Evaluation of Endocrine Disrupting Activities of Monohydroxylated Derivatives of 1-nitropyrene by Yeast Two-hybrid Assay

Kameda, Takayuki; Akiyama, Ayuko; Toriba, Akira; Tachikawa, Chihiro; Yoshita, Morio; Tang, Ning; Hayakawa, Kazuichi

doi:10.1248/jhs.54.118

Cited by 9 publications

(7 citation statements)

References 20 publications

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“…The photochemical formation of hydroxynitropyrene isomers from 1-nitropyrene in diesel exhaust and airborne particles has been recently reported (Kameda et al, 2011). Most hydroxynitropyrene isomers as well as the diones (Benson et al, 1985) show lower mutagenicity (Manabe et al, 1985; Ball et al, 1984; Kameda et al, 2008) than the parent nitropyrene. Thus, the present results indicate that during the atmospheric transport of the DNPs, these strong bacterial mutagens can be phototransform into less biologically active intermediates.…”

Section: Discussionmentioning

confidence: 99%

Phototransformations of dinitropyrene isomers on models of the atmospheric particulate matter

Arce

Morel

2013

Atmospheric Environment

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The 1,6 and 1,8-dinitropyrenes (DNP) isomers are strong mutagens and carcinogens encountered in diesel exhaust and airborne particles. Relative photodegradation rates were determined and some products were characterized when these isomers were irradiated adsorbed onto models of the atmospheric matter. These are compared to their photochemical behavior in a polar nonprotic solvent. The 1,8-DNP isomer is three times more reactive than the 1,6-DNP when irradiated adsorbed onto silica gel surfaces, while the reverse order is observed in solution, demonstrating the influence of structural differences and environmental effects on the photoreactivity. Oxygen is a key factor in the formation of pyrenediones from 1,8-DNP in solution and on silica gel which is not the case for 1,6-DNP. The average pore diameter (2.5 versus 6.0 nm) of the silica surfaces induces a significant change in the product distribution and relative yields of 1,8-DNP because pyrenediones or 8-hydroxy-1-nitropyrene are not produced in the smaller pore silica. A 6-hydroxy-1-nitropyrene product is observed both in acidic alumina and silica (6.0 nm) surfaces. On acidic alumina the rates of phototransformation of the isomers are equal, a significant increase in the relative yield of the hydroxynitropyrene product is observed compared to the silica and unidentified products in which the absence of NO2 and pyrene absorption bands were observed, demonstrating the surface effect on the photodegradation. Overall, the presence of some products indicates the occurrence of a nitro-nitrite rearrangement on the surface with the participation of a pyrenoxy radical as their precursor.

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Section: Discussionmentioning

confidence: 99%

Phototransformations of dinitropyrene isomers on models of the atmospheric particulate matter

Arce

Morel

2013

Atmospheric Environment

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“…23,27,28) Recently, however, OHNPs such as 1-OH-3-NP, 1-OH-6-NP, and 1-OH-8-NP have been found to act as endocrine disruptors, i.e. they act as estrogenic, anti-estrogenic, and anti-androgenic compounds, 29,30) which may cause dysfunction of human and wildlife endocrine systems, abnormal development of reproductive systems, and immunodeficiencies. In view of the influence of OHNPs on human health, we need to learn more about their environmental concentration levels, sources and behavior.…”

Section: Atmospheric Formation Of Hydroxynitropyrenes From a Photochementioning

confidence: 99%

Atmospheric Chemistry of Polycyclic Aromatic Hydrocarbons and Related Compounds

Kameda

2011

JOURNAL OF HEALTH SCIENCE

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Polycyclic aromatic compounds are ubiquitous atmospheric pollutants with toxic, mutagenic, and carcinogenic properties. They are produced from chemical reactions of their parent compounds in the atmosphere as well as from a wide variety of anthropogenic sources such as fuel combustions. The present review is mainly concerned with several reaction pathways regarding secondary formation of atmospheric polycyclic aromatic hydrocarbon (PAH) derivatives, i.e., formation of mutagenic nitrated PAHs, 1-and 2-nitrotriphenylene, via gas-phase OH or NO 3 radical-initiated reactions of the parent triphenylene, atmospheric formation of hydroxynitropyrenes from a photochemical reaction of 1-nitropyrene, and photochemical degradation of selected nitrated and oxygenated PAHs on airborne particles under simulated solar UV-irradiation.

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“…Several studies have found that most OHNP isomers have lower mutagenic activity than the parent 1-NP (Rosser et al, 1996;Manabe et al, 1985;Ball et al, 1985). Recently, however, OHNPs such as 1-OH-3-NP, 1-OH-6-NP, and 1-OH-8-NP have been found to act as endocrine disruptors: they act as estrogenic, anti-estrogenic, and anti-androgenic compounds (Kameda et al, 2008;Kameda et al, 2011a) that may cause dysfunction of human and wildlife endocrine systems, abnormal development of reproductive systems, and immunodeficiencies. In view of the influence of OHNPs on human health, we need to learn more about their environmental concentration levels, sources, and behaviors.…”

Section: Atmospheric Formation Of Hydroxynitropyrenes From a Photochementioning

confidence: 99%

Atmospheric Reactions of PAH Derivatives: Formation and Degradation

Kameda

2018

Polycyclic Aromatic Hydrocarbons

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Polycyclic aromatic compounds are ubiquitous atmospheric pollutants with toxic, mutagenic, and carcinogenic properties. They are produced from chemical reactions of their parent or related compounds in the atmosphere as well as from a wide variety of anthropogenic sources such as fuel combustions. In this chapter, chemical reaction pathways for the atmospheric secondary formation of several polycyclic aromatic hydrocarbon (PAH) derivatives, i.e., gas-phase formation of mutagenic 1-and 2-nitrotriphenylene via OH or NO3 radical-initiated reactions of the parent triphenylene, formation of carcinogenic 1-nitropyrene from heterogeneous nitration of pyrene on mineral dust aerosols, atmospheric formation of hydroxynitropyrenes from a photochemical reaction of 1-nitropyrene, and photochemical degradation of selected nitrated and oxygenated PAHs on airborne particles under simulated solar UV-irradiation, are addressed.

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Evaluation of Endocrine Disrupting Activities of Monohydroxylated Derivatives of 1-nitropyrene by Yeast Two-hybrid Assay

Cited by 9 publications

References 20 publications

Phototransformations of dinitropyrene isomers on models of the atmospheric particulate matter

Phototransformations of dinitropyrene isomers on models of the atmospheric particulate matter

Atmospheric Chemistry of Polycyclic Aromatic Hydrocarbons and Related Compounds

Atmospheric Reactions of PAH Derivatives: Formation and Degradation

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