메뉴 건너뛰기




Volumn 15, Issue 12, 2002, Pages 1495-1503

Correlations of nitrenium ion selectivities with quantitative mutagenicity and carcinogenicity of the corresponding amines

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE; AZIDE; HETEROCYCLIC AMINE; SOLVENT;

EID: 0036913640     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx025584s     Document Type: Article
Times cited : (30)

References (45)
  • 1
    • 0034301460 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships of mutagenic and carcinogenic aromatic amines
    • Benigni, R., Giuliani, A., Franke, R., and 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
  • 2
    • 0032565512 scopus 로고    scopus 로고
    • Chemical and biological factors affecting mutagen potency
    • Colvin, M. E., Hatch, F. T., and Felton, J. S. (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
  • 3
    • 0030841105 scopus 로고    scopus 로고
    • Review of the mutagenicity of monocyclic aromatic amines: Quantitative structure-activity relationships
    • Chung, K.-T., Kirkovsky, L., Kirkovsky, A., and Purcell, W. P. (1997) Review of the mutagenicity of monocyclic aromatic amines: Quantitative structure-activity relationships. 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
  • 4
    • 0026516590 scopus 로고
    • A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test: I. Mutagenicity of aromatic and heterocyclic amines in Salmonella typhimurium TA 98 and TA 100
    • Debnath, A. K., Debnath, G., Shusterman, A. J., and Hansch, C. (1992) A QSAR investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test: I. Mutagenicity of aromatic and heterocyclic amines in Salmonella typhimurium TA 98 and TA 100. 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
  • 5
    • 0026022636 scopus 로고
    • Quantitative structure-activity relationships of heterocyclic amine mutagens formed during the cooking of foods
    • Hatch, F. T., Knize, M. G., and Felton, J. S. (1991) Quantitative structure-activity relationships of heterocyclic amine mutagens formed during the cooking of foods. Environ. Mol. Mutagen. 17, 4-19.
    • (1991) Environ. Mol. Mutagen. , vol.17 , pp. 4-19
    • Hatch, F.T.1    Knize, M.G.2    Felton, J.S.3
  • 6
    • 0030017378 scopus 로고    scopus 로고
    • Structural and quantum chemical factors affecting mutagenic potency of aminoimidazoazaarenes
    • Hatch, F. T., Colvin, M. E., and Seidl, E. T. (1996) Structural and quantum chemical factors affecting mutagenic potency of aminoimidazoazaarenes. Environ. Mol. Mutagen. 27, 314-330.
    • (1996) Environ. Mol. Mutagen. , vol.27 , pp. 314-330
    • Hatch, F.T.1    Colvin, M.E.2    Seidl, E.T.3
  • 7
    • 0030914841 scopus 로고    scopus 로고
    • Quantitative structure-activity (QSAR) relationships of mutagenic aromatic and heterocyclic amines
    • Hatch, F. T., and Colvin, M. E. (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
  • 8
    • 0035687627 scopus 로고    scopus 로고
    • Extended quantitative structure-activity relationships for 80 aromatic and heterocyclic amines: Structural, electronic, and hydropathic factors affecting mutagen potency
    • Hatch, F. T., Knize, M. G., and Colvin, M. E. (2001) Extended quantitative structure-activity relationships for 80 aromatic and heterocyclic amines: Structural, electronic, and hydropathic factors affecting mutagen 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
  • 9
    • 0033043476 scopus 로고    scopus 로고
    • A comprehensive QSAR treatment of the genotoxicity of heteroaromatic and aromatic amines
    • Maran, U., Karelson, M., and Katritzky, A. R. (1999) A comprehensive QSAR treatment of the genotoxicity of heteroaromatic and aromatic amines. Quant. Struct.-Act. Relat. 18, 3-10.
    • (1999) Quant. Struct.-Act. Relat. , vol.18 , pp. 3-10
    • Maran, U.1    Karelson, M.2    Katritzky, A.R.3
  • 10
    • 0026584188 scopus 로고
    • Relative stabilities of nitrenium ions derived from polycyclic aromatic amines: Relationship to mutagenicity
    • Ford, G. P., and Herman, P. S. (1992) Relative stabilities of nitrenium ions derived from polycyclic aromatic amines: Relationship to mutagenicity. Chem.-Biol. Interact. 81, 1-18.
    • (1992) Chem.-Biol. Interact. , vol.81 , pp. 1-18
    • Ford, G.P.1    Herman, P.S.2
  • 11
    • 0026512204 scopus 로고
    • Relative stabilities of nitrenium ions derived from heterocyclic amine food carcinogens: Relationship to mutagenicity
    • Ford, G. P., and Griffin, G. R. (1992) Relative stabilities of nitrenium ions derived from heterocyclic amine food carcinogens: Relationship to mutagenicity. Chem. Biol. Interact. 81, 19-33.
    • (1992) Chem. Biol. Interact. , vol.81 , pp. 19-33
    • Ford, G.P.1    Griffin, G.R.2
  • 12
    • 0026521971 scopus 로고
    • Quantitative structure-activity relationships of mutagenic aromatic and heteroaromatic azides and amines
    • Sabbioni, G., and Wild, P. (1992) Quantitative structure-activity relationships of mutagenic aromatic and heteroaromatic azides and amines. Carcinogenesis 13, 709-713.
    • (1992) Carcinogenesis , vol.13 , pp. 709-713
    • Sabbioni, G.1    Wild, P.2
  • 13
    • 0026647386 scopus 로고
    • Quantitative correlation of mutagenic and carcinogenic potencies for heterocyclic amines from cooked foods and additional aromatic amines
    • Hatch, F. T., Knize, M. G., Moore, D. H., II, and Felton, J. S. (1992) Quantitative correlation of mutagenic and carcinogenic potencies for heterocyclic amines from cooked foods and additional aromatic amines. Mutat. Res. 271, 269-287.
    • (1992) Mutat. Res. , vol.271 , pp. 269-287
    • Hatch, F.T.1    Knize, M.G.2    Moore D.H. II3    Felton, J.S.4
  • 14
    • 0000037422 scopus 로고
    • Metabolic activation and DNA-adducts of aromatic amines and nitroaromatic hydrocarbons
    • Cooper, C. S., and Grover, P. L., Eds., Springer-Verlag, Berlin
    • Beland, F. A., and Kadlubar, F. F. (1990) Metabolic activation and DNA-adducts of aromatic amines and nitroaromatic hydrocarbons. In Handbook of Experimental Pharmacology (Cooper, C. S., and Grover, P. L., Eds.) Vol. 94/1, pp 267-325, Springer-Verlag, Berlin.
    • (1990) Handbook of Experimental Pharmacology , vol.94 , Issue.1 , pp. 267-325
    • Beland, F.A.1    Kadlubar, F.F.2
  • 16
    • 84954615220 scopus 로고
    • Selective trapping of N-acetyl-N-(4-biphenylyl)-nitrenium and N-acetyl-N-(2-fluorenyl)-nitrenium ions by 2′-deoxyguanosine in aqueous solution
    • Novak, M., and Kennedy, S. A. (1995) Selective trapping of N-acetyl-N-(4-biphenylyl)-nitrenium and N-acetyl-N-(2-fluorenyl)-nitrenium ions by 2′-deoxyguanosine in aqueous solution. J. Am. Chem. Soc. 117, 574-575.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 574-575
    • Novak, M.1    Kennedy, S.A.2
  • 17
    • 0030929002 scopus 로고    scopus 로고
    • Reactions of ester derivatives of carcinogenic N-(4-biphenylyl)hydroxylamine and the corresponding hydroxamic acid with purine nucleosides
    • Kennedy, S. A., Novak, M., and Kolb, B. A. (1997) Reactions of ester derivatives of carcinogenic N-(4-biphenylyl)hydroxylamine and the corresponding hydroxamic acid with purine nucleosides. J. Am. Chem. Soc. 119, 7654-7664.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7654-7664
    • Kennedy, S.A.1    Novak, M.2    Kolb, B.A.3
  • 18
    • 0033553130 scopus 로고    scopus 로고
    • Spectroscopic characterization of the initial C8 intermediate in the reaction of the 2-fluorenylnitrenium ion with 2′-deoxyguanosine
    • McClelland, R. A., Ahmad, A., Dicks, A. P., and Licence, V. P. (1999) Spectroscopic characterization of the initial C8 intermediate in the reaction of the 2-fluorenylnitrenium ion with 2′-deoxyguanosine. J. Am. Chem. Soc. 121, 3303-3310.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 3303-3310
    • McClelland, R.A.1    Ahmad, A.2    Dicks, A.P.3    Licence, V.P.4
  • 19
    • 0020533372 scopus 로고
    • Revised methods for the salmonella mutagenicity test
    • Maron, D. M., and Ames, B. N. (1983) Revised methods for the salmonella mutagenicity test. Mutat. Res. 113, 173-215.
    • (1983) Mutat. Res. , vol.113 , pp. 173-215
    • Maron, D.M.1    Ames, B.N.2
  • 20
    • 0033529812 scopus 로고    scopus 로고
    • Hydrolysis reactions of N-sulfonatooxy-N-acetyl-1-aminonaphthalene and N-sulfonatooxy-N-acetyl-2-aminonaphthalene: Limited correlation of nitrenium ion azide/solvent selectivities and mutagenicities of the corresponding amines
    • Novak, M., VandeWater, A. J., Brown, A. J., Sanzenbacher, S. A., Hunt, L. A., Kolb, B. A., and Brooks, M. E. (1999) Hydrolysis reactions of N-sulfonatooxy-N-acetyl-1-aminonaphthalene and N-sulfonatooxy-N-acetyl-2-aminonaphthalene: Limited correlation of nitrenium ion azide/solvent selectivities and mutagenicities of the corresponding amines. J. Org. Chem. 64, 6023-6031.
    • (1999) J. Org. Chem. , vol.64 , pp. 6023-6031
    • Novak, M.1    VandeWater, A.J.2    Brown, A.J.3    Sanzenbacher, S.A.4    Hunt, L.A.5    Kolb, B.A.6    Brooks, M.E.7
  • 21
    • 0001652916 scopus 로고
    • Reactivity and selectivity of nitrenium ions derived from ester derivatives of carcinogenic N-(4-biphenylyl)hydroxylamine and the corresponding hydroxamic acid
    • Novak, M., Kahley, M. J., Eiger, E., Helmick, J. S., and Peters, H. E. (1993) Reactivity and selectivity of nitrenium ions derived from ester derivatives of carcinogenic N-(4-biphenylyl)hydroxylamine and the corresponding hydroxamic acid. J. Am. Chem. Soc. 115, 9453-9460.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 9453-9460
    • Novak, M.1    Kahley, M.J.2    Eiger, E.3    Helmick, J.S.4    Peters, H.E.5
  • 23
    • 0018774149 scopus 로고
    • Mechanisms of action of carcinogenic aromatic amines: An investigation using mutagenesis in bacteria
    • Scribner, J. D., Fisk, S. R., and Scribner, N. K. (1979) Mechanisms of action of carcinogenic aromatic amines: An investigation using mutagenesis in bacteria. Chem.-Biol. Interact. 26, 11-25.
    • (1979) Chem.-Biol. Interact. , vol.26 , pp. 11-25
    • Scribner, J.D.1    Fisk, S.R.2    Scribner, N.K.3
  • 24
    • 0023526324 scopus 로고
    • Mutagenicity of choroaniline/lignin metabolities in the Salmonella/microsome assay
    • Rashid, K. A., Arjmand, M., Sandermann, H., Mumma, R. O. (1987) Mutagenicity of choroaniline/lignin metabolities in the Salmonella/microsome assay. J. Environ. Sci. Health B22, 721-729.
    • (1987) J. Environ. Sci. Health , vol.B22 , pp. 721-729
    • Rashid, K.A.1    Arjmand, M.2    Sandermann, H.3    Mumma, R.O.4
  • 26
    • 0023704076 scopus 로고
    • Salmonella mutagenicity tests: IV. Results from the testing of 300 chemicals
    • Zeiger, E., Anderson, B., Haworth, S., Lawlor, K., and Mortelmans, K. (1988) Salmonella mutagenicity tests: IV. Results from the testing of 300 chemicals. Environ. Mol. Mutagen. 11 (Suppl. 12), 1-158.
    • (1988) Environ. Mol. Mutagen. , vol.11 , Issue.SUPPL. 12 , pp. 1-158
    • Zeiger, E.1    Anderson, B.2    Haworth, S.3    Lawlor, K.4    Mortelmans, K.5
  • 27
    • 0026503111 scopus 로고
    • Salmonella mutagenicity tests: V. Results from the testing of 311 chemicals
    • Zeiger, E., Anderson, B., Haworth, S., Lawlor, T., and Mortelmans, K. (1992) Salmonella mutagenicity tests: V. Results from the testing of 311 chemicals. Environ. Mol. Mutagen. 19 (Suppl. 2), 2-141.
    • (1992) Environ. Mol. Mutagen. , vol.19 , Issue.SUPPL. 2 , pp. 2-141
    • Zeiger, E.1    Anderson, B.2    Haworth, S.3    Lawlor, T.4    Mortelmans, K.5
  • 28
    • 0022458177 scopus 로고
    • Salmonella mutagenicity tests: 11. Results from the testing of 270 chemicals
    • Mortelmans, K., Haworth, S., Lawlor, T., Speck, W., Tainer, B., and Zeiger, E. (1986) Salmonella mutagenicity tests: 11. Results from the testing of 270 chemicals. Environ. Mutagen. 8 (Suppl. 7), 1-119.
    • (1986) Environ. Mutagen. , vol.8 , Issue.SUPPL. 7 , pp. 1-119
    • Mortelmans, K.1    Haworth, S.2    Lawlor, T.3    Speck, W.4    Tainer, B.5    Zeiger, E.6
  • 29
    • 0030189661 scopus 로고    scopus 로고
    • Halide ion trapping of nitrenium ions formed in the Bamberger rearrangement of N-arylhydroxylamines. Lifetime of the parent phenylnitrenium ion in water
    • Fishbein, J. C., and McClelland, R. A. (1996) Halide ion trapping of nitrenium ions formed in the Bamberger rearrangement of N-arylhydroxylamines. Lifetime of the parent phenylnitrenium ion in water. Can. J. Chem. 74, 1321-1328.
    • (1996) Can. J. Chem. , vol.74 , pp. 1321-1328
    • Fishbein, J.C.1    McClelland, R.A.2
  • 31
    • 0032564841 scopus 로고    scopus 로고
    • Nitrenium ions from food-derived heterocyclic arylamine mutagens
    • Novak, M., Xu, L., and Wolf, R. A. (1998) Nitrenium ions from food-derived heterocyclic arylamine mutagens. J. Am. Chem. Soc. 120, 1643-1644.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 1643-1644
    • Novak, M.1    Xu, L.2    Wolf, R.A.3
  • 32
    • 0000133260 scopus 로고
    • Involvement of free nitrenium ions, ion pairs, and preassociation trapping in the reactions of ester derivatives of N-arylhydroxylamines and N-arylhydroxamic acids in aqueous solution
    • Novak, M., Kahley, M. J., Lin, J., Kennedy, S. A., and James, T. G. (1995) Involvement of free nitrenium ions, ion pairs, and preassociation trapping in the reactions of ester derivatives of N-arylhydroxylamines and N-arylhydroxamic acids in aqueous solution. J. Org. Chem. 60, 8294-8304.
    • (1995) J. Org. Chem. , vol.60 , pp. 8294-8304
    • Novak, M.1    Kahley, M.J.2    Lin, J.3    Kennedy, S.A.4    James, T.G.5
  • 33
    • 0034685435 scopus 로고    scopus 로고
    • Characterization of the 2-(α-carbolinyl) nitrenium ion and its conjugate base produced during the decomposition of the model carcinogen 2-N-(pivaloyloxy)-2-amino-α-carboline in aqueous solution
    • Novak, M., and Kazerani, S. (2000) Characterization of the 2-(α-carbolinyl) nitrenium ion and its conjugate base produced during the decomposition of the model carcinogen 2-N-(pivaloyloxy)-2-amino-α-carboline in aqueous solution. J. Am. Chem. Soc. 122, 3606-3616.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 3606-3616
    • Novak, M.1    Kazerani, S.2
  • 34
    • 0000774184 scopus 로고    scopus 로고
    • Spectroscopic characterization by laser flash photolysis of electrophilic intermediates derived from 4-aminostilbenes. Stilbene "nitrenium" ions and quinone methide imines
    • Bose, R., Ahmad, A. R., Dicks, A. P., Novak, M., Kayser, K. J., and McClelland, R. A. (1999) Spectroscopic characterization by laser flash photolysis of electrophilic intermediates derived from 4-aminostilbenes. Stilbene "nitrenium" ions and quinone methide imines. J. Chem. Soc., Perkin Trans. 2, 1591-1599.
    • (1999) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1591-1599
    • Bose, R.1    Ahmad, A.R.2    Dicks, A.P.3    Novak, M.4    Kayser, K.J.5    McClelland, R.A.6
  • 35
    • 0031673418 scopus 로고    scopus 로고
    • Carbocation-like reactivity patterns in X′-substituted-4-biphenylylnitrenium ions
    • Ren, D., and McClelland, R. A. (1998) Carbocation-like reactivity patterns in X′-substituted-4-biphenylylnitrenium ions. Can. J. Chem. 76, 78-84.
    • (1998) Can. J. Chem. , vol.76 , pp. 78-84
    • Ren, D.1    McClelland, R.A.2
  • 36
    • 0000315234 scopus 로고
    • Electron-deficient strong bases-generation of the 4-biphenylylnitrenium and 2-fluorenylnitrenium ions by nitrene protonation in water
    • McClelland, R. A., Davidse, P. A., and Hadzialic, G. (1995) Electron-deficient strong bases-generation of the 4-biphenylylnitrenium and 2-fluorenylnitrenium ions by nitrene protonation in water. J. Am. Chem. Soc. 117, 4173-4174.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4173-4174
    • McClelland, R.A.1    Davidse, P.A.2    Hadzialic, G.3
  • 37
    • 54249150617 scopus 로고    scopus 로고
    • Direct observation of 4-alkoxyphenylnitrenium ions upon irradiation of 4-alkoxyphenyl azides in aqueous solution
    • Sukhai, P., and McClelland, R. A. (1996) Direct observation of 4-alkoxyphenylnitrenium ions upon irradiation of 4-alkoxyphenyl azides in aqueous solution. J. Chem. Soc., Perkin Trans. 2, 1529-1530.
    • (1996) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 1529-1530
    • Sukhai, P.1    McClelland, R.A.2
  • 38
    • 0001297315 scopus 로고    scopus 로고
    • Photochemical generation and lifetimes in water of p-aryloxy- and p-alkoxyphenylnitrenium ions
    • Ramlall, P., and McClelland, R. A, (1999) Photochemical generation and lifetimes in water of p-aryloxy- and p-alkoxyphenylnitrenium ions. J. Chem. Soc., Perkin Trans. 2, 225-232.
    • (1999) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 225-232
    • Ramlall, P.1    McClelland, R.A.2
  • 39
    • 0037055097 scopus 로고    scopus 로고
    • Reactivity and Selectivity of the N-acetyl-Glu-P-1, N-acetyl-Glu-P-2, N-acetyl-MelQx, and N-acetyl-IQx nitrenium ions: Comparison to carbocyclic N-arylnitrenium ions
    • Novak, M., Toth, K., Rajagopal, S., Brooks, M., Hott, L. L., and Moslener, M. (2002) Reactivity and Selectivity of the N-acetyl-Glu-P-1, N-acetyl-Glu-P-2, N-acetyl-MelQx, and N-acetyl-IQx nitrenium ions: comparison to carbocyclic N-arylnitrenium ions. J. Am. Chem. Soc. 124, 7972-7981.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 7972-7981
    • Novak, M.1    Toth, K.2    Rajagopal, S.3    Brooks, M.4    Hott, L.L.5    Moslener, M.6
  • 41
    • 0000066384 scopus 로고
    • Comparison of the relative stabilities of polycyclic arylnitrenium ions and arylmethyl cations: Ab initio and semiempirical molecular orbital calculations
    • Ford, G. P., and Herman, P. S. (1991) Comparison of the relative stabilities of polycyclic arylnitrenium ions and arylmethyl cations: Ab initio and semiempirical molecular orbital calculations. THEOCHEM 236, 269-282.
    • (1991) THEOCHEM , vol.236 , pp. 269-282
    • Ford, G.P.1    Herman, P.S.2
  • 42
    • 0033529745 scopus 로고    scopus 로고
    • Correlation of azide/solvent selectivities for nitrenium ions with ab initio hydration energies: Understanding the kinetic lability of nitrenium ions in aqueous solution
    • Novak, M., and Lin, J. (1999) Correlation of azide/solvent selectivities for nitrenium ions with ab initio hydration energies: Understanding the kinetic lability of nitrenium ions in aqueous solution. J. Org. Chem. 64, 6032-6040.
    • (1999) J. Org. Chem. , vol.64 , pp. 6032-6040
    • Novak, M.1    Lin, J.2
  • 43
    • 0021667179 scopus 로고    scopus 로고
    • http://potency.berkeley.edu/cpdb.html. See Gold, L. S., Sawyer, C. B., Magaw, R., Backman, G. M., deVeciana, M., Levinson, R., Hooper, N. K., Havender, W. R., Bernstein, L., Petro, R., Pike, M. C., and Ames, B. N. (1984) A Carcinogenic potency database of the standardized results of animal bioassays. Environ. Health Perspect. 58, 9-319.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.