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Volumn 26, Issue 4, 2015, Pages 301-323

Interspecies quantitative structure–activity–activity relationships (QSAARs) for prediction of acute aquatic toxicity of aromatic amines and phenols

Author keywords

acute aquatic toxicity; applicability; aromatic amines and phenols; interspecies QSAR; QSAAR

Indexed keywords

ALGAE; AMINES; AROMATIZATION; COMPUTATIONAL CHEMISTRY; FISH; MOLECULAR GRAPHICS; MOLECULAR WEIGHT; TOXICITY;

EID: 84928927772     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/1062936X.2015.1032347     Document Type: Article
Times cited : (36)

References (47)
  • 1
    • 0026785215 scopus 로고
    • Classifying environmental pollutants. 1: Structure–activity relationships for prediction of aquatic toxicity
    • H.J.M. Verhaar, C.J. Vanleeuwen, and J.L.M. Hermens, Classifying environmental pollutants. 1: Structure–activity relationships for prediction of aquatic toxicity, Chemosphere 25 (1992), pp. 471–491.
    • (1992) Chemosphere , vol.25 , pp. 471-491
    • Verhaar, H.J.M.1    Vanleeuwen, C.J.2    Hermens, J.L.M.3
  • 2
    • 0025071340 scopus 로고
    • Rules for distinguishing toxicants that cause type-I and type-II narcosis syndromes
    • G.D. Veith and S.J. Broderius, Rules for distinguishing toxicants that cause type-I and type-II narcosis syndromes, Environ. Health Perspect. 87 (1990), pp. 207–211.
    • (1990) Environ. Health Perspect. , vol.87 , pp. 207-211
    • Veith, G.D.1    Broderius, S.J.2
  • 3
    • 79952492543 scopus 로고    scopus 로고
    • Reactivity and aquatic toxicity of aromatic compounds transformable to quinone-type Michael acceptors
    • F. Bajot, M.T.D. Cronin, D.W. Roberts, and T.W. Schultz, Reactivity and aquatic toxicity of aromatic compounds transformable to quinone-type Michael acceptors, SAR QSAR Environ. Res. 22 (2011), pp. 51–65.
    • (2011) SAR QSAR Environ. Res. , vol.22 , pp. 51-65
    • Bajot, F.1    Cronin, M.T.D.2    Roberts, D.W.3    Schultz, T.W.4
  • 4
    • 0036294887 scopus 로고    scopus 로고
    • Interspecies sensitivity in the aquatic toxicity of aromatic amines
    • E.U. Ramos, M.A. Vaal, and J.L.M. Hermens, Interspecies sensitivity in the aquatic toxicity of aromatic amines, Environ. Toxicol. Pharmacol. 11 (2002), pp. 149–158.
    • (2002) Environ. Toxicol. Pharmacol. , vol.11 , pp. 149-158
    • Ramos, E.U.1    Vaal, M.A.2    Hermens, J.L.M.3
  • 5
    • 79961207063 scopus 로고    scopus 로고
    • Toxicity of 58 substituted anilines and phenols to algae Pseudokirchneriella subcapitata and bacteria Vibrio fischeri: Comparison with published data and QSARs
    • V. Aruoja, M. Sihtmäe, H.-C. Dubourguier, and A. Kahru, Toxicity of 58 substituted anilines and phenols to algae Pseudokirchneriella subcapitata and bacteria Vibrio fischeri: Comparison with published data and QSARs, Chemosphere 84 (2011), pp. 1310–1320.
    • (2011) Chemosphere , vol.84 , pp. 1310-1320
    • Aruoja, V.1    Sihtmäe, M.2    Dubourguier, H.-C.3    Kahru, A.4
  • 6
    • 1942453814 scopus 로고    scopus 로고
    • Assessment and modeling of the toxicity of organic chemicals to Chlorella vulgaris: Development of a novel database
    • M.T.D. Cronin, T.I. Netzeva, J.C. Dearden, R. Edwards, and A.D.P. Worgan, Assessment and modeling of the toxicity of organic chemicals to Chlorella vulgaris: Development of a novel database, Chem. Res. Toxicol. 17 (2004), pp. 545–554.
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 545-554
    • Cronin, M.T.D.1    Netzeva, T.I.2    Dearden, J.C.3    Edwards, R.4    Worgan, A.D.P.5
  • 7
    • 84897560487 scopus 로고    scopus 로고
    • Biological read-across: Mechanistically-based species-species and endpoint-endpoint extrapolations
    • Cronin M. T. D., Madden J. C., (eds), Royal Society of Chemistry, Cambridge: Chapter 18
    • M.T.D. Cronin, Biological read-across: Mechanistically-based species-species and endpoint-endpoint extrapolations, in In Silico Toxicology: Principles and Applications, M. T. D. Cronin and J. C. Madden, eds., Royal Society of Chemistry, Cambridge, 2010, Chapter 18, pp. 446–477.
    • (2010) In Silico Toxicology: Principles and Applications , pp. 446-477
    • Cronin, M.T.D.1
  • 8
    • 1442311046 scopus 로고    scopus 로고
    • Quantitative inter-specific chemical activity relationships of pesticides in the aquatic environment
    • P. Tremolada, A. Finizio, S. Villa, C. Gaggi, and M. Vighi, Quantitative inter-specific chemical activity relationships of pesticides in the aquatic environment, Aquat. Toxicol. 67 (2004), pp. 87–103.
    • (2004) Aquat. Toxicol. , vol.67 , pp. 87-103
    • Tremolada, P.1    Finizio, A.2    Villa, S.3    Gaggi, C.4    Vighi, M.5
  • 9
    • 84878140376 scopus 로고    scopus 로고
    • Daphnia and fish toxicity of (benzo)triazoles: Validated QSAR models, and interspecies quantitative activity-activity modelling
    • S. Cassani, S. Kovarich, E. Papa, P.P. Roy, L. van der Wal, and P. Gramatica, Daphnia and fish toxicity of (benzo)triazoles: Validated QSAR models, and interspecies quantitative activity-activity modelling, J. Hazard. Mater. 258 (2013), pp. 50–60.
    • (2013) J. Hazard. Mater. , vol.258 , pp. 50-60
    • Cassani, S.1    Kovarich, S.2    Papa, E.3    Roy, P.P.4    van der Wal, L.5    Gramatica, P.6
  • 10
    • 33646359947 scopus 로고    scopus 로고
    • Interspecies correlation estimates predict protective environmental concentrations
    • S.D. Dyer, D.J. Versteeg, S.E. Belanger, J.G. Chaney, and F.L. Mayer, Interspecies correlation estimates predict protective environmental concentrations, Environ. Sci. Technol. 40 (2006), pp. 3102–3111.
    • (2006) Environ. Sci. Technol. , vol.40 , pp. 3102-3111
    • Dyer, S.D.1    Versteeg, D.J.2    Belanger, S.E.3    Chaney, J.G.4    Mayer, F.L.5
  • 11
    • 84928934686 scopus 로고    scopus 로고
    • The US Environmental Protection Agency, Web-ICE v3.2.1; available at http://www.epa.gov/ceampubl/fchain/webice/.
    • Web-ICE v3.2.1
  • 12
    • 84928923734 scopus 로고    scopus 로고
    • Interspecies correlations for predicting the acute toxicity of xenobiotics
    • Devillers J., (ed), Springer, New York:
    • J. Devillers, P. Pandard, E. Thybaud, and A. Merle, Interspecies correlations for predicting the acute toxicity of xenobiotics, in Ecotoxicology Modeling, J. Devillers, ed., Springer, New York, 2009, pp. 85–115.
    • (2009) Ecotoxicology Modeling , pp. 85-115
    • Devillers, J.1    Pandard, P.2    Thybaud, E.3    Merle, A.4
  • 13
    • 70649105422 scopus 로고    scopus 로고
    • Prediction of acute mammalian toxicity from QSARs and interspecies correlations
    • J. Devillers and H. Devillers, Prediction of acute mammalian toxicity from QSARs and interspecies correlations, SAR QSAR Environ. Res. 20 (2009), pp. 467–500.
    • (2009) SAR QSAR Environ. Res. , vol.20 , pp. 467-500
    • Devillers, J.1    Devillers, H.2
  • 14
    • 33749680786 scopus 로고    scopus 로고
    • Quantitative structure–activity–activity and quantitative structure–activity investigations of human and rodent toxicity
    • I. Lessigiarska, A.P. Worth, T.I. Netzeva, J.C. Dearden, and M.T.D. Cronin, Quantitative structure–activity–activity and quantitative structure–activity investigations of human and rodent toxicity, Chemosphere 65 (2006), pp. 1878–1887.
    • (2006) Chemosphere , vol.65 , pp. 1878-1887
    • Lessigiarska, I.1    Worth, A.P.2    Netzeva, T.I.3    Dearden, J.C.4    Cronin, M.T.D.5
  • 15
    • 34247101873 scopus 로고    scopus 로고
    • Comparative quantitative structure-activity-activity relationships for toxicity to Tetrahymena pyriformis and Pimephales promelas, ATLA
    • I. Kahn, U. Maran, E. Benfenati, T.I. Netzeva, T.W. Schultz, and M.T.D. Cronins, Comparative quantitative structure-activity-activity relationships for toxicity to Tetrahymena pyriformis and Pimephales promelas, ATLA, Altern. Lab. Anim. 35 (2007), pp. 15–24.
    • (2007) Altern. Lab. Anim. , vol.35 , pp. 15-24
    • Kahn, I.1    Maran, U.2    Benfenati, E.3    Netzeva, T.I.4    Schultz, T.W.5    Cronins, M.T.D.6
  • 17
    • 33646836776 scopus 로고    scopus 로고
    • Discriminating toxicant classes by mode of action: 1. (Eco)toxicity profiles
    • M. Nendza and A. Wenzel, Discriminating toxicant classes by mode of action: 1. (Eco)toxicity profiles, Environ. Sci. Pollut. Res. 13 (2006), pp. 192–203.
    • (2006) Environ. Sci. Pollut. Res. , vol.13 , pp. 192-203
    • Nendza, M.1    Wenzel, A.2
  • 18
    • 0035069685 scopus 로고    scopus 로고
    • Discriminating toxicant classes by mode of action: 2. Physico-chemical descriptors
    • M. Nendza and M. Müller, Discriminating toxicant classes by mode of action: 2. Physico-chemical descriptors, Quant. Struct.-Act. Relatsh. 19 (2000), pp. 581–598.
    • (2000) Quant. Struct.-Act. Relatsh , vol.19 , pp. 581-598
    • Nendza, M.1    Müller, M.2
  • 19
    • 85194976299 scopus 로고    scopus 로고
    • Results of eco-toxicity tests data conducted by Ministry of the Environment in Japan, 2014; available at http://www.env.go.jp/chemi/sesaku/02e.pdf.
    • (2014)
  • 24
    • 0023965741 scopus 로고
    • SMILES, A chemical language and information-system.1. Introduction to methodology and encoding rules
    • D. Weininger, SMILES, A chemical language and information-system.1. Introduction to methodology and encoding rules, J. Chem. Inf. Comput. Sci. 28 (1988), pp. 31–36.
    • (1988) J. Chem. Inf. Comput. Sci. , vol.28 , pp. 31-36
    • Weininger, D.1
  • 28
    • 79957609261 scopus 로고    scopus 로고
    • Triclosan: Environmental exposure, toxicity and mechanisms of action
    • A.B. Dann and A. Hontela, Triclosan: Environmental exposure, toxicity and mechanisms of action, J. Appl. Toxicol. 31 (2011), pp. 285–311.
    • (2011) J. Appl. Toxicol. , vol.31 , pp. 285-311
    • Dann, A.B.1    Hontela, A.2
  • 29
    • 0342657075 scopus 로고    scopus 로고
    • Towards the primary target of chloroacetamides – new findings pave the way
    • P. Boger, B. Matthes, and J. Schmalfuss, Towards the primary target of chloroacetamides – new findings pave the way, Pest Manag. Sci. 56 (2000), pp. 497–508.
    • (2000) Pest Manag. Sci. , vol.56 , pp. 497-508
    • Boger, P.1    Matthes, B.2    Schmalfuss, J.3
  • 31
    • 77956404390 scopus 로고    scopus 로고
    • Development of an ecotoxicity QSAR model for the KAshinhou Tool for Ecotoxicity (KATE) system, version
    • A. Furuhama, T. Toida, N. Nishikawa, Y. Aoki, Y. Yoshioka, and H. Shiraishi, Development of an ecotoxicity QSAR model for the KAshinhou Tool for Ecotoxicity (KATE) system, version, SAR QSAR Environ. Res. 21(2010), pp. 403–413.
    • SAR QSAR Environ. Res. , vol.21 , Issue.2010 , pp. 403-413
    • Furuhama, A.1    Toida, T.2    Nishikawa, N.3    Aoki, Y.4    Yoshioka, Y.5    Shiraishi, H.6
  • 33
    • 84863304598 scopus 로고    scopus 로고
    • R Foundation for Statistical Computing, Vienna:
    • R Development Core Team, R: A language and environment for statistical computing, R Foundation for Statistical Computing, Vienna, 2013; available at http://www.R-project.org.
    • (2013) R: A language and environment for statistical computing
  • 34
    • 84869473298 scopus 로고    scopus 로고
    • Development of ecotoxicity QSAR models based on partial charge descriptors for acrylate and related compounds
    • A. Furuhama, Y. Aoki, and H. Shiraishi, Development of ecotoxicity QSAR models based on partial charge descriptors for acrylate and related compounds, SAR QSAR Environ. Res. 23 (2012), pp. 731–749.
    • (2012) SAR QSAR Environ. Res. , vol.23 , pp. 731-749
    • Furuhama, A.1    Aoki, Y.2    Shiraishi, H.3
  • 35
    • 0043132440 scopus 로고    scopus 로고
    • Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs
    • L. Eriksson, J. Jaworska, A.P. Worth, M.T.D. Cronin, R.M. McDowell, and P. Gramatica, Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs, Environ. Health Perspect. 111 (2003), pp. 1361–1375.
    • (2003) Environ. Health Perspect. , vol.111 , pp. 1361-1375
    • Eriksson, L.1    Jaworska, J.2    Worth, A.P.3    Cronin, M.T.D.4    McDowell, R.M.5    Gramatica, P.6
  • 37
    • 27744590591 scopus 로고    scopus 로고
    • QSAR applicability domain estimation by projection of the training set in descriptor space: A review, ATLA
    • J. Jaworska, N. Nikolova-Jeliazkova, and T. Aldenberg, QSAR applicability domain estimation by projection of the training set in descriptor space: A review, ATLA, Altern. Lab. Anim. 33 (2005), pp. 445–459.
    • (2005) Altern. Lab. Anim. , vol.33 , pp. 445-459
    • Jaworska, J.1    Nikolova-Jeliazkova, N.2    Aldenberg, T.3
  • 38
    • 84887612987 scopus 로고    scopus 로고
    • Measurement of baseline toxicity and QSAR analysis of 50 non-polar and 58 polar narcotic chemicals for the alga Pseudokirchneriella subcapitata
    • V. Aruoja, M. Moosus, A. Kahru, M. Sihtmaee, and U. Maran, Measurement of baseline toxicity and QSAR analysis of 50 non-polar and 58 polar narcotic chemicals for the alga Pseudokirchneriella subcapitata, Chemosphere 96 (2014), pp. 23–32.
    • (2014) Chemosphere , vol.96 , pp. 23-32
    • Aruoja, V.1    Moosus, M.2    Kahru, A.3    Sihtmaee, M.4    Maran, U.5
  • 39
    • 3042549719 scopus 로고    scopus 로고
    • Montreal, Canada:
    • Molecular Operating Environment (MOE), 2013.0801, Chemical Computing Group Inc., Montreal, Canada, 2013.
    • (2013) Chemical Computing Group Inc.
  • 40
    • 85194974944 scopus 로고    scopus 로고
    • CIMPL, 2.04, CimplSoft Inc.; available at http://www.cimplsoft.com/.
    • CimplSoft Inc.
  • 41
    • 49149147973 scopus 로고
    • Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges
    • J. Gasteiger and M. Marsili, Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges, Tetrahedron 36 (1980), pp. 3219–3228.
    • (1980) Tetrahedron , vol.36 , pp. 3219-3228
    • Gasteiger, J.1    Marsili, M.2
  • 44
    • 0013650912 scopus 로고    scopus 로고
    • Toronto, Canada: details about the log D prediction module calculation are
    • ACD/LogD, version 2014, Advanced Chemistry Development, Inc., Toronto, Canada; details about the log D prediction module calculation are available at http://www.acdlabs.com/products/percepta/predictors/logd/.
    • Advanced Chemistry Development, Inc.
  • 46
    • 0030981036 scopus 로고    scopus 로고
    • Predicting modes of toxic action from chemical structure: Acute toxicity in the fathead minnow (Pimephales promelas)
    • C.L. Russom, S.P. Bradbury, S.J. Broderius, D.E. Hammermeister, and R.A. Drummond, Predicting modes of toxic action from chemical structure: Acute toxicity in the fathead minnow (Pimephales promelas), Environ. Toxicol. Chem. 16 (1997), pp. 948–967.
    • (1997) Environ. Toxicol. Chem. , vol.16 , pp. 948-967
    • Russom, C.L.1    Bradbury, S.P.2    Broderius, S.J.3    Hammermeister, D.E.4    Drummond, R.A.5
  • 47
    • 85194979940 scopus 로고    scopus 로고
    • The US Environmental Protection Agency, ECOSAR; available at http://www.epa.gov/oppt/newchems/tools/21ecosar.htm.
    • ECOSAR


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