Analysis of nitrated polycyclic aromatic hydrocarbons in diesel particulates

Abstract

The analysis of nitrated polycyllc aromatic hydrocarbons (nltro-PAH) In diesel particulate extracts using a combination of high-performance liquid chromatography, gas chromatography/mass spectrometry, hlgh-resolutlon mass spectrometry, and mass spectrometry/mass spectrometry (MS/MS) techniques Is described. Triple stage quadrupole (TSQ)-MSZMS operated In the constant neutral loss mode Is described for the rapid qualitative screening of nltro-PAH Isomer groups In solvent extracts of diesel particulates. Twenty such Isomer groups of nltro-PAH derivatives were found, many of these groups containing a large number of possible compounds.Mass analyzed Ion kinetic energy spectrometry (MIKES)-MS/MS was found to be much less selective than the TSQ-MS/MS for the analysis of nltro-PAH In unfractionated diesel extracts. HPLC prefractlonatlon was required to remove Interferences In the MIKES analysis. Fused silica capillary GC/MS using on-column Injection was found to be necessary for Indentlfylng specific nltro-PAH Isomers and minimizing decomposition. The highly mutagenic 1-nltropyrene (1-NP) was the only compound found In the nltro(pyrenes and fluoranthenes) Isomer group. The MIKES and TSQ techniques gave comparable results for the quantitation of 1-NP.Organic solvent extracts of diesel exhaust particulates exhibit direct-acting (i.e., activation by mammalian tissue homogenate is not required) mutagenicity (1-5) using the Ames assay (6). High-performance liquid chromatography (HPLC) (1,2,4,5), thin-layer chromatography (TLC) (7,8), and liquid chromatography (9) have been used to fractionate diesel particulate extracts for subsequent mutagenicity testing.

Mutagenicities and Endocrine-disrupting Activities of 1-Hydroxy-2-nitropyrene and 1-Hydroxy-5-nitropyrene

“…Nitrated polycyclic aromatic hydrocarbons (NPAHs) are also a class of mutagens/carcinogens found in the atmosphere, and some of them exhibit stronger mutagenicity/carcinogenicity than their parent PAHs. 1) 1-Nitropyrene (1-NP) is believed to be emitted into the atmosphere from combustion processes of fossil fuel such as diesel fuel 2) and is one of the most abundant NPAHs in the atmosphere. 3) 1-NP taken up by humans and animals is metabolized to hydroxynitropyrenes (OHNPs; Fig.…”

Transfer of Polycyclic Aromatic Hydrocarbons to Fetuses and Breast Milk of Rats Exposed to Diesel Exhaust

“…5) Particulates in DE adsorb many chemicals, such as polycyclic aromatic hydrocarbons (PAHs). [6][7][8][9] We previously showed that several PAHs and monohydroxy PAHs (OHPAHs) have estrogenic/antiestrogenic and antiandrogenic activities in vitro. [10][11][12][13] Though the inhalation of DE during the formative period affects the differentiation process of the fetal organs, little is known about whether PAHs transfer from mother to offspring and act as endocrine disrupters in the offspring.…”

Detection of Mutagenic 1-Chloro-3-, -6-, and -8-Nitropyrenes in Surface Soil Collected in Kyoto, Japan

“…Nitroarenes are produced by the incomplete combustion of organic compounds such as fossil fuels, [1][2][3] and are also produced in the atmosphere from parent arenes and nitrogen oxides. [4][5][6] Nitroarenes are widespread environmental pollutants [7][8][9] and some are suspected human carcinogens.…”