메뉴 건너뛰기




Volumn 9, Issue 1, 1996, Pages 99-108

Synthesis, characterization, and conformational analysis of DNA adducts from methylated anilines present in tobacco smoke

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLANILINE; 2,3 DIMETHYLANILINE; 2,4 DIMETHYLANILINE; 3 METHYLANILINE; 4 METHYLANILINE; ANILINE DERIVATIVE; AROMATIC AMINE; TOBACCO SMOKE; UNCLASSIFIED DRUG;

EID: 0030034422     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx950044z     Document Type: Article
Times cited : (42)

References (77)
  • 1
    • 0011859974 scopus 로고
    • Occupational carcinogens
    • (Cooper, C. S., and Grover, P. L., Eds.) Springer-Verlag, Heidelberg
    • Searle, C. E., and Teale, O J. (1990) Occupational carcinogens. In Handbook of Experimental Pharmacology. Carcinogenesis and Mutagenesis (Cooper, C. S., and Grover, P. L., Eds.) Vol. 94/I, pp 103-151, Springer-Verlag, Heidelberg.
    • (1990) Handbook of Experimental Pharmacology. Carcinogenesis and Mutagenesis , vol.94 , Issue.1 , pp. 103-151
    • Searle, C.E.1    Teale, O.J.2
  • 2
    • 0018291014 scopus 로고
    • Chemical studies on tobacco smoke. LXIV. On the analysis of aromatic amines in cigarette smoke
    • Patrianakos, C., and Hoffmann, D. (1979) Chemical studies on tobacco smoke. LXIV. On the analysis of aromatic amines in cigarette smoke J. Anal. Toxicol 3, 150-154.
    • (1979) J. Anal. Toxicol , vol.3 , pp. 150-154
    • Patrianakos, C.1    Hoffmann, D.2
  • 3
    • 0027246519 scopus 로고
    • Primary aromatic amines from side-stream cigarette smoke are common contaminants of indoor air
    • Luceri, F., Pieraccini, G., Moneti, G., and Dolara, P. (1993) Primary aromatic amines from side-stream cigarette smoke are common contaminants of indoor air. Toxicol. Ind. Health 9, 405-413.
    • (1993) Toxicol. Ind. Health , vol.9 , pp. 405-413
    • Luceri, F.1    Pieraccini, G.2    Moneti, G.3    Dolara, P.4
  • 4
    • 9044236287 scopus 로고
    • The health consequences of smoking - Cancer
    • Washington, DC
    • U.S. Surgeon General (1982) The health consequences of smoking - Cancer. DHHS (OHS) 82-50179, Washington, DC.
    • (1982) DHHS (OHS) 82-50179
  • 5
    • 0003502258 scopus 로고
    • The health consequences of involuntary smoking
    • Washington, DC
    • U.S. Surgeon General (1986) The health consequences of involuntary smoking. DHHS (CDC) 87-8398, Washington, DC.
    • (1986) DHHS (CDC) 87-8398
  • 7
    • 0020960482 scopus 로고
    • Tobacco as a risk factor in bladder cancer
    • Mommsen, S., and Aagaard, J. (1983) Tobacco as a risk factor in bladder cancer. Carcinogenesis 4, 335-338.
    • (1983) Carcinogenesis , vol.4 , pp. 335-338
    • Mommsen, S.1    Aagaard, J.2
  • 8
    • 0024383693 scopus 로고
    • Histologic changes in the urinary bladder in relation to cigarette smoking and use of artificial sweeteners
    • Auerbach, O., and Garfinkel, L. (1989) Histologic changes in the urinary bladder in relation to cigarette smoking and use of artificial sweeteners. Cancer 64, 983-987.
    • (1989) Cancer , vol.64 , pp. 983-987
    • Auerbach, O.1    Garfinkel, L.2
  • 9
    • 0002256633 scopus 로고
    • Advances in tobacco carcinogenesis
    • (Cooper, C. S., and Grover, P. L., Eds.) Springer-Verlag, Heidelberg
    • Hoffmann, D., and Hecht, S. S. (1990) Advances in tobacco carcinogenesis. In Handbook of Experimental Pharmacology. Carcinogenesis and Mutagenesis (Cooper, C. S., and Grover, P. L., Eds.) Vol. 94/I, pp 63-102, Springer-Verlag, Heidelberg.
    • (1990) Handbook of Experimental Pharmacology. Carcinogenesis and Mutagenesis , vol.94 , Issue.1 , pp. 63-102
    • Hoffmann, D.1    Hecht, S.S.2
  • 10
    • 0026618193 scopus 로고
    • Epidemiological models of carcinogenesis: The example of bladder cancer
    • Vineis, P. (1992) Epidemiological models of carcinogenesis: the example of bladder cancer. Cancer Epidemiol. Biomarkers Prev. 1, 149-153.
    • (1992) Cancer Epidemiol. Biomarkers Prev. , vol.1 , pp. 149-153
    • Vineis, P.1
  • 11
    • 0000037422 scopus 로고
    • Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons
    • (Cooper, C. S., and Grover, P. L., Eds.) Springer-Verlag, Heidelberg
    • Beland, F. A., and Kadlubar, F. F. (1990) Metabolic activation and DNA adducts of aromatic amines and nitroaromatic hydrocarbons. In Handbook of Experimental Pharmacology. Carcinogenesis and Mutagenesis (Cooper, C. S., and Grover, P. L., Eds.) Vol. 94/I, pp 267-325, Springer-Verlag, Heidelberg.
    • (1990) Handbook of Experimental Pharmacology. Carcinogenesis and Mutagenesis , vol.94 , Issue.1 , pp. 267-325
    • Beland, F.A.1    Kadlubar, F.F.2
  • 12
    • 0028705750 scopus 로고
    • DNA adducts of carcinogenic aromatic amines
    • (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartech, H., Eds) IARC Scientific Publications No. 125, International Agency for Research on Cancer, Lyon
    • Kadlubar, F. F. (1994) DNA adducts of carcinogenic aromatic amines. In DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., and Bartech, H., Eds) IARC Scientific Publications No. 125, pp 199-216, International Agency for Research on Cancer, Lyon.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 199-216
    • Kadlubar, F.F.1
  • 13
    • 0027975141 scopus 로고
    • Mutations induced by aromatic amine DNA adducts in pBR322
    • Melchior, W. B., Jr., Marques, M. M., and Beland, F. A. (1994) Mutations induced by aromatic amine DNA adducts in pBR322. Carcinogenesis 15, 889-899.
    • (1994) Carcinogenesis , vol.15 , pp. 889-899
    • Melchior Jr., W.B.1    Marques, M.M.2    Beland, F.A.3
  • 14
    • 0024843623 scopus 로고
    • Minor-groove binding models for acetylaminofluorene modified DNA
    • Shapiro, R., Hingerty, B. E., and Broyde, S. (1989) Minor-groove binding models for acetylaminofluorene modified DNA. J. Biomol. Struct. Dyn. 7, 493-513.
    • (1989) J. Biomol. Struct. Dyn. , vol.7 , pp. 493-513
    • Shapiro, R.1    Hingerty, B.E.2    Broyde, S.3
  • 15
    • 0026795019 scopus 로고
    • NMR structural studies of a 15-mer DNA sequence from a ras protooncogene, modified at the first base of codon 61 with the carcinogen 4-aminobiphenyl
    • Cho, B. P., Beland, F. A., and Marques, M. M. (1992) NMR structural studies of a 15-mer DNA sequence from a ras protooncogene, modified at the first base of codon 61 with the carcinogen 4-aminobiphenyl. Biochemistry 31, 9587-9602.
    • (1992) Biochemistry , vol.31 , pp. 9587-9602
    • Cho, B.P.1    Beland, F.A.2    Marques, M.M.3
  • 16
    • 0028323638 scopus 로고
    • NMR structural studies of a 15-mer DNA duplex from a ras protooncogene modified with the carcinogen 2-aminofluorene: Conformational heterogeneity
    • Cho, B. P., Beland, F. A., and Marques, M. M. (1994) NMR structural studies of a 15-mer DNA duplex from a ras protooncogene modified with the carcinogen 2-aminofluorene: conformational heterogeneity. Biochemistry 33, 1373-1384.
    • (1994) Biochemistry , vol.33 , pp. 1373-1384
    • Cho, B.P.1    Beland, F.A.2    Marques, M.M.3
  • 17
    • 0028294041 scopus 로고
    • Conformation of amine- modified DNA. 2-Aminofluorene- and 2-(acetylamino)fluorene- modified deoxydinucleoside monophosphates with all possible nearest neighbors. A comparison of search and optimization methods
    • Shapiro, R., Sidawi, D., Miao, Y.-S., Hingerty, B. E., Schmidt, K. E., Moskowitz, J., and Broyde, S. (1994) Conformation of amine- modified DNA. 2-Aminofluorene- and 2-(acetylamino)fluorene- modified deoxydinucleoside monophosphates with all possible nearest neighbors. A comparison of search and optimization methods. Chem. Res. Toxicol. 7, 239-253.
    • (1994) Chem. Res. Toxicol. , vol.7 , pp. 239-253
    • Shapiro, R.1    Sidawi, D.2    Miao, Y.-S.3    Hingerty, B.E.4    Schmidt, K.E.5    Moskowitz, J.6    Broyde, S.7
  • 18
    • 0028382509 scopus 로고
    • 2-Aminofluorene modified DNA duplex exists in two interchangeable conformations
    • Eckel, L. M., and Krugh, T. R. (1994) 2-Aminofluorene modified DNA duplex exists in two interchangeable conformations. Nature. Struct. Biol. 1, 89-94.
    • (1994) Nature. Struct. Biol. , vol.1 , pp. 89-94
    • Eckel, L.M.1    Krugh, T.R.2
  • 19
    • 0028033727 scopus 로고
    • Structural characterization of two interchangeable conformations of a 2-aminofluorene- modified DNA oligomer by NMR and energy minimization
    • Eckel, L. M., and Krugh, T. H. (1994) Structural characterization of two interchangeable conformations of a 2-aminofluorene- modified DNA oligomer by NMR and energy minimization. Biochemistry 33, 13611-13624.
    • (1994) Biochemistry , vol.33 , pp. 13611-13624
    • Eckel, L.M.1    Krugh, T.H.2
  • 21
    • 0025255481 scopus 로고
    • DNA adducts in different tissues of smokers and non-smokers
    • Cuzick, J., Routledge, M. N., Jenkins, D., and Garner, R. C. (1990) DNA adducts in different tissues of smokers and non-smokers. Int. J. Cancer 45, 673-678.
    • (1990) Int. J. Cancer , vol.45 , pp. 673-678
    • Cuzick, J.1    Routledge, M.N.2    Jenkins, D.3    Garner, R.C.4
  • 22
    • 0026056501 scopus 로고
    • Smoking related carcinogen - DNA adducts in biopsy samples of human urinary bladder: Identification of N-(deoxyguanosin-8- yl)-4-aminobiphenyl as a major adduct
    • Talaska, G., Al-Juburi, A. Z. S. S., and Kadlubar, F. F. (1991) Smoking related carcinogen - DNA adducts in biopsy samples of human urinary bladder: identification of N-(deoxyguanosin-8- yl)-4-aminobiphenyl as a major adduct Proc. Natl. Acad. Sci. U.S.A. 88, 5350-5354.
    • (1991) Proc. Natl. Acad. Sci. U.S.A. , vol.88 , pp. 5350-5354
    • Talaska, G.1    Al-Juburi, A.Z.S.S.2    Kadlubar, F.F.3
  • 24
    • 0028149727 scopus 로고
    • Analysis of 4-aminobiphenyl - DNA adducts in human urinary bladder and lung by alkaline hydrolysis and negative ion gas chromatography - mass spectrometry
    • Lin, D., Lay, J. O., Jr., Bryant, M. S., Malaveille, C., Friesen, M., Bartsch, H., Lang, N. P., and Kadlubar, F. F. (1993) Analysis of 4-aminobiphenyl - DNA adducts in human urinary bladder and lung by alkaline hydrolysis and negative ion gas chromatography - mass spectrometry. Environ. Health Perspect. 106 (Suppl. 6), 11-16.
    • (1993) Environ. Health Perspect. , vol.106 , Issue.6 SUPPL. , pp. 11-16
    • Lin, D.1    Lay Jr., J.O.2    Bryant, M.S.3    Malaveille, C.4    Friesen, M.5    Bartsch, H.6    Lang, N.P.7    Kadlubar, F.F.8
  • 25
    • 0023143658 scopus 로고
    • Hemoglobin adducts of 4-aminobiphenyl in smokers and nonsmokers
    • Bryant, M. S., Skipper, P. L., Tannenbaum, S. R., and Maclure, M. (1987) Hemoglobin adducts of 4-aminobiphenyl in smokers and nonsmokers. Cancer Res. 47, 602-608.
    • (1987) Cancer Res. , vol.47 , pp. 602-608
    • Bryant, M.S.1    Skipper, P.L.2    Tannenbaum, S.R.3    Maclure, M.4
  • 26
    • 0001643274 scopus 로고
    • Carcinogenic aromatic amines and related compounds
    • Chemical Carcinogens (Searle, C. E., Ed.) American Chemical Society, Washington, DC
    • Garner, R. C., Martin, C. N., and Clayson, D. B. (1984) Carcinogenic aromatic amines and related compounds. In Chemical Carcinogens (Searle, C. E., Ed.) ACS Monograph 182, pp 175-276, American Chemical Society, Washington, DC.
    • (1984) ACS Monograph 182 , pp. 175-276
    • Garner, R.C.1    Martin, C.N.2    Clayson, D.B.3
  • 27
    • 9044237830 scopus 로고
    • Health and environmental effects profile for toluidines
    • National Technical Information Service, Springfield, VA
    • Environmental Criteria and Assessment Office (1988) Health and environmental effects profile for toluidines. NTIS/PB88-130075, National Technical Information Service, Springfield, VA.
    • (1988) NTIS/PB88-130075
  • 28
    • 9044225271 scopus 로고
    • Health and environmental effects profile for 2,4-dimethylamline and 2,4- dimethylaniline hydrochloride
    • National Technical Information Service, Springfield, VA
    • Environmental Criteria and Assessment Office (1989) Health and environmental effects profile for 2,4-dimethylamline and 2,4- dimethylaniline hydrochloride. NTIS/PBS9-123004, National Technical Information Service, Springfield, VA.
    • (1989) NTIS/PBS9-123004
  • 29
    • 0025830122 scopus 로고
    • Excess number of bladder cancers in workers exposed to ortho-toluidine and aniline
    • Ward, E., Carpenter, A., Markowitz, S., Roberts, D., and Halperin, W. (1991) Excess number of bladder cancers in workers exposed to ortho-toluidine and aniline. J. Natl. Cancer Inst. 83, 501-506.
    • (1991) J. Natl. Cancer Inst. , vol.83 , pp. 501-506
    • Ward, E.1    Carpenter, A.2    Markowitz, S.3    Roberts, D.4    Halperin, W.5
  • 30
    • 0023238507 scopus 로고
    • GC/MS analysis of biologically important aromatic amines. Application to human dosimetry
    • Stillwell, W. G., Bryant, M. S., and Wishnok, J. S. (1987) GC/MS analysis of biologically important aromatic amines. Application to human dosimetry. Biomed. Environ. Mass Spectrom. 14, 221-227.
    • (1987) Biomed. Environ. Mass Spectrom. , vol.14 , pp. 221-227
    • Stillwell, W.G.1    Bryant, M.S.2    Wishnok, J.S.3
  • 31
    • 0024237525 scopus 로고
    • Hemoglobin adducts of aromatic amines: Associations with smoking status and type of tobacco
    • Bryant, M. S., Vineis, P., Skipper, P. L., and Tannenbaum, S. R. (1988) Hemoglobin adducts of aromatic amines: associations with smoking status and type of tobacco. Proc. Natl. Acad. Sci. U.S.A. 85, 9788-9791.
    • (1988) Proc. Natl. Acad. Sci. U.S.A. , vol.85 , pp. 9788-9791
    • Bryant, M.S.1    Vineis, P.2    Skipper, P.L.3    Tannenbaum, S.R.4
  • 33
    • 84990158064 scopus 로고
    • Formation of N-(deoxyguanosin-8-yl)aniline in the in vitro reaction of N-acetoxyaniline with deoxyguanosine and DNA
    • Famulok, M., and Boche, G. (1989) Formation of N-(deoxyguanosin-8-yl)aniline in the in vitro reaction of N-acetoxyaniline with deoxyguanosine and DNA. Angew. Chem., Int. Ed. Engl. 28, 468-469.
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 468-469
    • Famulok, M.1    Boche, G.2
  • 34
    • 84985651797 scopus 로고
    • N-Aryl-O-(α-aminoacyl)- hydroxylamine: Modellreaktionen mit Desoxyguanosin, Guanosin und 5′-Guanosinmonophosphat zur Aktivierung monocyclischer aromatischer Amine (z.B. Phenacetin) zu Ultimaten Carcinogenen
    • Meier, C., and Boche, G. (1990) N-Aryl-O-(α-aminoacyl)- hydroxylamine: Modellreaktionen mit Desoxyguanosin, Guanosin und 5′-Guanosinmonophosphat zur Aktivierung monocyclischer aromatischer Amine (z.B. Phenacetin) zu Ultimaten Carcinogenen [N-aryl-O-(α-aminoacyl)hydroxylamines: model reactions with deoxyguanosine, guanosine and 5′-guanosine monophosphate for the activation of monocyclic aromatic amines (e.g. phenacetin) into ultimate carcinogens]. Chem. Ber. 123, 1699-1705.
    • (1990) Chem. Ber. , vol.123 , pp. 1699-1705
    • Meier, C.1    Boche, G.2
  • 36
    • 0019275121 scopus 로고
    • Sensitivity of the conformation of deoxyguanosine to binding at the C-8 position by N-acetylated and unacetylated 2-aminofluorene
    • Evans, F. E., Miller, D. W., and Beland, F. A. (1980) Sensitivity of the conformation of deoxyguanosine to binding at the C-8 position by N-acetylated and unacetylated 2-aminofluorene. Carcinogenesis 1, 955-959.
    • (1980) Carcinogenesis , vol.1 , pp. 955-959
    • Evans, F.E.1    Miller, D.W.2    Beland, F.A.3
  • 37
    • 0001938636 scopus 로고
    • Arylamine - DNA adduct formation in relation to urinary bladder carcinogenesis and Salmonella typhimurium mutagenesis
    • (Sugimura, T., Kondo, S., and Takebe, H., Eds.) Liss, New York
    • Kadlubar, F. F., Beland, F. A., Beranek, D. T., Dooley, K. L., Heflich, R. H., and Evans, F. E. (1982) Arylamine - DNA adduct formation in relation to urinary bladder carcinogenesis and Salmonella typhimurium mutagenesis. In Environmental Mutagens and Carcinogens (Sugimura, T., Kondo, S., and Takebe, H., Eds.) pp 385-396, Liss, New York.
    • (1982) Environmental Mutagens and Carcinogens , pp. 385-396
    • Kadlubar, F.F.1    Beland, F.A.2    Beranek, D.T.3    Dooley, K.L.4    Heflich, R.H.5    Evans, F.E.6
  • 38
    • 0025820806 scopus 로고
    • The modification of guanine nucleosides and nucleotides by the borderline arylamine carcinogens 4-methyl- and 4-methoxyaniline: Chemistry and structural characterization
    • Meier, C., and Boche, G. (1991) The modification of guanine nucleosides and nucleotides by the borderline arylamine carcinogens 4-methyl- and 4-methoxyaniline: chemistry and structural characterization. Carcinogenesis 12, 1633-1640.
    • (1991) Carcinogenesis , vol.12 , pp. 1633-1640
    • Meier, C.1    Boche, G.2
  • 39
    • 0014821810 scopus 로고
    • Carbon-13 magnetic resonance. XVII. Pyrimidine and purine nucleosides
    • Jones, A. J., Grant, D. M., Winkley, M. W., and Robins, R. K. (1970) Carbon-13 magnetic resonance. XVII. Pyrimidine and purine nucleosides. J. Am. Chem. Soc. 92, 4079-4087.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 4079-4087
    • Jones, A.J.1    Grant, D.M.2    Winkley, M.W.3    Robins, R.K.4
  • 40
    • 0021155362 scopus 로고
    • Conformation and dynamics of the 8-substituted deoxyguanosine 5′-monophosphate adduct of the carcinogen 2-(acetylamino)fluorene
    • Evans, F. E., Miller, D. W., and Levine, R. A. (1984) Conformation and dynamics of the 8-substituted deoxyguanosine 5′-monophosphate adduct of the carcinogen 2-(acetylamino)fluorene. J. Am. Chem., Soc. 106, 396-401.
    • (1984) J. Am. Chem., Soc. , vol.106 , pp. 396-401
    • Evans, F.E.1    Miller, D.W.2    Levine, R.A.3
  • 41
    • 85066073517 scopus 로고
    • Synthese von Acylcyaniden (α-Oxonitrilen) mit Cyanotrimethylsilan
    • Herrmann, K., and Simchen, G. (1979) Synthese von Acylcyaniden (α-Oxonitrilen) mit Cyanotrimethylsilan [Synthesis of acyl cyanides (α-oxonitriles) with cyanotrimethylsilane]. Synthesis, 204-205.
    • (1979) Synthesis , pp. 204-205
    • Herrmann, K.1    Simchen, G.2
  • 42
    • 84943834540 scopus 로고
    • Einfluss von Methyl auf die Reactions-geschwindigkeit der Arylhydroxylamine
    • Bamberger, E., and Rising, A. (1901) Einfluss von Methyl auf die Reactions-geschwindigkeit der Arylhydroxylamine [Influence of methyl on the reactivity of arylhydroxylamines]. Liebigs Ann. Chem. 316, 257-295.
    • (1901) Liebigs Ann. Chem. , vol.316 , pp. 257-295
    • Bamberger, E.1    Rising, A.2
  • 43
    • 84978592732 scopus 로고
    • Ueber die Reduction aromatischer Nitroverbindungen
    • Bamberger, E. (1895) Ueber die Reduction aromatischer Nitroverbindungen [On the reduction of aromatic nitro compounds]. Ber. 28, 245-251.
    • (1895) Ber. , vol.28 , pp. 245-251
    • Bamberger, E.1
  • 44
    • 9044235712 scopus 로고
    • Ueber 2,4-Dimethylphenylhydroxylamin und uber 2,4-Dimethylchinol
    • Bamberger, E., and Brady, F. (1900) Ueber 2,4-Dimethylphenylhydroxylamin und uber 2,4-Dimethylchinol [On 2,4-dimethylphenylhydroxylamine and on 2,4-dimethylquinol]. Ber. 33, 3642-3658.
    • (1900) Ber. , vol.33 , pp. 3642-3658
    • Bamberger, E.1    Brady, F.2
  • 45
    • 0001391308 scopus 로고
    • β-Phenylhydroxylamine
    • (Blatt, A. H., Ed.) Wiley, New York
    • Kamm, O. (1941) β-Phenylhydroxylamine. In Organic Syntheses (Blatt, A. H., Ed.) Collect. Vol. I, 445-447, Wiley, New York.
    • (1941) Organic Syntheses , vol.1 , pp. 445-447
    • Kamm, O.1
  • 46
    • 37049105414 scopus 로고
    • Tetrahedral intermediates formed during acyl transfer. Reactions of acetyl cyanide
    • Lobo, A. M., Marques, M. M., Prabhakar, S., and Rzepa, H. S. (1985) Tetrahedral intermediates formed during acyl transfer. Reactions of acetyl cyanide. J. Chem. Soc., Chem. Commun., 1113-1115.
    • (1985) J. Chem. Soc., Chem. Commun. , pp. 1113-1115
    • Lobo, A.M.1    Marques, M.M.2    Prabhakar, S.3    Rzepa, H.S.4
  • 47
    • 0000195484 scopus 로고
    • Tetrahedral intermediates formed by nitrogen and oxygen attack of aromatic hydroxylamines on acetyl cyanide
    • Lobo, A. M., Marques, M. M., Prabhakar, S., and Rzepa, H. S. (1987) Tetrahedral intermediates formed by nitrogen and oxygen attack of aromatic hydroxylamines on acetyl cyanide. J. Org. Chem. 52, 2925-2927.
    • (1987) J. Org. Chem. , vol.52 , pp. 2925-2927
    • Lobo, A.M.1    Marques, M.M.2    Prabhakar, S.3    Rzepa, H.S.4
  • 48
    • 0022492733 scopus 로고
    • Relationships between the DNA adducts and sister-chromatid exchanges produced in Chinese hamster ovary cells by N-hydroxy-2-aminofluorene, N- hydroxy-N′-acetylbenzidine and 1-nitrosopyrene
    • Heflich, R. H., Morris,. S. M., Beranek, D. T., McGarrity, L. J., Chen, J. J., and Beland, F. A. (1986) Relationships between the DNA adducts and sister-chromatid exchanges produced in Chinese hamster ovary cells by N-hydroxy-2-aminofluorene, N- hydroxy-N′-acetylbenzidine and 1-nitrosopyrene. Mutagenesis 1, 201-206.
    • (1986) Mutagenesis , vol.1 , pp. 201-206
    • Heflich, R.H.1    Morris, S.M.2    Beranek, D.T.3    McGarrity, L.J.4    Chen, J.J.5    Beland, F.A.6
  • 49
    • 0026735982 scopus 로고
    • Computer graphics presentations and analysis of hydrogen bonds from molecular dynamics simulation
    • Shibata, M., and Zielinski, T. J. (1992) Computer graphics presentations and analysis of hydrogen bonds from molecular dynamics simulation. J. Mol. Graphics 10, 88-95.
    • (1992) J. Mol. Graphics , vol.10 , pp. 88-95
    • Shibata, M.1    Zielinski, T.J.2
  • 50
    • 84990148608 scopus 로고
    • Synthesis of O-acetyl-N-(4-biphenylyl)hydroxylamine ("N-acetoxy-4-aminobiphenyl"), an ultimate metabolite of carcinogenic 4-aminobiphenyl, and its reaction with deoxyguanosine
    • Famulok, M., Bosold, F., and Boche, G. (1989) Synthesis of O-acetyl-N-(4-biphenylyl)hydroxylamine ("N-acetoxy-4-aminobiphenyl"), an ultimate metabolite of carcinogenic 4-aminobiphenyl, and its reaction with deoxyguanosine. Angew. Chem., Int. Ed. Engl. 28, 337-338.
    • (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 337-338
    • Famulok, M.1    Bosold, F.2    Boche, G.3
  • 51
    • 0012755026 scopus 로고
    • Synthesis of N-acetoxy-2-aminonaphthaline, an ultimate carcinogen of the carcinogenic 2-naphthylamine, and its in vitro reactions with (bio)nucleophiles
    • Famulok, M., Bosold, F., and Boche, G. (1989) Synthesis of N-acetoxy-2-aminonaphthaline, an ultimate carcinogen of the carcinogenic 2-naphthylamine, and its in vitro reactions with (bio)nucleophiles. Tetrahedron Lett. 30, 321-324.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 321-324
    • Famulok, M.1    Bosold, F.2    Boche, G.3
  • 52
    • 0025342116 scopus 로고
    • The ultimate carcinogen, O-acetyl-N-(2-fluorenyl)hydroxylamine ("N-acetoxy-2-aminofluorene"), and its reaction in vitro to form 2-[N-(deoxyguanosin-8- yl)amino]fluorene
    • Bosold, F., and Boche, G. (1990) The ultimate carcinogen, O-acetyl-N-(2-fluorenyl)hydroxylamine ("N-acetoxy-2-aminofluorene"), and its reaction in vitro to form 2-[N-(deoxyguanosin-8- yl)amino]fluorene. Angew. Chem., Int. Ed. Engl. 29, 63-64.
    • (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 63-64
    • Bosold, F.1    Boche, G.2
  • 53
    • 33845278615 scopus 로고
    • 2+- induced reduction of N-aryl-O-pivaloylhydroxylamines: Aqueous solution chemistry of model carcinogens
    • 2+- induced reduction of N-aryl-O-pivaloylhydroxylamines: aqueous solution chemistry of model carcinogens. J. Org. Chem. 53, 4762-4769.
    • (1988) J. Org. Chem. , vol.53 , pp. 4762-4769
    • Novak, M.1    Lagerman, R.K.2
  • 54
    • 0026512811 scopus 로고
    • Hemoglobin binding of monocyclic aromatic amines: Molecular dosimetry and quantitative structure activity relationships for the N-oxidation
    • Sabbioni, G (1992) Hemoglobin binding of monocyclic aromatic amines: molecular dosimetry and quantitative structure activity relationships for the N-oxidation. Chem.-Biol. Interact. 81, 91-117.
    • (1992) Chem.-Biol. Interact. , vol.81 , pp. 91-117
    • Sabbioni, G.1
  • 55
    • 0019394168 scopus 로고
    • New syntheses of N-(guanosin-8-yl)-4-aminobiphenyl and its 5′-monophosphate
    • Lee, M.-S., and King, C. M. (1981) New syntheses of N-(guanosin-8-yl)-4-aminobiphenyl and its 5′-monophosphate. Chem.-Biol. Interact. 34, 239-248.
    • (1981) Chem.-Biol. Interact. , vol.34 , pp. 239-248
    • Lee, M.-S.1    King, C.M.2
  • 56
    • 0023735197 scopus 로고
    • A new synthetic route to nucleotide adducts derived from N-acetylated and unacetylated 4-aminobiphenyl
    • Underwood, G. R., Price, M. F., and Shapiro, R. (1988) A new synthetic route to nucleotide adducts derived from N-acetylated and unacetylated 4-aminobiphenyl. Carcinogenesis 9, 1817-1821.
    • (1988) Carcinogenesis , vol.9 , pp. 1817-1821
    • Underwood, G.R.1    Price, M.F.2    Shapiro, R.3
  • 57
    • 0025126254 scopus 로고
    • Facile aerial oxidation of the DNA-base adduct N-(2′-deoxyguanosin-8-yl)-2-aminofluorene [dG(C8)AF]
    • Shibutani, S., Gentles, R. G., Iden, C. R., and Johnson, F. (1990) Facile aerial oxidation of the DNA-base adduct N-(2′-deoxyguanosin-8-yl)-2-aminofluorene [dG(C8)AF]. J. Am. Chem. Soc. 112, 5667-5668.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 5667-5668
    • Shibutani, S.1    Gentles, R.G.2    Iden, C.R.3    Johnson, F.4
  • 58
    • 0000215867 scopus 로고
    • Synthesis and properties of purine nucleosides and nucleotides
    • (Townsend, L. B., Ed) Plenum Press, New York
    • Srivastava, P. C., Robins, R. K. and Meyer, R. B., Jr. (1988) Synthesis and properties of purine nucleosides and nucleotides. In Chemistry of Nucleosides and Nucleotides (Townsend, L. B., Ed) pp 113-281, Plenum Press, New York.
    • (1988) Chemistry of Nucleosides and Nucleotides , pp. 113-281
    • Srivastava, P.C.1    Robins, R.K.2    Meyer Jr., R.B.3
  • 59
    • 0025790114 scopus 로고
    • Enzymatic synthesis of purine deoxynucleoside adducts
    • Chapeau, M.-C., and Marnett, L. J. (1991) Enzymatic synthesis of purine deoxynucleoside adducts. Chem. Res. Toxicol. 4, 636-638.
    • (1991) Chem. Res. Toxicol. , vol.4 , pp. 636-638
    • Chapeau, M.-C.1    Marnett, L.J.2
  • 60
    • 0017387514 scopus 로고
    • C8-Amino purine nucleosides. A well-defined steric determinant of glycosyl conformational preferences
    • Jordan, F., and Niv, H. (1977) C8-Amino purine nucleosides. A well-defined steric determinant of glycosyl conformational preferences. Biochim Biophys. Acta 476, 265-271.
    • (1977) Biochim Biophys. Acta , vol.476 , pp. 265-271
    • Jordan, F.1    Niv, H.2
  • 61
    • 0018899928 scopus 로고
    • NMR studies of the syn-anti dynamic equilibrium in purine nucleosides and nucleotides
    • Stolarski, R., Dudycz, L., and Shugar, D. (1980) NMR studies of the syn-anti dynamic equilibrium in purine nucleosides and nucleotides. Eur. J. Biochem. 108, 111-121.
    • (1980) Eur. J. Biochem. , vol.108 , pp. 111-121
    • Stolarski, R.1    Dudycz, L.2    Shugar, D.3
  • 63
    • 49349134796 scopus 로고
    • Conformations of nucleosides and nucleotides
    • Davies, D. B. (1978) Conformations of nucleosides and nucleotides. Prog. Nucl. Magn. Reson. Spectrosc. 12, 135-225.
    • (1978) Prog. Nucl. Magn. Reson. Spectrosc. , vol.12 , pp. 135-225
    • Davies, D.B.1
  • 64
    • 0020055717 scopus 로고
    • Force field conformational analysis of aminofluorene and acetylaminofluorene substituted deoxyguanosine
    • Lipkowitz, K. B., Chevalier, T., Widdifield, M., and Beland, F. A. (1982) Force field conformational analysis of aminofluorene and acetylaminofluorene substituted deoxyguanosine. Chem.-Biol. Interact. 40, 57-76.
    • (1982) Chem.-Biol. Interact. , vol.40 , pp. 57-76
    • Lipkowitz, K.B.1    Chevalier, T.2    Widdifield, M.3    Beland, F.A.4
  • 65
    • 0020854692 scopus 로고
    • Conformation of 2-aminofluorene-modified DNA
    • Broyde, S., and Hingerty, B. (1983) Conformation of 2-aminofluorene-modified DNA. Biopolymers 22, 2423-2441.
    • (1983) Biopolymers , vol.22 , pp. 2423-2441
    • Broyde, S.1    Hingerty, B.2
  • 66
    • 0022838294 scopus 로고
    • Energy minimized structures of carcinogen - DNA adducts: 2-acetylaminofluorene and 2-aminofluorene
    • Hingerty, B. E., and Broyde, S. (1986) Energy minimized structures of carcinogen - DNA adducts: 2-acetylaminofluorene and 2-aminofluorene. J. Biomol. Struct. Dyn. 4, 365-372.
    • (1986) J. Biomol. Struct. Dyn. , vol.4 , pp. 365-372
    • Hingerty, B.E.1    Broyde, S.2
  • 67
    • 0022261401 scopus 로고
    • Influence of the carcinogen 4-aminobiphenyl on DNA conformation
    • Broyde, S., Hingerty, B. E., and Srinivasan, A. R. (1985) Influence of the carcinogen 4-aminobiphenyl on DNA conformation. Caranagenesis 6, 719-725.
    • (1985) Caranagenesis , vol.6 , pp. 719-725
    • Broyde, S.1    Hingerty, B.E.2    Srinivasan, A.R.3
  • 68
    • 33845375943 scopus 로고
    • Conformation of d(CpG) modified by the carcinogen 4-aminobiphenyl: A combined experimental and theoretical analysis
    • Shapiro, R., Underwood, G. R., Zawadzka, H., Broyde, S., and Hingerty, B. E. (1986) Conformation of d(CpG) modified by the carcinogen 4-aminobiphenyl: a combined experimental and theoretical analysis. Biochemistry 25, 2198-2205.
    • (1986) Biochemistry , vol.25 , pp. 2198-2205
    • Shapiro, R.1    Underwood, G.R.2    Zawadzka, H.3    Broyde, S.4    Hingerty, B.E.5
  • 69
    • 0028813112 scopus 로고
    • Major and minor groove conformations of DNA trimers modified on guanine or adenine by 4-aminobiphenyl: Adenine adducts favor the minor groove
    • Shapiro, R., Ellis, S., Hingerty, B. E., and Broyde, S. (1995) Major and minor groove conformations of DNA trimers modified on guanine or adenine by 4-aminobiphenyl: adenine adducts favor the minor groove. Chem. Res. Toxicol. 8, 117-127.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 117-127
    • Shapiro, R.1    Ellis, S.2    Hingerty, B.E.3    Broyde, S.4
  • 70
    • 0024428898 scopus 로고
    • NMR and computational characterization of the N-(deoxyguanosin-8-yl)aminofluorene adduct [(AF)G] opposite adenosine in DNA: (AF)G[syn]-A[anti] pair formation and its pH dependence
    • Norman, D., Abuaf, P., Hingerty, B. E., Live, D., Grunberger, D., Broyde, S., and Patel, D. J. (1989) NMR and computational characterization of the N-(deoxyguanosin-8-yl)aminofluorene adduct [(AF)G] opposite adenosine in DNA: (AF)G[syn]-A[anti] pair formation and its pH dependence. Biochemistry 28, 7462-7476.
    • (1989) Biochemistry , vol.28 , pp. 7462-7476
    • Norman, D.1    Abuaf, P.2    Hingerty, B.E.3    Live, D.4    Grunberger, D.5    Broyde, S.6    Patel, D.J.7
  • 71
    • 0028901297 scopus 로고
    • Solution conformation of the N-(deoxyguanosin-8-yl)aminofluorene adduct opposite deoxyinosine and deoxyguanosine in DNA by NMR and computational characterization
    • Abuaf, P., Hingerty, B. E., Broyde, S., and Grunberger, D. (1995) Solution conformation of the N-(deoxyguanosin-8-yl)aminofluorene adduct opposite deoxyinosine and deoxyguanosine in DNA by NMR and computational characterization. Chem. Res. Toxicol. 8, 369-378.
    • (1995) Chem. Res. Toxicol. , vol.8 , pp. 369-378
    • Abuaf, P.1    Hingerty, B.E.2    Broyde, S.3    Grunberger, D.4
  • 73
    • 0018699168 scopus 로고
    • Structure - Mutagenicity relationships of N-oxidized derivatives of aniline, o-totuidine, 2′-methyl-4-aminobiphenyl, and 3,2′-dimethyl-4-aminobiphenyl
    • Hecht, S. S., El-Bayoumy, K., Tulley, L., and LaVoie, E. (1979) Structure - mutagenicity relationships of N-oxidized derivatives of aniline, o-totuidine, 2′-methyl-4-aminobiphenyl, and 3,2′-dimethyl-4-aminobiphenyl. J. Med. Chem. 22, 981-987.
    • (1979) J. Med. Chem. , vol.22 , pp. 981-987
    • Hecht, S.S.1    El-Bayoumy, K.2    Tulley, L.3    Lavoie, E.4
  • 74
    • 49049145952 scopus 로고
    • Efiects of ortho-methyl substituents on the mutagenicity of aminobiphenyls and aminonaphthalenes
    • El-Bayoumy, K., LaVoie, E. J., Tulley-Freiler, L., and Hecht, S. S. (1981) Efiects of ortho-methyl substituents on the mutagenicity of aminobiphenyls and aminonaphthalenes. Mutat. Res. 90, 340-354.
    • (1981) Mutat. Res. , vol.90 , pp. 340-354
    • El-Bayoumy, K.1    Lavoie, E.J.2    Tulley-Freiler, L.3    Hecht, S.S.4
  • 76
    • 0020644905 scopus 로고
    • In vivo metabolism of 3,2′-dimethyl-4- aminobiphenyl (DMAB) bearing on its organotropism in the Syrian golden hamster and the F344 rat
    • Nussbaum, M., Fiala, E S., Kulkarni, B., El-Bayoumy, K., and Weisburger, J. H. (1983) In vivo metabolism of 3,2′-dimethyl-4- aminobiphenyl (DMAB) bearing on its organotropism in the Syrian golden hamster and the F344 rat. Environ. Health Perspect. 49, 223-231.
    • (1983) Environ. Health Perspect. , vol.49 , pp. 223-231
    • Nussbaum, M.1    Fiala, E.S.2    Kulkarni, B.3    El-Bayoumy, K.4    Weisburger, J.H.5
  • 77
    • 0028690578 scopus 로고
    • DNA adducts of aromatic amines present in tobacco smoke
    • (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerback, D., and Bartsch, H., Eds) IARC Scientific Publications No. 125, International Agency for Research on Cancer, Lyon
    • Marques, M. M., and Beland, F. A. (1994) DNA adducts of aromatic amines present in tobacco smoke. In DNA Adducts: Identification and Biological Significance (Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerback, D., and Bartsch, H., Eds) IARC Scientific Publications No. 125, pp 453-456, International Agency for Research on Cancer, Lyon.
    • (1994) DNA Adducts: Identification and Biological Significance , pp. 453-456
    • Marques, M.M.1    Beland, F.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.