421
Views
19
CrossRef citations to date
0
Altmetric
Original Articles

Chlorinated Polycyclic Aromatic Hydrocarbons Associated with Drinking Water Disinfection: Synthesis, Formation under Aqueous Chlorination Conditions and Genotoxic Effects

, , , , , , & show all
Pages 356-371 | Received 01 Aug 2013, Accepted 01 Feb 2014, Published online: 13 Jun 2014

REFERENCES

  • Richardson, S.D., M.J. Plewa, E.D. Wagner, R. Schoeny, and D.M. Demarini. “Occurrence, Genotoxicity, and Carcinogenicity of Regulated and Emerging Disinfection by-Products in Drinking Water: A Review and Roadmap for Research.” Mutation Research 636 (2007): 178–242.
  • IARC. “Some Drinking-Water Disinfectants and Contaminants, Including Arsenic.” IARC Monographs on the Evaluation of Carcinogenic Risks 84 (2004): 1–477.
  • King, W.D., L.D. Marrett, and C.G. Woolcott. “Case-Control Study of Colon and Rectal Cancers and Chlorination By-Products in Treated Water.” Cancer Epidemiology, Biomarkers & Prevention 9 (2000): 813–8.
  • Nikolaou, A.D., S.K. Golfinopoulos, T.D. Lekkas, and M.N. Kostopoulou. “DBP Levels in Chlorinated Drinking Water: Effect of Humic Substances.” Environmental Monitoring Assesment. 93 (2004): 301–19.
  • Oyler, A.R., R.J. Liukkonen, M.K. Lukasewycz, D.A. Cox, D.A. Peake, and R.M. Carlson. “Implications of Treating Water Containing Polynuclear Aromatic-Hydrocarbons with Chlorine—A Gas Chromatographic-Mass Spectrometric Study.” Environmental Health Perspectives 46 (1982): 73–86.
  • Mori, Y., S. Goto, S. Onodera, S. Naito, and H. Matsushita. “Aqueous Chlorination of Tetracyclic Aromatic-Hydrocarbons – Reactivity And Product Distribution.” Chemosphere 22 (1991): 495–501.
  • Onodera, S., K. Igarashi, A. Fukuda, J. Ouchi, and S. Suzuki. “Chemical Changes of Organic Compounds in Chlorinated Water. XVI. Gas Chromatographic-Mass Spectrometric Studies of Reactions of Tricyclic Aromatic Hydrocarbons with Hypochlorite in Dilute Aqueous Solution.” Journal of Chromatography 466 (1989): 233–49.
  • Shiraishi, H., N.H. Pilkington, A. Otsuki, and K. Fuwa. “Occurrence of Chlorinated Polynuclear Aromatic-Hydrocarbons in Tap Water.” Environmental Science and Technology 19 (1985): 585–90.
  • Ohura, T., K.-I. Sawada, T. Amagai, and M. Shinomiya. “Discovery of Novel Halogenated Polycyclic Aromatic Hydrocarbons in Urban Particulate Matters: Occurrence, Photostability, and AhR Activity.” Environmental Science and Technology 43 (2009): 2269–75.
  • Majer, B.J., V. Mersch-Sundermann, F. Darroudi, B. Laky, K. de Wit, and S. Knasmuller. “Genotoxic Effects of Dietary and Lifestyle Related Carcinogens in Human Derived Hepatoma (HepG2, Hep3B) Cells.” Mutation Research—Fundamental and Molecular Mechanisms of Mutagenesis 551 (2004): 153–66.
  • Lin, T. and M.S. Yang. “Benzo[a]pyrene-induced Necrosis in the HepG(2) Cells via PARP-1 Activation and NAD(+) Depletion.” Toxicology 245 (2008): 147–53.
  • Spink, D.C., S.J. Wu, B.C. Spink, M.M. Hussain, D.D. Vakhania, B.T. Pentecost, and L.S. Kaminsky. “Induction of CYP1A1 and CYP1B1 by benzo[k]fluoranthene and benzo[a]pyrene in T-47D Human Breast Cancer Cells: Roles of PAH Interactions and PAH Metabolites.” Toxicological and Applied Pharmacology 226 (2008): 213–24.
  • Roth, M.J., W.-Q. Wei, J. Baer, C.C. Abnet, G.-Q. Wang, L.R. Sternberg, A.C. Warner, L.L. Johnson, N. Lu, C.A. Giffen, S.M. Dawsey, Y.-L. Qiao, and J. Cherry. “Aryl Hydrocarbon Receptor Expression Is Associated with a Family History of Upper Gastrointestinal Tract Cancer in a High-Risk Population Exposed to Aromatic Hydrocarbons.” Cancer Epidemiology, Biomarkers & Prevention 18 (2009): 2391–6.
  • Colmsjo, A., A. Rannug, and U. Rannug. “Some Chloro Derivatives of Polynuclear Aromatic-Hydrocarbons are Potent Mutagens in Salmonella-Typhimurium.” Mutation Research 135 (1984): 21–9.
  • Lofroth, G., L. Nilsson, E. Agurell, and T. Sugiyama. “Salmonella Microsome Mutagenicity of Monochloro Derivatives of Some Di-tetracyclic, Tri-tetracyclic and Tetracyclic Aromatic-Hydrocarbons.” Mutation Research 155 (1985): 91–4.
  • IARC. “A Review of Human Carcinogens – Chemical Agents and Related Occupations.” IARC Monographs on the Evaluation of Carcinogenic Risks 100, F (2012): 111–44.
  • Stocker, K.J., W.R. Howard, J. Statham, and R.J. Proudlock. “Assessment of the Potential in vivo Genotoxicity of Fluoranthene.” Mutagenesis 11 (1996): 493–6.
  • Audebert, M., A. Riu, C. Jacques, A. Hillenweck, E.L. Jamin, D. Zalko, and J.P. Cravedi. “Use of the Gamma H2AX Assay for Assessing the Genotoxicity of Polycyclic Aromatic Hydrocarbons in Human Cell Lines.” Toxicology Letters 199 (2010): 182–92.
  • Knasmüller, S., V. Mersch–Sundermann, S. Kevekordes, F. Darroudi, W.W. Huber, C. Hoelzl, J. Bichler, and B.J. Majer. “Use of Human–Derived Liver Cell Lines for the Detection of Environmental and Dietary Genotoxicants; Current State of Knowledge.” Toxicology 198 (2004): 315–28.
  • Tice, R.R., E. Agurell, D. Anderson, B. Burlinson, A. Hartmann, H. Kobayashi, Y. Miyamae, E. Rojas, J.C. Ryu, and Y.F. Sasaki. “Single Cell Gel/Comet Assay: Guidelines for in vitro and in vivo genetic toxicology testing.” Environmental and Molecular Mutagenesis 35 . (200): 206–21.
  • Van Haeringen, C.J., J. Lugtenburg, and J. Cornelisse. “Synthesis and Characterization of Chloro-, Bromo-, Cyano-, Formyl-, and Methylfluoranthenes.” Polycyclic Aromatic Compounds 8 (1996): 9–22.
  • Oyler, A.R., R.J. Liukkonen, M.T. Lukasewycz, K.E. Helkklla, D.A. Cox, and R.M. Carlson. “Chorine “Disinfection” Chemistry of Aromatic Compouns. Polynuclear Aromatic Hydrocarbons: Rates, Products, and Mechanisms.” Environmental Science and Technology 17 (1983): 334–42.
  • Repetto, G., A. del Peso, and J.L. Zurita. “Neutral Red Uptake Assay for the Estimation of Cell Viability/Cytotoxicity.” Nature Protocols 3 (2008): 1125–31.
  • Liviac, D., A. Creus, and R. Marcos. “Genotoxicity Analysis of Two Halonitromethanes, a Novel Group of Disinfection By-products (DBPs), in Human Cells Treated in vitro.” Environmental Research 109 (2009): 232–8.
  • Mulder, P.P. J., N.V. S. Ramakrishna, P. Cremonesi, E.G. Rogan, and E.L. Cavalieri. “Synthesis of 1- and 3-fluorobenzo[a]pyrene.” Chemical Research in Toxicology 6 (1993): 657–61.
  • Mirafzal, G.A. and A.M. Lozeva. “Phase Transfer Catalyzed Oxidation of Alcohols with Sodium Hypochlorite.” Tetrahedron Letters 39 (1998): 7263–6.
  • Ogba, N., C.M. Wang, and S. Raychoudhury. “Differential Effects of Fluoranthene and benzo[a]pyrene in MCF-7 cells.” Journal of Environmental Science and Health A 40 (2005): 927–36.
  • Kirsch-Volders, M., G. Plas, A. Elhajouji, M. Lukamowicz, L. Gonzalez, K. Vande Loock, and I. Decordier. “The in vitro MN Assay in 2011: Origin and Fate, Biological Significance, Protocols, High Throughput Methodologies and Toxicological Relevance.” Archives of Toxicology 85 (2011): 873–99.
  • Dipple, A. “Reactions of Polycyclic Aromatic Hydrocarbons with DNA.” IARC Scientific Publications (1994): 107–29.
  • Chen, Y.Y., L.Z. Zhu, and R.B. Zhou. “Characterization and Distribution of Polycyclic Aromatic Hydrocarbon in Surface Water and Sediment from Qiantang River, China”. Journal of Hazardous Materials 141 (2007): 148–55.
  • Deng, H.M., P.A. Peng, W.L. Huang, and H.Z. Song. “Distribution and Loadings of Polycyclic Aromatic Hydrocarbons in the Xijiang River in Guangdong, South China.” Chemosphere 64 (2006): 1401–11.
  • An, T., M. Qiao, G. Li, H. Sun, X. Zeng, and J.Fu. “Distribution, Sources, and Potential Toxicological Significance of PAHs in Drinking Water Sources within the Pearl River Delta.” Journal of Environmental Monitoring 13 (2011): 1457–63.
  • Ma, Y.G., J.P. Cheng, F. Jiao, K.X. Duo, Z. Rong, M. Li, and W.H. Wang. “Distribution, Sources, and Potential Risk of Polycyclic Aromatic Hydrocarbons (PAHs) in Drinking Water Resources from Henan Province in Middle of China.” Environmental Monitoring and Assessment 146 (2008): 127–38.
  • Zhang, D., T. An, M. Qiao, B.G. Loganathan, X. Zeng, G. Sheng, and J.Fu. “Source Identification and Health Risk of Polycyclic Aromatic Hydrocarbons Associated with Electronic Dismantling in Guiyu town, South China.” Journal of Hazardous Materials 192 (2011):1–7.
  • Sun, J.L., H. Zeng, and H.G. Ni. “Halogenated Polycyclic Aromatic Hydrocarbons in the Environment.”.Chemosphere 90 (2013): 1751–9.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.