Evaluation of the OECD QSAR Application Toolbox and Toxtree for estimating the mutagenicity of chemicals. Part 1. Aromatic amines

References

• Worth , AP , Hartung , T and van Leeuwen , CJ . 2004 . The role of the European centre for the validation of alternative methods (ECVAM) in the validation of (Q)SARs . SAR QSAR Environ. Res. , 15 : 345 – 358 .
   PubMed Web of Science ®Google Scholar
• Moudgal , CJ , Young , D , Nichols , T , Martin , T , Harten , P , Venkatapathy , R , Stelma , G , Siddhanti , S , Baier-Anderson , C and Wolfe , M . 2008 . Application of QSARs and VFARs to the rapid risk assessment process at US EPA . SAR QSAR Environ. Res. , 19 : 579 – 587 .
   PubMed Web of Science ®Google Scholar
• Zachary , M and Greeway , GM . 2009 . Comparative PBT screening using (Q)SAR tools within REACH legislation . SAR QSAR Environ. Res. , 20 : 145 – 157 .
   PubMed Web of Science ®Google Scholar
• Gorrod , JW and Manson , D . 1986 . The metabolism of aromatic amines . Xenobiotica , 16 : 933 – 955 .
   PubMed Web of Science ®Google Scholar
• Lai , DY , Woo , YT , Argus , MF and Arcos , JC . 1996 . “ Cancer risk reduction through mechanism-based molecular design of chemical ” . In Designing Safer Chemicals , Edited by: DeVito , SC and Garrett , RL . 62 – 73 . Washington : ACS Symposium Series 640, American Chemical Society .
   Google Scholar
• Rehn , L . 1895 . Blasengeschwuelste bei Fuchsin-Arbeiten . Arch. Klin. Chir. , 50 : 588 – 600 .
   Google Scholar
• Leuenberger , SG . 1912 . Die unter dem Einfluss der synthetischen Farbeindustrie beobachete Geschwulstentwicklung . Beiträge Z. Klin. Chir. , 80 : 208 – 316 .
   Google Scholar
• Vineis , P and Pirastu , R . 1997 . Aromatic amines and cancer . Cancer Causes Control , 8 : 346 – 355 .
   PubMed Web of Science ®Google Scholar
• Bi , W , Hayes , RB , Feng , P , Qi , Y , You , X , Zhen , J , Zhang , M , Qu , B , Fu , Z , Chen , M , Chien , HTC and Blot , WJ . 1992 . Mortality and incidence of bladder cancer in benzidine-exposed workers in China . Am. J. Ind. Med. , 21 : 481 – 489 .
   PubMed Web of Science ®Google Scholar
• Singh , H , Purnell , E and Smith , C . 2007 . Mechanistic study on aniline-induced erythrocyte toxicity . Arch. Hig. Rada Toksikol. , 58 : 275 – 285 .
   PubMedGoogle Scholar
• Hatch , FT and Colvin , ME . 1997 . Quantitative structure-activity (QSAR) relationships of mutagenic aromatic and heterocyclic amines . Mutat. Res. , 376 : 87 – 96 .
   PubMed Web of Science ®Google Scholar
• Klopman , G , Tonucci , DA , Holloway , M and Rosenkranz , HS . 1984 . Relationship between polarographic reduction potential and mutagenicity of nitroaromatics . Mutat. Res. , 126 : 139 – 144 .
   PubMed Web of Science ®Google Scholar
• Compadre , RL , Byrd , C and Compadre , CM . 1998 . “ Comparative QSAR and 3-D-QSAR analysis of the mutagenicity of nitroaromatic compounds ” . In Comparative QSAR , Edited by: Devillers , J . 111 – 136 . Washington : Taylor & Francis .
   Google Scholar
• Basak , SC , Gute , BD and Grunwald , GD . 1999 . Assessment of the mutagenicity of aromatic amines from theoretical structural parameters: A hierarchical approach . SAR QSAR Environ. Res. , 10 : 117 – 129 .
   PubMed Web of Science ®Google Scholar
• Basak , SC and Mills , D . 2001 . Prediction of mutagenicity utilizing a hierarchical QSAR approach . SAR QSAR Environ. Res. , 12 : 491 – 496 .
   Web of Science ®Google Scholar
• Vračko , M . 2006 . QSAR approach in study of mutagenicity of aromatic and heteroaromatic amines . Top. Heterocycl. Chem. , 4 : 85 – 106 .
   Google Scholar
• Benigni , R , Bossa , C , Netzeva , T , Rodomonte , A and Tsakovska , I . 2007 . Mechanistic QSAR of aromatic amines: New models for discriminating between homocyclic mutagens and nonmutagens, and validation of models for carcinogens . Environ. Mol. Mutag. , 48 : 754 – 771 .
   PubMed Web of Science ®Google Scholar
• OECD QSAR Application Toolbox, http://www.oecd.org/document/54/0,3343,en_2649_34379_42923638_1_1_1_1,00.html
   Google Scholar
• Toxtree, http://ecb.jrc.it/qsar/qsar-tools/index.php?c=TOXTREE
   Google Scholar
• Anonymous, The Principles for Establishing the Status of Development and Validation of (Quantitative) Structure-Activity Relationships (Q)SARs, OECD document, ENV/JM/TG(2004)27
   Google Scholar
• R. Benigni, C. Bossa, N. Jeliazkova, T. Netzeva, and A. Worth, The Benigni / Bossa Rulebase for Mutagenicity and Carcinogenicity – A Module of Toxtree, JRC European Commission, Ispra, EUR 23241 EN, 2008
   Google Scholar
• de Flora , S . 1981 . Study of 106 organic and inorganic compounds in the Salmonella/microsome test . Carcinogenesis , 2 : 283 – 298 .
   PubMed Web of Science ®Google Scholar
• de Flora , S , Zanacchi , P , Camoirano , A , Bennicelli , C and Badolati , GS . 1984 . Genotoxic activity and potency of 135 compounds in the Ames reversion test and in a bacterial DNA-repair test . Mutat. Res. , 133 : 161 – 198 .
   PubMed Web of Science ®Google Scholar
• Shahin , MM , Bugaut , A and Kalopissis , G . 1982 . Mutagenic evaluation of the hair-dye component 2,4-diaminophenoxyethanol in Salmonella typhimurium/microsome plate test and Saccharomyces cerevisiae strain D4 and XV185-14C . Mutat. Res. , 102 : 319 – 329 .
   PubMed Web of Science ®Google Scholar
• Shahin , MM . 1985 . “ Dependence of mutagen activity on chemical structure in two series of related amines ” . In Environmental Mutagens and Carcinogens , Edited by: Sugimura , T , Kondo , S and Takebe , H . 379 – 383 . New York : Liss Press .
   Google Scholar
• Haworth , S , Lawlor , T , Mortelmans , K , Speck , W and Zeiger , E . 1983 . Salmonella mutagenicity test results for 250 chemicals . Environ. Mutag. Supl. , 1 : 3 – 142 .
   Google Scholar
• Takahashi , K , Kaiya , T and Kawazoe , Y . 1987 . Structure-mutagenicity relationship among aminoquinolines, aza-analogues of naphthylamine, and their N-acetyl derivatives . Mutat. Res. , 187 : 191 – 197 .
   PubMed Web of Science ®Google Scholar
• André , V , Boissart , C , Sichel , F , Gauduchon , P , Talaër , JY , Le Lancelot , JC , Mercier , C , Chemtob , S and Tallec , A . 1997 . Mutagenicity of nitro- and amino-substituted carbazoles in Salmonella typhimurium. III. Methylated derivatives of 9H-carbazole . Mutat. Res. , 389 : 247 – 260 .
   PubMed Web of Science ®Google Scholar
• Chung , KT , Murdock , CA , Stevens , SE , Li , YS , Wei , CI , Huang , TS and Chou , MW . 1995 . Mutagenicity and toxicity studies of p-phenylenediamine and its derivatives . Toxicol. Lett. , 81 : 23 – 32 .
   PubMed Web of Science ®Google Scholar
• Chung , KT , Kirkovsky , L , Kirkovsky , A and Purcell , WP . 1997 . Review of mutagenicity of monocyclic aromatic amines: Quantitative structure-activity relationships . Mutat. Res. , 387 : 1 – 16 .
   PubMed Web of Science ®Google Scholar
• Chung , KT , Chen , SC and Claxton , LD . 2006 . Review of the Salmonella typhimurium mutagenicity of benzidine, benzidine analogues, and benzidine-based dyes . Mutat. Res. , 612 : 58 – 76 .
   PubMed Web of Science ®Google Scholar
• Haack , T , Erdinger , L and Boche , G . 2001 . Mutagenicity in Salmonella typhimurium TA98 and TA100 of nitroso and respective hydroxylamine compounds . Mutat. Res. , 491 : 183 – 193 .
   PubMed Web of Science ®Google Scholar
• Catterall , FS , Coombs , MM , Ioannides , C , Sepiol , JJ and Wilson , J . 2001 . Mutagenicity of bay-region amino-substituted cyclopenta[a]phenanthrenes and 2- and 5-aminochrysene . Mutat Res. , 492 : 7 – 11 .
   PubMed Web of Science ®Google Scholar
• Heyden , WF . 1998 . Summary of Toxicology Studies with Alachlor , Toxicology Division, Monsanto Company .
   Google Scholar
• Anonymous . 1997 . Public Health Goal for Alachlor in Drinking Water , California EPA, , USA : Pesticide and Environmental Toxicology Section, Office of Environmental Health Hazard Assessment .
   Google Scholar
• Anonymous, Toxicology of Carbetamide, Department for Environment, Food and Rural Affairs, Pesticides Safety Directorate, UK, n° 125, 1995
   Google Scholar
• de Lorenzo , F , Staiano , N , Silengo , L and Cortese , R . 1978 . Mutagenicity of diallate, sulfallate, and triallate and relationship between structure and mutagenic effects of carbamates used widely in agriculture . Cancer Res. , 38 : 13 – 15 .
   PubMed Web of Science ®Google Scholar
• Van Engelen , J . 2009 . Pesticide Residues in Food 2000: Chlorpropham , IPCS, INCHEM .
   Google Scholar
• Anonymous, Evaluation on: Dimefuron, Department for Environment, Food and Rural Affairs, Pesticides Safety Directorate, UK, n° 79, 1993
   Google Scholar
• Anonymous, Evaluation on: Flufenoxuron (2) Use as a Wood Preservative, Department for Environment, Food and Rural Affairs, Pesticides Safety Directorate, UK, n° 180, 1998
   Google Scholar
• Adhikari , N and Grover , IS . 1993 . “ Genotoxic appraisal of pesticides in environment ” . In Advances in Environmental Sciences , Edited by: Tripathi , AK , Srivastava , AK and Pandey , SN . 311 – 323 . New Delhi, , India : Ashish Publishing House .
   Google Scholar
• Moriya , M and Ohta , T . 1981 . NNF-136: Microbial Mutagenicity Study , Tokyo, Japan : Institute of Environmental Toxicology .
   Google Scholar
• I. Dewhurst, Flutolanil, Pesticide Residues in Food, Joint FAO/WHO Meeting on Pesticide Residues, IPCS, INCHEM, 2002
   Google Scholar
• Zhao , Y , Dong , D , Zhao , S , Zhang , L , Ren , L , Yang , X , Xu , Y and Chen , X . 2006 . Detection of mutagenicity of hexaflumuron . J. Zhengzhou Univ. , 41 : 901 – 903 .
   Google Scholar
• Anonymous, Evaluation on: Linuron, Department for Environment, Food and Rural Affairs, Pesticides Safety Directorate, UK, n° 132, 1995
   Google Scholar
• Anonymous, FAO Specifications and Evaluations for Agricultural Pesticides. Lifenuron, Food and Agriculture Organization of the United Nations, 2008
   Google Scholar
• Anonymous, FAO Specifications and Evaluations for Agricultural Pesticides. Metazachlor, Food and Agriculture Organization of the United Nations, 2008
   Google Scholar
• Anonymous, Evaluation on: Monolinuran, Department for Environment, Food and Rural Affairs, Pesticides Safety Directorate, UK, n° 133, 1995
   Google Scholar
• Ryu , JC and Kim , YJ . 2004 . Evaluation of the genetic toxicity of synthetic chemicals (IX). A synthetic selective herbicide, pretilachlor . J. Environ. Toxicol. , 19 : 93 – 100 .
   Google Scholar
• Dearfield , KL , McCarroll , NC , Protzel , A , Stack , HF , Jackson , MA and Waters , MD . 1999 . A survey of EPA/OPP and open literature on selected chemicals. II. Mutagenicity and carcinogenicity of selected chloroacetanilides and related compounds . Mutat. Res. , 443 : 183 – 221 .
   PubMed Web of Science ®Google Scholar
• McMillan , DC , Shaddock , JG , Heflich , RH , Casciano , DA and Hinson , JA . 1988 . Evaluation of propanil and its N-oxidized derivatives for genotoxicity in the Salmonella typhimurium reversion, Chinese hamster ovary/hypoxanthine guanine phosphoribosyl transferase, and rat hepatocyte/DNA repair assays . Fundam. Appl. Toxicol. , 11 : 429 – 439 .
   PubMedGoogle Scholar
• D.C.L. Jones, V.F. Simmon, K.E. Mortelmans, A.D. Mitchell, E.L. Evans, M.M. Jotz, E.S. Riccio, D.E. Robinson, and B.A. Kirkhart, In Vitro and in Vivo Mutagenicity Studies of Environmental Chemicals, EPA-600/S1-84-003, EPA Research Triangle Park, 1984
   Google Scholar
• Kamoshita , M , Kosaka , K , Endo , O , Asami , M and Aizawa , T . 2010 . Mutagenic activities of a chlorination by-product of butamifos, its structural isomer, and their related compounds . Chemosphere , 78 : 482 – 487 .
   PubMed Web of Science ®Google Scholar
• Esancy , JF , Freeman , HS and Claxton , LD . 1990 . The effect of alkoxy substituents on the mutagenicity of some aminoazobenzene dyes and their reductive-cleavage products . Mutat. Res. , 238 : 1 – 22 .
   PubMed Web of Science ®Google Scholar
• Jeong , E , Freeman , HS and Claxton , LD . 2010 . Synthesis and characterization of selected 4,4′-diaminoalkoxyazobenzenes . Dyes Pigments , 87 : 100 – 108 .
   Web of Science ®Google Scholar
• Toxtree User Manual, Ideaconsult, Bulgaria, version of 15 July 2009
   Google Scholar
• Vracko , M , Bandelj , V , Barbieri , P , Benfenati , E , Chaudry , Q , Cronin , M , Devillers , J , Gallegos , A , Gini , G , Gramatica , P , Helma , C , Mazzatorta , P , Neagu , D , Netzeva , T , Pavan , M , Patlewicz , G , Randic , M , Tsakovska , I and Worth , A . 2006 . Validation of counter propagation neural network models for predictive toxicology according to the OECD principles: A case study . SAR QSAR Environ. Res. , 17 : 265 – 384 .
   PubMed Web of Science ®Google Scholar
• Benigni , R and Bossa , C . 2008 . Structure alerts for carcinogenicity, and the Salmonella assay system: A novel insight through the chemical relational databases technology . Mutat. Res. , 659 : 248 – 261 .
   PubMed Web of Science ®Google Scholar
• Devillers , J and Mombelli , E . 2010 . Evaluation of the OECD QSAR application toolbox and toxtree for estimating the mutagenicity of chemicals. Part 2. α, β unsaturated aldehydes . SAR QSAR Environ. Res. , 21 : 771 – 783 .
   PubMed Web of Science ®Google Scholar