Isolation and structural identification of a direct-acting mutagen derived from N-nitroso-N-methylpentylamine and Fenton's reagent with copper ion

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 18, 2011, Pages 5693-5697

  Miura, Motofumi ^a,d   Inami, Keiko ^a,b   Yoshida, Masafumi ^b   Yamaguchi, Kentaro ^c   Mashino, Tadahiko ^a   Mochizuki, Masataka ^a,b  

^a KEIO UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF SCIENCE   (Japan)

^c TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^d NIHON UNIVERSITY   (Japan)

Author keywords

Fenton's reagent; Hydroxyl radical; Metabolic activation; N Nitrosodialkylamine; Nitric oxide; Pyrazoline

Indexed keywords

3 ETHYL 3 NITRO 1 PYRAZOLINE; 5 ETHYL 5 NITRO 1 PYRAZOLINE 1 OXIDE; COPPER ION; FERROUS GLUCONATE; MUTAGENIC AGENT; N METHYL N PENTYLNITROSAMINE; NITRIC OXIDE; NITROSAMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROSCOPY; ISOLATION PROCEDURE; MUTAGENICITY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SALMONELLA TYPHIMURIUM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

COPPER; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; FERROUS COMPOUNDS; HYDROGEN PEROXIDE; IONS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUTAGENS; MUTATION; NITRIC OXIDE; NITROSAMINES; SALMONELLA TYPHIMURIUM; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

RATTUS; SALMONELLA TYPHIMURIUM;

EID: 80052580696     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.07.012     Document Type: Article

References (39)

1. R. Preussmann, and Eisenbrand C.B. Searle, Chemical Carcinogens 2nd ed. 1984 American Chemical Society Washington, DC 829 868
2. P.N. Magee, and J.M. Barnes Adv. Cancer Res. 10 1967 163
3. A.R. Tricker, and R. Preussmann Mutat. Res. 259 1991 277
4. W. Lijinsky Mutat. Res. 443 1999 129
5. J.H. Hotchkiss Cancer Surveys 8 1989 295
6. W. Lijinsky Food Chem. Toxicol. 22 1984 715
7. H. Bartsch, and B. Spiegelhalder Eur. J. Cancer Prev. 5 1996 11
8. A.R. Tricker Eur. J. Cancer Prev. 6 1997 226
9. S.S. Hecht, and J.B. Morrison Cancer Res. 44 1984 2873
10. M.A. Marletta Chem. Res. Toxicol. 1 1988 249
11. M. Miwa, D.J. Stuehr, M.A. Marletta, J.S. Wishnok, and S.R. Tannenbaum Carcinogenesis 8 1987 955
12. H. Druckrey, R. Preussmann, S. Ivankovic, and D. Schmahl Zeitschrift Krebsforsch. 69 1967 103
13. H. Bartsch, and R. Montesano Carcinogenesis 5 1984 1381
14. P. Jakszyn, and C.A. González World J. Gastroenterol. 12 2006 4296
15. R. Preussmann Arzneim.-Forsch. 14 1964 769
16. M. Jarman, and D. Manson Carcinogenesis 7 1986 559
17. Y. Heur, A.J. Streeter, R.W. Nims, and L.K. Keefer Chem. Res. Toxicol. 2 1989 247
18. K. Hiramoto, Y. Ryuno, and K. Kikugawa Mutat. Res. 520 2002 103
19. E. Suzuki, M. Mochizuki, K. Shibuya, and M. Okada Gann 74 1983 41
20. S.T. Hsieh, P.L. Kraft, M.C. Archer, and S.R. Tannenbaum Mutat. Res. 35 1976 23
21. K. Inami, S. Ishimura, Y. Akaike, E. Suzuki, N. Tsutsumi, K. Takeda, and M. Mochizuki J. Health Sci. 56 2010 576
22. N. Tsutsumi, K. Inami, and M. Mochizuki Bioorg. Med. Chem. 18 2010 8284
23. J.B. Guttenplan Mutat. Res. 186 1987 81
24. M. Mancera, E. Rodriguez, R. Isaac, and J.A. Galbis J. Org. Chem. 53 1988 5648
25. M. Mochizuki, C.C. Irving, T. Anjo, Y. Wakabayashi, E. Suzuki, and M. Okada Cancer Res. 40 1980 162
26. K. Leung, and M.C. Arther Carcinogenesis 6 1985 189
27. http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?GENETOX Genetic Toxicology Data Bank (GENE-TOX), US National Library of Medicine.
28. http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?CCRIS, Chemical Carcinogenesis Research Information System (CCRIS), US National Library of Medicine.
29. C. Ji, S.S. Mirvish, J. Nickols, H. Ishizaki, M.J. Lee, and C.S. Yang Cancer Lett. 49 1989 5299
30. G. Bellec, T. Goasduff, J.F. Ménez, and F. Berthou Cancer Lett. 100 1996 115
31. G. Bellec, Y. Dreano, P. Lozach, J.F. Ménes, and F. Berthou Carcinogenesis 17 1996 2029
32. G. Halliwell, and J.M.C. Gutteridge Free Radicals and Biology and Medicine 3rd ed. 1998 Oxford University Press London pp 36-104
33. G.L. Brewer Chem. Res. Toxicol. 23 2010 319
34. W.W. Hartman, and L.J. Roll A.H. Blatt, Organic Synthesis Collective Vol. 2 1950 John Wiley & Sons New York 460
35. H. Feuer, R. Miller, and C.B. Lawyer J. Org. Chem. 26 1961 1357
36. M. Miyashita, T. Yanami, and A. Yoshikoshi O.L. Chapman, Organic Synthesis Vol. 60 1981 John Wiley & Sons New York 101 103
37. D.M. Maron, and B.N. Ame Mutat. Res. 113 1983 173
38. K. Mortelmans, and E. Zeiger Mutat. Res. 455 2000 29
39. J.A. Moore, and D.E. Reed H. Baumgarten, Organic Synthesis Collective Vol. 5 1973 John Wiley & Sons New York 351