Relationships among direct-acting mutagenicity, nitro group orientation and polarographic reduction potential of 6-nitrobenzo[a]pyrene, 7-nitrobenz[a]anthracene and their derivatives

Fu, Peter P.; Heflich, Robert H.; Unruh, Leonard E.; Shaikh, Ali U.; Wu, Yu-Sen; Lai, Ching-Cheng; Lai, Jin‐Shin

doi:10.1016/0165-7992(88)90027-9

Cited by 30 publications

(17 citation statements)

References 22 publications

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“…Thus, stereoselective metabolism of a halogenated PAH, 7-Cl-BA was reported in 1985, which is three years earlier than the first report of 7-Cl-BA being found in municipal incinerator fly ash [136]. Subsequent studies demonstrated that (i) 7-chloro-BA trans-3,4-dihydrodiol was the proximate induced a unique type of ras (K-ras) oncogene activation, with 95% of the mutations being GGC → CGC at the first base of K-ras codon 13 in liver tumors of B6C3F 1 mice [127,144,145]. The mechanism by which 7-chloro-BA induces liver tumors in the male B6C3F1 mice is shown in Figure 10.…”

Section: Formation Of Halogenated Pahsmentioning

confidence: 96%

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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

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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: Formation Of Halogenated Pahsmentioning

confidence: 96%

“…Many nitro-PAHs are highly mutagenic and believed to account for a significant part of the mutagenicity of air-borne particulate matter [10,126,[182][183][184][185][186][187]. In diesel exhaust particulates, approximately 40% of the directacting mutagenicity is believed to be due to nitro-PAHs [10,182].…”

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

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196

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“…We also determined that the level of lipid peroxidation formation was independent of the geometrical location and orientation of the nitro group, or the size of the PAH moiety in geenral. This is drastically different from the structure-activity study of mutagenicity and tumorigenicity of nitro-PAHs from which good correlations were observed [12,13,14,15,16,17,18]. For example, when assayed in Salmonella typhimurium tester strain TA98 in the absence of an exogenous S9 activation enzymes, nitro‑PAHs with the nitro substituent situated at the longest molecular axis, such as 2-nitro-BaP, exhibited the highest mutagenicity among the geometrical nitro-PAH isomers [17].…”

Section: Discussionmentioning

confidence: 74%

“…We have long been interested in studying nitro-PAH induced mutagenesis and carcinogenesis on the basis of structure-activity relationship [12,13,14,15,16,17,18]. To date, the study on nitro-PAH induced phototoxicity on the basis of structure-activity relationship has been limited [14,19,20].…”

Section: Introductionmentioning

confidence: 99%

UVA Photoirradiation of Nitro-Polycyclic Aromatic Hydrocarbons—Induction of Reactive Oxygen Species and Formation of Lipid Peroxides †

Xia¹,

Yin²,

Zhao³

et al. 2013

IJERPH

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Nitro-polycyclic aromatic hydrocarbons (nitro-PAHs) are a class of genotoxic environmental contaminants. We have long been interested in determining the mechanisms by which nitro-PAHs induce genotoxicity. Although the metabolic activation of nitro-PAHs leading to toxicological activities has been well studied, the photo-induced activation of nitro-PAHs has seldom been reported. In this paper, we report photo-induced lipid peroxidation by 19 nitro-PAHs. The results indicated that all but two of the nitro-PAHs can induce lipid peroxidation. Mechanistic studies suggest that lipid peroxidation by nitro-PAHs is mediated by free radicals generated in the reaction. There was no structural correlation between the nitro-PAHs and their ability to induce lipid peroxidation upon UVA irradiation, or between the HOMO-LUMO gap and the ability to cause lipid peroxidation. Most of the nitro-PAHs are less potent in terms of causing lipid peroxidation than their parent PAHs. The lack of correlation is attributed to the complex photophysics and photochemistry of the nitro-PAHs and the yield of reactive oxygen species (ROS) and other factors.

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“…More than 40 structurally related nitroPAHs were used to determine the relationships among direct-acting mutagenicity, orientation of the nitro group, and reduction potential of the nitro group (13,14,17). The compounds consisted of isomeric mononitrated and dinitrated B[a]P, benzo[e]pyrenes, their derivatives, and other nitro-PAHs containing from two to five aromatic rings.…”

Section: Nitro Orientation and Mutagenicity In Salmonellamentioning

confidence: 99%

DNA Adducts and Carcinogenicity of Nitro-Polycyclic Aromatic Hydrocarbons

Fu¹,

Herreno-Sáenz²,

Tungeln³

et al. 1994

Environmental Health Perspectives

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Relationships among direct-acting mutagenicity, nitro group orientation and polarographic reduction potential of 6-nitrobenzo[a]pyrene, 7-nitrobenz[a]anthracene and their derivatives

Cited by 30 publications

References 22 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

UVA Photoirradiation of Nitro-Polycyclic Aromatic Hydrocarbons—Induction of Reactive Oxygen Species and Formation of Lipid Peroxides †

DNA Adducts and Carcinogenicity of Nitro-Polycyclic Aromatic Hydrocarbons

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