Quantitative structure—activity relationships for the prediction of relative in vitro potencies (REPs) for chloronaphthalenes

References

• Falandysz , J. 2003 . Chloronaphthalenes as food-chain contaminants: A review . Food Addit. Contam. , 20 : 995 – 1014 .
   PubMed Web of Science ®Google Scholar
• Falandysz , J. , Nose , K. , Ishikawa , Y. , Łukaszewicz , E. , Yamashita , N. and Noma , Y . 2006 . Chloronaphthalenes composition of several batches of Halowax 1051 . J. Environ. Sci. & Health. , A41 : 291 – 301 .
   Web of Science ®Google Scholar
• Falandysz , J. , Nose , K. , Ishikawa , Y. , Łukaszewicz , E. , Yamashita , N. and Noma , Y . 2006 . HRGC/HRMS analysis of chloronaphthalenes in several batches of Halowax 1000, 1001, 1013, 1014 and 1099 . J. Environ. Sci. Health. , A41 : 2237 – 2253 .
   Web of Science ®Google Scholar
• Falandysz , J. , Kawano , M. , Ueda , M. , Matsuda , M. , Kannan , K. , Giesy , J. P. and Wakimoto , T. 2000 . Composition of chloronaphthalene congeners in technical chloronaphthalene formulations of the Halowax series . J. Environ. Sci. Health , A35 : 281 – 298 .
   Web of Science ®Google Scholar
• Falandysz , J. and Rappe , C. 1996 . Spatial distribution in plankton and bioaccumulation features of polychlorinated naphthalenes in a pelagic food chain in southern part of the Baltic Proper . Environ. Sci. Technol. , 30 : 3362 – 3370 .
   Web of Science ®Google Scholar
• Noma , Y. , Yamamoto , T. and Sakai , S. I. 2004 . Congener-specific composition of polychlorinated naphthalenes, coplanar PCBs, dibenzo-p-dioxins, and dibenzofurans in the Halowax series . Environ. Sci. Technol. , 38 : 1675 – 1680 .
   PubMed Web of Science ®Google Scholar
• Falandysz , J. 1998 . Polychlorinated naphthalenes: An environmental update . Environ. Pollut. , 101 : 77 – 90 .
   PubMed Web of Science ®Google Scholar
• Falandysz , J. , Taniyasu , S. , Flisak , M. , Swietojanska , A. , Horii , Y. , Hanari , N. and Yamashita , N. 2004 . Highly toxic chlorobiphenyl and by-side impurities content and composition of technical chlorofen formulation . J. Environ. Sci. Health , A39 : 2773 – 2782 .
   Web of Science ®Google Scholar
• Horii , Y. , Kannan , K. , Petrick , G. , Gamo , T. , Falandysz , J. and Yamashita , N. 2005 . Congener-specific carbon isotopic analysis of technical PCB and PCN mixtures using two-dimensional gas chromatography—isotope ratio mass spectrometry . Environ. Sci. Technol. , 39 : 4206 – 4212 .
   PubMed Web of Science ®Google Scholar
• Taniyasu , S. , Falandysz , J. , Swietojanska , A. , Flisak , M. , Horii , Y. , Hanari , N. and Yamashita , N. 2005 . Clophen A60 composition and content of CBs, CNs, CDFs, and CDDs after 2D-HPLC, HRGC/LRMS, and HRGC/HRMS separation and quantification . J. Environ. Sci. Health , A40 : 43 – 61 .
   Web of Science ®Google Scholar
• Yamashita , N. , Taniyasu , S. , Hanari , N. , Horii , Y. and Falandysz , J. 2003 . Polychlorinated naphthalene contamination of some recently manufactured industrial products and commercial goods in Japan . J. Environ. Sci. Health , A38 : 1745 – 1759 .
   Web of Science ®Google Scholar
• Domingo , J. L. , Falcó , J. , Llobert , J. M. , Casas , C. , Teixidó , A. and Müller , L. 2003 . Polychlorinated naphthalenes in foods: Estimated dietary intake by the population of Catalonia, Spain . Environ. Sci. Technol. , 37 : 2332 – 2335 .
   PubMed Web of Science ®Google Scholar
• Horii , Y. , Falandysz , J. , Hanari , N. , Rostkowski , P. , Puzyn , T. , Okada , M. , Amano , K. , Naya , T. , Taniyasu , S. and Yamashita , N. 2004 . Concentrations and fluxes of chloronaphthalenes in sediments from the Lake Kitaura in Japan in recent 15 centuries . J. Environ. Sci. Health. , A39 : 587 – 609 .
   Google Scholar
• Olson , C. 1969 . Bovine hyperkeratosis (X-disease, highly chlorinated naphthalene poisoning). Historical review , Adv. Vet. Sci. Comp. Med. Edited by: B. C. A. and C. O.E. Vol. 13 , 101 – 157 . New York : Academic Press .
   Google Scholar
• Blankenship , A. L. , Kannan , K. , Villalobos , S. A. , Villeneuve , D. L. , Falandysz , J. , Imagawa , T. , Jakobsson , E. and Giesy , J. P. 2000 . Relative potencies of individual polychlorinated naphthalenes and Halowax mixtures to induce Ah receptor-mediated responses . Environ. Sci. Technol. , 34 : 3153 – 3158 .
   Web of Science ®Google Scholar
• Nebert , D. W. and Gelboin , H. V. 1968 . Substrate-inducible microsomal aryl hydroxylase in mamalian cell culture: Assay and properties of induced enzyme . J. Biol. Chem. , 242 : 6242 – 6249 .
   Google Scholar
• Villeneuve , D. L. , Kannan , K. , Khim , J. S. , Falandysz , J. , Nikiforov , V. A. , Blankenship , A. L. and Giesy , J. P. 2000 . Relative potencies of individual polychlorinated naphthalenes to induce dioxin-like responses in fish and mammalian in vitro bioassays . Arch. Environ. Contam. Toxicol. , 39 : 273 – 281 .
   PubMed Web of Science ®Google Scholar
• van Berg der , M. L. , Brinbaum , L. , Bosveld , B. T.C. , Brumström , B. , Cook , P. , Feely , M. , Giesy , J. P. , Hanberg , A. , Hasegawa , R. , Kennedy , S. W. , Kubiak , T. , Larsen , J. C. , van Leeuwen , F. X.R. , Djien Liem , A. K. , Nolt , C. , Peterson , R. E. , Pollinger , L. , Safe , S. , Schrenk , D. , Tillitt , D. , Tysklind , M. , Younes , M. , Waren , F. and Zacharewski , T. 1998 . Toxic Equivalency Factors (TEFs) for PCBs, PCDDs, PCDFs for humans and wildlife . Environ. Health Perspect. , 106 : 775 – 792 .
   PubMed Web of Science ®Google Scholar
• Blankenship , A. L. and Giesy , J. P. 2002 . “ Use of biomarkers of exposure and vertebrate tissue residues in the hazard characterization of PCBs at contaminated sites: Application to birds and mammals ” . In Environmental Analysis of Contaminated Sites: Toxicological Methods and Approaches , Edited by: Sunahra , G. I. , Renoux , A. Y. , Thellen , C. , Gaudet , C. L. and Pilon , A. New York : John Wiley and Sons .
   Google Scholar
• Sanderson , J. T. and Giesy , J. P. 1998 . “ Functional response assays in wildlife toxicology ” . In Encyclopedia of Environmental Analysis and Remediation , Edited by: Meyers , R. A. 5272 – 5297 . New York : Wiley & Sons Inc. .
   Google Scholar
• Hilscherova , K. , Machala , M. , Kannan , K. , Blankenship , A. L. and Giesy , J. P. 2000 . Cell bioassays for detection of aryl hydrocarbon (AhR) and estrogen receptor (ER) mediated activity in environmental samples . Environ. Sci. Pollut. Res. , 7 : 159 – 171 .
   PubMed Web of Science ®Google Scholar
• Aarts , J. M.M.J.G. , Denison , M. S. , De Haan , L. H.J. , Schalk , J. A.C. , Cox , M. A. and Brouwer , A. 1993 . Ah receptor-mediated luciferase expression: a tool for monitoring dioxin-like toxicity . Organohalogen Compd. , 13 : 361 – 364 .
   Google Scholar
• Akerblom , N. , Olsson , K. , Berg , A. H. , Andersson , P. L. , Tysklind , M. , Forlin , L. and Norrgren , L. 2000 . Impact of polychlorinated naphthalenes (PCNs) in juvenile Baltic salmon, Salmo salar: Evaluation of estrogenic effects, development, and CYP1 A induction . Arch. Environ. Contam. Toxicol. , 38 : 225 – 233 .
   PubMed Web of Science ®Google Scholar
• Handberg , A. , Waern , F. , Asplund , L. , Haglund , E. and Safe , S. 1990 . Swedish dioxin survey: determination of 2,3,7,8-TCDD toxic equivalent factors for some chlorinated biphenyls and naphtalenes using biological tests . Chemosphere, , 20 : 1161 – 1164 .
   Google Scholar
• Hayward , D. 1998 . Identification of bioaccumulating polychlorinated naphtalenes and their toxicological significance . Environ. Res. , 76 : 1 – 18 .
   PubMed Web of Science ®Google Scholar
• Pesonen , M. , Teivainen , P. , Lundstrom , J. , Jakobsson , E. and Norrgren , L. 2000 . Biochemical responses of fish sac fry and a primary cell culture of fish hepatocytes exposed to polychlorinated naphthalenes . Arch. Environ. Contam. Toxicol. , 38 : 52 – 58 .
   PubMed Web of Science ®Google Scholar
• Ruzo , L. , Jones , D. , Safe , S. and Hutzinger , O. 1976 . Metabolism of chlorinated naphthalenes . J. Agric. Food Chem. , 24 : 581 – 583 .
   PubMed Web of Science ®Google Scholar
• Ruzo , L. , Safe , S. and Hutzinger , O. 1975 . Hydroxylated metabolites of chloronaphthalenes (Halowax 1031) in pig urine . Chemosphere, , 3 : 121 – 123 .
   Google Scholar
• Villalobos , S. A. , Papoulias , D. M. , Meadows , J. , Blankenship , A. L. , Pastva , S. D. , Kannan , K. , Hinton , D. E. , Tillitt , D. E. and Giesy , J. P. 2000 . Toxic responses of medaka, d-rR strain, to polychlorinated naphthalene mixtures after embryonic exposure by in ovo nanoinjection: A partial life-cycle assessment . Environ. Toxicol. Chem. , 19 : 432 – 440 .
   Web of Science ®Google Scholar
• Falandysz , J. and Puzyn , T. 2004 . Computational prediction of 7-ethoxyresorufin-O-diethylase (EROD) and luciferase (luc) inducing potency for 75 congeners of chloronaphthalene . J. Environ. Sci. Health. , A39 : 1505 – 1523 .
   Google Scholar
• Olivero-Verbel , J. , Vivas-Reyes , R. , Pacheco-Londoño , L. , Johnson-Restrepo , B. and Kannan , K. 2004 . Discriminant analysis for activation of the aryl hydrocarbon receptor by polychlorinated naphthalenes . J. Mol. Struct. (THEOCHEM), , 678 : 157 – 161 .
   Web of Science ®Google Scholar
• Cronin , M. T.D. 2002 . The current status and future applicability of Quantitative Structure – Activity Relationships (QSARs) in predicting toxicology . ATLA , : 81 – 84 . Supplement 2
   Google Scholar
• Jaworska , J. , Nikolova-Jeliazkova , N. and Aldenberg , T. 2005 . QSAR applicability domain estimation by projection of the training set in descriptor space: A review . ATLA, , 33 : 445 – 459 .
   Google Scholar
• Netzeva , T. I. , Worth , A. P. , Aldenberg , T. , Benigni , R. , Cronin , M. T.D. , Gramatica , P. , Jaworska , J. , Kahn , S. , Klopman , G. , Marchant , C. A. , Myatt , G. , Nikolova-Jeliazkova , N. , Patlewicz , G. Y. , Perkins , R. , Roberts , D. W. , Schultz , T. W. , Stanton , D. T. , van de Sandt , J. J.M. , Tong , W. , Veith , G. and Yang , C. 2005 . Current status of methods for defining the applicability domain of (Quantitative) Structure–Activity Relationships . ATLA, , 33 : 1 – 19 .
   Google Scholar
• Frisch , M. J. , Trucks , G. W. , Schlegel , H. B. , Scuseria , G. E. , Robb , M. A. , Cheeseman , J. R. , Montgomery , J. A. , Vreven , T. , Kudin , K. N. , Burant , J. C. , Millam , J. M. , Iyengar , S. S. , Tomasi , J. , Barone , V. , Mennucci , B. , Cossi , M. , Scalmani , G. , Rega , N. , Petersson , G. A. , Nakatsuji , H. , Hada , M. , Ehara , M. , Toyota , K. , Fukuda , R. , Hasegawa , J. , Ishida , M. , Nakajima , Y. , Honda , Y. , Kitao , O. , Nakai , H. , Klene , M. , Li , X. , Knox , J. E. , Hratchian , H. P. , Cross , J. B. , Adamo , C. , Jaramillo , J. , Gomperts , R. , Stratmann , R. E. , Yazyev , O. , Austin , A. J. , Cammi , R. , Pomelli , C. , Ochterski , J. W. , Ayala , P. Y. , Morokuma , K. , Voth , G. A. , Salvador , P. , Dannenberg , J. J. , Zakrzewski , V. G. , Dapprich , S. , Daniels , A. D. , Strain , M. C. , Farkas , O. , Malick , D. K. , Rabuck , A. D. , Raghavachari , K. , Foresman , J. B. , Ortiz , J. V. , Cui , Q. , Baboul , A. G. , Clifford , S. , Cioslowski , J. , Stefanov , B. B. , Liu , G. , Liashenko , A. , Piskorz , P. , Komaromi , I. , Martin , R. L. , Fox , D. J. , Keith , T. , Al-Laham , M. A. , Peng , C. Y. , Nanayakkara , A. , Challacombe , M. , Gill , P. M.W. , Johnson , B. , Chen , W. , Wong , M. W. , Gonzalez , C. and Pople , J. A. 2003 . GAUSSIAN 03 , Pittsburgh : Gaussian Inc. .
   Google Scholar
• Jensen , F. 1999 . Introduction to Computational Chemistry , Chichester : John Wiley & Sons .
   Google Scholar
• Ochterski , J. W. 2000 . Thermochemistry in Gaussian , Gaussian Inc. . http://gaussian.com
   Google Scholar
• Todeschini , R. and Consonni , V. 2000 . Handbook of Molecular Descriptors , Weinheim : Wiley-VCH Verlag .
   Google Scholar
• Todeschini , R. , Consonni , V. , Mauri , A. and Pavan , M. 2003 . DRAGON . Milano Chemometrics ,
   Google Scholar
• Chabanet , C. 2000 . Statistical analysis of sensory profiling data . Graphs for presenting results (PCA and ANOVA). Food Qualit. Perform. , 11 : 159 – 162 .
   Web of Science ®Google Scholar
• Sharaf , M. A. , Illman , D. H. and Kowalski , B. R. 1986 . Chemometrics , John Wiley & Sons Inc. .
   Google Scholar
• StatSoft. STATICTICA (data analysis software system) . 2004 . version 6.1 , StatSoft Inc. . http://www.statsoft.com
   Google Scholar
• Duch , W. , Korbicz , J. , Rutkowski , L. and Tadeusiewicz , R. 2000 . Sieci neuronowe , Akademicka Oficyna Wydawnicza EXIT Warszawa . (in Polish)
   Google Scholar
• Kosiński , R. 2004 . Sztuczne sieci neuronowe , Warszawa : Wydawnictwo Naukowo-Techniczne . (in Polish)
   Google Scholar
• Holland , J. H. 1992 . Adaptiation in natural and atrificials systems , MIT Press .
   Google Scholar
• Behnish , P. A. , Hosoe , K. and Sakai , S. 2001 . Bioanalytical screening methods for dioxins and dioxin-like compounds—A review of bioassay/biomarker technology . Environ. Internat. , 27 : 413 – 439 .
   PubMed Web of Science ®Google Scholar
• Petrulis , J. R. and Bunce , N. J. 1999 . Competitive inhibition by inducer as a confounding factor in the use of the etoxyresorufin-O-deethylase (EROD) assay to estimate exposure to dioxin-like compounds . Toxicol. Lett. , 105 : 251 – 260 .
   PubMed Web of Science ®Google Scholar
• Campbell , M. A. , Bandiera , S. , Robertson , L. , Parkinson , A. and Safe , S. 1981 . Octachloronaphtalene induction of hepatic microsomal aryl hydrocarbon hydroxylase activity in the immature male rat . Toxicology , 22 : 123 – 132 .
   PubMed Web of Science ®Google Scholar
• Villeneuve , D. L. , Khim , J. S. , Kannan , K. , Falandysz , J. , Nikiforov , V. A. , Blankenship , A. and Giesy , J. 2000 . Relative potencies of individual polychlorinated naphthalenes to induce dioxin-like responses in fish and mammalian in vitro bioassays . Organohalogen Compd. , 47 : 5 – 8 .
   Google Scholar