Chemistry of carcinogenic and mutagenic metabolites of heterocyclic aromatic amines

Journal of Physical Organic Chemistry

Volumn 17, Issue 6-7 SPEC.ISS., 2004, Pages 615-624

  Novak, Michael ^a   Rajagopal, Sridharan ^a   Xu, Lulu ^a   Kazerani, Shahrokh ^a   Toth, Krisztina ^a   Brooks, Michael ^a   Nguyen, Thach Mien ^a  

^a MIAMI UNIVERSITY   (United States)

Author keywords

2 deoxyguanosine adducts; Azide clock; Carcinogens; Decomposition kinetics; Heterocyclic aromatic amines; Mutagens; Nitrenium ions

Indexed keywords

AMINES; CARCINOGENS; CHEMICAL BONDS; DECOMPOSITION; DNA; ESTERS; IONS; METABOLITES; MUTAGENS; ORGANIC ACIDS; REACTION KINETICS;

AZIDE CLOCK; DECOMPOSITION KINETICS; HETEROCYCLIC AROMATIC AMINES; NITRENIUM IONS;

AROMATIC COMPOUNDS;

EID: 2942756009     PISSN: 08943230     EISSN: None     Source Type: Journal    
DOI: 10.1002/poc.765     Document Type: Article

References (63)

1. Sugimura T, Nagao M, Kawachi T, Honda M, Yahagi T, Seino Y, Sato S, Matsukura N, Matsushima T, Shirai A, Sawamura M, Matsumoto H. In Origins of Human Cancer, Hiatt HH, Watson JD, Winsten JA (eds). Cold Spring Harbor Laboratory Press: Cold Spring Harbor, NY, 1977; 1561-1577.
2. Eisenbrand G, Tang W. Toxicology 1993; 84: 1-82; Hatch FT, Knize MG, Felton JS. Environ. Mol. Mutagen. 1991; 17: 4-19; Layton DW, Bogen KT, Knize MG, Hatch FT, Johnson VM, Felton JS. Carcinogenesis 1995; 16: 39-52; Sugimura T. Environ. Health Perspect. 1986; 67: 5-10.
3. Eisenbrand G, Tang W. Toxicology 1993; 84: 1-82; Hatch FT, Knize MG, Felton JS. Environ. Mol. Mutagen. 1991; 17: 4-19; Layton DW, Bogen KT, Knize MG, Hatch FT, Johnson VM, Felton JS. Carcinogenesis 1995; 16: 39-52; Sugimura T. Environ. Health Perspect. 1986; 67: 5-10.
4. Eisenbrand G, Tang W. Toxicology 1993; 84: 1-82; Hatch FT, Knize MG, Felton JS. Environ. Mol. Mutagen. 1991; 17: 4-19; Layton DW, Bogen KT, Knize MG, Hatch FT, Johnson VM, Felton JS. Carcinogenesis 1995; 16: 39-52; Sugimura T. Environ. Health Perspect. 1986; 67: 5-10.
5. Eisenbrand G, Tang W. Toxicology 1993; 84: 1-82; Hatch FT, Knize MG, Felton JS. Environ. Mol. Mutagen. 1991; 17: 4-19; Layton DW, Bogen KT, Knize MG, Hatch FT, Johnson VM, Felton JS. Carcinogenesis 1995; 16: 39-52; Sugimura T. Environ. Health Perspect. 1986; 67: 5-10.
6. Felton JS, Jägerstad M, Knize MG, Skog K, Wakabayashi K, In Food Borne Carcinogens: Heterocyclic Amines, Nagao M, Sugimura T (eds). Wiley: New York, 2000; 31-71.
7. Ohgaki H, Matsukura N, Morino K, Kanachi T, Sugimura T, Takayama S. Carcinogenesis 1984; 5: 815-819; Sugimura T. Mutat. Res. 1985; 150: 33-41.
8. Ohgaki H, Matsukura N, Morino K, Kanachi T, Sugimura T, Takayama S. Carcinogenesis 1984; 5: 815-819; Sugimura T. Mutat. Res. 1985; 150: 33-41.
9. Shinohara A, Saito K, Yamazoe Y, Kamataki T, Kato R. Cancer Res. 1986; 46: 4362-4367; Snyderwine EG, Wirth PJ, Roller PP, Adamson RH, Sato S, Thorgiersson SS. Carcinogenesis 1988; 9: 411-418; Meerman JHN, Ringer DP, Coughtrie MWH, Bamforth KJ, Gilissen RAH. J. Chem.-Biol. Interact. 1994; 92: 321-328.
10. Shinohara A, Saito K, Yamazoe Y, Kamataki T, Kato R. Cancer Res. 1986; 46: 4362-4367; Snyderwine EG, Wirth PJ, Roller PP, Adamson RH, Sato S, Thorgiersson SS. Carcinogenesis 1988; 9: 411-418; Meerman JHN, Ringer DP, Coughtrie MWH, Bamforth KJ, Gilissen RAH. J. Chem.-Biol. Interact. 1994; 92: 321-328.
11. Shinohara A, Saito K, Yamazoe Y, Kamataki T, Kato R. Cancer Res. 1986; 46: 4362-4367; Snyderwine EG, Wirth PJ, Roller PP, Adamson RH, Sato S, Thorgiersson SS. Carcinogenesis 1988; 9: 411-418; Meerman JHN, Ringer DP, Coughtrie MWH, Bamforth KJ, Gilissen RAH. J. Chem.-Biol. Interact. 1994; 92: 321-328.
12. Yamazoe Y, Nagata K. In Food Borne Carcinogens: Heterocyclic Amines, Nagao M, Sugimura T (eds). Wiley: New York, 2000; 74-89; King RS, Kadlubar FF, Turesky RJ. In Food Borne Carcinogens: Heterocyclic Amines, Nagao M, Sugimura T (eds). Wiley: New York, 2000; 90-111.
13. Yamazoe Y, Nagata K. In Food Borne Carcinogens: Heterocyclic Amines, Nagao M, Sugimura T (eds). Wiley: New York, 2000; 74-89; King RS, Kadlubar FF, Turesky RJ. In Food Borne Carcinogens: Heterocyclic Amines, Nagao M, Sugimura T (eds). Wiley: New York, 2000; 90-111.
14. Miller JA. Cancer Res. 1970; 30: 559-576; Lotlikar PD, Scribner JD, Miller JA, Miller EC. Life Sci. 1966; 5: 1263-1269.
15. Miller JA. Cancer Res. 1970; 30: 559-576; Lotlikar PD, Scribner JD, Miller JA, Miller EC. Life Sci. 1966; 5: 1263-1269.
16. Novak M, Rajagopal S. Adv. Phys. Org. Chem. 2001; 36: 167-254.
17. Novak M, Kennedy SA. J. Am. Chem. Soc. 1995; 117: 574-575; Kennedy SA, Novak M, Kolb BA. J. Am. Chem. Soc. 1997; 119: 7654-7664.
18. Novak M, Kennedy SA. J. Am. Chem. Soc. 1995; 117: 574-575; Kennedy SA, Novak M, Kolb BA. J. Am. Chem. Soc. 1997; 119: 7654-7664.
19. McClelland RA, Ahmad A, Dicks AP, Licence VP. J. Am. Chem. Soc. 1999; 121: 3303-3310.
20. Falvey DE. J. Phys. Org. Chem. 1999; 12: 589-596; Srivastava S, Ruane PH, Toscano JP, Sullivan MB, Cramer CJ, Chiapperino D, Reed EC, Falvey DE. J. Am. Chem. Soc. 2000; 122: 8271-8278; Chiapperino D, McIlroy S, Falvey DE. J. Am. Chem. Soc. 2002; 124: 3567-3577.
21. Falvey DE. J. Phys. Org. Chem. 1999; 12: 589-596; Srivastava S, Ruane PH, Toscano JP, Sullivan MB, Cramer CJ, Chiapperino D, Reed EC, Falvey DE. J. Am. Chem. Soc. 2000; 122: 8271-8278; Chiapperino D, McIlroy S, Falvey DE. J. Am. Chem. Soc. 2002; 124: 3567-3577.
22. Falvey DE. J. Phys. Org. Chem. 1999; 12: 589-596; Srivastava S, Ruane PH, Toscano JP, Sullivan MB, Cramer CJ, Chiapperino D, Reed EC, Falvey DE. J. Am. Chem. Soc. 2000; 122: 8271-8278; Chiapperino D, McIlroy S, Falvey DE. J. Am. Chem. Soc. 2002; 124: 3567-3577.
23. Novak M, Xu L, Wolf RA. J. Am. Chem. Soc. 1998; 120: 1643-1644.
24. Novak M, Kazerani S. J. Am. Chem. Soc. 2000; 122: 3606-3616.
25. Novak M, Toth K, Rajagopal S, Brooks M, Hott LL, Moslener M. J. Am. Chem. Soc. 2002; 124: 7972-7981.
26. Novak M, Nguyen T-M. J. Org. Chem. 2003; 68: 9875-9881.
27. Rajagopal S, Brooks ME, Nguyen T-M, Novak M. Tetrahedron 2003; 59: 8003-8010.
28. Novak M, Kahley MJ, Eiger E, Helmick JS, Peters HE. J. Am. Chem. Soc. 1993; 115: 9453-9460.
29. Grivas S. In Food Borne Carcinogens: Heterocyclic Amines, Nagao M, Sugimura T (eds). Wiley: New York, 2000; 5-29.
30. Novak M, Kahley MJ, Lin J, Kennedy SA, Swanegan LA. J. Am. Chem. Soc. 1994; 116: 11626-11627.
31. Srivastava S, Falvey DE. J. Am. Chem. Soc. 1995; 117: 10186-10193.
32. Zhang X-M, Bruno JW, Enyinnaya E. J. Org. Chem. 1998; 63: 4671-4678; Freedman HH. In Carbonium Ions, vol. IV, Olah GA, Schleyer PvR (eds). Wiley: New York, 1973; Chapt. 28.
33. Zhang X-M, Bruno JW, Enyinnaya E. J. Org. Chem. 1998; 63: 4671-4678; Freedman HH. In Carbonium Ions, vol. IV, Olah GA, Schleyer PvR (eds). Wiley: New York, 1973; Chapt. 28.
34. Rangappa KS, Novak M. J. Org. Chem. 1992; 57: 1285-1290; Novak M, Rangappa KS, Manitsas RK. J. Org. Chem. 1993; 58: 7813-7821.
35. Rangappa KS, Novak M. J. Org. Chem. 1992; 57: 1285-1290; Novak M, Rangappa KS, Manitsas RK. J. Org. Chem. 1993; 58: 7813-7821.
36. Williams KB, Richard JP. J. Phys. Org. Chem. 1998; 11:701-706.
37. Richard JP, Jencks WP. J. Am. Chem. Soc. 1982; 104: 4689-4691; 1982; 104: 4691-4692; 1984; 106: 1383-1396; Richard JP, Rothenberg ME, Jencks WP. J. Am. Chem. Soc. 1984; 106: 1361-1372; Kemp DS, Casey ML. J. Am. Chem. Soc. 1973; 95: 6670-6680; Rappaport Z. Tetrahedron Lett. 1979; 2559-2562; Richard JP, Amyes TL, Vontor T. J. Am. Chem. Soc. 1991; 113: 5871-5873; McClelland RA, Kanagasabapathy VM, Banait NS, Steenken S. J. Am. Chem. Soc. 1989; 111: 3966-3972; 1991; 113: 1009-1014.
38. Richard JP, Jencks WP. J. Am. Chem. Soc. 1982; 104: 4689-4691; 1982; 104: 4691-4692; 1984; 106: 1383-1396; Richard JP, Rothenberg ME, Jencks WP. J. Am. Chem. Soc. 1984; 106: 1361-1372; Kemp DS, Casey ML. J. Am. Chem. Soc. 1973; 95: 6670-6680; Rappaport Z. Tetrahedron Lett. 1979; 2559-2562; Richard JP, Amyes TL, Vontor T. J. Am. Chem. Soc. 1991; 113: 5871-5873; McClelland RA, Kanagasabapathy VM, Banait NS, Steenken S. J. Am. Chem. Soc. 1989; 111: 3966-3972; 1991; 113: 1009-1014.
39. Richard JP, Jencks WP. J. Am. Chem. Soc. 1982; 104: 4689-4691; 1982; 104: 4691-4692; 1984; 106: 1383-1396; Richard JP, Rothenberg ME, Jencks WP. J. Am. Chem. Soc. 1984; 106: 1361-1372; Kemp DS, Casey ML. J. Am. Chem. Soc. 1973; 95: 6670-6680; Rappaport Z. Tetrahedron Lett. 1979; 2559-2562; Richard JP, Amyes TL, Vontor T. J. Am. Chem. Soc. 1991; 113: 5871-5873; McClelland RA, Kanagasabapathy VM, Banait NS, Steenken S. J. Am. Chem. Soc. 1989; 111: 3966-3972; 1991; 113: 1009-1014.
40. Richard JP, Jencks WP. J. Am. Chem. Soc. 1982; 104: 4689-4691; 1982; 104: 4691-4692; 1984; 106: 1383-1396; Richard JP, Rothenberg ME, Jencks WP. J. Am. Chem. Soc. 1984; 106: 1361-1372; Kemp DS, Casey ML. J. Am. Chem. Soc. 1973; 95: 6670-6680; Rappaport Z. Tetrahedron Lett. 1979; 2559-2562; Richard JP, Amyes TL, Vontor T. J. Am. Chem. Soc. 1991; 113: 5871-5873; McClelland RA, Kanagasabapathy VM, Banait NS, Steenken S. J. Am. Chem. Soc. 1989; 111: 3966-3972; 1991; 113: 1009-1014.
41. Richard JP, Jencks WP. J. Am. Chem. Soc. 1982; 104: 4689-4691; 1982; 104: 4691-4692; 1984; 106: 1383-1396; Richard JP, Rothenberg ME, Jencks WP. J. Am. Chem. Soc. 1984; 106: 1361-1372; Kemp DS, Casey ML. J. Am. Chem. Soc. 1973; 95: 6670-6680; Rappaport Z. Tetrahedron Lett. 1979; 2559-2562; Richard JP, Amyes TL, Vontor T. J. Am. Chem. Soc. 1991; 113: 5871-5873; McClelland RA, Kanagasabapathy VM, Banait NS, Steenken S. J. Am. Chem. Soc. 1989; 111: 3966-3972; 1991; 113: 1009-1014.
42. Richard JP, Jencks WP. J. Am. Chem. Soc. 1982; 104: 4689-4691; 1982; 104: 4691-4692; 1984; 106: 1383-1396; Richard JP, Rothenberg ME, Jencks WP. J. Am. Chem. Soc. 1984; 106: 1361-1372; Kemp DS, Casey ML. J. Am. Chem. Soc. 1973; 95: 6670-6680; Rappaport Z. Tetrahedron Lett. 1979; 2559-2562; Richard JP, Amyes TL, Vontor T. J. Am. Chem. Soc. 1991; 113: 5871-5873; McClelland RA, Kanagasabapathy VM, Banait NS, Steenken S. J. Am. Chem. Soc. 1989; 111: 3966-3972; 1991; 113: 1009-1014.
43. Richard JP, Jencks WP. J. Am. Chem. Soc. 1982; 104: 4689-4691; 1982; 104: 4691-4692; 1984; 106: 1383-1396; Richard JP, Rothenberg ME, Jencks WP. J. Am. Chem. Soc. 1984; 106: 1361-1372; Kemp DS, Casey ML. J. Am. Chem. Soc. 1973; 95: 6670-6680; Rappaport Z. Tetrahedron Lett. 1979; 2559-2562; Richard JP, Amyes TL, Vontor T. J. Am. Chem. Soc. 1991; 113: 5871-5873; McClelland RA, Kanagasabapathy VM, Banait NS, Steenken S. J. Am. Chem. Soc. 1989; 111: 3966-3972; 1991; 113: 1009-1014.
44. Richard JP, Jencks WP. J. Am. Chem. Soc. 1982; 104: 4689-4691; 1982; 104: 4691-4692; 1984; 106: 1383-1396; Richard JP, Rothenberg ME, Jencks WP. J. Am. Chem. Soc. 1984; 106: 1361-1372; Kemp DS, Casey ML. J. Am. Chem. Soc. 1973; 95: 6670-6680; Rappaport Z. Tetrahedron Lett. 1979; 2559-2562; Richard JP, Amyes TL, Vontor T. J. Am. Chem. Soc. 1991; 113: 5871-5873; McClelland RA, Kanagasabapathy VM, Banait NS, Steenken S. J. Am. Chem. Soc. 1989; 111: 3966-3972; 1991; 113: 1009-1014.
45. Richard JP, Jencks WP. J. Am. Chem. Soc. 1982; 104: 4689-4691; 1982; 104: 4691-4692; 1984; 106: 1383-1396; Richard JP, Rothenberg ME, Jencks WP. J. Am. Chem. Soc. 1984; 106: 1361-1372; Kemp DS, Casey ML. J. Am. Chem. Soc. 1973; 95: 6670-6680; Rappaport Z. Tetrahedron Lett. 1979; 2559-2562; Richard JP, Amyes TL, Vontor T. J. Am. Chem. Soc. 1991; 113: 5871-5873; McClelland RA, Kanagasabapathy VM, Banait NS, Steenken S. J. Am. Chem. Soc. 1989; 111: 3966-3972; 1991; 113: 1009-1014.
46. Fishbein JC, McClelland RA. J. Am. Chem. Soc. 1987; 109: 2824-2825.
47. McClelland RA, Licence VE. Arkivoc 2001; xii: 72-81 (http://www.arkat- usa.org/ark/journal/Volume2/Part3/Tee/OT-286C/OT-286C.pdf).
48. Davidse PA, Kahley MJ, McClelland RA, Novak M. J. Am. Chem. Soc. 1994; 116: 4513-4514.
49. McClelland RA, Gadosy TA, Ren D. Can. J. Chem. 1998; 76: 1327-1337.
50. McClelland RA, Davidse PA, Hadzialic G. J. Am. Chem. Soc. 1995; 117: 4173-4174.
51. Ren D, McClelland RA. Can. J. Chem. 1998; 76: 78-84; Bose R, Ahmad AR, Dicks AP, Novak M, Kayser KJ, McClelland RA. J. Chem. Soc., Perkin Trans. 2 1999; 1591-1599.
52. Ren D, McClelland RA. Can. J. Chem. 1998; 76: 78-84; Bose R, Ahmad AR, Dicks AP, Novak M, Kayser KJ, McClelland RA. J. Chem. Soc., Perkin Trans. 2 1999; 1591-1599.
53. Novak M, Lin J. J. Org. Chem. 1999; 64: 6032-6040.
54. Turesky RJ, Rossi SC, Welti DH, Lay JO Jr, Kadlubar FF. Chem. Res. Toxicol. 1992; 5: 479-490.
55. Snyderwine EG, Turtletaub KW. In Food Borne Carcinogens: Heterocyclic Amines, Nagao M, Sugimura T (eds). Wiley: New York, 2000; 131-161.
56. Ramlall P, McClelland RA. J. Chem. Soc., Perkin Trans. 2 1999; 225-232.
57. Novak M, Roy AK. J. Org. Chem. 1985; 50: 571-580; 1985; 50: 4884-4888.
58. Novak M, Roy AK. J. Org. Chem. 1985; 50: 571-580; 1985; 50: 4884-4888.
59. Muckel E, Frandsen H, Glatt HR. Food Chem. Toxicol. 2002; 40: 1063-1068; Meinl W, Meerman JHN, Glatt HR. Pharmacogenetics 2002; 12: 677-689.
60. Muckel E, Frandsen H, Glatt HR. Food Chem. Toxicol. 2002; 40: 1063-1068; Meinl W, Meerman JHN, Glatt HR. Pharmacogenetics 2002; 12: 677-689.
61. Novak M, Rajagopal S. Chem. Res. Toxicol. 2002; 15:1495-1503.
62. Leo AJ. Chem. Rev. 1993; 93: 1281-1306.
63. Benigni R, Giuliani A, Franke R, Gruska A. Chem. Rev. 2000; 100: 3697-3714.