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Chlorinated Polycyclic Aromatic Hydrocarbons Associated with Drinking Water Disinfection: Synthesis, Formation under Aqueous Chlorination Conditions and Genotoxic Effects
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Advisor(s)
Abstract(s)
Polycyclic aromatic hydrocarbons (PAHs) are among the most persistent and toxic organic
micropollutants present in water and several of them are mutagenic and carcinogenic.
Although it has been shown that chlorinated derivatives of PAHs (Cl-PAHs)
may be formed during the water chlorination procedure, little is known about their
potential genotoxic and carcinogenic effects. The objectives of the present work were
to prepare and characterize the major chlorinated derivatives of benzo[a]pyrene (BaP)
and fluoranthene (Fluo), to develop an analytical methodology for their quantification
in water samples and to analyse their potential genotoxicity. Chlorinated standards
were prepared by a newly developed two phase method (water/n-hexane) using sodium hypochlorite. 6-Chloro-benzo[a]pyrene was selectively obtained from BaP, while 1,3-
dichloro-fluoranthene and 3-chloro-fluoranthene were obtained from Fluo. All products
were isolated and characterized by nuclear magnetic resonance and mass spectrometry.
The formation of BaP- and Fluo-chlorinated derivatives under aqueous chlorination
conditions was observed using a SPE-HPLC-FLD methodology. In addition, the
cytotoxic and genotoxic activities of the three chlorinated derivatives were analyzed in
comparison to their parent compounds, in a human-derived hepatoma cell line using
the neutral red uptake and comet assays, respectively. The results showed that, at the
equimolar doses of 100 and 125 μM, 6-Cl-BaP was able to induce a significantly higher
level of DNA damage than BaP, suggesting a more potent genotoxic effect. In contrast,
neither Fluo nor its chlorinated derivatives were genotoxic in the same cell line. The
identification of new and possibly hazardous water chlorination by-product from PAHs
emphasizes the need to minimize total organic carbon content of raw water and the
implementation of safer water disinfection methods.
Description
Keywords
Água e Solo Genotoxicidade Ambiental Benzo[a]pyrene Chlorinated Polycyclic Aromatic Hydrocarbons Chromatographic Methodology Fluoranthene Genotoxicity Water Disinfection By-products
Pedagogical Context
Citation
Polycyclic Aromatic Compounds. 2014;34(4):356-371. doi:10.1080/10406638.2014.891143
Publisher
Taylor & Francis