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Volumn 412, Issue 1, 1998, Pages 99-107

Mutagenicity of isomeric alkanediazotates, precursors for ultimate alkylating species of carcinogenic N-nitroso compounds

Author keywords

Alkanediazotate; Geometrical isomerism; Mutagenicity; N nitroso compound; Ultimate alkylating species

Indexed keywords

ALKANE DERIVATIVE; ALKYL GROUP; ALKYLATING AGENT; CARCINOGEN; NITROSO DERIVATIVE; PYRAZINE DIAZOHYDROXIDE;

EID: 0031931293     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1383-5718(97)00180-0     Document Type: Article
Times cited : (10)

References (41)
  • 1
    • 0026038948 scopus 로고
    • Biological and chemical properties of alkanediazotates as active species of N-nitroso compounds
    • in: I.K. O'Neill, J. Chen, H. Bartsch (Eds.), IARC Scientific Publications No. 105, International Agency for Research on Cancer, Lyon
    • S. Ukawa, M. Mochizuki, Biological and chemical properties of alkanediazotates as active species of N-nitroso compounds, in: I.K. O'Neill, J. Chen, H. Bartsch (Eds.), Relevance to Human Cancer of N-Nitroso Compounds, Tobacco Smoke and Mycotoxins, IARC Scientific Publications No. 105, International Agency for Research on Cancer, Lyon, 1991 pp. 404-406.
    • (1991) Relevance to Human Cancer of N-Nitroso Compounds, Tobacco Smoke and Mycotoxins , pp. 404-406
    • Ukawa, S.1    Mochizuki, M.2
  • 2
    • 0011278203 scopus 로고
    • N-Nitroso carcinogens in the environment
    • in: C.E. Searle (Ed.), ACS Monograph No. 182, American Chemical Society, Washington, DC
    • R. Preussmann, G. Eisenbrand, N-Nitroso carcinogens in the environment, in: C.E. Searle (Ed.), Chemical Carcinogens, 2nd ed., ACS Monograph No. 182, American Chemical Society, Washington, DC, 1984 pp. 829-868.
    • (1984) Chemical Carcinogens, 2nd Ed. , pp. 829-868
    • Preussmann, R.1    Eisenbrand, G.2
  • 3
    • 0021266410 scopus 로고
    • A sensitive method for detecting in vivo formation of N-nitrosomorpholine and its application to rats given low doses of morpholine and sodium nitrite
    • Hecht S.S., Morrison J.B. A sensitive method for detecting in vivo formation of N-nitrosomorpholine and its application to rats given low doses of morpholine and sodium nitrite. Cancer Res. 44:1984;2873-2877.
    • (1984) Cancer Res. , vol.44 , pp. 2873-2877
    • Hecht, S.S.1    Morrison, J.B.2
  • 4
    • 0021677262 scopus 로고
    • Induction of tumours in rats by feeding nitrosatable amines together with sodium nitrite
    • Lijinsky W. Induction of tumours in rats by feeding nitrosatable amines together with sodium nitrite. Food Chem. Toxicol. 22:1984;715-720.
    • (1984) Food Chem. Toxicol. , vol.22 , pp. 715-720
    • Lijinsky, W.1
  • 5
    • 0023685375 scopus 로고
    • Mammalian synthesis of nitrite, nitrate, nitric oxide, and N-nitrosating agents
    • Marletta M.A. Mammalian synthesis of nitrite, nitrate, nitric oxide, and N-nitrosating agents. Chem. Res. Toxicol. 1:1988;249-257.
    • (1988) Chem. Res. Toxicol. , vol.1 , pp. 249-257
    • Marletta, M.A.1
  • 7
    • 0021680014 scopus 로고
    • Relevance of nitrosamines to human cancer
    • Bartsch H., Montesano R. Relevance of nitrosamines to human cancer. Carcinogenesis. 5:1984;1381-1393.
    • (1984) Carcinogenesis , vol.5 , pp. 1381-1393
    • Bartsch, H.1    Montesano, R.2
  • 8
    • 0002624810 scopus 로고
    • N-Nitroso carcinogens
    • in: C.E. Searle (Ed.), ACS Monograph No. 182, American Chemical Society, Washington, DC
    • R. Preussmann, B.W. Stewart, N-Nitroso carcinogens, in: C.E. Searle (Ed.), Chemical Carcinogens, 2nd ed., ACS Monograph No. 182, American Chemical Society, Washington, DC, 1984 pp. 643-828.
    • (1984) Chemical Carcinogens, 2nd Ed. , pp. 643-828
    • Preussmann, R.1    Stewart, B.W.2
  • 9
    • 0021242082 scopus 로고
    • Species differences in nitrosamine carcinogenesis
    • Lijinsky W. Species differences in nitrosamine carcinogenesis. J. Cancer Res. Clin. Oncol. 108:1984;46-55.
    • (1984) J. Cancer Res. Clin. Oncol. , vol.108 , pp. 46-55
    • Lijinsky, W.1
  • 10
    • 0018601031 scopus 로고
    • Mutagenic and DNA-damaging effects of N-alkyl-N-(α-acetoxyalkyl)nitrosamines, models for metabolically activated N,N-dialkylnitrosamines
    • Mochizuki M., Suzuki E., Anjo T., Wakabayashi Y., Okada M. Mutagenic and DNA-damaging effects of N-alkyl-N-(α-acetoxyalkyl)nitrosamines, models for metabolically activated N,N-dialkylnitrosamines. Gann. 70:1979;663-670.
    • (1979) Gann , vol.70 , pp. 663-670
    • Mochizuki, M.1    Suzuki, E.2    Anjo, T.3    Wakabayashi, Y.4    Okada, M.5
  • 11
    • 0000641793 scopus 로고
    • Formation of N-alkyl-N-(1-hydroperoxyalkyl)nitrosamines from N-alkyl-N-(1-acetoxyalkyl)nitrosamines
    • Mochizuki M., Anjo T., Wakabayashi Y., Sone T., Okada M. Formation of N-alkyl-N-(1-hydroperoxyalkyl)nitrosamines from N-alkyl-N-(1-acetoxyalkyl)nitrosamines. Tetrahedron Lett. 21:1980;1761-1764.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 1761-1764
    • Mochizuki, M.1    Anjo, T.2    Wakabayashi, Y.3    Sone, T.4    Okada, M.5
  • 12
    • 0007606114 scopus 로고
    • Synthesis of N-alkyl-N-(1-hydroperoxyalkyl)nitrosamines by oxygenation of lithiated dialkylnitrosamines
    • Mochizuki M., Sone T., Anjo T., Okada M. Synthesis of N-alkyl-N-(1-hydroperoxyalkyl)nitrosamines by oxygenation of lithiated dialkylnitrosamines. Tetrahedron Lett. 21:1980;1765-1766.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 1765-1766
    • Mochizuki, M.1    Sone, T.2    Anjo, T.3    Okada, M.4
  • 13
    • 0019268860 scopus 로고
    • Formation, deoxygenation and mutagenicity of α-hydroperoxydialkylnitrosamines
    • in: E.A. Walker, M. Castegnaro, L. Griciute, M. Börzsönyi (Eds.), IARC Scientific Publications No. 31, International Agency for Research on Cancer, Lyon
    • M. Okada, M. Mochizuki, T. Anjo, T. Sone, Y. Wakabayashi, E. Suzuki, Formation, deoxygenation and mutagenicity of α-hydroperoxydialkylnitrosamines, in: E.A. Walker, M. Castegnaro, L. Griciute, M. Börzsönyi (Eds.), N-Nitroso Compounds: Analysis, Formation and Occurrence, IARC Scientific Publications No. 31, International Agency for Research on Cancer, Lyon, 1980 pp. 71-82.
    • (1980) N-Nitroso Compounds: Analysis, Formation and Occurrence , pp. 71-82
    • Okada, M.1    Mochizuki, M.2    Anjo, T.3    Sone, T.4    Wakabayashi, Y.5    Suzuki, E.6
  • 14
    • 0001760345 scopus 로고
    • Isolation and characterization of N-alkyl-N-(hydroxymethyl)nitrosamines from N-alkyl-N-(hydroperoxymethyl)nitrosamines by deoxygenation
    • Mochizuki M., Anjo T., Okada M. Isolation and characterization of N-alkyl-N-(hydroxymethyl)nitrosamines from N-alkyl-N-(hydroperoxymethyl)nitrosamines by deoxygenation. Tetrahedron Lett. 21:1980;3693-3696.
    • (1980) Tetrahedron Lett. , vol.21 , pp. 3693-3696
    • Mochizuki, M.1    Anjo, T.2    Okada, M.3
  • 15
    • 0020349072 scopus 로고
    • Chemistry and mutagenicity of α-hydroxy nitrosamines
    • in: H. Bartsch, I.K. O'Neill, M. Castegnaro, M. Okada (Eds.), IARC Scientific Publications No. 41, International Agency for Research on Cancer, Lyon
    • M. Mochizuki, T. Anjo, K. Takeda, E. Suzuki, N. Sekiguchi, G.F. Huang, M. Okada, Chemistry and mutagenicity of α-hydroxy nitrosamines, in: H. Bartsch, I.K. O'Neill, M. Castegnaro, M. Okada (Eds.), N-Nitroso Compounds: Occurrence and Biological Effects, IARC Scientific Publications No. 41, International Agency for Research on Cancer, Lyon, 1982 pp. 553-559.
    • (1982) N-Nitroso Compounds: Occurrence and Biological Effects , pp. 553-559
    • Mochizuki, M.1    Anjo, T.2    Takeda, K.3    Suzuki, E.4    Sekiguchi, N.5    Huang, G.F.6    Okada, M.7
  • 16
    • 0002091886 scopus 로고
    • Chemistry of some alkanediazotates
    • Moss R.A. Chemistry of some alkanediazotates. Acc. Chem. Res. 7:1974;421-427.
    • (1974) Acc. Chem. Res. , vol.7 , pp. 421-427
    • Moss, R.A.1
  • 17
    • 84941058871 scopus 로고
    • Über Nitrosohydrazine. Isoazotate und Azoverbindungen der Fettreihe
    • Thiele J. Über Nitrosohydrazine. Isoazotate und Azoverbindungen der Fettreihe. Justus Liebigs Ann. Chem. 376:1910;239-268.
    • (1910) Justus Liebigs Ann. Chem. , vol.376 , pp. 239-268
    • Thiele, J.1
  • 18
    • 0344518480 scopus 로고
    • Über Diazoverbindungen, : XX. Struktur isomerer Diazotate: Das Hantzschsche Methyldiazotat
    • Müller E., Hoppe W., Hagenmaier H., Haiss H., Huber R., Rundel W., Suhr H. Über Diazoverbindungen, XX. Struktur isomerer Diazotate: das Hantzschsche Methyldiazotat Chem. Ber. 96:1963;1712-1719.
    • (1963) Chem. Ber. , vol.96 , pp. 1712-1719
    • Müller, E.1    Hoppe, W.2    Hagenmaier, H.3    Haiss, H.4    Huber, R.5    Rundel, W.6    Suhr, H.7
  • 20
    • 0023684093 scopus 로고
    • Quantum chemical studies of the products of decomposition of anticancer (2-haloethyl)nitrosoureas under physiological conditions
    • Sapse A.-M., Allen E.B., Lown J.W. Quantum chemical studies of the products of decomposition of anticancer (2-haloethyl)nitrosoureas under physiological conditions. J. Am. Chem. Soc. 110:1988;5671-5675.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 5671-5675
    • Sapse, A.-M.1    Allen, E.B.2    Lown, J.W.3
  • 21
    • 0001112652 scopus 로고
    • Rate constants for the decomposition of a simple alkanediazoate at physiological pH
    • Hovinen J., Fishbein J.C. Rate constants for the decomposition of a simple alkanediazoate at physiological pH. J. Am. Chem. Soc. 114:1992;366-367.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 366-367
    • Hovinen, J.1    Fishbein, J.C.2
  • 23
    • 0001095787 scopus 로고
    • Rate-limiting formation of diazonium ions in the aqueous decomposition of primary alkanediazoates
    • Ho J., Fishbein J.C. Rate-limiting formation of diazonium ions in the aqueous decomposition of primary alkanediazoates. J. Am. Chem. Soc. 116:1994;6611-6621.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 6611-6621
    • Ho, J.1    Fishbein, J.C.2
  • 24
    • 0020634705 scopus 로고
    • Mutagenicity of potassium alkanediazotates and their use as model compounds for activated nitrosamines
    • Hecker L.I., Saavedra J.E., Farrelly J.G., Andrews A.W. Mutagenicity of potassium alkanediazotates and their use as model compounds for activated nitrosamines. Cancer Res. 43:1983;4078-4082.
    • (1983) Cancer Res. , vol.43 , pp. 4078-4082
    • Hecker, L.I.1    Saavedra, J.E.2    Farrelly, J.G.3    Andrews, A.W.4
  • 27
    • 84948748025 scopus 로고
    • Thermal decomposition of higher sulphonylalkylnitrosamides
    • Hey D.H., De Boer Th.J. Thermal decomposition of higher sulphonylalkylnitrosamides. Recl. Trav. Chim. 73:1954;686-694.
    • (1954) Recl. Trav. Chim. , vol.73 , pp. 686-694
    • Hey, D.H.1    De Boer, Th.j.2
  • 28
    • 0020533372 scopus 로고
    • Revised methods for the Salmonella mutagenicity test
    • Maron D.M., Ames B.N. Revised methods for the Salmonella mutagenicity test. Mutation Res. 113:1983;173-215.
    • (1983) Mutation Res. , vol.113 , pp. 173-215
    • Maron, D.M.1    Ames, B.N.2
  • 30
    • 33847800887 scopus 로고
    • The hard soft acids bases (HSAB). Principle and organic chemistry
    • Ho T.-L. The hard soft acids bases (HSAB). Principle and organic chemistry. Chem. Rev. 75:1975;1-20.
    • (1975) Chem. Rev. , vol.75 , pp. 1-20
    • Ho, T.-L.1
  • 31
    • 0345114077 scopus 로고
    • Hard and soft acids and bases
    • Pearson R.G. Hard and soft acids and bases. J. Am. Chem. Soc. 85:1963;3533-3539.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 3533-3539
    • Pearson, R.G.1
  • 32
    • 0018118260 scopus 로고
    • Biochemical significance of the hard and soft acids and bases principle
    • Ho T.-L., Ho H.C., Hamilton L.D. Biochemical significance of the hard and soft acids and bases principle. Chem.-Biol. Interact. 23:1978;65-84.
    • (1978) Chem.-Biol. Interact. , vol.23 , pp. 65-84
    • Ho, T.-L.1    Ho, H.C.2    Hamilton, L.D.3
  • 33
    • 0023263169 scopus 로고
    • N-Nitrosamines: Bacterial mutagenesis and in vitro metabolism
    • Guttenplan J.B. N-Nitrosamines: Bacterial mutagenesis and in vitro metabolism. Mutation Res. 186:1987;81-134.
    • (1987) Mutation Res. , vol.186 , pp. 81-134
    • Guttenplan, J.B.1
  • 34
    • 0018585949 scopus 로고
    • Some biochemical aspects of N-nitroso compounds
    • Digenis G.A., Issidorides C.H. Some biochemical aspects of N-nitroso compounds. Bioorg. Chem. 8:1979;97-137.
    • (1979) Bioorg. Chem. , vol.8 , pp. 97-137
    • Digenis, G.A.1    Issidorides, C.H.2
  • 35
    • 0001406666 scopus 로고
    • Detection of carcinogens as mutagens in the Salmonella/microsome test: Assay of 300 chemicals
    • McCann J., Choi E., Yamasaki E., Ames B.N. Detection of carcinogens as mutagens in the Salmonella/microsome test: Assay of 300 chemicals. Proc. Natl. Acad. Sci. USA. 72:1975;5135-5139.
    • (1975) Proc. Natl. Acad. Sci. USA , vol.72 , pp. 5135-5139
    • McCann, J.1    Choi, E.2    Yamasaki, E.3    Ames, B.N.4
  • 36
    • 0018407137 scopus 로고
    • The mutagenicity of nitrosamides in Salmonella typhimurium
    • Lijinsky W., Andrews A.W. The mutagenicity of nitrosamides in Salmonella typhimurium. Mutation Res. 68:1979;1-8.
    • (1979) Mutation Res. , vol.68 , pp. 1-8
    • Lijinsky, W.1    Andrews, A.W.2
  • 37
    • 0018774045 scopus 로고
    • Mutagenicity of methyl-, ethyl-, propyl- And butylnitrosourea towards Escherichia coli WP2 strains with varying DNA repair capabilities
    • Garner R.C., Pickering C., Martin C.N. Mutagenicity of methyl-, ethyl-, propyl- and butylnitrosourea towards Escherichia coli WP2 strains with varying DNA repair capabilities. Chem.-Biol. Interact. 26:1979;197-205.
    • (1979) Chem.-Biol. Interact. , vol.26 , pp. 197-205
    • Garner, R.C.1    Pickering, C.2    Martin, C.N.3
  • 38
    • 0018216943 scopus 로고
    • Syntheses of N-alkyl-N-(α-acetoxyalkyl)nitrosamine, model compounds for metabolically activated N,N-dialkylnitrosamines
    • Mochizuki M., Anjo T., Okada M. Syntheses of N-alkyl-N-(α-acetoxyalkyl)nitrosamine, model compounds for metabolically activated N,N-dialkylnitrosamines. Chem. Pharm. Bull. 26:1978;3905-3908.
    • (1978) Chem. Pharm. Bull. , vol.26 , pp. 3905-3908
    • Mochizuki, M.1    Anjo, T.2    Okada, M.3
  • 39
    • 0022997420 scopus 로고
    • Solvolysis of N-nitroso-N-(1-acetoxyalkyl)alkylamines in phosphate buffer: Characterization and mutagenicity of N-nitroso-N-(1-phosphonooxyalkyl)alkylamines
    • Mochizuki M., Anjo T., Sekiguchi N., Ikarashi A., Wakabayashi Y., Okada M. Solvolysis of N-nitroso-N-(1-acetoxyalkyl)alkylamines in phosphate buffer: Characterization and mutagenicity of N-nitroso-N-(1-phosphonooxyalkyl)alkylamines. Chem. Pharm. Bull. 34:1986;3956-3959.
    • (1986) Chem. Pharm. Bull. , vol.34 , pp. 3956-3959
    • Mochizuki, M.1    Anjo, T.2    Sekiguchi, N.3    Ikarashi, A.4    Wakabayashi, Y.5    Okada, M.6
  • 40
    • 0023927935 scopus 로고
    • Metabolism of the Z and E isomers of N-nitroso-N-methyl-(2-oxopropyl)amine by rat hepatocytes
    • Farrelly J.G., Stewart M.L., Farnsworth D.W., Saavedra J.E. Metabolism of the Z and E isomers of N-nitroso-N-methyl-(2-oxopropyl)amine by rat hepatocytes. Cancer Res. 48:1988;3347-3349.
    • (1988) Cancer Res. , vol.48 , pp. 3347-3349
    • Farrelly, J.G.1    Stewart, M.L.2    Farnsworth, D.W.3    Saavedra, J.E.4
  • 41
    • 0024405947 scopus 로고
    • Microsomal metabolism of the Z and E isomers of N-nitroso-N-methyl-N-n-pentylamine
    • He C., Farrelly J.G. Microsomal metabolism of the Z and E isomers of N-nitroso-N-methyl-N-n-pentylamine. Cancer Lett. 45:1989;189-194.
    • (1989) Cancer Lett. , vol.45 , pp. 189-194
    • He, C.1    Farrelly, J.G.2


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