메뉴 건너뛰기




Volumn 48, Issue 9, 2007, Pages 754-771

Mechanistic QSAR of aromatic amines: New models for discriminating between homocyclic mutagens and nonmutagens, and validation of models for carcinogens

Author keywords

Aromatic amines; Cancer; Genotoxicity; In silico; Risk assessment; Structure activity

Indexed keywords

1 AMINO 2 METHYLNAPHTHALENE; 1 AMINOANTHRACENE; 1 AMINOCARBAZOLE; 1 AMINOFLUORANTHENE; 1 AMINOFLUORENE; 1 AMINOPHENANTHRENE; 1 AMINOPHENAZINE; 1 AMINOPYRENE; 1 NAPHTHYLAMINE; 1,7 DIAMINOPHENAZINE; 1,9 DIAMINOPHENAZINE; 2 AMINO 1 METHYLNAPHTHALENE; 2,2' DIAMINOBIPHENYL; 2,3 DIMETHYLANILINE; 2,4 DIAMINO N BUTYLBENZENE; 2,4 DIFLUOROANILINE; 2,4 DIMETHYLANILINE; 2,4 DINITROANILINE; 2,4' DIAMINODIPHENYL; 2,4,5 TRIMETHYLANILINE; 2,5 DIMETHYLANILINE; 2,6 CHLORO 1,4 PHENYLENEDIAMINE; 2,7 DIAMINOFLUORENE; 2,7 DIAMINOPHENAZINE; 4 ISOPROPYL 1,3 BENZENEDIAMINE; 4 NITRO 1 NAPHTHYLAMINE; AROMATIC AMINE; CARCINOGEN; MUTAGENIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 37349002009     PISSN: 08936692     EISSN: 10982280     Source Type: Journal    
DOI: 10.1002/em.20355     Document Type: Article
Times cited : (73)

References (41)
  • 2
    • 0000037422 scopus 로고
    • Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons
    • Cooper CS, Grover PL, editors, Berlin: Springer Verlag. pp
    • Beland FA, Kadlubar FF. 1990. Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. In: Cooper CS, Grover PL, editors. Chemical Carcinogenesis and Mutagenesis I. Berlin: Springer Verlag. pp 265-325.
    • (1990) Chemical Carcinogenesis and Mutagenesis I , pp. 265-325
    • Beland, F.A.1    Kadlubar, F.F.2
  • 3
    • 20044383057 scopus 로고    scopus 로고
    • Structure-activity relationship studies of chemical mutagens and carcinogens: Mechanistic investigations and prediction approaches
    • Benigni, R. 2005. Structure-activity relationship studies of chemical mutagens and carcinogens: Mechanistic investigations and prediction approaches. Chem Rev 105:1767-1800.
    • (2005) Chem Rev , vol.105 , pp. 1767-1800
    • Benigni, R.1
  • 4
    • 33749859175 scopus 로고    scopus 로고
    • Structure-activity models of chemical carcinogens: State of the art, and new directions
    • Benigni R, Bossa C. 2006. Structure-activity models of chemical carcinogens: State of the art, and new directions. Ann Ist Super Sanità 42:118-126.
    • (2006) Ann Ist Super Sanità , vol.42 , pp. 118-126
    • Benigni, R.1    Bossa, C.2
  • 5
    • 0028079977 scopus 로고
    • QSAR models for both mutagenic potency and activity: Application to nitroarenes and aromatic amines
    • Benigni R, Andreoli C, Giuliani A. 1994. QSAR models for both mutagenic potency and activity: Application to nitroarenes and aromatic amines. Environ Mol Mutagen 24:208-219.
    • (1994) Environ Mol Mutagen , vol.24 , pp. 208-219
    • Benigni, R.1    Andreoli, C.2    Giuliani, A.3
  • 6
    • 0031904573 scopus 로고    scopus 로고
    • QSAR models for discriminating between mutagenic and nonmutagenic aromatic and heteroaromatic amines
    • Benigni R, Passerini L, Gallo G, Giorgi F, Cotta-Ramusino M. 1998. QSAR models for discriminating between mutagenic and nonmutagenic aromatic and heteroaromatic amines. Environ Mol Mutagen 32:75-83.
    • (1998) Environ Mol Mutagen , vol.32 , pp. 75-83
    • Benigni, R.1    Passerini, L.2    Gallo, G.3    Giorgi, F.4    Cotta-Ramusino, M.5
  • 7
    • 0034301460 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships of mutagenic and carcinogenic aromatic amines
    • Benigni R, Giuliani A, Franke R, Gruska A. 2000. Quantitative structure-activity relationships of mutagenic and carcinogenic aromatic amines. Chem Rev 100:3697-3714.
    • (2000) Chem Rev , vol.100 , pp. 3697-3714
    • Benigni, R.1    Giuliani, A.2    Franke, R.3    Gruska, A.4
  • 10
    • 0030841105 scopus 로고    scopus 로고
    • Review of mutagenicity of monocyclic aromatic amines: Quantitative structure-activity relations
    • Chung K-T, Kirkovsky L, Kirkovsky A, Purcell WP. 1997. Review of mutagenicity of monocyclic aromatic amines: Quantitative structure-activity relations. Mutat Res 387:1-16.
    • (1997) Mutat Res , vol.387 , pp. 1-16
    • Chung, K.-T.1    Kirkovsky, L.2    Kirkovsky, A.3    Purcell, W.P.4
  • 11
    • 0032565512 scopus 로고    scopus 로고
    • Chemical and biological factors affecting mutagen potency
    • Colvin ME, Hatch FT, Felton JS. 1998. Chemical and biological factors affecting mutagen potency. Mutat Res 400:479-492.
    • (1998) Mutat Res , vol.400 , pp. 479-492
    • Colvin, M.E.1    Hatch, F.T.2    Felton, J.S.3
  • 12
    • 0023261761 scopus 로고
    • The effect of biotransformation of 2,4-dinitrotoluene on its mutagenic potential
    • Couch DB, Abernethy DJ, Allen PF. 1987. The effect of biotransformation of 2,4-dinitrotoluene on its mutagenic potential. Mutag 2:415-418.
    • (1987) Mutag , vol.2 , pp. 415-418
    • Couch, D.B.1    Abernethy, D.J.2    Allen, P.F.3
  • 13
    • 0026516590 scopus 로고
    • A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test, Part 1: Mutagenicity of aromatic and heteroaromatic amines in Salmonella typhimurium TA98 and TA100
    • Debnath AK, Debnath G, Shusterman AJ, Hansch C. 1992. A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test, Part 1: Mutagenicity of aromatic and heteroaromatic amines in Salmonella typhimurium TA98 and TA100. Environ Mol Mutagen 19:37-52.
    • (1992) Environ Mol Mutagen , vol.19 , pp. 37-52
    • Debnath, A.K.1    Debnath, G.2    Shusterman, A.J.3    Hansch, C.4
  • 14
    • 0027008363 scopus 로고
    • Toxicology and hazard potential of trifluralin
    • Ebert E, Leist KH, Ehling G. 1992. Toxicology and hazard potential of trifluralin. Food Chem Toxicol 30:1031-1044.
    • (1992) Food Chem Toxicol , vol.30 , pp. 1031-1044
    • Ebert, E.1    Leist, K.H.2    Ehling, G.3
  • 15
  • 16
    • 0034807089 scopus 로고    scopus 로고
    • Prediction of rodent carcinogenicity of aromatic amines: A quantitative structure-activity relationships model
    • Franke R, Gruska A, Giuliani A, Benigni R. 2001. Prediction of rodent carcinogenicity of aromatic amines: A quantitative structure-activity relationships model. Carcinogenesis 22:1561-1571.
    • (2001) Carcinogenesis , vol.22 , pp. 1561-1571
    • Franke, R.1    Gruska, A.2    Giuliani, A.3    Benigni, R.4
  • 17
    • 0023267180 scopus 로고
    • Mutagenicity of selected aniline derivatives to Salmonella following plant activation and mammalian hepatic activation
    • Gentile JM, Gentile GJ, Plewa MJ. 1987. Mutagenicity of selected aniline derivatives to Salmonella following plant activation and mammalian hepatic activation. Mutat Res 188:185-196.
    • (1987) Mutat Res , vol.188 , pp. 185-196
    • Gentile, J.M.1    Gentile, G.J.2    Plewa, M.J.3
  • 18
    • 0035889635 scopus 로고    scopus 로고
    • Transformation of mutagenic aromatic amines into non-mutagenic species by alkyl substituents. I. Alkylation ortho to the amino function
    • Glende C, Schmitt H, Erdinger L, Engelhardt G, Boche G. 2001. Transformation of mutagenic aromatic amines into non-mutagenic species by alkyl substituents. I. Alkylation ortho to the amino function. Mutat Res 498:19-37.
    • (2001) Mutat Res , vol.498 , pp. 19-37
    • Glende, C.1    Schmitt, H.2    Erdinger, L.3    Engelhardt, G.4    Boche, G.5
  • 19
    • 0037170698 scopus 로고    scopus 로고
    • Transformation of mutagenic aromatic amines into non-mutagenic species by alkyl substituents. II. Alkylation far away from the amino function
    • Glende C, Klein M, Schmitt H, Erdinger L, Boche G. 2002. Transformation of mutagenic aromatic amines into non-mutagenic species by alkyl substituents. II. Alkylation far away from the amino function. Mutat Res 515:15-38.
    • (2002) Mutat Res , vol.515 , pp. 15-38
    • Glende, C.1    Klein, M.2    Schmitt, H.3    Erdinger, L.4    Boche, G.5
  • 20
    • 0033173147 scopus 로고    scopus 로고
    • Supplement to the Carcinogenic Potency Database (CPDB): Results of animal bioassays published in the general literature in 1993 to 1994 and by the National Toxicology Program in 1995 to 1996
    • Gold LS, Manley NB, Slone TH, Rohrbach L. 1999. Supplement to the Carcinogenic Potency Database (CPDB): Results of animal bioassays published in the general literature in 1993 to 1994 and by the National Toxicology Program in 1995 to 1996. Environ Health PerspectSuppl 107 (Suppl 4):527-600.
    • (1999) Environ Health PerspectSuppl , vol.107 , Issue.SUPPL. 4 , pp. 527-600
    • Gold, L.S.1    Manley, N.B.2    Slone, T.H.3    Rohrbach, L.4
  • 23
    • 0036516054 scopus 로고    scopus 로고
    • Chembioinformatics: Comparative QSAR at the interface between chemistry and biology
    • Hansch C, Hoekman D, Leo A, Weininger D, Selassie CD. 2002. Chembioinformatics: Comparative QSAR at the interface between chemistry and biology. Chem Rev 102:783-812.
    • (2002) Chem Rev , vol.102 , pp. 783-812
    • Hansch, C.1    Hoekman, D.2    Leo, A.3    Weininger, D.4    Selassie, C.D.5
  • 24
    • 0030914841 scopus 로고    scopus 로고
    • Quantitative structure-activity (QSAR) relationships of mutagenic aromatic and heterocyclic amines
    • Hatch FT, Colvin ME. 1997. Quantitative structure-activity (QSAR) relationships of mutagenic aromatic and heterocyclic amines. Mutat Res 376:87-96.
    • (1997) Mutat Res , vol.376 , pp. 87-96
    • Hatch, F.T.1    Colvin, M.E.2
  • 25
    • 0035687627 scopus 로고    scopus 로고
    • Extended quantitative structure-activity relationships for 80 aromatic and heterocyclic amines: Structural, electronic, and hydropathic factors affecting mutagenic potency
    • Hatch FT, Knize MG, Colvin ME. 2001. Extended quantitative structure-activity relationships for 80 aromatic and heterocyclic amines: Structural, electronic, and hydropathic factors affecting mutagenic potency. Environ Mol Mutagen 38:268-291.
    • (2001) Environ Mol Mutagen , vol.38 , pp. 268-291
    • Hatch, F.T.1    Knize, M.G.2    Colvin, M.E.3
  • 26
    • 0022267040 scopus 로고
    • Chemical properties of ultimate carcinogenic metabolites of arylamines and arylamides
    • Harvey RG, editor, Washington, D.C, American Chemical Society. pp
    • Kadlubar FF, Beland FA. 1985. Chemical properties of ultimate carcinogenic metabolites of arylamines and arylamides. In: Harvey RG, editor. Polyciclic Hydrocarbons and Carcinogenesis. Washington, D.C.: American Chemical Society. pp 341-370.
    • (1985) Polyciclic Hydrocarbons and Carcinogenesis , pp. 341-370
    • Kadlubar, F.F.1    Beland, F.A.2
  • 27
    • 0002844452 scopus 로고
    • The role of ctochrome P-450 in the metabolism of chemical carcinogens
    • Guengerich FP, editor, Boca Raton: CRC Press. pp
    • Kadlubar FF, Hammons GJ. 1987. The role of ctochrome P-450 in the metabolism of chemical carcinogens. In: Guengerich FP, editor. Mammalian Cytochromes P-450, vol. II. Boca Raton: CRC Press. pp 81-130.
    • (1987) Mammalian Cytochromes P-450 , vol.2 , pp. 81-130
    • Kadlubar, F.F.1    Hammons, G.J.2
  • 28
    • 33644607911 scopus 로고    scopus 로고
    • A QSAR for the mutagenic potency of twelve 2-amino-trimethylimidazopyridine isomers: Structural, quantum-chemical, and hydropathic factors
    • Knize MG, Hatch FT, Tanga MJ, Lau EY, Colvin ME. 2006. A QSAR for the mutagenic potency of twelve 2-amino-trimethylimidazopyridine isomers: Structural, quantum-chemical, and hydropathic factors. Environ Mol Mutagen 47:132-146.
    • (2006) Environ Mol Mutagen , vol.47 , pp. 132-146
    • Knize, M.G.1    Hatch, F.T.2    Tanga, M.J.3    Lau, E.Y.4    Colvin, M.E.5
  • 29
    • 0002082587 scopus 로고    scopus 로고
    • Cancer risk reduction through mechanism-based molecular design of chemicals
    • DeVito SC, Garrett RL, editors, Washington, D.C, American Chemical Society. pp
    • Lai DY, Woo YT, Argus MF, Arcos JC. 1996. Cancer risk reduction through mechanism-based molecular design of chemicals. In: DeVito SC, Garrett RL, editors. Designing Safer Chemicals. Green Chemistry for Pollution Prevention. Washington, D.C.: American Chemical Society. pp 1-13.
    • (1996) Designing Safer Chemicals. Green Chemistry for Pollution Prevention , pp. 1-13
    • Lai, D.Y.1    Woo, Y.T.2    Argus, M.F.3    Arcos, J.C.4
  • 30
    • 37349011135 scopus 로고    scopus 로고
    • OECD. Report on the Regulatory Uses and Applications in OECD Member Countries of (Quantitative) Structure-Activity Relationship [(Q)SAR] Models in the Assessment of New and Existing Chemicals. 58. Paris: Organisation of Economic Cooperation and Development. 2006. OECD Series on Testing and Assessment.
    • OECD. Report on the Regulatory Uses and Applications in OECD Member Countries of (Quantitative) Structure-Activity Relationship [(Q)SAR] Models in the Assessment of New and Existing Chemicals. 58. Paris: Organisation of Economic Cooperation and Development. 2006. OECD Series on Testing and Assessment.
  • 31
    • 0022516588 scopus 로고
    • Mutagenicity testing of selected analgesics in Ames Salmonella strains
    • Oldham JW, Preston RF, Paulson JD. 1986. Mutagenicity testing of selected analgesics in Ames Salmonella strains. J Appl Toxicol 6:237-243.
    • (1986) J Appl Toxicol , vol.6 , pp. 237-243
    • Oldham, J.W.1    Preston, R.F.2    Paulson, J.D.3
  • 32
    • 0031657862 scopus 로고    scopus 로고
    • Carcinogenic heterocyclic amines in model system and cooked foods: A review on formation, occorrence and intake
    • Skog KI, Johansson MA, Jagerstad MI. 1998. Carcinogenic heterocyclic amines in model system and cooked foods: A review on formation, occorrence and intake. Food Chem Toxicol 36:879-896.
    • (1998) Food Chem Toxicol , vol.36 , pp. 879-896
    • Skog, K.I.1    Johansson, M.A.2    Jagerstad, M.I.3
  • 33
    • 0030981184 scopus 로고    scopus 로고
    • Overview of carcinogenic heterocyclic amines
    • Sugimura T. 1997. Overview of carcinogenic heterocyclic amines. Mutat Res 376:211-219.
    • (1997) Mutat Res , vol.376 , pp. 211-219
    • Sugimura, T.1
  • 34
    • 0021883903 scopus 로고
    • Mutagenicity of N-acetyl and N,N′-diacetyl derivatives of 3 aromatic amines used as epoxy-resin hardeners
    • Tanaka K, Ino T, Sawahata T, Marui S, Igaki H, Yashima H. 1985. Mutagenicity of N-acetyl and N,N′-diacetyl derivatives of 3 aromatic amines used as epoxy-resin hardeners. Mutat Res 143:11-15.
    • (1985) Mutat Res , vol.143 , pp. 11-15
    • Tanaka, K.1    Ino, T.2    Sawahata, T.3    Marui, S.4    Igaki, H.5    Yashima, H.6
  • 37
    • 0006022855 scopus 로고    scopus 로고
    • Aromatic amino and nitro-amino compounds and their halogenated derivatives
    • Bingham E, Cohrssen B, Powell CH, editors, New York: Wiley. pp
    • Woo YT, Lai DY. 2001. Aromatic amino and nitro-amino compounds and their halogenated derivatives. In: Bingham E, Cohrssen B, Powell CH, editors. Patty's Toxicology. New York: Wiley. pp 969-1105.
    • (2001) Patty's Toxicology , pp. 969-1105
    • Woo, Y.T.1    Lai, D.Y.2
  • 38
    • 0024467886 scopus 로고
    • Genotoxicity and effects on rat liver drug-metabolizing enzymes by possible substitutes for 4,4′-methylene bis(2-chloroaniline)
    • Wu K, Bonin AM, Leslie CL, Baker RSU, Stacey NH. 1989. Genotoxicity and effects on rat liver drug-metabolizing enzymes by possible substitutes for 4,4′-methylene bis(2-chloroaniline). Carcinogenesis 10:2119-2122.
    • (1989) Carcinogenesis , vol.10 , pp. 2119-2122
    • Wu, K.1    Bonin, A.M.2    Leslie, C.L.3    Baker, R.S.U.4    Stacey, N.H.5
  • 39
    • 33646844277 scopus 로고    scopus 로고
    • The art of data mining the minefields of toxicity databases to link chemistry to biology
    • Yang C, Richard AM, Cross KP. 2006. The art of data mining the minefields of toxicity databases to link chemistry to biology. Curr Comput Aid Drug Design 2:135-150.
    • (2006) Curr Comput Aid Drug Design , vol.2 , pp. 135-150
    • Yang, C.1    Richard, A.M.2    Cross, K.P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.