Airborne Polycyclic Aromatic Hydrocarbons and Their Derivatives

Finlayson-Pitts, B. J.

doi:10.1016/b978-012257060-5/50012-5

Cited by 18 publications

(19 citation statements)

References 497 publications

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“…Atmospheric oxidation reactions of BaP and other PAH copollutants yield several of the same PAH oxidation species produced by enzymatic oxidation (Yang et al, 1975;Shen et al, 1979;Van Cauwenberghe, 1985;Cavalieri & Rogan, 1995;Finlayson-Pitts & Pitts, 1999). Therefore, atmospheric chemistry and biological oxidation (oxidation reactions) of PAHs may lead to the production of oxy-PAH species (PAH diones) that produce toxicological responses in respiratory epithelium.…”

Section: Discussionmentioning

confidence: 95%

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Benzo[a]Pyrene Diones are Produced by Photochemical and Enzymatic Oxidation and Induce Concentration-Dependent Decreases in the Proliferative State of Human Pulmonary Epithelial Cells

Reed

Monske

Lauer

et al. 2003

Journal of Toxicology and Environmental Health, Part A

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Organic components within mixtures of combustion-derived materials may play an important role in the correlation between air pollution and adverse cardio/respiratory health. One class of these organic components, polycyclic aromatic hydrocarbons (PAHs), has been shown to produce a wide variety of adverse health effects. An air toxic and a model PAH, benzo[a]pyrene (BaP), is a component of combustion-derived particulate matter (PM). Although most biological effects associated with BaP have been attributed to the cytochrome P-450 derived BaP 7,8-diol 9,10-epoxide, many other BaP oxidation products are formed in atmospheric and biological reactions and may contribute to PAH-induced adverse health effects. In an ambient environment, BaP and other PAHs undergo oxidation in the presence of ultraviolet light, O(2), O(3), NO(2), or OH(*). Biological peroxidase- and P-450 mediated conversion of BaP produces an extensive metabolic profile of BaP oxidation products that significantly outnumber the 7,8-diol/diol epoxide. The data herein show that in addition to near-ultraviolet light and P-450 isozymes, lactoperoxidase (airway peroxidase) converted BaP into a mixture of three diones, the 1,6-, 3,6-, and 6,12-BaP dione (BPD). In addition, it was found that low concentrations of BPDs induced a concentration-dependent decrease in the proliferation state of human pulmonary epithelial cells in vitro. Nanomolar concentrations of BPDs mediated cell growth inhibition, which was partially reversed by co-incubation with N-acetyl-L-cysteine and ascorbate. BPDs induced the formation of reactive oxygen species as measured by the fluorophore 2,7-dichloro-fluorescein. Together, these results may indicate a role for PAH oxidation products (PAH diones) in the adverse health effects associated with combustion-derived PM and semivolatile organic compounds.

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Section: Discussionmentioning

confidence: 95%

“…Organic oxidation by photochemistry, hydroxyl radicals, nitration, and ozonolysis lead to a variety of oxidized polycyclics that may interact with the respiratory tract cells (Van Cauwenberghe, 1985;Finlayson-Pitts & Pitts, 1999). A congruent, oxidized PAH (oxy-PAH) class formed by all of these processes is PAH diones (Finlayson-Pitts & Pitts, 1999).…”

mentioning

confidence: 98%

Benzo[a]Pyrene Diones are Produced by Photochemical and Enzymatic Oxidation and Induce Concentration-Dependent Decreases in the Proliferative State of Human Pulmonary Epithelial Cells

Reed

Monske

Lauer

et al. 2003

Journal of Toxicology and Environmental Health, Part A

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“…The biosphere intercepts these contaminants during atmospheric deposition: wet deposition and dry deposition (Finlayson-Pitts and Pitts, 2000). In this way, biomonitors like conifer needles (Ratola et al, 2010), deciduous leaves (De Nicola et al, 2013), lichens (Blasco et al, 2011) and mosses/bryophytes (Foan et al, 2014) can be a useful strategy to monitor the exposure of wildlife and human populations to these pollutants.…”

Section: Introductionmentioning

confidence: 99%

Mosses as an integrating tool for monitoring PAH atmospheric deposition: Comparison with total deposition and evaluation of bioconcentration factors. A year-long case-study

et al. 2015

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Polycyclic aromatic hydrocarbon (PAH) atmospheric deposition was evaluated at a remote site in Northern Spain using moss biomonitoring with Hylocomium splendens (Hedw.) Schimp., and by measuring the total deposition fluxes of PAHs. The year-long study allowed seasonal variations of PAH content in mosses to be observed, and these followed a similar trend to those of PAH fluxes in total deposition. Generally, atmospheric deposition of PAHs is greater in winter than in summer, due to more PAH emissions from domestic heating, less photoreactivity of the compounds, and intense leaching of the atmosphere by wet deposition. However, fractionation of these molecules between the environmental compartments occurs: PAH fluxes in total deposition and PAH concentrations in mosses are correlated with their solubility (r=0.852, p<0.01) and lipophilic properties (KOW, r=0.768, p<0.01), respectively. This annual study therefore showed that atmospheric PAH fluxes can be estimated with moss biomonitoring data if the bioconcentration or 'enriching' factors are known.

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“…The sources of NPAHs are similar to those of PAHs, including coal production, incomplete combustion of organic matter, fuel exhaust, petroleum‐derived products, and some industrial processes [3]. Finlayson‐Pitts and Pitts [4] reported formation of NPAHs during the incomplete combustion of nitrogen‐containing organic substances in the presence of NOx. The presence of NPAHs has been documented in air, groundwater, and both marine and freshwater environments [1].…”

Section: Introductionmentioning

confidence: 99%

Toxic effects and oxidative stress in higher plants exposed to polycyclic aromatic hydrocarbons and their N‐heterocyclic derivatives

Pašková

Hilscherová

Feldmannová

et al. 2006

Enviro Toxic and Chemistry

101

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N-heterocyclic derivatives of polycyclic aromatic hydrocarbons (NPAHs) are widespread concomitantly with their parent analogues and have been detected in air, water, sediments, and soil. Although they were shown to be highly toxic to some organisms, our understanding of their occurrence, environmental fate, biological metabolism, and effects is limited. This study evaluated toxic effects of three homocyclic aromatic hydrocarbons (PAHs-phenanthrene, anthracene, fluorene) and their seven N-heterocyclic derivates on higher terrestrial plants Sinapis alba, Triticum aestivum, and Phaseolus vulgaris. Germinability, morphological endpoints, parameters of detoxification, and antioxidant components of plant metabolism as well as lipid peroxidation were studied in acute phytotoxicity tests. Phytotoxicity of NPAHs was generally more pronounced than the effects of parent PAHs, and it significantly differed with respect to the structure of individual NPAHs. Sinapis alba and T. aestivum were more sensitive plant species than P. vulgaris. Chemicals with the strongest inhibition effect on germination and growth of plants were phenanthridine, acridine, benzo[h]quinoline, and 1,10- and 1,7-phenanthroline. All tested chemicals significantly induced activities of detoxification and antioxidant enzymes (glutathione reductase, glutathione peroxidase, and glutathione-S-transferase) at nanomolar to low micromolar concentrations. Levels of reduced glutathione were induced by all tested chemicals except 1,10- and 4,7-phenanthroline. Furthermore, fluorene, carbazole, acridine, phenanthrene, phenanthridine, benzo[h]quinoline, and 1,7-phenanthroline significantly increased lipid peroxidation. The results of our study newly demonstrate significant toxicity of NPAHs to plants and demonstrate suitability of multiple biomarker assessment to characterize mechanisms of oxidative stress and to serve as an early warning of phytotoxicity in vivo.

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Airborne Polycyclic Aromatic Hydrocarbons and Their Derivatives

Cited by 18 publications

References 497 publications

Benzo[a]Pyrene Diones are Produced by Photochemical and Enzymatic Oxidation and Induce Concentration-Dependent Decreases in the Proliferative State of Human Pulmonary Epithelial Cells

Benzo[a]Pyrene Diones are Produced by Photochemical and Enzymatic Oxidation and Induce Concentration-Dependent Decreases in the Proliferative State of Human Pulmonary Epithelial Cells

Mosses as an integrating tool for monitoring PAH atmospheric deposition: Comparison with total deposition and evaluation of bioconcentration factors. A year-long case-study

Toxic effects and oxidative stress in higher plants exposed to polycyclic aromatic hydrocarbons and their N‐heterocyclic derivatives

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