Studies on the Aromatic Nitro Compounds in Air. III. Determination of 1-Nitropyrene in Airborne Particulate Matter and Automobile Emissions

邦正, 森田; 和美, 深町; 寛, 常盤

doi:10.1248/jhs1956.29.4_199

Cited by 18 publications

(4 citation statements)

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“…The crude product was purified on Florisil by eluting with benzene and was then recrystallized from benzene as yellowish needles: mp 197-198 °C [lit. (15) mp 196-197.5 °C]; MS (70 eV): m/z 247; 500-MHz NMR (acetone-*): ó 8.25 (t, 1H, H7), 8.27 (t, 1H, H2), 8.30 (AB pattern, 2H, H940), 8.50 (d, 1H, Hi), 8.55 (d, 1H, He), 8.62 (d, 1H, He), 8.81 (d, 1H, H3), 9.05 (s, 1H, Hg); *,2 = *|7 = *8 = 7.7, *3 = 8.2, *,io = 9.0 Hz. Synthesis of 4-(Acetylamino)pyrene (4-AAP).…”

Section: Methodsmentioning

confidence: 99%

“…7.61 (s, 1H, H10), 8.14 (t, 1H, H2), 8.25 (dd, 1H, Hi), 8.27 (t, 1H, H7), 8.56 (dd, 1H, H6), 8.64 (dd, 1H, H8), 8.85 (dd, 1H, H3), 9.01 (s, 1H, Hg); *,2 = 7.9, *,3 = 0.9, *,3 = 8.0, *,8 = 7.8, *,8 = 1.2 Hz. 10-OH-4-NP (CDC13):…”

Section: Methodsmentioning

confidence: 99%

“…It has been demonstrated that the mutagenic and carcinogenic potencies of N02-PAH are strongly dependent on their structure. Among the three isomers of mononitropyrene that occur in urban air (7,8), the levels of 2-nitropyrene (2-NP) and 4-NP are about the same; however, there is far less of these than of 1-NP and the latter is the only isomer detected in combustion materials (1).…”

Section: Introductionmentioning

confidence: 99%

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In vitro and In vivo Metabolism of the Carcinogen 4-Nitropyrene

Upadhyaya

et al. 1994

Chem. Res. Toxicol.

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The in vitro and in vivo metabolism of the potent mutagen and carcinogen, 4-nitropyrene, was studied. 4-Aminopyrene, 4-(acetylamino)pyrene, 9,10-epoxy-9,10-dihydro-4-nitropyrene, cis- and trans-9,10-dihydro-9,10-dihydroxy-4-nitropyrene, 9- and 10-hydroxy-4-nitropyrene, and 9- and 10-hydroxy-4-(acetylamino)pyrene were synthesized to serve as markers for the identification of 4-nitropyrene metabolites. Initially, 4-nitropyrene was metabolized by rat liver microsomes, or rat liver 9000g supernatant, to yield primarily two metabolites; one of these was identified as 4-nitropyrene-9,10-dione. The major metabolite of 4-nitropyrene in the presence of 3,3,3-trichloropropylene-1,2-oxide was 9,10-epoxy-9,10-dihydro-4-nitropyrene. In parallel studies, oral administration of 58 mg (0.3 mCi/mmol)/kg body weight of [3H]4-nitropyrene to female Sprague-Dawley rats, which are susceptible to mammary carcinogenesis by this agent, yielded 32% and 30.6% of the dose after 48 h as urinary and fecal excretion products, respectively. Excretion of the radioactivity remained slightly higher in the urine than in feces throughout 168 h after administration. Some of the fecal metabolites (isolated amounts expressed as % of dose) were identified as 4-aminopyrene (5.4), 9(10)-hydroxy-4-(acetylamino)pyrene (3.3), and unmetabolized 4-nitropyrene (2.4). Sulfates (3.3) and glucuronides (2.4) of 9(10)-hydroxy-4-(acetylamino)pyrene were identified in the urine. This study indicates that nitroreduction and ring oxidation are metabolic pathways of 4-nitropyrene in vivo; similar findings were obtained previously with its structural isomers 1- and 2-nitropyrene. However, the pattern of excretion of 4-nitropyrene is different; the significance of this observation in relation to tumor induction is discussed.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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In vitro and In vivo Metabolism of the Carcinogen 4-Nitropyrene

Upadhyaya

et al. 1994

Chem. Res. Toxicol.

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“…Ambient air contains carcinogenic and mutagenic compounds such as polycyclic aromatic hydrocarbons (PAHs) and their nitro derivatives as a result of air pollution derived from combustion emission ( − ). These compounds are suspected to be a contributing factor in human lung cancer, especially in industrial and urban areas ( − ).…”

Section: Introductionmentioning

confidence: 99%

Presence of 1-Hydroxypyrene Conjugates in Woody Plant Leaves and Seasonal Changes in Their Concentrations

Nakajima

Kojima

Iwaya

et al. 1996

Environ. Sci. Technol.

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β-O-Glucoside and β-O-glucuronide conjugates of 1-hydroxypyrene (OHPy) were found in the leaves of four kinds of woody plant; cherry, maple, ginkgo, and camphor. The conjugates were quantified by measuring OHPy liberated from the water-soluble fraction of leaves treated with β-O-glucosidase and β-O-glucuronidase. Concentrations of β-O-glucuronide and β-O-glucoside ranged from 0 to 358 and from 0 to 129 pmol/g of fresh leaves, respectively, in monthly measurement over a period of 1 year. The amounts of glucuronide conjugates were greater than those of glucoside conjugates in most plants examined. Both conjugates were detected at the highest concentrations in summer to autumn. For most plants, the total amounts of the conjugates were greater than that of free OHPy in the leaves in all seasons, and the differences reached 30-fold in maple leaves in September. From these results, the source of the OHPy conjugates in leaves and their implications are discussed.

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