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ToxSci Advance Access originally published online on March 10, 2006
Toxicological Sciences 2006 91(2):440-447; doi:10.1093/toxsci/kfj151
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© The Author 2006. Published by Oxford University Press on behalf of the Society of Toxicology. All rights reserved. For Permissions, please email: journals.permissions@oxfordjournals.org

Formation of Genotoxic Nitro-PAH Compounds in Fish Exposed to Ambient Nitrite and PAH

M. S. Shailaja1, Rani Rajamanickam and Solimabi Wahidulla

Chemical Oceanography Division, National Institute of Oceanography, Dona Paula, Goa 403004, India

Received December 5, 2005; accepted February 20, 2006

Mutagenic nitrated polycyclic aromatic hydrocarbons (nitro-PAHs) have been known to arise in the environment through direct emissions from combustion sources and nitration of PAHs, primarily in the atmosphere. Here, we report the formation of nitro-PAH compounds in fish contaminated with PAH and exposed to nitrite Formula in the ambient water. Electrospray ionization mass spectrometric analysis of the bile of the euryhaline fish Oreochromis mossambicus exposed simultaneously to field-relevant, sublethal concentrations of phenanthrene (1 µg/g) and Formula (1µM) and collision-induced dissociation of selected ions revealed the presence of two strongly genotoxic nitro-PAH metabolites, namely phenanthrene-6-nitro-1,2-dihydrodiol-3,4-epoxide (mass/charge [m/z] 273) and dihydrodihydroxy acetylamino nitrophenanthrene (m/z 359). These two metabolite peaks present only in the bile of fish exposed simultaneously to phenanthrene and Formula constituted, respectively, about 3.1 and 2.7% of the highest peak among the putative unconjugated phenanthrene metabolites in the mass spectrum. The presence of the oxidized phenanthrene metabolite dihydroxyphenanthrene (m/z 233) in fish exposed to phenanthrene alone as well as phenanthrene plus Formula suggested that oxidation of phenanthrene precedes nitration in the sequence of reactions leading to the formation of the observed nitrophenanthrene metabolites. However, the route of PAH administration seems to determine the nature of metabolites formed. Nearly 92% of the hepatic cells of the fish exposed to phenanthrene in the presence of Formula were found to have suffered extensive DNA fragmentation on comet assay.

Key Words: nitrite; coastal waters; nitro-PAH; fish; genotoxicity.


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