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| Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula (CH2OH)2. It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid. It has a sweet taste, but is toxic in high concentrations. This molecule has been observed in outer space. |
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Read full article at Wikipedia
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| InChI=1S/C2H6O2/c3-1-2-4/h3-4H,1-2H2 |
| LYCAIKOWRPUZTN-UHFFFAOYSA-N |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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solvent
A liquid that can dissolve other substances (solutes) without any change in their chemical composition.
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toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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solvent
A liquid that can dissolve other substances (solutes) without any change in their chemical composition.
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View more via ChEBI Ontology
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ethane-1,2-diol
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ethylene glycol
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1,2-Dihydroxyethane
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NIST Chemistry WebBook
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1,2-Ethanediol
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KEGG COMPOUND
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1,2-ETHANEDIOL
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PDBeChem
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2-Hydroxyethanol
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NIST Chemistry WebBook
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Ethanediol
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NIST Chemistry WebBook
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Ethylene glycol
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KEGG COMPOUND
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ethylene glycol
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UniProt
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Glycol
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KEGG COMPOUND
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HO‒CH2‒CH2‒OH
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IUPAC
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Monoethylene glycol
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NIST Chemistry WebBook
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1310
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PPDB
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C00007409
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KNApSAcK
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C01380
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KEGG COMPOUND
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c0542
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UM-BBD
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C15588
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KEGG COMPOUND
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EDO
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PDBeChem
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Ethylene_Glycol
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Wikipedia
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GLYCOL
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MetaCyc
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| View more database links |
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107-21-1
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CAS Registry Number
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ChemIDplus
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107-21-1
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CAS Registry Number
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ChemIDplus
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107-21-1
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CAS Registry Number
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NIST Chemistry WebBook
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505945
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Reaxys Registry Number
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Reaxys
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943
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Gmelin Registry Number
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Gmelin
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Ravi G, Venkatesh YP (2014)
Recognition of flavin mononucleotide, Haemophilus influenzae type b and its capsular polysaccharide vaccines by antibodies specific to D-ribitol-5-phosphate.
Glycoconjugate journal 31, 573-585 [PubMed:25108762]
[show Abstract]
D-Ribitol-5-phosphate (Rbt-5-P) is an important metabolite in the pentose phosphate pathway and an integral part of bacterial cell wall polysaccharides, specifically as polyribosyl ribitol phosphate (PRP) in Haemophilus influenzae type b (Hib). The major objective of this study was to investigate whether an antibody specific to Rbt-5-P can recognize the PRP of Hib. D-Ribose-5-phosphate was reacted with proteins in the presence of sodium cyanoborohydride to obtain Rbt-5-P epitopes; 120 h reaction resulted in conjugation of ~30 and ~17 moles of Rbt-5-P/mole of BSA and OVA, respectively, based on decrease in amino groups, MALDI-TOF analyses, an increase in apparent molecular weight (SDS-PAGE) and glycoprotein staining. Immunization of rabbits with Rbt-5-P-BSA conjugate generated antibodies to Rbt-5-P as demonstrated by dot immunoblot and non-competitive ELISA. Homogeneous Rbt-5-P-specific antibody was purified from Rbt-5-P-BSA antiserum subjected to caprylic acid precipitation followed by hapten-affinity chromatography; its affinity constant is 7.1 × 10(8) M(-1). Rbt-5-P antibody showed 100 % specificity to Rbt-5-P, ~230 %, 10 % and 3.4 % cross-reactivity to FMN, riboflavin and FAD, respectively; the antibody showed ~4 % cross-reactivity to D-ribitol and <3 % to other sugars/sugar alcohols. Rbt-5-P-specific antibody recognized Hib conjugate vaccines containing PRP which was inhibited specifically by Rbt-5-P, and also detected Hib cell-surface capsular polysaccharides by immunofluorescence. In conclusion, Rbt-5-P-protein conjugate used as an immunogen elicited antibodies binding to an epitope also present in PRP and Hib bacteria. Rbt-5-P-specific antibody has potential applications in the detection and quantification of free/bound Rbt-5-P and FMN as well as immunological recognition of Hib bacteria and its capsular polysaccharide. | Ravi G, Venkatesh YP (2014)
Recognition of riboflavin and the capsular polysaccharide of Haemophilus influenzae type b by antibodies generated to the haptenic epitope D-ribitol.
Glycoconjugate journal 31, 247-258 [PubMed:24643482]
[show Abstract]
D-Ribitol, a five-carbon sugar alcohol, is an important metabolite in the pentose phosphate pathway; it is an integral part of riboflavin (vitamin B2) and cell wall polysaccharides in most Gram-positive and a few Gram-negative bacteria. Antibodies specific to D-ribitol were generated in New Zealand white rabbits by using reductively aminated D-ribose-BSA conjugate as the immunogen. MALDI-TOF and amino group analyses of ribitol-BSA conjugate following 120 h reaction showed ~27-30 mol of ribitol conjugated per mole BSA. The presence of sugar alcohol in the conjugates was also confirmed by an increase in molecular mass and a positive periodic acid-Schiff staining in SDS-PAGE. Caprylic acid precipitation of rabbit serum followed by hapten affinity chromatography on ribitol-KLH-Sepharose CL-6B resulted in pure ribitol-specific antibodies (~45-50 μg/mL). The affinity constant of ribitol antibodies was found to be 2.9 × 10(7) M(-1) by non-competitive ELISA. Ribitol antibodies showed 100% specificity towards ribitol, ~800% cross-reactivity towards riboflavin, 10-15% cross-reactivity with sorbitol, xylitol and mannitol, and 5-7% cross-reactivity with L-arabinitol and meso-erythritol. The specificity of antibody to ribitol was further confirmed by its low cross-reactivity (0.4%) with lumichrome. Antibodies to D-ribitol recognized the purified capsular polysaccharide of Haemophilus influenzae type b, which could be specifically inhibited by ribitol. In conclusion, antibodies specific to D-ribitol have been generated and characterized, which have potential applications in the detection of free riboflavin and ribitol in biological samples, as well as identification of cell-surface macromolecules containing ribitol. | Monet C, Richard E, Missonnier S, Rebouissoux L, Llanas B, Harambat J (2013)
[Secondary hyperoxaluria and nephrocalcinosis due to ethylene glycol poisoning].
Archives de pediatrie : organe officiel de la Societe francaise de pediatrie 20, 863-866 [PubMed:23827374]
[show Abstract]
We report the case of a 3-year-old boy admitted to the pediatric emergency department for ethylene glycol poisoning. During hospitalization, he presented dysuria associated with crystalluria. Blood tests showed metabolic acidosis with an elevated anion gap. A renal ultrasound performed a few weeks later revealed bilateral medullary hyperechogenicity. Urine microscopic analysis showed the presence of weddellite crystals. Secondary nephrocalcinosis due to ethylene glycol intoxication was diagnosed. Hyperhydration and crystallization inhibition by magnesium citrate were initiated. Despite this treatment, persistent weddellite crystals and nephrocalcinosis were seen more than 2years after the intoxication. Ethylene glycol is metabolized in the liver by successive oxidations leading to its final metabolite, oxalic acid. Therefore, metabolic acidosis with an elevated anion gap is usually found following ethylene glycol intoxication. Calcium oxalate crystal deposition may occur in several organs, including the kidneys. The precipitation of calcium oxalate in renal tubules can lead to nephrocalcinosis and acute kidney injury. The long-term renal prognosis is related to chronic tubulointerstitial injury caused by nephrocalcinosis. Treatment of ethylene glycol intoxication is based on specific inhibitors of alcohol dehydrogenase and hemodialysis in the most severe forms, and should be started promptly. | Zhang J, Yuan Q, Zhang J, Li T, Guo H (2013)
Direct synthesis of ethylene glycol from methanol by dielectric barrier discharge.
Chemical communications (Cambridge, England) 49, 10106-10108 [PubMed:24045699]
[show Abstract]
Ethylene glycol (EG) has been obtained with 71.53% selectivity and 15.77% methanol conversion under optimized conditions using a double dielectric barrier discharge (DDBD) reactor. The importance of the discharge intensity and the obvious catalytic effect of the hydrogen co-feed were observed. | Li Z, Kay BD, Dohnálek Z (2013)
Dehydration and dehydrogenation of ethylene glycol on rutile TiO2(110).
Physical chemistry chemical physics : PCCP 15, 12180-12186 [PubMed:23764541]
[show Abstract]
The interactions of ethylene glycol with a partially reduced rutile TiO2(110) surface have been studied using temperature programmed desorption (TPD). The saturation coverage on surface Ti rows is determined to be 0.43 monolayer (ML), slightly less than one ethylene glycol per two Ti sites. Most of the adsorbed ethylene glycol (∼80%) undergoes further reactions to yield other products. Two major channels are observed, dehydration yielding ethylene and water and dehydrogenation yielding acetaldehyde and hydrogen. Hydrogen formation is rather surprising as it has not been observed previously on TiO2(110) from simple organic molecules. The coverage dependent yields of ethylene and acetaldehyde correlate well with those of water and hydrogen, respectively. Dehydration dominates at lower ethylene glycol coverages (<0.2 ML) and plateaus as the coverage is increased to saturation. Dehydrogenation is observed primarily at higher ethylene glycol coverages (>0.2 ML). Our results suggest that the observed dehydration and dehydrogenation reactions proceed via different surface intermediates. | Sreenath K, Venkatesh YP (2007)
Reductively aminated D-xylose-albumin conjugate as the immunogen for generation of IgG and IgE antibodies specific to D-xylitol, a haptenic allergen.
Bioconjugate chemistry 18, 1995-2003 [PubMed:17979222]
[show Abstract]
Sugar alcohols are widely used as food additives and drug excipients. Xylitol, a five-carbon sugar alcohol, and a low-calorie alternative sweetener to sucrose (approx 40% fewer calories), has enjoyed an enviable record of safety, and allergic reactions to xylitol are very rare. A case of oral erosive eczema to xylitol has been reported recently [Hanakawa, Y., Hanakawa, Y., Tohyama, M., Yamasaki, K., Hashimoto, K. (2005) Xylitol as a causative agent of oral erosive eczema. Brit. J. Dermatol. 152, 821-822]. Xylitol does not contain any reactive groups; hence, it is nonimmunogenic. In order to explain the immunogenicity of xylitol, polyclonal antibodies to xylitol have been raised using the reductive aminated product of D-xylose conjugated to bovine serum albumin (BSA) as the immunogen. Rabbits immunized with xylitol-BSA conjugate (52 haptens/molecule) gave a good antibody response. Purification of antixylitol antibodies was carried out using hapten-affinity chromatography on xylitol-keyhole limpet hemocyanin-Sepharose CL-6B; the yield was approximately 40 microg/mL of rabbit immune serum. Purified xylitol-specific antibodies appeared to be homogeneous by native PAGE with a pI of approximately 7.2 by isoelectric focusing. Although the purified antibodies are specific for the xylitoyl moiety of xylitol-protein conjugates, they reacted equally well with the Schiff base conjugate of xylosyl-protein conjugates (68% cross-reactivity) indicating that carbons 2 to 5 of xylitol act as an epitope. Xylitol antibodies showed excellent specificity towards xylitol and <4.4% cross-reactivity with D-xylose and various sugar alcohols except ribitol and galactitol, which showed approximately 11% and 8% cross-reactivity, respectively. D-Xylitol-BSA conjugate was used to raise IgE antibodies in BALB/c mice by repeated intradermal administration. Passive cutaneous anaphylaxis using the immune sera confirmed the haptenic nature of xylitol. | Reddy NJ, Lewis LD, Gardner TB, Osterling W, Eskey CJ, Nierenberg DW (2007)
Two cases of rapid onset Parkinson's syndrome following toxic ingestion of ethylene glycol and methanol.
Clinical pharmacology and therapeutics 81, 114-121 [PubMed:17186009]
[show Abstract]
Ethylene glycol and methanol are toxic alcohols commonly found in a variety of commercial products. We report two cases, one associated with ethylene glycol and one with methanol poisoning, which both led to acute hemorrhagic necrosis of the basal ganglia and resulted in acute Parkinson's syndrome. It is unlikely that oxalate crystal deposition is the only mechanism for such basal ganglia necrosis, because similar findings were seen following methanol intoxication. We discuss other possible mechanisms that may contribute towards this unusual neurotoxicity. Both of our patients survived their toxic ingestions, but then developed acute Parkinson's syndrome within 10 days of the ingestion. However, the patient who ingested methanol developed respiratory muscle stiffness/weakness, which responded poorly to anti-Parkinsonian drug therapy. Treatment with carbidopa/levodopa improved cogwheel rigidity and bradykinesia in both patients. We conclude that acute Parkinsonism is one of the lesser-recognized devastating complications of both ethylene glycol and methanol poisoning. | Hegde VL, Venkatesh YP (2007)
Generation of antibodies specific to D-mannitol, a unique haptenic allergen, using reductively aminated D-mannose-bovine serum albumin conjugate as the immunogen.
Immunobiology 212, 119-128 [PubMed:17336832]
[show Abstract]
D-mannitol is commonly used as a food additive and excipient due to its sweetness, non-toxicity, and low calorific value. However, several cases of hypersensitivity reactions to mannitol have been reported. Owing to its inert nature, mannitol cannot produce an immunological response. In order to explain the mechanism of immunogenicity of mannitol, a method to obtain mannitol epitopes on a carrier protein, which serves as an immunogen to generate antibodies against mannitol, is described. In the present investigation, D-mannitol-specific polyclonal antibodies were generated by immunizing rabbits with reductively aminated mannose-bovine serum albumin (BSA) (33 haptens/molecule) as the hapten-carrier conjugate. Anti-mannitol IgG antibodies were purified from the immune serum by hapten-affinity chromatography on a D-mannitol-keyhole limpet hemocyanin (KLH)-Sepharose CL-6B affinity matrix. The yield of mannitol-specific antibodies was approximately 40 microg per mL of rabbit antiserum. The specificity of the purified antibodies towards D-mannitol was demonstrated by hapten-inhibition in enzyme-linked immunosorbent assay (ELISA). The affinity-purified antibodies were found to be very specific to D-mannitol showing less than 5% cross-reactivity with other sugars and sugar alcohols, with the exception of its epimer, sorbitol, which showed 8.8% cross-reactivity. Importantly, the antibodies showed <1% cross-reactivity with L-mannitol epitope, thus exhibiting configurational specificity. The inhibition studies provided evidence for the haptenic nature of mannitol and confirmed that the mannitoyl group is a single epitope. The reaction scheme utilized here for the generation of mannitol epitopes provides the basis for the immunogenicity of mannitol. | Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG (2007)
Growth control of the eukaryote cell: a systems biology study in yeast.
Journal of biology 6, 4 [PubMed:17439666]
[show Abstract]
BackgroundCell growth underlies many key cellular and developmental processes, yet a limited number of studies have been carried out on cell-growth regulation. Comprehensive studies at the transcriptional, proteomic and metabolic levels under defined controlled conditions are currently lacking.ResultsMetabolic control analysis is being exploited in a systems biology study of the eukaryotic cell. Using chemostat culture, we have measured the impact of changes in flux (growth rate) on the transcriptome, proteome, endometabolome and exometabolome of the yeast Saccharomyces cerevisiae. Each functional genomic level shows clear growth-rate-associated trends and discriminates between carbon-sufficient and carbon-limited conditions. Genes consistently and significantly upregulated with increasing growth rate are frequently essential and encode evolutionarily conserved proteins of known function that participate in many protein-protein interactions. In contrast, more unknown, and fewer essential, genes are downregulated with increasing growth rate; their protein products rarely interact with one another. A large proportion of yeast genes under positive growth-rate control share orthologs with other eukaryotes, including humans. Significantly, transcription of genes encoding components of the TOR complex (a major controller of eukaryotic cell growth) is not subject to growth-rate regulation. Moreover, integrative studies reveal the extent and importance of post-transcriptional control, patterns of control of metabolic fluxes at the level of enzyme synthesis, and the relevance of specific enzymatic reactions in the control of metabolic fluxes during cell growth.ConclusionThis work constitutes a first comprehensive systems biology study on growth-rate control in the eukaryotic cell. The results have direct implications for advanced studies on cell growth, in vivo regulation of metabolic fluxes for comprehensive metabolic engineering, and for the design of genome-scale systems biology models of the eukaryotic cell. | Sreenath K, Prabhasankar P, Venkatesh YP (2006)
Generation of an antibody specific to erythritol, a non-immunogenic food additive.
Food additives and contaminants 23, 861-869 [PubMed:16901854]
[show Abstract]
Erythritol, a simple sugar alcohol, is widely used as a food and drug additive owing to its chemical inertness, sweetness and non-toxicity. Adverse reactions to erythritol are rare and only three cases of allergic reactions to foods containing erythritol have been reported. Being inert, erythritol cannot produce an immunological response. In order to explain the mechanism of immunogenicity of erythritol, a method to obtain erythritol epitopes on a carrier protein, which can serve as an immunogen to develop antibodies against erythritol, is described. D-Erythrose was conjugated to bovine serum albumin at pH 8 by reductive amination. The reduction product of the Schiff base of D-erythrose-bovine serum albumin conjugate creates erythritoyl groups. Rabbits immunized with erythritol-bovine serum albumin conjugate (29 haptens/molecule) showed good antibody response (detection of 1 microg antigen, erythritol-keyhole limpet haemocyanin conjugate possessing 50% modified amino groups, at 1 : 50,000 dilution). Anti-erythritol immunoglobulin-G antibodies were purified from the immune serum using hapten-affinity chromatography on an erythritol-keyhole limpet haemocyanin-Sepharose CL-6B affinity matrix. The yield of erythritol-specific antibody was approximately 40 microg ml-1 of rabbit antiserum. Enzyme-linked immunobsorbant assay inhibition studies using sugars, sugar alcohols and L-lysine showed minimal cross-reactivity (approximately 4%) when compared with erythritol; only dithioerythritol showed a cross-reactivity of approximately 33%. D-Threitol and L-threitol (isomers of erythritol) had cross-reactivities of 15 and 11%, respectively. The inhibition studies confirmed the haptenic nature of erythritol and indicated that the erythritoyl group is a single epitope. The reaction scheme outlined here for the generation of erythritol epitopes appears to provide a basis for the immunogenicity of erythritol. | Corley RA, Bartels MJ, Carney EW, Weitz KK, Soelberg JJ, Gies RA, Thrall KD (2005)
Development of a physiologically based pharmacokinetic model for ethylene glycol and its metabolite, glycolic Acid, in rats and humans.
Toxicological sciences : an official journal of the Society of Toxicology 85, 476-490 [PubMed:15716482]
[show Abstract]
An extensive database on the toxicity and modes of action of ethylene glycol (EG) has been developed over the past several decades. Although renal toxicity has long been recognized as a potential outcome, in recent years developmental toxicity, an effect observed only in rats and mice, has become the subject of extensive research and regulatory reviews to establish guidelines for human exposures. The developmental toxicity of EG has been attributed to the intermediate metabolite, glycolic acid (GA), which can become a major metabolite when EG is administered to rats and mice at high doses and dose rates. Therefore, a physiologically based pharmacokinetic (PBPK) model was developed to integrate the extensive mode of action and pharmacokinetic data on EG and GA for use in developmental risk assessments. The resulting PBPK model includes inhalation, oral, dermal, intravenous, and subcutaneous routes of administration. Metabolism of EG and GA were described in the liver with elimination via the kidneys. Metabolic rate constants and partition coefficients for EG and GA were estimated from in vitro studies. Other biochemical constants were optimized from appropriate in vivo pharmacokinetic studies. Several controlled rat and human metabolism studies were used to validate the resulting PBPK model. When internal dose surrogates were compared in rats and humans over a broad range of exposures, it was concluded that humans are unlikely to achieve blood levels of GA that have been associated with developmental toxicity in rats following occupational or environmental exposures. | Wiley JF (1999)
Novel therapies for ethylene glycol intoxication.
Current opinion in pediatrics 11, 269-273 [PubMed:10349109]
[show Abstract]
Ethylene glycol is a serious toxin that children frequently ingest. Diagnosis and treatment of this poisoning are challenging and frequently involve the use of novel therapies. In the past year, fomepizole (4-methylpyrazole) has been approved for use as an antidote in the treatment of ethylene glycol poisoning in adults, and the first article reporting the use of fomepizole in a pediatric ethylene glycol exposure was published. As a result, the therapy of ethylene glycol poisoning in children is likely to change from the traditional approach of ethanol administration coupled with hemodialysis to the administration of fomepizole with or without hemodialysis. | Lech J (1997)
Two solvents, dimethyl formamide (DMFA) and ethylene glycol (EG), induced the mRNA of vitellogenin in rainbow trout.
Chemico-biological interactions 108, 135 [PubMed:9463526] | Sode K, Nakasono S, Tanaka M, Matsunaga T (1993)
Subzero temperature operating biosensor utilizing an organic solvent and quinoprotein glucose dehydrogenase.
Biotechnology and bioengineering 42, 251-254 [PubMed:18612987]
[show Abstract]
A subzero temperature operating biosensor was constructed using immobilized quinoprotein glucose dehydrogenase (PQQGDH), glassy carbon electrode, soluble electron mediator (ferrocene monocarboxylic acid), and an organic solvent, ethylene glycol, as an antifreezing reagent. Using this biosensor, glucose concentration can be determined even at -7 degrees C. At this temperature, the response was 20% of that obtained at 20 degrees C. This is the first study describing a subzero temperature operating biosensor. |
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