Laboratory data base for isomer-specific determination of polychlorinated biphenyls

Schwartz, Ted R.; Campbell, Randolph D.; Stalling, David L.; Little, Robert L.; Petty, Jimmie D.; Hogan, James W.; Kaiser, Edwin M.

doi:10.1021/ac00272a025

Cited by 33 publications

(12 citation statements)

References 9 publications

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“…In this regard, PCB29 is a putative estrogen mimic because it has both ortho-and para-chlorine substituents. Aroclor 1242 is a mixture of 27-74 Cl 2 -Cl 4 congeners (Alford-Stevens, 1986), most of which have ortho-chlorine substituents (Rapaport and Eisenreich, 1984;Schwartz et al, 1984;Alder et al, 1993). It is not known whether a PCB congener's ability to affect molting in D. magna is also related to its pattern of chlorine substitution.…”

Section: Fig 3 Effects Of 4-octylphenol On Molting Of Daphnia Magnamentioning

confidence: 99%

Effects of Estrogenic Xenobiotics on Molting of the Water Flea,Daphnia magna

Zou

Fingerman

1997

Ecotoxicology and Environmental Safety

121

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Section: Fig 3 Effects Of 4-octylphenol On Molting Of Daphnia Magnamentioning

confidence: 99%

Effects of Estrogenic Xenobiotics on Molting of the Water Flea,Daphnia magna

Zou

Fingerman

1997

Ecotoxicology and Environmental Safety

121

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“…Quantitation of environmental samples as equivalents of tech-mixtures is altered (6). The correlation between the chromatogram of an Aroclor standard and that of PCB mixtures from an environmental sample is variable (7)(8)(9)(10)(11), and conventional quantitation methods permit considerable subjectivity on the part of the analyst (12)(13)(14). Ad-ditionally, reporting concentration data as total PCBs provides no information about the potential biological significance of the particular mixture of congeners in a sample and may be misleading.…”

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confidence: 99%

Environmental occurrence, abundance, and potential toxicity of polychlorinated biphenyl congeners: considerations for a congener-specific analysis.

McFarland

Clarke

1989

Environ Health Perspect

621

279

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Polychlorinated biphenyls (PCBs) as environmental contaminants often cannot be adequately described by reference to Aroclors or to total PCBs. Although there are 209 possible PCB configurations (congeners), perhaps half that number account for nearly all of the environmental contamination attributable to PCBs. Still fewer congeners are both prevalent and either demonstrably or potentially toxic. If potential toxicity, environmental prevalence, and relative abundance in animal tissues are used as criteria, the number of environmentally threatening PCB congeners reduces to about thirty-six. Twenty-five of these account for 50 to 75% of total PCBs in tissue samples of fish, invertebrates, birds, and mammals.A few PCB congeners that are sterically similar to 2,3,7,3,7, are directly toxic. Other PCB congeners, as well as those that are directly toxic, may also be involved in toxicity indirectly by stimulating the production of (inducing) bioactivating enzyme systems. The most consequential of these have the ability to induce aryl hydrocarbon metabolizing mixed-function oxidases (MFOs). A result can be an increased capacity for bioactivation of otherwise nontoxic foreign compounds such as certain polynuclear aromatic hydrocarbons (PAH) to cytotoxic or genotoxic metabolites. The effectiveness of specific PCB congeners as inducers of different types of cytochrome P-450-dependent MFO systems is determined by their stereochemistry. Although MFO induction is not a proximate cause, it is a strong correlate of certain kinds of toxicities. Structural patterns can thus be used to discriminate among PCB congeners on the basis of toxic potential, if not entirely on toxicity per se. Congeners that demonstrate 3-methylcholanthrene-type (3-MCtype) and mixed-type MFO induction have the greatest toxic potential. These congeners most closely resemble 2,3,7,8-TCDD in their structures and in their toxic effects. The larger group of phenobarbital-type (PBtype) inducers have considerably less potential for contributing to toxic effects. Weak inducers and noninducing congeners have the least potential for toxicity.Using the rationale described in this paper, we assigned the most environmentally threatening PCB congeners to four groups. Congeners assigned to Group 1 are considered most likely to contribute to adverse biological effects attributable to PCBs in an environmental sample. Group 1A contains the three most potent (pure 3-MC-type inducer) congeners, IUPAC numbers 77, 126, and 169. Six congeners, numbers 105, 118, 128, 138, 156, and 170, are assigned to Group 1B. These congeners are mixed-type inducers that have been reported frequently in environmental samples. Group 2 congeners are PB-type inducers that are also prevalent in the environment; these include numbers 87, 99, 101, 153, 180, 183, and 194. Group 3 congeners, numbers 18,44,49,52,70,74, 151, 177, 187, and 201, are weak or noninducers, but they occur frequently in the environment or in high concentrations in animal tissues relative to other PCB congeners, and so may be of ...

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“…For this analysis, energy values were used to evaluate the distribution of isomers using the Boltzmann distribution at 300, 600, and 900 K [40]. The results were compared to available data on the abundance of these compounds in nature [37,[40][41][42][43][44][45][46][47][48][49][50][51][52][53][54][55][56]. A brief review of these data in the literature is shown in Supplementary Table S7.…”

Section: Isomer Distributionmentioning

confidence: 99%

Quantum Chemical Investigation of Polychlorinated Dibenzodioxins, Dibenzofurans and Biphenyls: Relative Stability and Planarity Analysis

Datta

Limpanuparb

2020

Molecules

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All the possible polychlorinated aromatic compounds in the classes of dibenzodioxins (PCDDs), dibenzofurans (PCDFs), and biphenyls (PCBs) were studied by the quantum chemical methods of HF/6-311++G(d,p), B3LYP/6-311++G(d,p), and MP2/cc-pVTZ. The calculated stabilities and structures of these compounds were compared with the available data on their abundance and toxicity. Prediction models for trends in energy and planarity among these congeners were proposed. The results discussed here can help contribute to the understanding of the role of dioxin-like compounds (DLCs) in the environment.

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Laboratory data base for isomer-specific determination of polychlorinated biphenyls

Cited by 33 publications

References 9 publications

Effects of Estrogenic Xenobiotics on Molting of the Water Flea,Daphnia magna

Effects of Estrogenic Xenobiotics on Molting of the Water Flea,Daphnia magna

Environmental occurrence, abundance, and potential toxicity of polychlorinated biphenyl congeners: considerations for a congener-specific analysis.

Quantum Chemical Investigation of Polychlorinated Dibenzodioxins, Dibenzofurans and Biphenyls: Relative Stability and Planarity Analysis

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