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Volumn 22, Issue 1-2, 2011, Pages 89-106

Structural alerts for estimating the carcinogenicity of pesticides and biocides

Author keywords

Biocides; Carcinogenicity; External validation; OECD QSAR Application Toolbox; Pesticides; Structural alerts; Toxtree

Indexed keywords

COMPUTATIONAL CHEMISTRY; FORECASTING;

EID: 79952527126     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/1062936X.2010.548349     Document Type: Article
Times cited : (26)

References (63)
  • 2
    • 84858677046 scopus 로고    scopus 로고
    • Ten iterative steps in development and evaluation of environmental models
    • A.J. Jakeman, L.A. Letcher, and J.P. Norton, Ten iterative steps in development and evaluation of environmental models, Environ. Model. Soft. 21 (2006), pp. 602-614.
    • (2006) Environ. Model. Soft , vol.21 , pp. 602-614
    • Jakeman, A.J.1    Letcher, L.A.2    Norton, J.P.3
  • 3
    • 0028679436 scopus 로고
    • Predicting modes of toxic action from chemical structure: An overview
    • S.P. Bradbury, Predicting modes of toxic action from chemical structure: An overview, SAR QSAR Environ. Res. 2 (1994), pp. 89-104.
    • (1994) SAR QSAR Environ. Res , vol.2 , pp. 89-104
    • Bradbury, S.P.1
  • 4
    • 67949118928 scopus 로고    scopus 로고
    • How not to develop a quantitative structure-activity or structure-property relationship (QSAR/QSPR)
    • J.C. Dearden, M.T.D. Cronin, and K.L.E. Kaiser, How not to develop a quantitative structure-activity or structure-property relationship (QSAR/QSPR), SAR QSAR Environ. Res. 20 (2009), pp. 241-266.
    • (2009) SAR QSAR Environ. Res , vol.20 , pp. 241-266
    • Dearden, J.C.1    Cronin, M.T.D.2    Kaiser, K.L.E.3
  • 6
    • 0342442815 scopus 로고    scopus 로고
    • Environmental chemistry: QSAR
    • P.v.P. Schleyer, N.L. Allinger, T. Clark, J. Gasteiger, P.A. Kollman, H.F. Schaefer, and P.R. Schreiner, eds., John Wiley & Sons, Chichester
    • J. Devillers, Environmental chemistry: QSAR, in The Encyclopedia of Computational Chemistry, Vol. 2, P.v.P. Schleyer, N.L. Allinger, T. Clark, J. Gasteiger, P.A. Kollman, H.F. Schaefer, and P.R. Schreiner, eds., John Wiley & Sons, Chichester, 1998, pp. 930-941.
    • (1998) The Encyclopedia of Computational Chemistry , vol.2 , pp. 930-941
    • Devillers, J.1
  • 7
    • 0038724207 scopus 로고    scopus 로고
    • The importance of being earnest: Validation is the absolute essential for successful application and interpretation of QSPR models
    • A. Tropsha, P. Gramatica, and V.K. Gombar, The importance of being earnest: Validation is the absolute essential for successful application and interpretation of QSPR models, QSAR Comb. Sci. 22 (2003), pp. 69-77.
    • (2003) QSAR Comb. Sci , vol.22 , pp. 69-77
    • Tropsha, A.1    Gramatica, P.2    Gombar, V.K.3
  • 8
    • 8344277344 scopus 로고    scopus 로고
    • Building QSAR models: A practical guide
    • M.T.D. Cronin and D.J. Livingstone, CRC Press, Boca Raton
    • D.J. Livingstone, Building QSAR models: A practical guide, in Predicting Chemical Toxicity and Fate, M.T.D. Cronin and D.J. Livingstone, CRC Press, Boca Raton, 2004, pp. 151-170.
    • (2004) Predicting Chemical Toxicity and Fate , pp. 151-170
    • Livingstone, D.J.1
  • 10
    • 0141462446 scopus 로고    scopus 로고
    • Q SARs: Gatekeepers against risk on chemicals?
    • E.M. Hulzebos and R. Posthumus, (Q)SARs: Gatekeepers against risk on chemicals?, SAR QSAR Environ. Res. 14 (2003), pp. 285-316.
    • (2003) SAR QSAR Environ. Res , vol.14 , pp. 285-316
    • Hulzebos, E.M.1    Posthumus, R.2
  • 11
    • 42149153772 scopus 로고    scopus 로고
    • ECOSAR model performance with a large test set of industrial chemicals
    • P. Reuschenbach, M. Silvani, M. Dammann, D. Warnecke, and T. Knacker, ECOSAR model performance with a large test set of industrial chemicals, Chemosphere 71 (2008), pp. 1986-1995.
    • (2008) Chemosphere , vol.71 , pp. 1986-1995
    • Reuschenbach, P.1    Silvani, M.2    Dammann, M.3    Warnecke, D.4    Knacker, T.5
  • 12
    • 59049091844 scopus 로고    scopus 로고
    • Pharmaceuticals in the environment: Good practice in predicting acute ecotoxicological effects
    • J.C. Madden, S.J. Enoch, M. Hewitt, and M.T.D. Cronin, Pharmaceuticals in the environment: Good practice in predicting acute ecotoxicological effects, Toxicol. Lett. 185 (2009), pp. 85-101.
    • (2009) Toxicol. Lett , vol.185 , pp. 85-101
    • Madden, J.C.1    Enoch, S.J.2    Hewitt, M.3    Cronin, M.T.D.4
  • 14
    • 0033797060 scopus 로고    scopus 로고
    • Predicting ready biodegradability in the Japanese Ministry of International Trade and Industry test
    • J. Tunkel, P.H. Howard, R.S. Boethling, W. Stiteler, and H. Loonen, Predicting ready biodegradability in the Japanese Ministry of International Trade and Industry test, Environ. Toxicol. Chem. 19 (2000), pp. 2478-2485.
    • (2000) Environ. Toxicol. Chem , vol.19 , pp. 2478-2485
    • Tunkel, J.1    Howard, P.H.2    Boethling, R.S.3    Stiteler, W.4    Loonen, H.5
  • 15
    • 77956416097 scopus 로고    scopus 로고
    • Domain of EPI suite biotransformation models
    • R.S. Boethling and J. Costanza, Domain of EPI suite biotransformation models, SAR QSAR Environ. Res. 21 (2010), pp. 415-443.
    • (2010) SAR QSAR Environ. Res , vol.21 , pp. 415-443
    • Boethling, R.S.1    Costanza, J.2
  • 16
    • 0030022676 scopus 로고    scopus 로고
    • On the usefulness and reliabiltity of existing QSBRs for risk assessment and priority setting
    • J.H. Langenberg, W.J.GM. Peijnenburg, and E. Rorije, On the usefulness and reliabiltity of existing QSBRs for risk assessment and priority setting, SAR QSAR Environ. Res. 5 (1996), pp. 1-16.
    • (1996) SAR QSAR Environ. Res , vol.5 , pp. 1-16
    • Langenberg, J.H.1    Peijnenburg, W.J.G.M.2    Rorije, E.3
  • 17
    • 0033103838 scopus 로고    scopus 로고
    • Evaluation and application of models for the prediction of ready biodegradability in the MITI-test
    • E. Rorije, H. Loonen, M. Müller, G Klopman, and W.J.GM. Peijnenburg, Evaluation and application of models for the prediction of ready biodegradability in the MITI-test, Chemosphere 38 (1999), pp. 1409-1417.
    • (1999) Chemosphere , vol.38 , pp. 1409-1417
    • Rorije, E.1    Loonen, H.2    Müller, M.3    Klopman, G.4    Peijnenburg, W.J.G.M.5
  • 20
    • 85195102987 scopus 로고    scopus 로고
    • OECD, software available at
    • OECD QSAR Application Toolbox, software available at http://www.oecd.org/document/54/0,3343,en_2649_34379_42923638_1_1_1_1,00.html
    • QSAR Application Toolbox
  • 21
    • 85195056643 scopus 로고    scopus 로고
    • software available at
    • Toxtree, software available at http://www.ecb.jrc.it/qsar/qsar-tools/index.php?c=TOXTREE
    • Toxtree
  • 22
    • 78649794120 scopus 로고    scopus 로고
    • Evaluation of the OECD QSAR application toolbox and Toxtree for estimating the mutagenicity of chemicals. Part 1. Aromatic amines
    • J. Devillers and E. Mombelli, Evaluation of the OECD QSAR application toolbox and Toxtree for estimating the mutagenicity of chemicals. Part 1. Aromatic amines, SAR QSAR Environ. Res. 21 (2010), pp. 753-769.
    • (2010) SAR QSAR Environ. Res , vol.21 , pp. 753-769
    • Devillers, J.1    Mombelli, E.2
  • 23
    • 37349002009 scopus 로고    scopus 로고
    • Mechanistic QSAR of aromatic amines: New models for discriminating between homocyclic mutagens and nonmutagens, and validation of models for carcinogens
    • R. Benigni, C. Bossa, T. Netzeva, A. Rodomonte, and I. Tsakovska, Mechanistic QSAR of aromatic amines: New models for discriminating between homocyclic mutagens and nonmutagens, and validation of models for carcinogens, Environ. Mol. Mutag. 48 (2007), pp. 754-771.
    • (2007) Environ. Mol. Mutag , vol.48 , pp. 754-771
    • Benigni, R.1    Bossa, C.2    Netzeva, T.3    Rodomonte, A.4    Tsakovska, I.5
  • 24
    • 0242509805 scopus 로고    scopus 로고
    • Structure-activity relationships for the mutagenicity and carcinogenicity of simple and α-ß unsaturated aldehydes
    • R. Benigni, L. Passerini, and A. Rodomonte, Structure-activity relationships for the mutagenicity and carcinogenicity of simple and α-ß unsaturated aldehydes, Environ. Mol. Mutagen. 42 (2003), pp. 136-143.
    • (2003) Environ. Mol. Mutagen , vol.42 , pp. 136-143
    • Benigni, R.1    Passerini, L.2    Rodomonte, A.3
  • 25
    • 30844471959 scopus 로고    scopus 로고
    • Simple and α-ß unsaturated aldehydes: Correct prediction of genotoxic activity through structure-activity relationship models
    • R. Benigni, L. Conti, R. Crebelli, A. Rodomonte, and M.R. Vari, Simple and α-ß unsaturated aldehydes: Correct prediction of genotoxic activity through structure-activity relationship models, Environ. Mol. Mutagen. 46 (2005), pp. 268-280.
    • (2005) Environ. Mol. Mutagen , vol.46 , pp. 268-280
    • Benigni, R.1    Conti, L.2    Crebelli, R.3    Rodomonte, A.4    Vari, M.R.5
  • 26
    • 78649803919 scopus 로고    scopus 로고
    • Evaluation of the OECD QSAR application toolbox and Toxtree for estimating the mutagenicity of chemicals. Part 2. α-ß unsaturated aliphatic aldehydes
    • J. Devillers and E. Mombelli, Evaluation of the OECD QSAR application toolbox and Toxtree for estimating the mutagenicity of chemicals. Part 2. α-ß unsaturated aliphatic aldehydes, SAR QSAR Environ. Res. 21 (2010), pp. 771-783.
    • (2010) SAR QSAR Environ. Res , vol.21 , pp. 771-783
    • Devillers, J.1    Mombelli, E.2
  • 28
    • 49849084348 scopus 로고    scopus 로고
    • Structure alerts for carcinogenicity, and the Salmonella assay system: A novel insight through the chemical relational databases technology
    • R. Benigni and C. Bossa, Structure alerts for carcinogenicity, and the Salmonella assay system: A novel insight through the chemical relational databases technology, Mutat. Res. 659 (2008), pp. 248-261.
    • (2008) Mutat. Res , vol.659 , pp. 248-261
    • Benigni, R.1    Bossa, C.2
  • 29
    • 78649771172 scopus 로고    scopus 로고
    • Evaluation of the OECD (Q)SAR Application Toolbox and Toxtree for predicting and profiling the carcinogenic potential of chemicals
    • E. Mombelli and J. Devillers, Evaluation of the OECD (Q)SAR Application Toolbox and Toxtree for predicting and profiling the carcinogenic potential of chemicals, SAR QSAR Environ. Res. 21 (2010), pp. 731-752.
    • (2010) SAR QSAR Environ. Res , vol.21 , pp. 731-752
    • Mombelli, E.1
  • 31
    • 28944440014 scopus 로고    scopus 로고
    • Prediction of the rodent carcinogenicity of 60 pesticides by the DEREKfW expert system
    • P. Crettaz and R. Benigni, Prediction of the rodent carcinogenicity of 60 pesticides by the DEREKfW expert system, J. Chem. Inf. Model. 45 (2005), pp. 1864-1873.
    • (2005) J. Chem. Inf. Model , vol.45 , pp. 1864-1873
    • Crettaz, P.1    Benigni, R.2
  • 32
    • 0032619762 scopus 로고    scopus 로고
    • Knowledge-based expert systems for toxicity and metabolism prediction: DEREK, StAR and METEOR
    • N. Greene, P.N. Judson, J.J. Langowski, and CA. Marchant, Knowledge-based expert systems for toxicity and metabolism prediction: DEREK, StAR and METEOR, SAR QSAR Environ. Res. 10 (1999), pp. 299-314.
    • (1999) SAR QSAR Environ. Res , vol.10 , pp. 299-314
    • Greene, N.1    Judson, P.N.2    Langowski, J.J.3    Marchant, C.A.4
  • 34
    • 85195047213 scopus 로고    scopus 로고
    • available at
    • EXTONET, available at http://www.extoxnet.orst.edu/
    • EXTONET
  • 38
    • 84874704646 scopus 로고    scopus 로고
    • available at
    • FAO Corporate Document Repository, available at http://www.fao.org/documents/en/docrep.jsp;jsessionid=B12541B6EF0F239157182A33058A0385
    • FAO Corporate Document Repository
  • 42
    • 85195053340 scopus 로고    scopus 로고
    • U.S. Environmental Protection Agency, Washington, DC, 738-F-93-014, 1993, available at
    • U.S. Environmental Protection Agency. R.E.D. Facts: Butylate, Office of Pesticides and Toxic Substances, Washington, DC, 738-F-93-014, 1993, available at http://www.epa.gov/oppsrrd1/REDs/factsheets/0071fact.pdf
    • R.E.D. Facts: Butylate, Office of Pesticides and Toxic Substances
  • 43
    • 0042035954 scopus 로고
    • Carcinogenicity and Pesticides. Principles, Issues, and Relationships
    • American Chemical Society, Washington, DC
    • N.N. Ragsdale and R.E. Menzer, Carcinogenicity and Pesticides. Principles, Issues, and Relationships, ACS Symposium series, Vol. 414, American Chemical Society, Washington, DC, 1989.
    • (1989) ACS Symposium Series , vol.414
    • Ragsdale, N.N.1    Menzer, R.E.2
  • 44
    • 0031677817 scopus 로고    scopus 로고
    • Mode of carcinogenic action of pesticides inducing thyroid follicular cell tumors in rodents
    • P.M. Hurley, R.N. Hill, and R.J. Whiting, Mode of carcinogenic action of pesticides inducing thyroid follicular cell tumors in rodents, Environ. Health Perspect. 106 (1998), pp. 437-445.
    • (1998) Environ. Health Perspect , vol.106 , pp. 437-445
    • Hurley, P.M.1    Hill, R.N.2    Whiting, R.J.3
  • 46
    • 85195093683 scopus 로고
    • Anonymous, Health Canada, E95-03, December 29, available at
    • Anonymous, Triasulfuron, Pest Management Regulatory Agency, Health Canada, E95-03, December 29, 1995, available at http://dsp-psd.pwgsc.gc.ca/Collection/H113-4-95-03E.pdf
    • (1995) Triasulfuron, Pest Management Regulatory Agency
  • 47
    • 0032442832 scopus 로고    scopus 로고
    • Carcinogenicity and co-carcinogenicity studies on propoxur in mouse skin
    • Y. Shukla, S.M. Baqar, and N.K. Mehrotra, Carcinogenicity and co-carcinogenicity studies on propoxur in mouse skin, Food Chem. Toxicol. 36 (1998), pp. 1125-1130.
    • (1998) Food Chem. Toxicol , vol.36 , pp. 1125-1130
    • Shukla, Y.1    Baqar, S.M.2    Mehrotra, N.K.3
  • 50
    • 0033565724 scopus 로고    scopus 로고
    • A survey of EPA/OPP and open literature on selected pesticide chemicals. II. Mutagenicity and carcinogenicity of selected chloroacetanilides and related compounds
    • K.L. Dearfield, N.E. McCarroll, A. Protzel, H.F. Stack, M.A. Jackson, and M.D. Waters, A survey of EPA/OPP and open literature on selected pesticide chemicals. II. Mutagenicity and carcinogenicity of selected chloroacetanilides and related compounds, Mutat. Res. 443 (1999), pp. 183-221.
    • (1999) Mutat. Res , vol.443 , pp. 183-221
    • Dearfield, K.L.1    McCarroll, N.E.2    Protzel, A.3    Stack, H.F.4    Jackson, M.A.5    Waters, M.D.6
  • 51
    • 0004058001 scopus 로고
    • 10th ed., The Royal Society of Chemistry & The British Crop Protection Council, UK
    • C. Tomlin, The Pesticide Manual, 10th ed., The Royal Society of Chemistry & The British Crop Protection Council, UK, 1994.
    • (1994) The Pesticide Manual
    • Tomlin, C.1
  • 52
    • 85195097713 scopus 로고    scopus 로고
    • available at
    • Biocidal Products Directive 98/8/EC, available at http://www.ec.europa.eu/environment/biocides/pdf/98_8_ec_web.pdf#page=48
    • Biocidal Products Directive 98/8/EC
  • 53
    • 85195077202 scopus 로고    scopus 로고
    • Règlement (ce) no 2032/2003 de la commission du 4 novembre 2003 concernant la seconde phase du programme de travail de dix ans visé à l'article 16, paragraphe 2, de la directive 98/8/CE du Parlement Européen et du Conseil concernant la mise sur le marché des produits biocides, et modifiant le règlement (CE) no 1896/2000
    • Règlement (ce) no 2032/2003 de la commission du 4 novembre 2003 concernant la seconde phase du programme de travail de dix ans visé à l'article 16, paragraphe 2, de la directive 98/8/CE du Parlement Européen et du Conseil concernant la mise sur le marché des produits biocides, et modifiant le règlement (CE) no 1896/2000, Journal officiel de l'Union europeenne, 24.11.2003.
    • (2003) Journal Officiel De L'Union Europeenne , vol.24 , pp. 11
  • 55
    • 0033867269 scopus 로고    scopus 로고
    • Nongenotoxic (epigenetic) carcinogens: Pesticides as an example. A critical review
    • V.N. Rakitsky, V.A. Koblyakov, and V.S. Turusov, Nongenotoxic (epigenetic) carcinogens: Pesticides as an example. A critical review, Teratogenesis. Carcinog. Mutagen 20 (2000), pp. 229-240.
    • (2000) Teratogenesis. Carcinog. Mutagen , vol.20 , pp. 229-240
    • Rakitsky, V.N.1    Koblyakov, V.A.2    Turusov, V.S.3
  • 57
    • 85195021491 scopus 로고
    • Mechanisms of chemical carcinogenicity, in Carcinogenicity and Pesticides
    • N.N. Ragsdale and R.E. Menzer, eds., ACS Symposium series, American Chemical Society, Washington, DC
    • W.T. Stott, T.R. Fox, R.H. Reitz, and P.G. Watanabe, Mechanisms of chemical carcinogenicity, in Carcinogenicity and Pesticides. Principles, Issues, and Relationships, N.N. Ragsdale and R.E. Menzer, eds., ACS Symposium series, Vol. 414, American Chemical Society, Washington, DC, 1989, pp. 43-77.
    • (1989) Principles, Issues, and Relationships , vol.414 , pp. 43-77
    • Stott, W.T.1    Fox, T.R.2    Reitz, R.H.3    Watanabe, P.G.4
  • 58
    • 0026802250 scopus 로고
    • Modulation of carcinogenicity in 1,2,3,4-tetrahydro-7,12-dimethylbenz[a]anthra-cene (THDMBA) by fluorine substitution: Crystal structures of the 5- and 6-fluoro regioisomers
    • S.D. Black, P.K. Sharma, J.C. Gallucci, A.C. Blackburn, J.W. Downs, S.J. Rinderle, and D.T. Witiak, Modulation of carcinogenicity in 1,2,3,4-tetrahydro-7,12-dimethylbenz[a]anthra-cene (THDMBA) by fluorine substitution: Crystal structures of the 5- and 6-fluoro regioisomers, Carcinogenesis 13 (1992), pp. 1337-1343.
    • (1992) Carcinogenesis , vol.13 , pp. 1337-1343
    • Black, S.D.1    Sharma, P.K.2    Gallucci, J.C.3    Blackburn, A.C.4    Downs, J.W.5    Rinderle, S.J.6    Witiak, D.T.7
  • 59
    • 0032819702 scopus 로고    scopus 로고
    • Three-dimensional structure of anti-5,6-dimethylchrysene-1,2-dihydrodiol-3,4-epoxide: A diol epoxide with a bay region methyl group
    • C.E. Afshar, A.K. Katz, H.L. Carrell, S. Amin, D. Desai, and J.P. Glusker, Three-dimensional structure of anti-5,6-dimethylchrysene-1,2-dihydrodiol-3,4-epoxide: A diol epoxide with a bay region methyl group, Carcinogenesis 20 (1999), pp. 1549-1554.
    • (1999) Carcinogenesis , vol.20 , pp. 1549-1554
    • Afshar, C.E.1    Katz, A.K.2    Carrell, H.L.3    Amin, S.4    Desai, D.5    Glusker, J.P.6
  • 60
    • 36448990057 scopus 로고    scopus 로고
    • Toxicity study of allelochemical-like pesticides by a combination of 3D-QSAR, docking, Local Binding Energy (LBE) and GRID approaches
    • F. Fratev, E. Lo Piparo, E. Benfenati, and E. Mihaylova, Toxicity study of allelochemical-like pesticides by a combination of 3D-QSAR, docking, Local Binding Energy (LBE) and GRID approaches, SAR QSAR Environ. Res. 18 (2007), pp. 675-692.
    • (2007) SAR QSAR Environ. Res , vol.18 , pp. 675-692
    • Fratev, F.1    Piparo, E.L.2    Benfenati, E.3    Mihaylova, E.4
  • 61
    • 52049085030 scopus 로고    scopus 로고
    • A combination of 3D-QSAR, docking, local binding energy (LBE) and GRID study of the species differences in the carcinogenicity of benzene derivatives chemicals
    • F. Fratev and E. Benfenati, A combination of 3D-QSAR, docking, local binding energy (LBE) and GRID study of the species differences in the carcinogenicity of benzene derivatives chemicals, J. Mol. Graph. Model. 27 (2008), pp. 147-160.
    • (2008) J. Mol. Graph. Model , vol.27 , pp. 147-160
    • Fratev, F.1    Benfenati, E.2
  • 62
    • 0029686995 scopus 로고    scopus 로고
    • Application of structural concepts to evaluate the potential carcinogenicity of natural products
    • H.S. Rosenkranz, M. Liu, A. Cunningham, and G. Klopman, Application of structural concepts to evaluate the potential carcinogenicity of natural products, SAR QSAR Environ. Res. 5 (1996), pp. 79-98.
    • (1996) SAR QSAR Environ. Res , vol.5 , pp. 79-98
    • Rosenkranz, H.S.1    Liu, M.2    Cunningham, A.3    Klopman, G.4
  • 63
    • 0041766208 scopus 로고    scopus 로고
    • In-silico screening of high production volume chemicals for mutagenicity using the MCASE QSAR expert system
    • G. Klopman, S.K. Chakravarti, N. Harris, J. Ivanov, and R.D. Saiakhov, In-silico screening of high production volume chemicals for mutagenicity using the MCASE QSAR expert system, SAR QSAR Environ. Res. 14 (2003), pp. 165-180.
    • (2003) SAR QSAR Environ. Res , vol.14 , pp. 165-180
    • Klopman, G.1    Chakravarti, S.K.2    Harris, N.3    Ivanov, J.4    Saiakhov, R.D.5


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