Identification of primary aromatic amines in mutagenically active subfractions from coal liquefaction materials

Wilson, Bary W.; Pelroy, R.A.; Cresto, James T.

doi:10.1016/0165-1218(80)90066-x

Cited by 80 publications

(33 citation statements)

References 4 publications

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“…The noncompetitive CYP1A inhibitor FL, for example, is one of the more prevalent PAHs found in marine sediments, lakes, and rainwater (Latimer and Zheng 2003; Van Metre et al 2000). Aminoanthracenes are components in coal liquefaction products (Pelroy and Wilson 1981; Wilson 1980) and may also be found in environmental mixtures. It is possible that other compounds found in environmental mixtures may also be as yet uncharacterized CYP1A inhibitors.…”

Section: Discussionmentioning

confidence: 99%

Synergistic Embryotoxicity of Polycyclic Aromatic Hydrocarbon Aryl Hydrocarbon Receptor Agonists with Cytochrome P4501A Inhibitors inFundulus heteroclitus

Wassenberg¹,

Giulio²

2004

Environ Health Perspect

188

175

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Widespread contamination of aquatic systems with polycyclic aromatic hydrocarbons (PAHs) has led to concern about effects of PAHs on aquatic life. Some PAHs have been shown to cause deformities in early life stages of fish that resemble those elicited by planar halogenated aromatic hydrocarbons (pHAHs) that are agonists for the aryl hydrocarbon receptor (AHR). Previous studies have suggested that activity of cytochrome P4501A, a member of the AHR gene battery, is important to the toxicity of pHAHs, and inhibition of CYP1A can reduce the early-life-stage toxicity of pHAHs. In light of the effects of CYP1A inhibition on pHAH-derived toxicity, we explored the impact of both model and environmentally relevant CYP1A inhibitors on PAH-derived embryotoxicity. We exposed Fundulus heteroclitus embryos to two PAH-type AHR agonists, β-naphthoflavone and benzo(a)pyrene, and one pHAH-type AHR agonist, 3,3′,4,4′,5-pentachlorobiphenyl (PCB-126), alone and in combination with several CYP1A inhibitors. In agreement with previous studies, coexposure of embryos to PCB-126 with the AHR antagonist and CYP1A inhibitor α-naphthoflavone decreased frequency and severity of deformities compared with embryos exposed to PCB-126 alone. In contrast, embryos coexposed to the PAHs with each of the CYP1A inhibitors tested were deformed with increased severity and frequency compared with embryos dosed with PAH alone. The mechanism by which inhibition of CYP1A increased embryotoxicity of the PAHs tested is not understood, but these results may be helpful in elucidating mechanisms by which PAHs are embryotoxic. Additionally, these results call into question additive models of PAH embryotoxicity for environmental PAH mixtures that contain both AHR agonists and CYP1A inhibitors.

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Section: Discussionmentioning

confidence: 99%

Synergistic Embryotoxicity of Polycyclic Aromatic Hydrocarbon Aryl Hydrocarbon Receptor Agonists with Cytochrome P4501A Inhibitors inFundulus heteroclitus

Wassenberg¹,

Giulio²

2004

Environ Health Perspect

188

175

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“…Some of these liquids have been found to be mutagenic in Salmonella typhimurium TA98 and to initiate tumor formation in mice (Wilson et al 1980;Pelroy and Petersen 1981;Pelroy and Wilson 1981;Mahlum and Wilson 1983;Mahlum 1983). Moreover, the mutagenicities of some coal liquids and other materials containing polycyclic aromatic compounds have been shown to increase during exposure to near-ultraviolet light (Larson et al 1977; Barnhart and Cox 1980;Strniste and Brake 1981;Strniste and Chen 1981;Chen and Strniste 1982;Strniste et al 1982aStrniste et al , 1982bSelby et al 1983 ).…”

Section: Introductionmentioning

confidence: 99%

Photodegradation of mutagens in solvent-refined coal liquids

Kalkwarf¹,

Stewart²,

Pelroy³

et al. 1984

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SUMMARYThe purpose of this investigation was to evaluate any changes in the chemical composition and microbial mutagenicities of two representative solventrefined coal (SRC) liquids as a function of exposure time to sunlight and air. This information was desired to assess potential health hazards arising from ground spills of these liquids during production, transport and use. Results of microbial mutagenicity assays using Salmonella typhimurium TA98, conducted after exposure, showed that the mutagenicities of both an SRC-II fuel oil blend and an SRC-1 process solvent decreased continuously with exposure time to air and that the decrease was accelerated by simultaneous exposure to simulated sunlight. The liquids were exposed as thin layers supported on surfaces of glass, paper, clay or aluminum; but the type of support had little effect on the results. The contrast between these results and the reported increases of mutagenesis in organisms exposed simultaneously to coal liquids and nearultraviolet light suggested that short-lived mutagenic intermediates, e.g., organic free radicals, were formed in the liquids during exposure to light.The highest activities of microbial mutagenicity in the SRC liquids were found in fractions rich in amino polycyclic aromatic hydrocarbons (amino PAH). After a 36-hour exposure of the fuel oil blend to air in the dark, the mutagenicity of its amine-rich fraction was reduced by 65%; whereas a 36-hour exposure in the light reduced the mutagenicity of this fraction by 92%. Similar rates of reduction in mutagenicity were achieved in exposures of the process solvent. The mutagenicities of other chemical fractions remained low during exposure. Analyses showed that most of the amine components of both liquids contained less than four aromatic rings and that their concentrations generally decreased with exposure time. These results indicate that the microbial mutagenicities of the two SRC liquids may be expected to gradually decrease if they are spilled out of doors, with the rate of decrease dependent on their access to air and sunlight. However, one cannot be sure that all of the potential health hazards of these materials are reduced by such exposures si nee the _i. typhimurium TA98 test system has been reported to be relatively insensitive to potential mutagens in fractions of SRC liquids rich in neutral aromatic compounds.Electron spin resonance (ESR) measurements on the liquids showed free radical concentrations on the order of 5xlo 16 unpaired spins per gram before exposure. In darkness, this concentration decreased continuously during exposure to air, paralleling the decrease in mutagenicities of the samples. In simulated sunlight, the concentration of paramagnetic species rapidly increased within the first few minutes of illumination and then decreased with continued exposure. This behavior suggested that organic free radicals were the major paramagnetic species, although charge-transfer complexes may have also been present. The ESR spectra were not sufficiently resolved to identi...

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“…A more elaborated thin-layer chromatographic fractionation of coal tar and the subsequent examination of mutagenicity was published by Wilson et al , in 1980 [70] and Bjorseth et al , in 1982 [71]. They also used the highly popular Ames-Test based on the mutation of strains of the bacterium Salmonella typhimurium [72–76].…”

Section: Reviews and Important Papers Of The Topicmentioning

confidence: 99%

A Unifying Review of Bioassay-Guided Fractionation, Effect-Directed Analysis and Related Techniques

Weller

2012

Sensors

155

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Abstract:The success of modern methods in analytical chemistry sometimes obscures the problem that the ever increasing amount of analytical data does not necessarily give more insight of practical relevance. As alternative approaches, toxicity-and bioactivity-based assays can deliver valuable information about biological effects of complex materials in humans, other species or even ecosystems. However, the observed effects often cannot be clearly assigned to specific chemical compounds. In these cases, the establishment of an unambiguous cause-effect relationship is not possible. Effect-directed analysis tries to interconnect instrumental analytical techniques with a biological/biochemical entity, which identifies or isolates substances of biological relevance. Successful application has been demonstrated in many fields, either as proof-of-principle studies or even for complex samples. This review discusses the different approaches, advantages and limitations and finally shows some practical examples. The broad emergence of effect-directed analytical concepts might lead to a true paradigm shift in analytical chemistry, away from ever growing lists of chemical compounds. The connection of biological effects with the identification and quantification of molecular entities leads to relevant answers to many real life questions.

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Identification of primary aromatic amines in mutagenically active subfractions from coal liquefaction materials

Cited by 80 publications

References 4 publications

Synergistic Embryotoxicity of Polycyclic Aromatic Hydrocarbon Aryl Hydrocarbon Receptor Agonists with Cytochrome P4501A Inhibitors inFundulus heteroclitus

Synergistic Embryotoxicity of Polycyclic Aromatic Hydrocarbon Aryl Hydrocarbon Receptor Agonists with Cytochrome P4501A Inhibitors inFundulus heteroclitus

Photodegradation of mutagens in solvent-refined coal liquids

A Unifying Review of Bioassay-Guided Fractionation, Effect-Directed Analysis and Related Techniques

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