Theoretical evaluation of substituted polycyclic aromatic hydrocarbons as emerging pollutant phototoxins

Rowberg, K. L.; Nataraj, Nakul; Saroian, W.; Kang, Lina

doi:10.2495/wp080321

Cited by 1 publication

(1 citation statement)

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“…The oxy-radical of BaP has been proposed to be responsible for DNA damage caused by the combination of UV light and BaP [99]. Molecular orbital calculations have been frequently used as a tool to correlate the chemical structures of PAH photoirradiation products, including both oxygenated PAHs and PAH quinones, with phototoxicity [77,[100][101][102].…”

Section: A Formation Of Oxygenated Pahs and Pah Quinonesmentioning

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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Section: A Formation Of Oxygenated Pahs and Pah Quinonesmentioning

confidence: 99%