polyethylene glycol-derivatized proteins. A mass spectrometric analysis of the attachment sites in polyethylene glycol-derivatized superoxide dismutase.

Base treatment of polyethylene glycol-derivatized superoxide dismutase in which the polyethylene glycol is linked to the protein via a succinyl bridge, removes the polyethylene glycol leaving a succinyl marker. Exhaustive succinylation with d4-succinic anhydride completes the derivatization in order to minimize fractionation in proteolysis, chromatography, and desorption in the mass spectrometer. Production of peptides from the derivatized protein for high resolution and high-resolution tandem MS allows identification of the site that had been derivatized by polyethylene glycol and the determination of the amount of polyethylene glycol originally at each site. The mass spectrometric strategy outlined herein can be applied to other proteins derivatized for therapeutic administration.

Amino Acid Sequence↗
PubMed1999

Toxicity of formulated glycol deicers and ethylene and propylene glycol to lactuca sativa, lolium perenne, selenastrum capricornutum, and lemna minor

Laboratory studies were conducted to determine the toxicity of ethylene glycol (EG) and propylene glycol (PG) as well as two formulated glycol aircraft deicing/anti-icing fluids (ADAFs) to lettuce (Lactuca sativa), perennial ryegrass (Lolium perenne), a green alga (Selenastrum capricornutum), and duckweed (Lemna minor). Seedling emergence, root length, and shoot length were measured in lettuce and ryegrass; cell growth of the alga and frond growth, chlorophyll a, and pheophytin a of the duckweed were measured. While both the ADAFs and pure glycols were toxic to the test species, there were substantial differences in how the organisms responded to the test materials. ADAFs affected emergence in ryegrass more than in lettuce. However, when considering the sublethal endpoints of root and shoot length, the ADAFs were significantly more toxic to lettuce. The root length 120-h IC25s for lettuce were 2,710 and 21, 270 mg EG/L for the ADAF and pure EG compound, respectively; the root length 120-h IC25s for ryegrass were 4,150 and 3,620 mg EG/L for the ADAF and pure EG compound, respectively. EG and PG ADAFs were more toxic than pure EG or PG to L. minor. To S. capricornutum, EG ADAF toxicity was similar to EG toxicity, however, PG ADAF was substantially more toxic to the alga than pure PG. The greater toxicity of ADAFs is reflective of other studies using animals and suggests that although glycols no doubt contribute to toxicity in deicer formulations, other compounds in the mixtures also contribute to the toxicity of the deicers. However, differences in responses between the four plant species suggest differences in modes of action and/or how the plants metabolize the compounds.http://link. springer-ny.com/link/service/journals/00244/bibs/37n1p29.html

Journal Article↗