Utilize este identificador para referenciar este registo: http://hdl.handle.net/10400.18/2725
Título: Chlorinated Polycyclic Aromatic Hydrocarbons Associated with Drinking Water Disinfection: Synthesis, Formation under Aqueous Chlorination Conditions and Genotoxic Effects
Autor: Pinto, Miguel
Rebola, Marlene
Louro, Henriqueta
Antunes, Alexandra M.M.
José, Silvia S.
Rocha, Maria
Silva, Maria João
Cardoso, Ana Sofia
Palavras-chave: Água e Solo
Genotoxicidade Ambiental
Benzo[a]pyrene
Chlorinated Polycyclic Aromatic Hydrocarbons
Chromatographic
Methodology
Fluoranthene
Genotoxicity
Water Disinfection By-products
Data: 13-Jun-2014
Editora: Taylor & Francis
Citação: Polycyclic Aromatic Compounds. 2014;34(4):356-371. doi:10.1080/10406638.2014.891143
Resumo: 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.
Peer review: yes
URI: http://hdl.handle.net/10400.18/2725
DOI: 10.1080/10406638.2014.891143
ISSN: 1040-6638 print
1563-5333 online
Versão do Editor: http://www.tandfonline.com/doi/abs/10.1080/10406638.2014.891143#.VMuDSdKsU0M
Aparece nas colecções:DSA - Artigos em revistas internacionais
DGH - Artigos em revistas internacionais

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