Disease relevance of 1,2-dichloroethane

• The first step in the utilization of the xenobiotic chlorinated hydrocarbon 1,2-dichloroethane by Xanthobacter autotrophicus is catalyzed by haloalkane dehalogenase (Dh1A) [1].
• Results of this study confirm that the episulfonium ion of CEG can adduct thioredoxin at the active site and may have important toxicologic significance regarding the mechanism of 1,2-dichloroethane toxicity [2].
• Monooxygenase-mediated 1,2-dichloroethane degradation by Pseudomonas sp. strain DCA1 [3].
• Here we report on the isolation of Desulfitobacterium dichloroeliminans strain DCA1, a nutritionally defined anaerobic dehalorespiring bacterium that selectively converts 1,2-dichloroethane and all possible vicinal dichloropropanes and -butanes into completely dechlorinated end products [4].
• GJ10 degrading 1,2-dichloroethane (DCE) and Burkholderia sp. JS150 degrading monochlorobenzene (MCB) [5].

Psychiatry related information on 1,2-dichloroethane

• Influence of organic nutrients and cocultures on the competitive behavior of 1,2-dichloroethane-degrading bacteria [6].

High impact information on 1,2-dichloroethane

• A self-consistent reaction field solvation model was used to examine the SN2 reactions between methyl chloride and hydroxide ion and between 1,2-dichloroethane and acetate in solution [7].
• In vivo genotoxicity and acute hepatotoxicity of 1,2-dichloroethane in mice: comparison of oral, intraperitoneal, and inhalation routes of exposure [8].
• In order to determine whether the covalent binding of the carcinogen 1,2-dichloroethane to macromolecules is dependent on microsomes or cytosol, microsomes and cytosol from lungs of C57BL/6 X C3H/He F1 (hereafter called B6C3F1) mice and Osborne-Mendel rats were incubated with [1,2-14C]dichloroethane and salmon sperm DNA [9].
• However, the rate-determining step in the conversion (kcat) of 1, 2-dibromoethane and 1,2-dichloroethane was found to be release of the charged halide ion out of the active site cavity, explaining the different Km but similar kcat values for these compounds [10].
• Rapid kinetics of electron transfer (ET) reactions across the interface between water and 1,2-dichloroethane were measured by steady-state voltammetry at nanopipet electrodes (50- to 400-nm orifice radius) [11].

Chemical compound and disease context of 1,2-dichloroethane

• We have found chlorine kinetic isotope effects on the dehalogenation catalyzed by haloalkane dehalogenase from Xanthobacter autotrophicus GJ10 to be 1.0045 +/- 0.0004 for 1,2-dichloroethane and 1.0066 +/- 0.0004 for 1-chlorobutane [12].
• Xanthobacter autotrophicus GJ10 needed biotin for optimal growth on 1,2-dichloroethane [6].
• The degradation of 1,2-dichloroethane (DCE) by Xanthobacter autotrophicus GJ10 proceeds via chloroacetaldehyde (CAA), a toxic intermediate in the cells if it is not metabolized further by the NAD(+)-dependent CAA dehydrogenases [13].
• X-ray-quality crystals of L-2-haloacid dehalogenase from the 1,2-dichloroethane-degrading bacterium Xanthobacter autotrophicus GJ10 have been grown at room temperature from 20% PEG 8000, 200 mM sodium formate at pH 6.8-7.0, using macroseeding techniques [14].
• Micronucleus induction in peripheral blood was examined during carcinogenicity assays of the genotoxic carcinogens 2-acetylaminofluorene (2-AAF), benzene, diethylnitrosamine (DEN) and 1,2-dichloroethane (1,2-DCE) in lymphoma prone E mu-PIM-1 transgenic mice [15].

Biological context of 1,2-dichloroethane

• The enzyme has a broad substrate specificity, but the kcat values of the enzyme for the best substrates 1,2-dichloroethane and 1,2-dibromoethane are rather low (3 and 3.5 s-1, respectively) [16].
• The rate law for the catalytic hydrogenation in 1,2-dichloroethane with complex [Ir2(mu-H)(mu-Pz)2H2(OSO2CF3)(NCMe)(PiPr3)2] (8) as catalyst precursor is rate = k[8]{p(H2)}; this is in agreement with the catalytic cycle deduced from the stochiometric experiments [17].
• DNA sequence changes produced by 1,2-dibromoethane (DBE), 1,2-dichloroethane (DCE) and 1-bromo-2-chloroethane (BCE) were analyzed using the vermilion locus of Drosophila melanogaster [18].
• A 200-kb plasmid, pXAU1, was isolated from this strain and shown to contain the dhlA gene, which codes for haloalkane dehalogenase, the first enzyme in the degradation pathway of 1,2-dichloroethane by GJ10 [19].
• In the present report the synthesis of the iodo compound is newly described, and it is established that HI- or HBr-mediated condensation and cyclization of malononitrile in 1,2-dichloroethane yield selectively the 5-cyanopyridine derivatives [20].

Anatomical context of 1,2-dichloroethane

• 1,2-Dichloroethane interacts 85% and 100% more with protein and DNA, respectively, in the presence of microsomes obtained from lung than from liver of B6C3F1 mice [9].
• Heparin, a highly negatively charged polysaccharide, which has been used widely as an anticoagulant and antithrombotic, was detected by ion-transfer voltammetry at the interface between 1,2-dichloroethane and an aqueous buffer solution or undiluted blood plasma [21].
• In vivo sister chromatid exchange induced by 1,2-dichloroethane on bone marrow cells of mice [22].
• Mutagenicity of 1,2-dichloroethane and 1,2-dibromoethane in two human lymphoblastoid cell lines [23].
• Rates of GSH-mediated conjugation, catalyzed by purified rat liver glutathione-S-transferase (GST), and binding of [35S]GSH-mediated conjugation products to calf thymus DNA were determined for 2CIEMS, 1,2-dichloroethane (EDC) and 1,2-dibromoethane (EDB) [24].

Associations of 1,2-dichloroethane with other chemical compounds

• The kinetics and the products of the bromination of several cyclic allenes, from C(9) to C(13) (1 a-e), with tetrabutylammonium tribromide (TBAT) and Br(2) have been investigated in 1,2-dichloroethane (DCE) and methanol [25].
• The importance of glutathione and glutathione transferase for somatic mutations in Drosophila melanogaster induced in vivo by 1,2-dichloroethane [26].
• Phenylalanine 172 is located in a helix-loop-helix structure that covers the active site cavity of the enzyme, interacts with the C1 beta of 1,2-dichloroethane during catalysis, and could be involved in stabilization of this helix-loop-helix region of the cap domain of the enzyme [27].
• The oxidation of diethyl and diphenyl sulfide photosensitized by dicyanoanthracene (DCA), N-methylquinolinium tetrafluoroborate (NMQ(+)), and triphenylpyrylium tetrafluoroborate (TPP(+)) has been explored by steady-state and laser flash photolysis studies in acetonitrile, methanol, and 1,2-dichloroethane [28].
• First, we performed a QSPR modeling of the distribution coefficient (logD) of uranyl extracted by phosphoryl-containing podands from water to 1,2-dichloroethane [29].

Gene context of 1,2-dichloroethane

• We have established that the episulfonium ion of CEG can adduct PDI and may have important toxicologic significance for 1,2-dichloroethane toxicity [30].
• For water/odichlorobenzene and water/1,2-dichloroethane interfaces [ET(30) of the oil > 35 kcal/mol], on the other hand, the interfacial polarity determined by TIR spectroscopy was lower than the ET(30)calc [31].
• Facilitated protamine transfer at polarized water/1,2-dichloroethane interfaces studied by cyclic voltammetry and chronoamperometry at micropipet electrodes [32].
• The haloalkane dehalogenase DhmA shows broad substrate specificity and good activity with the priority pollutant 1,2-dichloroethane [33].
• Sensitivity of transgenic Drosophila melanogaster with expression of a human gene encoding the glutathione S-transferase alpha subunit (GSTA1-1) to 1,2:5,6-dibenzanthracene (DBA) and 1,2-dichloroethane (DCE) was investigated in the somatic mutation and recombination test (SMART) [34].

Analytical, diagnostic and therapeutic context of 1,2-dichloroethane

• The lipophilicity of 28 acidic compounds with various functional groups was studied by potentiometry and cyclic voltammetry in the n-octanol/water and 1,2-dichloroethane/water systems in order to complement our understanding of the lipophilicity of neutral and ionized acids and to clarify the solvation mechanisms responsible for their partition [35].
• The solid could be recovered by centrifugation from the three-phase (solid-liquid-liquid) system containing 1,2-dichloroethane [36].
• 1,2-Dichloroethane (DCE) was reported to be carcinogenic in rats in a long-term bioassay using gavage in corn oil (24 and 48 mg/kg/day), but not by inhalation (up to 150-250 ppm, 7 h/day, 5 days/week) [37].
• Early pneumotoxic effects after oral administration of 1,2-dichloroethane [38].
• An extractive membrane bioreactor has been used to treat a synthetic waste-water containing a toxic volatile organic compound, 1,2-dichloroethane (DCE) [39].

References