Nitro‐polycyclic aromatic hydrocarbons: A class of genotoxic environmental pollutants

Fu, Peter P.; Herreno-Sáenz, Diógenes

doi:10.1080/10590509909373506

Cited by 55 publications

(42 citation statements)

References 150 publications

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“…Photochemically, the former nitro-PAHs react faster than the latter due to a light activated nitrite rearrangement mechanism as will be discussed later (87). It has long been recognized by Fu et al (18,22,83) that nitro-PAHs having perpendicular nitro groups are less mutagenic than nitro-PAHs having the nitro group parallel to the aromatic rings. This toxicity difference is attributed to their inability to be metabolized into reactive intermediates (N-hydroxyamino-PAH) that can form covalent DNA adducts.…”

Section: Pah Photochemistrymentioning

confidence: 99%

“…The photochemical reaction rate of nitro-PAHs depends on the position of the nitro-substitution (82,(84)(85)(86)(87). Nitro groups peri to two hydrogen atoms is forced to be in a perpendicular orientation to the aromatic ring due to steric hindrance while nitro groups peri only to one hydrogen atom stay in a parallel orientation to the aromatic ring (18,22,33,83) (Figure 9). Thus, nitro-PAHs can be divided into two categories: those with the perpendicular and others with the parallel nitro groups relative to the aromatic ring.…”

Section: Pah Photochemistrymentioning

confidence: 99%

“…Nitro-PAHs are a class of carcinogens detected in the atmosphere and some nitroPAHs are more carcinogenic than their parent PAHs (18,22,82,83). Amino-PAHs are usually the metabolite of nitro-PAHs.…”

Section: Pah Photochemistrymentioning

confidence: 99%

“…Rather, they require metabolic activation in order to exert genotoxicity, including mutagenicity and tumorigenicity (2,4,8,13,14,18,(21)(22)(23). Upon entering the body, the cellular defense system attempts to "remove" these foreign substances by metabolism.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

2002

Journal of Environmental Science and Health, Part C

341

252

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Section: Pah Photochemistrymentioning

confidence: 99%

Section: Pah Photochemistrymentioning

confidence: 99%

Section: Pah Photochemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

2002

Journal of Environmental Science and Health, Part C

341

252

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“…The S9-independent bacterial mutagenic activity in the polar fraction of combustion exhausts is primarily accounted for by the presence of nitro-PAH [46], which possess an extremely high mutagenic activity [30]. For instance, for 1-NP a direct-acting specific mutagenicity of 339 revertants/nmol (tester strain TA98) has been reported [47].…”

Section: Direct Mutagenicity Of 2 Andmentioning

confidence: 99%

Bacterial mutagenicity of the three isomeric dicyclopenta-fused pyrenes: the effects of dicyclopenta topology

Otero-Lobato

Jenneskens

Seinen

2004

Mutation Research/Genetic Toxicology and Environmental Mutagene

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Cyclopenta[cd]pyrene (1) and its congeners dicyclopenta [cd,mn]-(2), dicyclopenta [cd,fg]-(3), dicyclopenta [cd,jk]pyrene (4), which were all identified as constituents of combustion exhausts, as well as their partially hydrogenated derivatives 3,4-dihydrocyclopenta[cd]-(5), 1,2,4,5-tetrahydrodicyclopenta[cd,mn]-(6), 5,6,7,8-tetrahydrodicyclopenta[cd,fg]- (7) and 1,2,6,7-tetrahydrodicyclopenta[cd,jk]pyrene (8), were assayed for mutagenicity in the Salmonella typhimurium strain TA98 using different concentrations of microsomal protein in the metabolic activation system (S9-mix, with S9-fraction from liver of Aroclor-1254-treated rats: 2, 4 and 10% (v/v), respectively). Whereas a positive mutagenic response is found for 1-4 in the presence of S9-mix, 5-8 exert no mutagenicity either with or without S9-mix. Since for 1-4 the highest response is observed with S9-mix 2% (v/v) instead of the standard 4% (v/v), a one-step activation pathway, i.e. epoxidation of the five-membered ring olefinic bonds, appears to be operational. Surprisingly, 3 and, to a lesser extent, 2 (11.7 versus 4.2 His revertants/nmol) also give a positive response in the absence of S9-mix. Hence, 2 and 3 are expected to contribute to the direct-acting mutagenicity of the non-polar fraction of combustion exhausts. Presumably for the direct-acting mutagenicity one-electron transfer processes play a role in bioactivation. The experimental observations are supported by semi-empirical AM1 calculations on the possible ultimate metabolites, i.e. mono-epoxides (2a-4a), cis-di-epoxides (2b-4b) and trans-di-epoxides (2c-4c) and the related mono-hydroxy carbocations (2d-4d and 2e-4e), and the radical anions 1 •− -4 •− .

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PAHs: An Ecotoxicological Perspective

Douben¹

2003

120

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Nitro‐polycyclic aromatic hydrocarbons: A class of genotoxic environmental pollutants

Cited by 55 publications

References 150 publications

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

Environmental Carcinogenic Polycyclic Aromatic Hydrocarbons: Photochemistry and Phototoxicity

Bacterial mutagenicity of the three isomeric dicyclopenta-fused pyrenes: the effects of dicyclopenta topology

PAHs: An Ecotoxicological Perspective

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