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PubMed2001

Determination of short-chained poly(ethylene glycols) and ethylene glycol in environmental samples.

A method for the determination of ethylene glycol (EG), di(ethylene glycol) (E2) and tri(ethylene glycol) (E3) in environmental samples (raw and treated sewage, river water) has been developed. These substances are important by-products in the biotransformation of non-ionic surfactants (NS). The method is based on sequential liquid-liquid extraction with ethyl acetate and chloroform (resulting in the separation of poly(ethylene glycols) (PEG) and EG from the water matrix), precipitation of long-chained PEG (PEGlch) with Dragendorff reagent, extraction of short-chained PEG (PEGsh) (EG, E2 and E3) from a filtrate with chloroform and the final determination using alternating current voltammetry. The precision of the method is 7.3%, the recovery 95% and a detection limit of 1.5 microg in the sample, i.e. 10 microg l(-1) was achieved. As evidenced by F and t tests, the developed method is equivalent to the indirect PEGsh determination by the difference approach where concentration of PEGsh is determined by the difference of the total PEG and PEGlch. The PEGsh fraction was found to be present in considerable concentrations in raw and treated sewage, river water, as well as being a major biotransformation by-product in the continuous flow activated sludge testing of fatty alcohol ethoxylates.

Biotransformation↗

PubMed2006

Synthesis and characterization of poly(ethylene glycol)-poly(D,L-lactide-co-glycolide) poly(ethylene glycol) tri-block co-polymers modified with collagen: a model surface suitable for cell interaction.

This study focused on the synthesis and characterization of poly(ethylene glycol)-poly(D,L-lactide-co-glycolide)-poly(ethylene glycol) tri-block co-polymer (PEG-PDLLG-PEG), and its modification with type-I collagen. To this aim, a PEG-PDLLG-PEG tri-block co-polymer was synthesized in two steps by reacting poly(ethylene glycol)bis(carboxymethyl)ether with thionyl chloride to obtain an acyl-halide-terminated poly(ethylene glycol) and subsequently coupling this compound to hydroxyl-terminated poly(D,L-lactide-co-glycolide) (PDLLG). The new carboxyl endgroups of PEG-PDLLG-PEG were subsequently reacted with N-hydroxysuccinimide (NHS) in the presence of the hetero-bifunctional cross-linking agent dicyclohexylcarbodiimide (DCC) in order to activate the co-polymer for coupling with collagen. PEG-PDLLG-PEG and its activated form PEG-PDLLG-NHS were characterized by Fourier transform infrared (FT-IR) and 1H-NMR spectroscopy. Molecular weights of the polymeric products were determined by SEC. Type-I collagen in phosphate buffer was reacted with PEG-PDLLG-NHS. The resultant product, PEG-PDLLG-Col, was characterized by FT-IR. This biopolymer was used for preparation of a suitable surface for cell growth experiment. To measure the degree of cell proliferation, the films prepared with PDLLG, PEG-PDLLG-NHS and PEG-PDLLG-Col were seeded with L929 mouse fibroblasts. Cell growth was followed by SEM photography and quantitated by the neutral red uptake assay. It was shown that the attachment of collagen significantly increased the number of cells on the co-polymers.

Animals↗

PubMed1979

Quantitative structure-activity relationships involving the inhibition of glycolic acid oxidase by derivatives of glycolic and glyoxylic acids.

The enzyme glycolic acid oxidase oxidizes glycolate to glyoxylate and glyoxylate to oxalate. Three series of compounds related to the natural substrates, substituted glycolic, oxyacetic, and glyoxylic acids, have been investigated as inhibitors of this enzyme using the techniques of regression analysis and quantitative structure-activity relationships. The best overall correlation with inhibitory potencies was found with the Hansch hydrophobic parameter pi. The classical electronic parameters sigmap, sigmam, F, and R performed poorly. For the substituted glyoxylic acids, a dummy parameter relating to the presence of a nucleophilic group in close proximity to the alpha-carbonyl of the glyoxylate group was found to be highly significant. The syntheses of six novel glycolic and glyoxylic acids are described.

Acetates↗

PubMed2006

Effect of tocopheryl polyethylene glycol succinate on the percutaneous penetration of minoxidil from water/ethanol/polyethylene glycol 400 solutions.

We described to achieve the local retention of minoxidil which has penetrated the skin with minimization of its absorption into the general circulation and elimination of local irritation induced by propylene glycol. The effect of tocopheryl polyethylene glycol succinate (TPGS) on the penetration flux of minoxidil and its retention in the skin from topical minoxidil formulations consisting of water, alcohol, and polyethylene glycol 400 was characterized by an experimental design of ten solvent formulations in this study. Results show that the addition of TPGS was only able to improve the solubility of minoxidil in those solvent systems containing higher proportions of water and PEG 400, and the extent of improvement was also more profound with the addition of TPGS at concentrations higher than 5%. For those solvent systems containing a higher fraction of alcohol, an insignificant change in minoxidil solubility with increasing added amounts of TPGS was noted even with the tendency to decrease the solubility of minoxidil with higher amounts of TPGS. Increasing the amount of TPGS added gradually increased the flux and the corrected flux from solvent formulations with a lower solubility parameter, but decreased those from solvent systems with a higher solubility parameter. With the addition of TPGS, solvent formulation F6 (alcohol:PEG 400 of 50:50) was demonstrated to be the optimal choice by having an improved local effect and a reduced systemic effect compared to the reference of 2% Regaine((R)). Tocopheryl polyethylene glycol succinate (TPGS) was mainly retained locally in the stratum corneum, and the amount was proportional to the increase in the amount of TPGS added to these ten solvent formulations.

Administration, Cutaneous↗

PubMed1984

Review of glycol ether and glycol ether ester solvents used in the coating industry.

Ethylene oxide-based glycol ether and glycol ether ester solvents have been used in the coatings industry for the past fifty years. Because of their excellent performance properties (evaporation rate, blush resistance, flow-out and leveling properties, solubility for coating resins, solvent activity, mild odor, good coupling ability, good solvent release) a complete line of ethylene oxide-based solvents of various molecular weights has been developed. These glycol ether and glycol ether ester solvents have better solvent activity for coating resin than ester or ketone solvents in their evaporation rate range. The gloss, flow and leveling, and general performance properties of many coating systems are dependent on the use of these products in the coating formula. Because of the concern about the toxicity of certain ethylene oxide-based solvents, other products are being evaluated as replacements in coating formulas.

Chemical Phenomena↗

PubMed2006

Isolation of bacteria able to grow on both polyethylene glycol (PEG) and polypropylene glycol (PPG) and their PEG/PPG dehydrogenases.

Two bacterial consortia growing on a random copolymer of ethylene glycol and propylene glycol units were obtained by enrichment cultures from various microbial samples. Six major strains included in both consortia were purified and identified as Sphingomonads, Pseudomonas sp. and Stenotrophomonas maltophilia. Three of them (Sphingobium sp. strain EK-1, Sphingopyxis macrogoltabida strain EY-1, and Pseudomonas sp. strain PE-2) utilized both PEG and polypropylene glycol (PPG) as a sole carbon source. Four PEG-utilizing bacteria had PEG dehydrogenase (PEG-DH) activity, which was induced by PEG. PCR products from DNA of these bacteria generated with primers designed from a PEG-DH gene (AB196775 for S. macrogoltabida strain 103) indicated the presence of a sequence that is the homologous to the PEG-DH gene (99% identity). On the other hand, five PPG-utilizing bacteria had PPG dehydrogenase (PPG-DH) activity, but the activity was constitutive. PCR of a PPG-DH gene was performed using primers designed from a polyvinyl alcohol dehydrogenase (PVA-DH) gene (AB190288 for Sphingomonas sp. strain 113P3) because a PPG-DH gene has not been cloned yet, but both PPG-DH and PVA-DH were active toward PPG and PVA (Mamoto et al. 2006). PCR products of the five strains did not have similarity to each other or to oxidoreductases including PVA-DH.

Alcohol Oxidoreductases↗

PubMed1983

Comparative metabolism and disposition of ethylene glycol monomethyl ether and propylene glycol monomethyl ether in male rats.

Male Fischer 344 rats were given a single po dose of approximately 1 or 8.7 mmol/kg of [14C]EGME (ethylene glycol monomethyl ether) or [14C]PGME (propylene glycol monomethyl ether). After dosing, expired air, excreta, and tissues were analyzed for 14C; metabolites in urine were isolated and identified. There were pronounced differences in the metabolism and disposition of [14C]EGME and [14C]PGME. Approximately 50 to 60% of the administered 14C was excreted in urine, and about 12% was eliminated as 14CO2 within 48 hr after a single po dose of [14C]EGME. For PGME, only 10 to 20% of the administered 14C was excreted in urine, while 50 to 60% was eliminated as 14CO2 within 48 hr. Methoxyacetic acid was identified as the primary urinary metabolite of EGME, accounting for 80 to 90% of the total 14C in urine. PGME, propylene glycol(1,2-propanediol), and the sulfate and glucuronide conjugates of PGME were identified in urine of rats given PGME. Since methoxyacetic acid causes the same spectrum of toxicity as EGME in male rats, it is likely that the adverse effects of EGME are the result of its in vivo bioactivation to methoxyacetic acid. Hence, differences in routes of metabolism and types of metabolites appear to be the underlying basis for the remarkably different toxicologic properties of EGME and PGME, respectively.

Animals↗

PubMed1998

Drug compatibility with the sponge phases formed in monoolein, water, and propylene glycol or poly(ethylene glycol).

The liquid sponge phase, a bicontinuous lipid-water system, formed in solvent-monoolein-water systems was investigated with respect to drug compatibility. The solvents propylene glycol and poly(ethylene glycol) swell the bicontinuous cubic phase of the monoolein-water system and form the sponge phase at constant water contents, 40 and 30% w/w, respectively. Amphiphilic drugs such as lidocaine participate in the bilayer and act on the interfacial curvature according to the amphiphilic packing concept. The interfacial curvatures increase/decrease depending on the salt/base forms of the molecules. The quantity of lidocaine that can be incorporated into the sponge phase depends not only on the form of lidocaine but also on the lipid content and the solvent used in the sponge phase. Addition of the water-insoluble gramicidin S to the sponge phase resulted in a stiff isotropic phase, possibly a cubic phase, indicating interaction of gramicidin S with the lipid bilayer. The in vitro release of lidocaine was significantly faster from the sponge phase in the propylene glycol system than from the corresponding cubic phase without solvent.

Aminobutyrates↗

PubMed2003

Determination of ethanolamine, ethylene glycol and triethylene glycol by ion chromatography for laboratory and field biodegradation studies.

The determination of alkanolamines and glycols in groundwater and subsurface environments is essential for environmental assessment, remediation and monitoring for selected industrial sites. Monoethanolamine (MEA), ammonium, sodium, magnesium and calcium detection was performed using cation exchange chromatography (IC) with suppressed conductivity detection. Acetate, chloride, nitrite, nitrate, phosphate, sulfate and oxalate were monitored employing anion exchange chromatography with suppressed conductivity. Detection of ethylene glycol (MEG) and triethylene glycol (TEG) and ethanol was carried out using ion exclusion chromatography with pulsed amperometric detection. Effective determination of MEA, MEG and TEG in complex groundwater matrices without compound transformation offered improved monitoring capabilities. This study presents robust analytical tools for MEA, MEG and TEG determination in biodegradation studies. Using ion chromatography offered significant advantages for the analyses of groundwater samples and laboratory bioreactor monitoring.

Biodegradation, Environmental↗

PubMed1984

Ethylene glycol monomethyl ether and propylene glycol monomethyl ether: metabolism, disposition, and subchronic inhalation toxicity studies.

Short-term and subchronic vapor inhalation studies have shown that there are pronounced differences in the toxicological properties of ethylene glycol monomethyl ether (EGME) and propylene glycol monomethyl ether (PGME). Overexposure to EGME has resulted in adverse effects on testes, bone marrow and lymphoid tissues in laboratory animals. PGME does not affect these tissues, and instead, overexposure to PGME has been associated with increases in liver weight and central nervous system depression. EGME is primarily oxidized to methoxyacetic acid in male rats, while PGME apparently undergoes O-demethylation to form propylene glycol. Since methoxyacetic acid has been shown to have the same spectrum of toxicity as EGME in male rats, the observed differences in the toxicological properties of EGME and PGME are thought to be due to the fact that the two materials are biotransformed via different routes to different types of metabolites.

Air Pollutants↗

PubMed1989

Pharmacokinetics and biotransformation of diethylene glycol and ethylene glycol in the rat.

1. 14C-Diethylene glycol (DEG), administered orally to rats at 1, 5, and 10 ml/kg, gave elimination half-lives of 6, 6, and 10 h, respectively, from urinary excretion data. Half-logarithmic plots of urinary 14C excretion rates versus time indicated zero-order elimination for the first 9 and 18 h after oral doses of 5 and 10 ml of 14C-DEG/kg, respectively. 14C-DEG urinary elimination kinetics changed into first-order 6, 9, and 18 h after oral doses of 1, 5, and 10 ml/kg, with a half-life of 3 h. 2. After oral doses of 3 and 5 ml ethylene glycol (EG)/kg, half-lives of 4.5 and 4.1 h were estimated from cumulative urinary excretion data for non-metabolized EG. A half-life of 2 h was determined from half-logarithmic plots of urinary excretion rates of non-metabolized EG after the same oral doses of EG. 3. The urinary concentrations of non-metabolized DEG and its metabolite, 2-hydroxyethoxyacetic acid (2-HEAA), determined by high-resolution n.m.r. spectroscopy in the urine of rats doses with DEG were 61-68% and 16-31% dose, respectively. 4. Urinary concentrations of non-metabolized EG and its metabolite, glycolic acid (GA), determined by n.m.r., gave 62-67% for non-metabolized EG and 28.7% for GA following oral doses of EG. 5. Oxidation of DEG and EG in rats was accompanied by a change of urinary pH, reflecting metabolic acidosis. 6. Comparison of the KM for DEG oxidation in vitro by ADH with that of ethanol oxidation, showed a 680-fold difference in substrate affinity. DEG inhibited ethanol oxidation non-competitively, the Ki being 0.44 M.

Acidosis↗

PubMedDate not supplied

Gas chromatographic determination of monoethylene glycol and diethylene glycol in chocolate packaged in regenerated cellulose film.

A method for the quantitative determination of monoethylene glycol (MEG) and diethylene glycol (DEG) in chocolate is described. The procedure involves dissolving the chocolate in hot water, defatting with hexane, removing sugars by precipitation, and analyzing as trimethylsilyl (TMS) ether derivatives by capillary gas chromatography. The use of butan-1,4-diol as an internal standard corrects for recovery, which is between 50 and 60%, to give a relative standard deviation of 10-11% for the determination of both glycols at the level of 50 mg/kg. The presence of MEG and DEG in chocolate is confirmed by full scanning gas chromatography/mass spectrometry of the TMS derivatives.

Cacao↗

PubMed1997

Intravenous 4-methylpyrazole as an antidote for diethylene glycol and triethylene glycol poisoning: a case report.

Diethylene glycol (DEG) intoxication resembles that of ethylene glycol, with progressive inebriation, anion gap metabolic acidosis, renal failure, coma and death. DEG is oxidized by alcohol dehydrogenase (ADH) to more toxic byproducts, thus blockade of ADH might be beneficial. Triethylene glycol (TEG), also metabolized by ADH, is less toxic. A young female suicidally ingested DEG and TEG, presenting in metabolic acidosis with coma. Given 4-methylpyrazole (4-MP), an ADH inhibitor, the acidosis resolved, the patient recovered and was discharged without sequelae. 4-MP, if supported by further studies, may be useful in DEG poisoning.

Adolescent↗

PubMed1981

Simultaneous measurement of plasma 4-hydroxy-3-methoxyphenylethylene glycol and 3,4-dihydroxyphenylethylene glycol by gas chromatography mass spectrometry.

A sensitive gas chromatographic mass spectrometric assay has been developed to measure plasma 4-hydroxy-3-methoxyphenylethylene glycol and 3,4-dihydroxyphenylethylene glycol. Following addition of deuterated internal standards, the metabolites are propionylated to facilitate extraction with dichloromethane. After evaporation of the solvent, the residue is derivatized with t-butyldimethylsilylimidazole. The reaction product is washed with water, evaporated to dryness, and reconstituted with hexane for gas chromatography mass spectrometry. The single major fragment ion from each of the derivatized metabolites is monitored, yielding a sensitivity of approximately 3-5 pmol ml-1. Improved precision for the 3,4-dihydroxphenylethylene glycol assay may be facilitated by synthesis of a more stable internal standard.

Gas Chromatography-Mass Spectrometry↗

PubMed1990

Effect of ethylene glycol monomethyl ether and diethylene glycol monomethyl ether on hepatic metabolizing enzymes.

Glycol ethers have been extensively used in industry over the past 40-50 years. Numerous studies on the toxicity of glycol ethers have been performed, however, the effects of glycol ethers on the hepatic drug metabolizing enzymes are still unknown. We studied the changes of the putative metabolic enzymes, that is, the hepatic microsomal mixed function oxidase system and cytosolic alcohol dehydrogenase, by the oral administration of diEGME and EGME. Adult male Wistar rats were used. DiEGME was administered orally; 500, 1000, 2000 mg/kg for 1, 2, 5 or 20 days and EGME was 100, 300 mg/kg for 1, 2, 5 or 20 days. Decreases in liver weights were produced by highest doses of diEGME (2000 mg/kg body wt/day for 20 days) and EGME (300 mg/kg body wt/day for 20 days). DiEGME increased hepatic microsomal protein contents and induced cytochrome P-450, but not cytochrome b5 or NADPH-cytochrome c reductase. The activity of cytosolic ADH was not affected by diEGME administration. On the other hand, EGME did not change cytochrome P-450, cytochrome b5 or NADPH-cytochrome c reductase. The activity of cytosolic ADH was increased by repeated EGME treatment. Therefore it is suspected that the enzyme which takes part in the metabolism of diEGME is different from that of EGME, although diEGME is a structural homologue of EGME.

Administration, Oral↗

PubMed2006

Peptide-polyethylene glycol conjugates: synthesis and properties of peptides bearing a C-terminal polyethylene glycol chain.

The introduction of a polyethylene glycol chain has become a popular tool for increasing water solubility and bioavailability. Our interest in the development of catalytically active peptides and the selective recognition of peptides has led us to investigate strategies to increase the solubility of peptides in organic solvents. Specifically, we became interested in the introduction of solubilizing moieties at the C-terminus of two peptides. Here we present different synthetic strategies for the preparation of peptide-polyethylene glycol conjugates and discuss the effect of the polyethylene glycol chain on the solubility and other properties, such as the catalytic activity of these peptides.

Catalysis↗

PubMed1993

Use of polyethylene glycol-bound superoxide dismutase, polyethylene glycol-bound catalase, and nimodipine to prevent hypoxic ischemic injury to the brain of newborn pigs.

OBJECTIVE: To determine if polyethylene glycol-bound superoxide dismutase and catalase and nimodipine, alone or in combination, will ameliorate hypoxic ischemic injury to the brain. SUBJECTS: A total of 78 newborn (0 to 3 days) pigs were used. DESIGN: Prospective, blinded, randomized, controlled trial. INTERVENTIONS: The piglets were subjected to hypoxic ischemic brain injury. Carotid arteries were ligated at time 0 and BP was reduced one third by hemorrhage. At 15 mins, FIO2 was reduced to 0.6. At 30 mins, carotids were released, blood was reinfused, and FIO2 was increased to 1.0. Pigs were randomly assigned at time 35 mins to receive either: 10,000 U/kg of polyethylene glycol-bound superoxide dismutase and catalase (group 1); 0.5 mg/kg of nimodipine (group 2); both 10,000 U/kg of superoxide dismutase and catalase and 0.5 mg/kg of nimodipine (group 3); or no drugs (controls). MEASUREMENTS: The time after reoxygenation for return of electroencephalogram, respiration, blink and pain were recorded in minutes as well as a neurologic examination at 1, 2, and 3 days and pathologic examination of the brain at 3 days, both by blinded observers. MAIN RESULTS: There were no significant differences in the four groups. CONCLUSIONS: Polyethylene glycol-bound superoxide dismutase and catalase, and nimodipine, either alone or in combination, do not ameliorate hypoxic ischemic injury to the brain in the newborn pig when given 5 mins after reoxygenation.

Animals↗

PubMed1987

Glycol methacrylate embedding in histotechnology: the hematoxylin-eosin stain as a method for assessing the stability of glycol methacrylate sections.

Glycol methacrylate (GMA) samples containing inhibitor in the range of 200-300 ppm were included in a standard embedding mixture. The pH of the GMA samples was measured as a 10% solution of the sample in distilled water. The acidity of GMA due to methacrylic acid causes background staining of sections after basic dyes. The concentration of GMA and the amount of impurities such as methacrylic acid (MA) and ethylene glycol dimethacrylate (EDMA) were measured by gas chromatography. Distinct variations in purity were found among five samples of GMA. Sections derived from GMA samples containing more than 2% EDMA showed few, if any, minifolds after staining with hematoxylin and eosin and were more stable in alcoholic and basic solutions; sections from purer GMA showed minifolds and were less stable. Addition of crosslinkers, EDMA or triethylene glycol dimethacrylate (TEDMA) prevented these artifacts. Crosslinkers clearly influence dimensional changes in sections. Addition of crosslinkers to GMA samples containing minimal amounts of MA improved the results. The possibility of obtaining a high quality GMA embedding medium is discussed.

Acrylates↗