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PubMed1993

Mutagenic and lethal effects of halogenated methanes in the Ara test of Salmonella typhimurium: quantitative relationship with chemical reactivity.

The mutagenic and lethal effects of nine halogenated methanes (CCl4, carbon tetrachloride; CHCl3, chloroform; CH2Cl2, dichloromethane; CBr4, carbon tetrachloride; CHBr3, bromoform; CH2Br2, dibromomethane; CI4, carbon tetraiodide; CHI3, iodoform; and CH2I2, diiodomethane) have been investigated with the Ara forward-mutation assay of Salmonella typhimurium. Five substances (CH2Cl2, CBr4, CH2Br2, CHI3 and CH2I2) gave clear mutagenic responses. In all these cases the mutagenicity diminished in the presence of mammalian metabolic activation (S9 mixture). Two halomethanes (CCl4 and CHBr3) were classified as 'questionable' mutagens since they did not double the spontaneous value although a dose-response curve was obtained. All halomethanes tested exerted a lethal effect. A high concordance was found between lethality and chemical reactivity, as expected from the type and number of halogenated substituents. Compounds with equal numbers of substituents were lethal in the order I > Br > Cl. Additionally, the lethality of compounds with identical halogen substituents increased by successive halogenations. No such concordances were observed with respect to mutagenic activity. Structure-activity quantitative relationships were investigated by using the previously reported values of the polarographic half-wave reduction potential (-E1/2), a physicochemical parameter related to the energy required to put an electron into the lowest unoccupied molecular orbital. The lethality, quantified as LD37, correlated highly with the -E1/2 values for the nine halogenated compounds (r = -0.955 P < 0.001). These data suggest that halomethanes which are reduced easily will induce higher lethality than those with low reduction potential, in agreement with the predicted effects on lipid peroxidation and hepatotoxicity.(ABSTRACT TRUNCATED AT 250 WORDS)

Dose-Response Relationship, Drug↗
PubMed2001

Exudation of low molecular weight compounds (thiobismethane, methyl isocyanide, and methyl isothiocyanate) as a possible chemical defense mechanism in the marine sponge Ircinia felix.

The volatile constituents of the marine sponge Ircinia felix were obtained by dynamic headspace extraction and analyzed by HRGC, HRGC-MS and HRGC-Odor at sniffing port. Fifty-nine volatiles were identified for the first time in the odor of this sponge. Hydrocarbons (32.9%), alcohols (17.8%) and carbonyl compounds (16.0%) predominated in the sponge volatile profile, followed by esters (11.6%), halogen compounds (8.6%), ethers (7.7%), nitrogen and/or sulfur compounds (4.6%) and carboxylic acids (0.8%). Among the identified volatiles, thiobismethane (commonly known as dimethylsulfide), methyl isocyanide and methyl isothiocyanate were found to be responsible for the nauseating and toxic smell emitted by the sponge and for the antimicrobial activity detected in the volatile extract. Exudation experiments in aquarium and in situ conditions revealed that thiobismethane, methyl isocyanide and methyl isothiocyanate are continuously released by the sponge. Upon injury, the concentration of these volatiles increased strongly. Hence, these substances form a chemical protective barrier which may help these sponges avoid fouling, compete for space, prevent infection in the short term, and/or signal generalist predators regarding the existence of other toxic substances in the internal tissues.

Journal Article↗
PubMed1994

Metabolism of polyhalogenated compounds by a genetically engineered bacterium.

The decomposition of organic compounds by bacteria has been studied for almost a century, during which time selective enrichment culture has generated microorganisms capable of metabolizing thousands of organic compounds. But attempts to obtain pure cultures of bacteria that can metabolize highly halogenated compounds, a large and important class of pollutants, have been largely unsuccessful. Polyhalogenated compounds are most frequently metabolized by anaerobic bacteria as a result of reductive dehalogenation reactions, the products of which are typically substrates for bacterial oxygenases. Complete metabolism of polyhalogenated compounds therefore necessitates the sequential use of anaerobic and aerobic bacteria. Here we combine seven genes encoding two multi-component oxygenases in a single strain of Pseudomonas which as a result metabolizes polyhalogenated compounds by means of sequential reductive and oxidative reactions to yield non-toxic products. Cytochrome P450cam monooxygenase reduces polyhalogenated compounds, which are bound at the camphor-binding site, under subatmospheric oxygen tensions. We find that these reduction products are oxidizable substrates for toluene dioxygenase. Perhalogenated chlorofluorocarbons also act as substrates for the genetically engineered strain.

Camphor 5-Monooxygenase↗
PubMedDate not supplied

The lipid peroxidation model for halogenated hydrocarbon toxicity. Kinetics of peroxyl radical processes involving fatty acids and Fe(III) porphyrins.

The toxicity of halogenated alkanes originates from their metabolism by cytochrome P-450 which leads to the formation of reactive intermediates. In particular, peroxyl radicals derived from the halogenated compounds are believed to induce peroxidative chain degradation of lipids. To examine this hypothesis, radical reactions in a system involving FeIII-deuteroporphyrin as a model of cytochrome P-450, fatty acids or cholesterol, and carbon tetrachloride or the anesthetic agent halothane are studied by means of pulse radiolysis. It is shown that haloperoxyl radicals react with the fatty acids in competition with their reaction with the ferriporphyrin. Moreover, the secondary fatty acid peroxyl radicals also react efficiently with the porphyrin. A model for halogenated alkane toxicity is discussed in terms of these new findings. The importance of local oxygen concentration and structural arrangement of fatty acids around cytochrome P-450 are emphasized.

Cytochrome P-450 Enzyme System↗
PubMed1998

Detection of in vivo genotoxicity of haloalkanes and haloalkenes carcinogenic to rodents by the alkaline single cell gel electrophoresis (comet) assay in multiple mouse organs.

The micronucleus test is widely used to assess in vivo clastogenicity because of its convenience, but it is not appropriate for some carcinogenic chemical classes. Halogenated compounds, for example, are inconsistent micronucleus inducers. We assessed the genotoxicity of 7 haloalkanes and haloalkenes carcinogenic to rodents in 7 mouse organs-stomach, liver, kidney, bladder, lung, brain, and bone marrow-using the alkaline single cell gel electrophoresis (SCG) assay. The carcinogens we studied were 1, 2-dibromo-3-chloropropane (DBCP), 1,3-dichloropropene (mixture of cis and trans) (DCP), 1,2-dibromoethane (EDB), 1,2-dichloroethane (EDC), vinyl bromide, dichloromethane, and carbon tetrachloride; only DBCP induces micronuclei in mouse bone marrow. Except for carbon tetrachloride, halocompounds studied are mutagenic to Salmonella typhimurium. Mice were sacrificed 3 or 24 h after carcinogen administration. DCP and EDC induced DNA damage in all of the organs studied. Vinyl bromide yielded DNA damage in all of the organs except for bone marrow. DBCP induced DNA damage in the stomach, liver, kidney, lung, and bone marrow; EDB in the stomach, liver, kidney, bladder, and lung; and dichloromethane in the liver and lung. Since no deaths, morbidity, clinical signs, organ pathology, or microscopic signs of necrosis were observed, the DNA damage was not attributable to cytotoxicity. On the other hand, the positive response in the liver induced by carbon tetrachloride, which was accompanied by necrosis, was considered to be a false positive response. We suggest that the alkaline SCG assay can be used in multiple organs to detect in vivo genotoxicity that is not expressed in bone marrow cells in mice given non-necrogenic doses of halocompounds.

Alkanes↗
PubMed1987

In vivo measurement of unscheduled DNA synthesis and S-phase synthesis as an indicator of hepatocarcinogenesis in rodents.

Measurement of chemically induced DNA repair as unscheduled DNA synthesis in rodent liver following in vivo treatment is a useful screen for potential hepatocarcinogens. In addition to measurement of unscheduled DNA synthesis, examination of S-phase synthesis provides an indicator of chemically induced cell proliferation in the liver, which may be a basis for hepatic tumor promotion. Several chemicals and classes of chemicals have been examined using these end points. The pyrrolizidine alkaloid riddelline is a potent genotoxic agent in vitro, and in vivo studies confirm this response as riddelline induces significant elevations in unscheduled DNA synthesis and S-phase synthesis in rat liver. Conversely, H.C. Blue dyes #1 and #2 are both potent genotoxic agents in vitro but fail to express this genotoxicity in vivo. H.C. Blue #1 induces significant increases in S-phase synthesis in B6C3F1 mouse liver, which correlates with the observed carcinogenicity of this compound. Halogenated hydrocarbons likewise fail to induce unscheduled DNA synthesis in vivo, but many of these compounds do increase hepatic cell proliferation in mice, which may be the principal mechanism of hepatocarcinogenesis in this species.

Animals↗
PubMed2006

Elimination of organophosphate ester flame retardants and plasticizers in drinking water purification.

Organophosphate ester flame retardants and plasticizers like tris-(2-chloro-, 1-methyl-ethyl)phosphate (TCPP), tris-(2-chloro-, 1-chloromethyl-ethyl)phosphate (TDCP), tris-(2-chloroethyl)phosphate (TCEP), tributylphosphates, triphenylphosphate (TPP), ethylhexyldiphenylphosphate (EHDPP) and tris-(butoxyethyl)phosphate (TBEP) have been studied in diverse processes for drinking water purification. The elimination efficiency of these different treatment processes, e.g., biological active slow underground passage, soil passage and technical treatment processes such as ozonization or multilayer and activated carbon filtration have been studied in three waterworks in the catchment area of the river Ruhr. In the untreated surface water the concentrations of the chlorinated organophosphates ranged 50-150 ng L(-1) TCPP, 10-130 ng L(-1) TCEP and 10-40 ng L(-1) TDCP. The amounts of the non-chlorinated alkylphosphates were in the same order of magnitude (40 ng L(-1) of the tributylphosphates, 170 ng L(-1) of TBEP and 10 ng L(-1) TPP) depending on weather and water flow. EHDPP was detected in the range of 1 ng L(-1). After the drinking water purification process in all waterworks in this study, the concentrations of the selected substances were below the respective limit of quantification (0.3-3 ng L(-1)). While activated carbon filtration as well as extended passage through soil (10-15 days residence time) were effective in eliminating all selected compounds, ozonization and multilayer filtration did not contribute to the elimination of the chlorinated compounds. The elimination effect of slow underground passage combined with soil passage concerning the halogenated compounds seemed to depend on the hydraulic residence time.

Filtration↗
PubMed1997

Complete reductive dechlorination of 1,2-dichloropropane by anaerobic bacteria.

The transformation of 1,2-dichloropropane (1,2-D) was observed in anaerobic microcosms and enrichment cultures derived from Red Cedar Creek sediment. 1-Chloropropane (1-CP) and 2-CP were detected after an incubation period of 4 weeks. After 4 months the initial amount of 1,2-D was stoichiometrically converted to propene, which was not further transformed. Dechlorination of 1,2-D was not inhibited by 2-bromoethanesulfonate. Sequential 5% (vol/vol) transfers from active microcosms yielded a sediment-free, nonmethanogenic culture, which completely dechlorinated 1,2-D to propene at a rate of 5 nmol min(sup-1) mg of protein(sup-1). No intermediate formation of 1-CP or 2-CP was detected in the sediment-free enrichment culture. A variety of electron donors, including hydrogen, supported reductive dechlorination of 1,2-D. The highest dechlorination rates were observed between 20(deg) and 25(deg)C. In the presence of 1,2-D, the hydrogen threshold concentration was below 1 ppm by volume (ppmv). In addition to 1,2-D, the enrichment culture transformed 1,1-D, 2-bromo-1-CP, tetrachloroethene, 1,1,2,2-tetrachloroethane, and 1,2-dichloroethane to less halogenated compounds. These findings extend our knowledge of the reductive dechlorination process and show that halogenated propanes can be completely dechlorinated by anaerobic bacteria.

Journal Article↗
PubMed2005

Quantitative analysis of substrate specificity of haloalkane dehalogenase LinB from Sphingomonas paucimobilis UT26.

Haloalkane dehalogenases are microbial enzymes that cleave a carbon-halogen bond in halogenated compounds. The haloalkane dehalogenase LinB, isolated from Sphingomonas paucimobilis UT26, is a broad-specificity enzyme. Fifty-five halogenated aliphatic and cyclic hydrocarbons were tested for dehalogenation with the LinB enzyme. The compounds for testing were systematically selected using a statistical experimental design. Steady-state kinetic constants K(m) and k(cat) were determined for 25 substrates that showed detectable cleavage by the enzyme and low abiotic hydrolysis. Classical quantitative structure-activity relationships (QSARs) were used to correlate the kinetic constants with molecular descriptors and resulted in a model that explained 94% of the experimental data variability. The binding affinity of the tested substrates for this haloalkane dehalogenase correlated with hydrophobicity, molecular surface, dipole moment, and volume:surface ratio. Binding of the substrate molecules in the active site pocket of LinB depends nonlinearly on the size of the molecules. Binding affinity increases with increasing substrate size up to a chain length of six carbon atoms and then decreases. Comparative binding energy (COMBINE) analysis was then used to identify amino acid residues in LinB that modulate its substrate specificity. A model with three statistically significant principal components explained 95% of the experimental data variability. van der Waals interactions between substrate molecules and the enzyme dominated the COMBINE model, in agreement with the importance of substrate size in the classical QSAR model. Only a limited number of protein residues (6-8%) contribute significantly to the explanation of variability in binding affinities. The amino acid residues important for explaining variability in binding affinities are as follows: (i) first-shell residues Asn38, Asp108, Trp109, Glu132, Ile134, Phe143, Phe151, Phe169, Val173, Trp207, Pro208, Ile211, Leu248, and His272, (ii) tunnel residues Pro144, Asp147, Leu177, and Ala247, and (iii) second-shell residues Pro39 and Phe273. The tunnel and the second-shell residues represent the best targets for modulating specificity since their replacement does not lead to loss of functionality by disruption of the active site architecture. The mechanism of molecular adaptation toward a different specificity is discussed on the basis of quantitative comparison of models derived for two protein family members.

Alkanes↗
PubMed1991

Biodegradation of triiodophenol by cell-free extracts of a pentachlorophenol-degrading Flavobacterium sp.

Pentachlorophenol (PCP) degrading Flavobacterium sp. ATCC 39723 was found to degrade other polyhalogenated phenolic compounds, including triiodophenol, tribromophenol, and trichlorophenol. Each compound was able to induce the degradation of the other compounds. A PCP Flavobacterium sp. mutant, F-2, was unable to degrade any of the halogenated compounds. The results suggest that all of the polyhalogenated phenols were degraded by the same enzyme system. This observation led us to exploit the sensitive leuco crystal violet assay, which measures the iodide released from triiodophenol. Cell free extracts from PCP-induced cells were able to release iodide from triiodophenol. The reaction required NADPH and oxygen.

Biodegradation, Environmental↗
PubMed2004

Comparison of sampling efficiency and storage stability on different sorbents for determination of solvents in occupational air.

This study describes the sampling efficiency and storage stability of compounds typically present in occupational atmospheres on the sorbents Anasorb CSC, Anasorb 747, and Chromosorb 106. The selection of compounds included in the study contained aliphatic and aromatic hydrocarbons, alcohols, esters, glycol ethers, ketones, and halogenated compounds, thus representing a wide range of chemical and physical properties. The different sorbent tubes were simultaneously exposed to the selected compounds as three different mixtures of solvent vapours in air, and storage both at room temperature and at -22 degrees C was investigated. The sorbent tubes were stored and analyzed at two different laboratories. The sampling efficiencies of all the investigated compounds were excellent on Anasorb CSC and Anasorb 747, while Chromosorb 106 did not give such good results for the most volatile compounds under study. The room temperature storage stability on Chromosorb 106, however, was good for all compounds, although formation of artefacts was observed during storage, a disadvantage that was substantially reduced by storage at -22 degrees C. The room temperature storage stability on Anasorb CSC was good for all compounds except some of the ketones. The room temperature storage stability of these ketones, especially cyclohexanone and 2-butanone, was much better on Anasorb 747, which still showed the same excellent storage stability for the remaining compounds. When stored in a freezer, the storage stability of all compounds, including the ketones, was very good on all sorbents. Among the sorbents under study, Anasorb 747 appears to be the most suitable all-round sorbent for monitoring volatile compounds in occupational air, with satisfactory capabilities regarding both sampling efficiency and storage stability.

Air Pollutants, Occupational↗
PubMed1984

Isomer identification by kinetic energy release measurements using the voltage pulsed collision cell technique in mass-analysed ion kinetic energy spectrometry.

The voltage pulsing of the collision cell on a mass-analysed ion kinetic energy spectrometer allows simultaneous kinetic energy release measurements for unimolecular (T(V)), collision-induced (TCID(V)) and composite unimolecular and collision-induced (Tcomp(V)) decomposition processes in the time frame of a capillary gas chromatographic peak. The information gained by voltage pulsing sometimes allows more reliable isomer identification than by kinetic energy release measurements made in the non-pulsing mode alone. Presented are T(V), TCID(V) and Tcomp(V), and the ratio of their intensities for a number of isomeric halogenated compounds.

Hydrocarbons, Halogenated↗
PubMed1977

A multiclass, multiresidue analytical method for pesticides in water.

A procedure is reported for the multiclass, multiresidue analysis of pesticides in water. Compounds are extracted from water with methylene chloride, and the extract is concentrated by an evaporative technique utilizing reduced pressure and low temperature. Compounds are segregated into groups using a column of partially deactivated silica gel and sequential elution with four different solvent systems. Carbamate residues, converted to their 2,4-dinitrophenyl ether derivatives, are gas chromatographed via electron capture detection as are the parent compounds of the organohalogen compounds. Organophosphorus compounds are determined by gas chromatography using a flame photometric detector. Recovery studies were conducted on 42 halogenated compounds, 38 organophosphorus compounds, and 7 carbamates. Fifty-eight of 87 compounds tested produced recoveries in excess of 80%; another 13 compounds yielded recoveries exceeding 60%, while the recoveries on the remaining 16 compounds fell below 60%.

Carbamates↗
PubMed1988

Uroporphyria produced in mice by 20-methylcholanthrene and 5-aminolaevulinic acid.

Iron-loaded male C57BL/6 mice allowed free access to an aqueous solution of 5-aminolaevulinic acid (ALA) (2 mg/ml) as their only drink, develop severe uroporphyria within 9 days of a single intraperitoneal dose of 20-methylcholanthrene (MC) (125 mg/kg). At 21 days, uroporphyrinogen decarboxylase (EC 4.1.1.37) activities are less than 10% of control activities. The porphyria is not dependent on pretreatment with iron and persists for at least 21 days after withdrawal of ALA. The same intraperitoneal dose of MC does not produce porphyria within 21 days when given without ALA. Continuous administration of ALA markedly accelerates the onset of porphyria in iron-loaded male C57BL/6 mice after a single intraperitoneal dose of hexachlorobenzene (200 mg/kg); mice given phenobarbitone and ALA do not become porphyric. MC with ALA does not produce porphyria in iron-loaded male DBA/2 mice. At least two separate events are needed to produce uroporphyria in mammals: induction of a specific form of cytochrome P-450 and stimulation of the formation of intermediates of haem biosynthesis in the liver. These results show that severe, persistent porphyria can be produced in mammals by compounds other than polyhalogenated aromatic hydrocarbons and suggest that a similar mechanism underlies the porphyrogenic action of halogenated and non-halogenated compounds.

Aminolevulinic Acid↗
PubMed2003

Molecular markers of anthropogenic activity in sediments of the Havel and Spree Rivers (Germany).

Detailed gas chromatographic/mass spectrometric analyses have been applied to sediment samples of the Havel and Spree River, tributaries to the Elbe River, in order to identify specific molecular markers of anthropogenic activities. Despite a wide variety of lipophilic organic compounds from diffuse anthropogenic contamination, a local emission of an industrial point source was reflected by specific markers including halogenated compounds and nitrogen containing substances (4-ethylnitrobenzene, formyl piperidine, acetyl piperidine). In addition to well-known anthropogenic markers various new molecular tracers were detected and are discussed, namely plasticizers (alkylsulfonic acid aryl esters, tributyl and tricresyl phosphates), synthetic fragrances (galaxolide, tonalide, 4-oxoisophorone), additives of personal care products (4-methoxycinnamic acid 2-ethylhexyl ester, benzyl benzoate, dibenzyl ether, benzophenone), occurring due to sewage treatment plant input.

Cosmetics↗
PubMed2000

Antifungal properties of substituted 1-phenyl-5-mercaptotetrazoles and their oxidation product, 5-bis-(1-phenyltetrazolyl)disulfide.

The antifungal effect of substituted 1-phenyl-5-mercaptotetrazoles was tested with Candida tropicalis, C. pseudotropicalis, C. mogii, Trichosporon cutaneum, Cryptococcus albidus and S. cerevisiae. Candida strains exhibited the lowest sensitivity to the compounds; the most sensitive was S. cerevisiae. The MIC values ranged from 40 to > 1000 mg/mL. The antifungal effect of halogenated compounds decreased in the series of bromo > chloro > fluoro derivatives. The electrochemical oxidation of substituted 1-phenyl-5-mercaptotetrazole derivatives in an acetonitrile medium was studied as a model for the enzymic oxidation of the substance, including study of the effect of water, perchloric and trifluoromethanesulfuric acids on E1/2 and I1. 5-Bis-(1-phenyltetrazolyl)disulfide, the compound with no antifungal effect, has been identified as the main oxidation product of 1-phenyl-5-mercaptotetrazole.

Acetonitriles↗
PubMed2005

A field comparison of volatile organic compound measurements using passive organic vapor monitors and stainless steel canisters.

Concurrent field measurements of 10 volatile organic compounds (VOCs) were made using passive diffusion-based organic vapor monitors (OVMs) and the U.S. Federal Reference Method, which comprises active monitoring with stainless steel canisters (CANs). Measurements were obtained throughout a range of weather conditions, repeatedly over the course of three seasons, and at three different locations in the Minneapolis/St. Paul metropolitan area. Ambient concentrations of most VOCs as measured by both methods were low compared to those of other large metropolitan areas. For some VOCs a considerable fraction of measurements was below the detection limit of one or both methods. The observed differences between the two methods were similar across measurement sites, seasons, and meteorological variables. A Bayesian analysis with uniform priors on the differences was applied, with accommodation of sometimes heavy censoring (nondetection) in either device. The resulting estimates of bias and standard deviation of the OVM relative to the CAN were computed by tertile of the canister-measured concentration. In general, OVM and CAN measurements were in the best agreement for benzene and other aromatic compounds with hydrocarbon additions (ethylbenzene, toluene, and xylenes). The two methods were not in such good agreement for styrene and halogenated compounds (carbon tetrachloride, p-dichlorobenzene, methylene chloride, and trichloroethylene). OVMs slightly overestimated benzene concentrations and carbon tetrachloride at low concentrations, but in all other cases where significant differences were found, OVMs underestimated relative to canisters. Our study indicates that the two methods are in agreement for some compounds, but not all. We provide data and interpretation on the relative performance of the two VOC measurement methods, which facilitates intercomparisons among studies.

Air Pollutants↗