A rapid decay channel of the lowest excited singlet state of 9-benzoyl-10-nitroanthracene generating 9-benzoyl-10-anthryloxy radical and nitrogen (II) oxide

Hamanoue, Kumao; Nakayama, Toshihiro; Amijima, Yutaka; Ibuki, Kazuyasu

doi:10.1016/s0009-2614(97)00064-x

Cited by 17 publications

(30 citation statements)

References 16 publications

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“…The NO radical will react with the most stable carbon radical to form a nitroso ketone, which is usually unstable and continues on to become anthraquinone. In the reaction with 10-chloro, cyano, benzoyl, and nitro substituted 9-nitroanthracenes, such a nitroso ketone intermediate was observed [191,193].…”

Section: Photoirradiation Of Nitro-pahsmentioning

confidence: 99%

“…It has been shown that a nitro-PAH with its nitro group adopting a perpendicular orientation reacts faster under light irradiation [189][190][191][192][193]. Nitro-PAHs with a perpendicular nitro group are less mutagenic than those with a parallel nitro group due to their inability to be metabolized into reactive intermediates that form covalent DNA adducts [187,194].…”

Section: Photoirradiation Of Nitro-pahsmentioning

confidence: 99%

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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: Photoirradiation Of Nitro-pahsmentioning

confidence: 99%

Section: Photoirradiation Of Nitro-pahsmentioning

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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“…Upon absorption of light energy, the molecule is promoted to excited singlet state, which intersystem crosses to the excited triplet state. The nitro group rearranges to a nitrite in the excited triplet state24,31,35. Breaking of the N-O bond of nitrite forms a nitroso radical and an oxygen-centered radical in the anthracene moiety.…”

Section: Resultsmentioning

confidence: 99%

“…The NO radical will react with the most stable carbon radical on the opposite site of the nitro group in a concerted fashion and form a nitroso ketone, which is usually unstable and continues on to become anthraquinone. In the reaction with 10-chloro, cyano, benzoyl, and nitro substituted 9-nitroanthracenes, such a nitroso ketone intermediate was observed21,24,31.…”

Section: Introductionmentioning

confidence: 97%

“…Nitro groups with only one or no peri -hydrogen will maintain a parallel orientation to the aromatic moiety4. Nitro-PAHs with a perpendicular nitro group react faster under light irradiation due to a nitro to nitrite rearrangement as it was proposed20–24. Nitro-PAHs with a perpendicular nitro group are less mutagenic than those with a parallel nitro groups due to their inability to be metabolized into reactive intermediates that form covalent DNA adducts5,25.…”

Section: Introductionmentioning

confidence: 99%

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Photochemical reaction of 9-nitro-substituted anthracene-like molecules 9-methyl-10-nitroanthracene and 12-methyl-7-nitrobenz[a]anthracene

Stewart

Jiao

Valente

et al. 2009

Journal of Photochemistry and Photobiology A: Chemistry

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Photochemical reaction of nitro-polycyclic aromatic hydrocarbons: effect by solvent and structure

et al. 2009

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Photochemical degradation of 1-nitropyrene, 2-nitrofluorene, 2,7-dinitrofluorene, 6-nitrochrysene, 3-nitrofluoranthene, 5-nitroacenaphthene, and 9-nitroanthracene were examined in CHCl 3 , CH 2 Cl 2 , DMF, DMF/H 2 O (80/20), CH 3 CN, or CH 3 CN/H 2 O (80/20). The degradation follows mostly the 1 st order kinetics; but a few follow 2 nd order kinetics or undergo self-catalysis. The photodegradation rates follow the order: CHCl 3 > CH 2 Cl 2 > DMF > DMF/H 2 O > CH 3 CN > CH 3 CN/H 2 O. DMF is an exceptional solvent because 3 of the 7 compounds undergo self-catalytic reaction. 9-Nitroanthracene, which has a perpendicular nitro group, is the fastest, while the more compact 1-nitropyrene and 3-nitrofluoranthene, are the slowest degrading compounds.

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A rapid decay channel of the lowest excited singlet state of 9-benzoyl-10-nitroanthracene generating 9-benzoyl-10-anthryloxy radical and nitrogen (II) oxide

Cited by 17 publications

References 16 publications

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

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

Photochemical reaction of 9-nitro-substituted anthracene-like molecules 9-methyl-10-nitroanthracene and 12-methyl-7-nitrobenz[a]anthracene

Photochemical reaction of nitro-polycyclic aromatic hydrocarbons: effect by solvent and structure

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