dichloroethylenes

Summary

Summary: Toxic chlorinated unsaturated hydrocarbons. Include both the 1,1- and 1,2-dichloro isomers. Both isomers are toxic, but 1,1-dichloroethylene is the more potent CNS depressant and hepatotoxin. It is used in the manufacture of thermoplastic polymers.

Top Publications

  1. Morita Y, Futagami T, Goto M, Furukawa K. Functional characterization of the trigger factor protein PceT of tetrachloroethene-dechlorinating Desulfitobacterium hafniense Y51. Appl Microbiol Biotechnol. 2009;83:775-81 pubmed publisher
    ..On the other hand, PceT failed to bind the mature form of PceA that lost the TAT signal sequence. This is the first report in dehalorespiring bacteria, indicating that PceT is responsible for the correct folding of the precursor PceA...
  2. Shim H, Ryoo D, Barbieri P, Wood T. Aerobic degradation of mixtures of tetrachloroethylene, trichloroethylene, dichloroethylenes, and vinyl chloride by toluene-o-xylene monooxygenase of Pseudomonas stutzeri OX1. Appl Microbiol Biotechnol. 2001;56:265-9 pubmed
    ..015, 0.023. and 0.029 nmol/min x mg protein, respectively. This indicates that for the first time an aerobic enzyme can degrade mixtures of all chlorinated ethenes, including the once--so it was believed-completely recalcitrant PCE. ..
  3. Futagami T, Yamaguchi T, Nakayama S, Goto M, Furukawa K. Effects of chloromethanes on growth of and deletion of the pce gene cluster in dehalorespiring Desulfitobacterium hafniense strain Y51. Appl Environ Microbiol. 2006;72:5998-6003 pubmed
    ..Moreover, such a growth inhibitory effect was also observed in the presence of carbon tetrachloride at 1 microM, but not carbon dichloride even at 1 mM...
  4. Schafer D, Köber R, Dahmke A. Competing TCE and cis-DCE degradation kinetics by zero-valent iron-experimental results and numerical simulation. J Contam Hydrol. 2003;65:183-202 pubmed
    ..Even if TCE is present in only small concentrations (>3% of molar cis-DCE concentration) it is the contaminant limiting the residence time and the required thickness of the iron barrier. ..
  5. Albert D, Albert A, Vernace M, Sebastian J, Hsia E. Analysis of a cluster of cases of Wegener granulomatosis. J Clin Rheumatol. 2005;11:188-93 pubmed
    ..We encourage clinicians to seek data that suggests an unusual environmental exposure and to solicit information that might implicate an industrial source for these exposures. ..
  6. Miller T, Franklin M, Halden R. Bacterial community analysis of shallow groundwater undergoing sequential anaerobic and aerobic chloroethene biotransformation. FEMS Microbiol Ecol. 2007;60:299-311 pubmed
    ..The study shows that bacterial community structure is related to groundwater geochemistry and that Alphaproteobacteria are enriched in locales where cis-DCE removal occurs. ..
  7. Yan J, Şimşir B, Farmer A, Bi M, Yang Y, Campagna S, et al. The corrinoid cofactor of reductive dehalogenases affects dechlorination rates and extents in organohalide-respiring Dehalococcoides mccartyi. ISME J. 2016;10:1092-101 pubmed publisher
    ..These findings emphasize that the role of the corrinoid/lower base synthesizing community must be understood to predict strain-specific Dhc activity and achieve efficacious contaminated site cleanup. ..
  8. Simmonds A, Reilly C, Baldwin R, Ghanayem B, Lanza D, Yost G, et al. Bioactivation of 1,1-dichloroethylene to its epoxide by CYP2E1 and CYP2F enzymes. Drug Metab Dispos. 2004;32:1032-9 pubmed
    ..The results also demonstrated that CYP2E1 is the high-affinity enzyme involved in DCE bioactivation. ..
  9. Morrill P, Lacrampe Couloume G, Slater G, Sleep B, Edwards E, McMaster M, et al. Quantifying chlorinated ethene degradation during reductive dechlorination at Kelly AFB using stable carbon isotopes. J Contam Hydrol. 2005;76:279-93 pubmed
    ..Stable carbon isotopes can provide not only a sensitive means for early identification of the effects of biodegradation, but an additional means to quantify the rates of biodegradation in the field. ..

More Information

Publications62

  1. Clark R, Foley L. A matrix isolation study of the photochemically induced reactions of nitrogen dioxide with 1,2-dibromoethene and 1,2-dichloroethene using Fourier transform infrared spectroscopy. Spectrochim Acta A Mol Biomol Spectrosc. 2005;61:1389-93 pubmed
    ..The possible reaction pathway is discussed. ..
  2. Doughty D, Sayavedra Soto L, Arp D, Bottomley P. Effects of dichloroethene isomers on the induction and activity of butane monooxygenase in the alkane-oxidizing bacterium "Pseudomonas butanovora". Appl Environ Microbiol. 2005;71:6054-9 pubmed
    ..1,2-trans DCE was unique among the BMO substrates tested in its ability to induce lacZ expression. ..
  3. Rahm B, Richardson R. Dehalococcoides' gene transcripts as quantitative bioindicators of tetrachloroethene, trichloroethene, and cis-1,2-dichloroethene dehalorespiration rates. Environ Sci Technol. 2008;42:5099-105 pubmed
    ..8 x 10(9) copies/mL culture for every/eeq/ L/hr increase in respiration rate (R2 = 0.90). Although RDase transcripts may provide information on substrate range, H2ase transcripts may be better indicators of per cell respiration rates. ..
  4. Forkert P, Boyd S, Ulreich J. Pulmonary bioactivation of 1,1-dichloroethylene is associated with CYP2E1 levels in A/J, CD-1, and C57BL/6 mice. J Pharmacol Exp Ther. 2001;297:1193-200 pubmed
    ..These results showed differences in CYP2E1 levels in the lungs of A/J, CD-1, and C57BL/6 mice that correlated with the extent to which the DCE epoxide is formed as well as with the severity of lung cytotoxicity. ..
  5. Arulmozhiraja S, Ehara M, Nakatsuji H. Electronic transitions in cis- and trans-dichloroethylenes and tetrachloroethylene. J Chem Phys. 2008;129:174506 pubmed publisher
    Electronic structures of trans- and cis-dichloroethylenes and tetrachloroethylene were studied using symmetry-adapted cluster configuration interaction theory. Basis sets up to the aug-cc-pVTZ of Dunning, Jr...
  6. Lee J, Hiibel S, Reardon K, Wood T. Identification of stress-related proteins in Escherichia coli using the pollutant cis-dichloroethylene. J Appl Microbiol. 2010;108:2088-102 pubmed publisher
    ..Six previously uncharacterized proteins (YchH, YdeI, YgiW, YhcN, YjaA and YodD) were shown to be stress proteins. ..
  7. Lee P, Conrad M, Alvarez Cohen L. Stable carbon isotope fractionation of chloroethenes by dehalorespiring isolates. Environ Sci Technol. 2007;41:4277-85 pubmed
  8. Ma X, Novak P, Semmens M, Clapp L, Hozalski R. Comparison of pulsed and continuous addition of H2 gas via membranes for stimulating PCE biodegradation in soil columns. Water Res. 2006;40:1155-66 pubmed
    ..Unfortunately, this strategy has proven to be inefficient, with the bulk of the added H2 used to support methanogenesis. ..
  9. Jennings L, Chartrand M, Lacrampe Couloume G, Lollar B, Spain J, Gossett J. Proteomic and transcriptomic analyses reveal genes upregulated by cis-dichloroethene in Polaromonas sp. strain JS666. Appl Environ Microbiol. 2009;75:3733-44 pubmed publisher
    ..The results provide a significant step toward elucidation of cDCE degradation pathways and enhanced understanding of cDCE degradation in JS666. ..
  10. Liu Y, Xia F, Liu F, Chen H. [Effects of benzene, toluene on reductive dechlorination of trichloroethylene and its daughter product cis-1,2-dichloroethylene by granular iron]. Huan Jing Ke Xue. 2010;31:1526-32 pubmed
  11. Slikker W, Andersen M, Bogdanffy M, Bus J, Cohen S, Conolly R, et al. Dose-dependent transitions in mechanisms of toxicity: case studies. Toxicol Appl Pharmacol. 2004;201:226-94 pubmed
    ..The case studies formed the basis for technical discourse at two scientific workshops in 2003. ..
  12. Paolini M, Mesirca R, Pozzetti L, Sapone A, Cantelli Forti G. Induction of CYP2B1 mediated pentoxyresorufin O-dealkylase activity in different species, sex and tissue by prototype 2B1-inducers. Chem Biol Interact. 1995;95:127-39 pubmed
    ..Therefore, caution should be exercised when using PROD activity as specific enzymatic assay to probe CYP2B1-like induction. ..
  13. Martin E, Forkert P. Evidence that 1,1-dichloroethylene induces apoptotic cell death in murine liver. J Pharmacol Exp Ther. 2004;310:33-42 pubmed
    ..These data suggested that DCE produces apoptosis by inducing MPT, causing release of cytochrome c into the cytosol and caspase activation. ..
  14. Hendricks J, Shelton D, Loveland P, Pereira C, Bailey G. Carcinogenicity of dietary dimethylnitrosomorpholine, N-methyl-N'-nitro-N-nitrosoguanidine, and dibromoethane in rainbow trout. Toxicol Pathol. 1995;23:447-57 pubmed
    ..DCE and CP produced no neoplasms at the exposure levels used. No evidence of other chronic toxicity was seen for any of the 5 compounds. ..
  15. Sugimoto K, Hirota S, Imanaka K, Ohnishi H, Tomioka H, Tada K, et al. Covered Gianturco stent for tracheal stricture: application of polychlorovinylidene and polyurethane as covering materials. Eur Radiol. 2001;11:1933-8 pubmed
    ..However, the indications for its use are limited to patients with poor prognoses, because hemoptysis, granuloma formation, and bacterial propagation remain problematic. ..
  16. Godsy E, Warren E, Paganelli V. The role of microbial reductive dechlorination of TCE at a phytoremediation site. Int J Phytoremediation. 2003;5:73-87 pubmed
    ..Elsewhere at the site, transpiration and degradation by the cottonwood trees appears to be responsible for loss of chlorinated ethenes. ..
  17. Arcangeli J, Arvin E. Methanotrophic biodegradation of cis-1,2-dichloroethylene in a continuously fed fixed-film bioreactor. Water Sci Technol. 2004;49:231-6 pubmed
    ..On the basis of this study it is concluded that careful control of the oxygen and methane concentrations as well as of the biofilm thickness is necessary in order to optimise the biodegradation of cis-DCE in fixed film bioreactors. ..
  18. Chang Y, Kikuchi S, Kawauchi N, Sato T, Takamizawa K. Complete dechlorination of tetrachloroethylene by use of an anaerobic Clostridium bifermentans DPH-1 and zero-valent iron. Environ Technol. 2008;29:381-91 pubmed publisher
    ..It is thought that phosphoric acid iron contained in a medium forms film on the surface of iron particle, so oxidation of iron is inhibited...
  19. Marino J, Zou N. Chemoselective syntheses of gamma-butyrolactams using vinyl sulfilimines and dichloroketene. Org Lett. 2005;7:1915-7 pubmed
    ..Fine-tuning of substituents within vinyl sulfilimines results in reactions with good chemoselectivity and yield for lactams. ..
  20. Malley L, Hansen J, Everds N, Warheit D. 4-week inhalation toxicity study with a mixture of dichloroethylene and perfluorobutylethylene in rats. Inhal Toxicol. 2002;14:773-87 pubmed
    ..Under the conditions of the study, the no-observed-effect level (NOEL) was 400 ppm in males and females based on clinical signs of toxicity during exposure to 2000 or 8000 ppm. ..
  21. Takeuchi M, Nanba K, Iwamoto H, Nirei H, Kusuda T, Kazaoka O, et al. In situ bioremediation of a cis-dichloroethylene-contaminated aquifer utilizing methane-rich groundwater from an uncontaminated aquifer. Water Res. 2005;39:2438-44 pubmed
    ..The population of methanotrophs with high V(max) and K(m) for methane uptake increased, resulting in successful degradation of c-DCE at a monitoring well 2m downgradient of the injection well. ..
  22. Slater G, Lollar B, Sleep B, Edwards E. Variability in carbon isotopic fractionation during biodegradation of chlorinated ethenes: implications for field applications. Environ Sci Technol. 2001;35:901-7 pubmed
    ..Despite this variability, these results demonstrate that carbon isotopic analysis can provide qualitative evidence of the occurrence and relative extent of microbial reductive dechlorination of the chlorinated ethenes. ..
  23. Fletcher K, Ritalahti K, Pennell K, Takamizawa K, Löffler F. Resolution of culture Clostridium bifermentans DPH-1 into two populations, a Clostridium sp. and tetrachloroethene-dechlorinating Desulfitobacterium hafniense strain JH1. Appl Environ Microbiol. 2008;74:6141-3 pubmed publisher
    ..and PCE-dechlorinating Desulfitobacterium hafniense strain JH1. Strain JH1 carries pceA, encoding a PCE reductive dehalogenase, and shares other characteristics with Desulfitobacterium hafniense strain Y51...
  24. Heck K, Janesko B, Scuseria G, Halas N, Wong M. Observing metal-catalyzed chemical reactions in situ using surface-enhanced Raman spectroscopy on Pd-Au nanoshells. J Am Chem Soc. 2008;130:16592-600 pubmed publisher
    ..More broadly, the results highlight the exciting prospects of studying catalytic processes in water in situ, like those involved in biomass conversion and proton-exchange membrane fuel cells. ..
  25. Ye L, Schilhabel A, Bartram S, Boland W, Diekert G. Reductive dehalogenation of brominated ethenes by Sulfurospirillum multivorans and Desulfitobacterium hafniense PCE-S. Environ Microbiol. 2010;12:501-9 pubmed publisher
    ..hafniense PCE-S also formed ethene. With the purified enzymes from both organisms the kinetic properties of dehalogenation of brominated alkenes were studied and compared with those of their chlorinated analogues...
  26. Johnson P, Dawson B, Goldberg S. A review: trichloroethylene metabolites: potential cardiac teratogens. Environ Health Perspect. 1998;106 Suppl 4:995-9 pubmed
    ..Further studies of drinking-water exposure and potential mechanisms of action on the developing heart are proceeding. ..
  27. Imfeld G, Aragonés C, Fetzer I, Mészáros E, Zeiger S, Nijenhuis I, et al. Characterization of microbial communities in the aqueous phase of a constructed model wetland treating 1,2-dichloroethene-contaminated groundwater. FEMS Microbiol Ecol. 2010;72:74-88 pubmed publisher
    ..Based on a multiple-method approach, this study illustrates the linkage between microbial community dynamics and composition, changes of hydrochemical conditions and processes of DCE degradation in a wetland system. ..
  28. Olaniran A, Pillay D, Pillay B. Aerobic dechlorination of cis- and trans-dichloroethenes by some indigenous bacteria isolated from contaminated sites in Africa. J Environ Sci (China). 2004;16:968-72 pubmed
    ..These findings therefore indicated the important roles that these organisms may play in the bioremediation of sites polluted with chlorinated ethene compounds in Africa. ..
  29. Mathews J, Etheridge A, Raymer J, Black S, Pulliam D, Bucher J. Selective inhibition of cytochrome P450 2E1 in vivo and in vitro with trans-1,2-dichloroethylene. Chem Res Toxicol. 1998;11:778-85 pubmed
    ..DCE is an effective, relatively nontoxic inhibitor of P450 2E1 in vivo and in vitro that has greater selectivity than other agents currently used. ..
  30. Ban M, Hettich D, Bonnet P. Effect of inhaled industrial chemicals on systemic and local immune response. Toxicology. 2003;184:41-50 pubmed
  31. Kim Y, Istok J, Semprini L. Push-pull tests evaluating in situ aerobic cometabolism of ethylene, propylene, and cis-1,2-dichloroethylene. J Contam Hydrol. 2006;82:165-81 pubmed
    ..These results suggest that a series of push-pull tests performed with nontoxic chemical probes can be useful for detecting and monitoring in situ aerobic cometabolism of CAHs. ..
  32. Shang H, Yang Q, Zhang Y. Kinetic models of dichloroethylene biodegradation by two strains of aerobic bacteria. Biomed Environ Sci. 2011;24:261-7 pubmed publisher
    ..The substrate removal rates obtained from both bacterial strains in this study were higher than those reported in similar studies. ..
  33. Hrapovic L, Sleep B, Major D, Hood E. Laboratory study of treatment of trichloroethene by chemical oxidation followed by bioremediation. Environ Sci Technol. 2005;39:2888-97 pubmed
    ..Reduced conditions created by biostimulation were also conducive to reduction of Mn(IV) from MnO2 in both bioaugmented and nonbioaugmented columns resulting in an increased dissolved manganese (Mn2+) concentration in groundwater. ..
  34. Potyrailo R, Sivavec T. Boosting sensitivity of organic vapor detection with silicone block polyimide polymers. Anal Chem. 2004;76:7023-7 pubmed
    ..Water sensitivity is comparable with the sensor response to nonpolar organic vapors. The high sensitivity and long-term stability of these sensor materials make them attractive for ultrasensitive practical sensors. ..
  35. Waksman J, Phillips S. Biologic markers of exposure to chlorinated solvents. Clin Occup Environ Med. 2004;4:413-21, v pubmed
    ..Although some studies have shown that protein and DNA adducts may form with chlorinated hydrocarbons, their application has not been validated sufficiently to justify their use as biologic markers of exposure. ..
  36. Hata J, Takamizawa K, Miyata N, Iwahori K. Biodegradation of cis-1,2-dichloroethylene and vinyl chloride in anaerobic cultures enriched from landfill leachate sediment under Fe(III)-reducing conditions. Biodegradation. 2003;14:275-83 pubmed
    ..The traits of the culture described here are unusual in the anaerobic degradation of chlorinated ethenes and may be useful for searching an effective organism and mechanism regarding anaerobic cis-DCE and VC degradation. ..
  37. Jones J, Kaphalia L, Treinen Moslen M, Liebler D. Proteomic characterization of metabolites, protein adducts, and biliary proteins in rats exposed to 1,1-dichloroethylene or diclofenac. Chem Res Toxicol. 2003;16:1306-17 pubmed
    ..In addition, the results provide direct in vivo evidence for DCE metabolic routes proposed in the formation of covalent adducts. ..
  38. Fletcher K, Nijenhuis I, Richnow H, Löffler F. Stable carbon isotope enrichment factors for cis-1,2-dichloroethene and vinyl chloride reductive dechlorination by Dehalococcoides. Environ Sci Technol. 2011;45:2951-7 pubmed publisher
    ..As cis-DCE and VC ? values are all within the same order-of-magnitude and fractionation is always measured during Dhc dechlorination, CSIA may be a valuable approach for monitoring in situ cis-DCE and VC reductive dechlorination. ..
  39. Loreau O, Maret A, Chardigny J, Sebedio J, Noel J. Sequential substitution of 1,2-dichloro-ethene: a convenient stereoselective route to (9Z,11E)-, (10E,12Z)- and (10Z,12Z)-. Chem Phys Lipids. 2001;110:57-67 pubmed
    ..1% (10E,12Z); 17.2% (10Z,12Z)). Impurities (<2% if present) were identified as being (E,E) CLA isomers and were removed by RP-HPLC. Metabolism studies in animal are in progress. ..
  40. Hoarau P, Gnassia Barelli M, Romeo M, Girard J. Differential induction of glutathione S-transferases in the clam Ruditapes decussatus exposed to organic compounds. Environ Toxicol Chem. 2001;20:523-9 pubmed
    ..Results of these studies suggest that, in R. decussatus, organics may induce GSTs belonging to the pi class. ..
  41. Guiot S, Kuhn R, Levesque M, Cimpoia R. Ultrastructure of a bio-electrolytic methanogenic/methanotrophic granular biofilm for the complete degradation of tetrachloroethylene in contaminated groundwater. Water Sci Technol. 2007;55:465-71 pubmed
    ..It evidenced that with operational time, along with increasing oxygenation rate, methanotrophic communities were specifically colonising onto the outermost layer of the anaerobic/aerobic granule...
  42. Eger E, Halsey M, Koblin D, Laster M, Ionescu P, Königsberger K, et al. The convulsant and anesthetic properties of cis-trans isomers of 1,2-dichlorohexafluorocyclobutane and 1,2-dichloroethylene. Anesth Analg. 2001;93:922-7 pubmed
    ..Such isomeric effects may be as useful as those found with optical isomers in defining receptor-anesthetic interactions. ..
  43. Dorsi F, De Grandis D, Laurelli R, Narda R, Pietrantonio E, Scarlini E, et al. [Evaluation of professional exposure to chloride vinyl monomer and vinyl idene chloride for a pharmaceutical packaging worker]. G Ital Med Lav Ergon. 2007;29:262-4 pubmed
    ..We explain the evaluations by which we could consider the pollutant different distribution in workplaces. ..
  44. Coleman N, Mattes T, Gossett J, Spain J. Biodegradation of cis-dichloroethene as the sole carbon source by a beta-proteobacterium. Appl Environ Microbiol. 2002;68:2726-30 pubmed
    ..Epoxyethane was produced from ethene by cDCE-grown cells, suggesting that an epoxidation reaction is the first step in cDCE degradation. ..
  45. Zhang J, Joslyn A, Chiu P. 1,1-dichloroethene as a predominant intermediate of microbial trichloroethene reduction. Environ Sci Technol. 2006;40:1830-6 pubmed
    ..This study provides a possible biological mechanism forthe occurrence of 1,1-DCE in TCE-contaminated sites. ..
  46. Lee W, Batchelor B. Abiotic reductive dechlorination of chlorinated ethylenes by iron-bearing soil minerals. 2. Green rust. Environ Sci Technol. 2002;36:5348-54 pubmed
    ..These findings are relevant to the understanding of the role of abiotic reductive dechlorination during natural attenuation in environments that contain GR(SO4). ..
  47. Kageyama C, Ohta T, Hiraoka K, Suzuki M, Okamoto T, Ohishi K. Chlorinated aliphatic hydrocarbon-induced degradation of trichloroethylene in Wautersia numadzuensis sp. nov. Arch Microbiol. 2005;183:56-65 pubmed
    ..Based on these results and the proposal of transferring R. basilensis and related species to Wautersia gen. nov., we propose that these strains should be assigned to the genus Wautersia as Wautersia numadzuensis sp. nov. ..
  48. Broholm K, Ludvigsen L, Jensen T, Østergaard H. Aerobic biodegradation of vinyl chloride and cis-1,2-dichloroethylene in aquifer sediments. Chemosphere. 2005;60:1555-64 pubmed
    ..It seems like a potential for natural biodegradation exists at least for VC at these two sites and also to some degree for c-1,2-DCE. ..
  49. Cupples A, Spormann A, McCarty P. Vinyl chloride and cis-dichloroethene dechlorination kinetics and microorganism growth under substrate limiting conditions. Environ Sci Technol. 2004;38:1102-7 pubmed
    ..7 microM, regardless of electron donor levels. The ability to achieve sustainable bioremediation to acceptable levels can be greatly influenced by this threshold level. ..
  50. Cope D, Benson C. Grey-iron foundry slags as reactive media for removing trichloroethylene from groundwater. Environ Sci Technol. 2009;43:169-75 pubmed
    ..Calculations indicate a 2-m-thick slag PRB can degrade TCE to less than 0.005 mg/L for influent concentrations less than 2 mg/L at seepage velocities below 0.1 m/d. ..
  51. Salaices Avila M, Breiter R, Mott H. Development of a simple, accurate SPME-based method for assay of VOCs in column breakthrough experiments. Chemosphere. 2007;66:18-29 pubmed
    ..10 min for GC analysis. A linear calibration function in the gas phase was developed to analyse the breakthrough curve data, linear between a range of 0.9-236 microgl(-1), and a detection limit lower than 5 microgl(-1). ..
  52. Heimann A, Jakobsen R. Experimental evidence for a lack of thermodynamic control on hydrogen concentrations during anaerobic degradation of chlorinated ethenes. Environ Sci Technol. 2006;40:3501-7 pubmed
    ..We also present recalculated thermodynamic properties of aqueous chlorinated ethene species that allow for calculation of in-situ Gibbs free energy of dechlorination reactions at different temperatures. ..
  53. Suganthi G, Sivakolunthu S, Ramakrishnan V. Solvatochromic and preferential solvation studies on schiff base 1,4-bis(((2-methylthio)phenylimino)methyl) benzene in binary liquid mixtures. J Fluoresc. 2010;20:1181-9 pubmed publisher
    ..The dipole moment ratios between ground and excited states were deduced using the solvatochromic shifts of absorption and fluorescence spectra as a function of dielectric constant (?), refractive index (n) and it was found to be 1.25. ..