Effect of nitro substitution on the light-mediated mutagenicity of polycyclic aromatic hydrocarbons in Salmonella typhimurium TA98

White, Gail L.; Fu, Peter P.; Heflich, Robert H.

doi:10.1016/0165-7992(85)90115-0

Cited by 15 publications

(7 citation statements)

References 34 publications

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“…In another study, the direct photolysis of 7-NBaA resulted in increased direct-acting mutagenicity to TA98 in the Salmonella assay with increasing irradiation time. 47 The orientation of the nitro group has been related to the photochemical stability of NPAH, 48 and both 9-NAN and 7-NBaA have nitro group orientations that are out of the aromatic plane, reducing the steric effects exerted by two peri-hydrogens. This structure makes these PAHs less photochemically stable and may explain their significant degradation during the OH radical exposure (Figure 1B).…”

Section: Resultsmentioning

confidence: 99%

Heterogeneous Reactions of Particulate Matter-Bound PAHs and NPAHs with NO₃/N₂O₅, OH Radicals, and O₃ under Simulated Long-Range Atmospheric Transport Conditions: Reactivity and Mutagenicity

Jariyasopit

Zimmermann

Schrlau

et al. 2014

Environ. Sci. Technol.

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The heterogeneous reactions of ambient particulate matter (PM)-bound polycyclic aromatic hydrocarbons (PAHs) and nitro-PAHs (NPAHs) with NO3/N2O5, OH radicals, and O3 were studied in a laboratory photochemical chamber. Ambient PM2.5 and PM10 samples were collected from Beijing, China and Riverside, California, and exposed under simulated atmospheric long-range transport conditions for O3 and OH and NO3 radicals. Changes in the masses of 23 PAHs and 20 NPAHs, as well as the direct and indirect-acting mutagenicity of the PM (determined using the Salmonella mutagenicity assay with TA98 strain), were measured prior to and after exposure to NO3/N2O5, OH radicals, and O3. In general, O3 exposure resulted in the highest relative degradation of PM-bound PAHs with more than four rings (benzo[a]pyrene was degraded equally well by O3 and NO3/N2O5). However, NPAHs were most effectively formed during the Beijing PM exposure to NO3/N2O5. In ambient air 2-nitrofluoranthene (2-NF) is formed from gas-phase NO3 radical- and OH radical-initiated reactions of fluoranthene, and 2-nitropyrene (2-NP) is formed from gas-phase OH radical-initiated reaction of pyrene. There was no formation of 2-NF or 2-NP in any of the heterogeneous exposures, suggesting that gas-phase formation of NPAHs did not play an important role during chamber exposures. Exposure of Beijing PM to NO3/N2O5 resulted in an increase in direct-acting mutagenic activity which was associated with the formation of mutagenic NPAHs. No NPAH formation was observed in any of the exposures of the Riverside PM. This was likely due to the accumulation of atmospheric degradation products from gas-phase reactions of volatile species onto the surface of PM collected in Riverside prior to exposure in the chamber, thus decreasing the availability of PAHs for reaction.

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Section: Resultsmentioning

confidence: 99%

Heterogeneous Reactions of Particulate Matter-Bound PAHs and NPAHs with NO₃/N₂O₅, OH Radicals, and O₃ under Simulated Long-Range Atmospheric Transport Conditions: Reactivity and Mutagenicity

Jariyasopit

Zimmermann

Schrlau

et al. 2014

Environ. Sci. Technol.

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“…Some of the early studies focused on the impact of light and PAHs on the development of cancer [57][58][59][60]. Subsequently, work has been directed toward the study of molecular mechanism of phototoxicity of PAHs [61][62][63][64][65][66][67][68][69][70][71][72][73]. As a result of the photoreactions, singlet oxygen, superoxide radical, PAH radical, DNA radical, oxygenated PAH reactive intermediates, and other reactive intermediates are formed and can damage cellular constituents, resulting in either acute toxicity or genotoxicity [27].…”

Section: Mechanisms Of Pah Photoreactions In the Environmentmentioning

confidence: 99%

Phototoxicity and Environmental Transformation of Polycyclic Aromatic Hydrocarbons (PAHs)—Light-Induced Reactive Oxygen Species, Lipid Peroxidation, and DNA Damage

Xia

Sun

et al. 2012

Journal of Environmental Science and Health, Part C

196

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Polycyclic aromatic hydrocarbons (PAHs) are a class of mutagenic and tumorigenic environmental contaminants. Although the mechanisms by which PAHs induce cancer in experimental animals have been extensively studied and the metabolic activation pathways have been determined, the environmental fate of PAHs and the phototoxicity exerted by PAHs, as well as their photoreaction products formed in the environment, have received much less attention. In this review, the formation of oxygenated PAHs, PAH quinones, nitro-PAHs, and halogenated PAHs from photoreaction of environmental PAHs are addressed. Upon light irradiation, PAHs and all PAH photoreaction products can absorb light energy to reach photo-excited states, which react with molecular oxygen, medium, and coexisting chemicals to produce reactive oxygen species (ROS) and other reactive intermediates, such as oxygenated PAHs and free radicals. These intermediates, including ROS, induce lipid peroxidation, and DNA damage including DNA strand breakage, oxidation to 8-oxo-2'-deoxyguanosine, and DNA-adducts. Since these toxicological endpoints are associated with age-related diseases, including cancer, environmental PAHs concomitantly exposed to sunlight may potentially promote human skin damage, leading to ageing and skin cancers. Thus, we suggest that (i) in addition to the widely recognized metabolic pathways, more attention must be paid to photoreaction as an important activation pathway for PAHs, (ii) risk assessment of environmental PAHs should take into consideration the complex photochemical reactions leading to mixtures of products that are also phototoxic; and (iii) the study of structure-toxicity relationships should be expanded to cover the complex photoreactions and extrinsic factors that affect phototoxicity endpoints.

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“…Some of the early studies focused on the impact of light and PAH on the development of cancer (104)(105)(106)(107). Later on, more work have been directed toward the study of the molecular mechanism of phototoxicity of PAHs (40,73,95,97,101,(108)(109)(110)(111)(112)(113)(114)(115)(116)(117)(118). A review article on the effects of near ultraviolet radiation on the toxicity of PAHs in animals and plants appeared in 1996 (46).…”

Section: Pah Molecular Phototoxicitymentioning

confidence: 99%

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

2002

Journal of Environmental Science and Health, Part C

341

252

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Effect of nitro substitution on the light-mediated mutagenicity of polycyclic aromatic hydrocarbons in Salmonella typhimurium TA98

Cited by 15 publications

References 34 publications

Heterogeneous Reactions of Particulate Matter-Bound PAHs and NPAHs with NO₃/N₂O₅, OH Radicals, and O₃ under Simulated Long-Range Atmospheric Transport Conditions: Reactivity and Mutagenicity

Heterogeneous Reactions of Particulate Matter-Bound PAHs and NPAHs with NO₃/N₂O₅, OH Radicals, and O₃ under Simulated Long-Range Atmospheric Transport Conditions: Reactivity and Mutagenicity

Phototoxicity and Environmental Transformation of Polycyclic Aromatic Hydrocarbons (PAHs)—Light-Induced Reactive Oxygen Species, Lipid Peroxidation, and DNA Damage

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

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Effect of nitro substitution on the light-mediated mutagenicity of polycyclic aromatic hydrocarbons in Salmonella typhimurium TA98

Cited by 15 publications

References 34 publications

Heterogeneous Reactions of Particulate Matter-Bound PAHs and NPAHs with NO3/N2O5, OH Radicals, and O3 under Simulated Long-Range Atmospheric Transport Conditions: Reactivity and Mutagenicity

Heterogeneous Reactions of Particulate Matter-Bound PAHs and NPAHs with NO3/N2O5, OH Radicals, and O3 under Simulated Long-Range Atmospheric Transport Conditions: Reactivity and Mutagenicity

Phototoxicity and Environmental Transformation of Polycyclic Aromatic Hydrocarbons (PAHs)—Light-Induced Reactive Oxygen Species, Lipid Peroxidation, and DNA Damage

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

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Heterogeneous Reactions of Particulate Matter-Bound PAHs and NPAHs with NO₃/N₂O₅, OH Radicals, and O₃ under Simulated Long-Range Atmospheric Transport Conditions: Reactivity and Mutagenicity

Heterogeneous Reactions of Particulate Matter-Bound PAHs and NPAHs with NO₃/N₂O₅, OH Radicals, and O₃ under Simulated Long-Range Atmospheric Transport Conditions: Reactivity and Mutagenicity