Stable ion study of benzo[a]pyrene (BaP) derivatives: 7,8-dihydro-BaP, 9,10-dihydro-BaP and its 6-halo derivatives, 1- and 3-methoxy-9,10-dihydro- BaP-7(8H)-one, as well as the proximate carcinogen BaP 7,8-dihydrodiol and its dibenzoate, combined with a comparative DNA binding study of regioisomeric (1-, 4-, 2-) pyrenylcarbinols

Organic and Biomolecular Chemistry

Volumn 1, Issue 9, 2003, Pages 1509-1516

  Okazaki, Takao ^a   Laali, Kenneth K ^a   Zajc, Barbara ^b,c   Lakshman, Mahesh K ^b   Kumar, Subodh ^d   Baird, William M ^e   Dashwood, Wan Mohaiza ^e  

^a KENT STATE UNIVERSITY   (United States)

^b CITY COLLEGE OF NEW YORK   (United States)

^c UNIVERSITY OF LJUBLJANA   (Slovenia)

^d BUFFALO STATE COLLEGE   (United States)

^e OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING ENERGY; CARCINOGENS; DNA; IONS; REACTION KINETICS; SUBSTITUTION REACTIONS;

BENZOPYRENE; DIBENZOATE; DIHYDRODIOL; PYRENYLCARBINOLS;

HYDROCARBONS;

MINK CELL FOCUS-FORMING VIRUS;

EID: 0141940210     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b212412b     Document Type: Article

References (56)

1. R.G. Harvey, Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity, Cambridge University Press, Cambridge, UK, 1991.
2. R.G. Harvey and N.E. Geacintov, Acc. Chem. Res., 1988, 21, 66.
3. R.G. Harvey, Acc. Chem. Res., 1981, 14, 218.
4. T.M. Penning, M.E. Burczynski, C.-F. Hung, K.D. McCoull, N.T. Palackal and L.S. Tsuruda, Chem. Res. Toxicol., 1999, 12, 1.
5. N.T. Nashed, A. Bax, R.J. Loncharich, J.M. Sayer and D.M. Jerina, J. Am. Chem. Soc., 1993, 115, 1711.
6. N.T. Nashed, S.K. Balani, R.J. Loncharich, J.M. Sayer, D.Y. Shipley, D.L. Whalen and D.M. Jerina, J. Am. Chem. Soc., 1991, 113, 3910.
7. N.T. Nashed, T.V.S. Rao and D.M. Jerina, J. Org. Chem., 1993, 58, 6344.
8. J.W. Keller and C. Heidelberger, J. Am. Chem. Soc., 1976, 98, 2328.
9. For representative examples focusing on synthesis of diol epoxide-nucleoside and DNA lesions see: (a) S. Chaturvedi and M.K. Lakshman, Carcinogenesis, 1996, 17, 2747
10. (b) S.J. Kim, M.P. Stone, C.M. Harris and T.M. Harris, J. Am. Chem. Soc., 1992, 114, 5480
11. (c) T. Steinbrecher, A. Becker, J.J. Stezowski, F. Oesch and A. Seidel, Tetrahedron Lett., 1993, 34, 1773
12. (d) B. Mao, J. Xu, B. Li, L.A. Margulis, S. Smirnov, N.Q. Ya, S. Courtney and N.E. Geacintov, Carcinogenesis, 1995, 16, 357
13. (e) H. Kroth, H. Yagi, A. Seidel and D.M. Jerina, J. Org. Chem., 2000, 65, 5558
14. (f) G.R. Negrete and T. Meehan, Tetrahedron Lett., 1994, 35, 4727
15. (g) H. Lee, E. Luna, M. Hinz, J.J. Stezowski, A.S. Kiselyov and R.G. Harvey, J. Org. Chem., 1995, 60, 5604.
16. (a) N.B. Islam, D.L. Whalen and D.M. Jerina, J. Am. Chem. Soc., 1987, 109, 2108
17. (b) S.C. Gupta, N.B. Islam, D.L. Whalen, H. Yagi and D.M. Jerina, J. Org. Chem., 1987, 52, 3812.
18. (a) M.D. Hylarides, T.A. Lyle, G.H. Daub and D.L. Vander Jagt, J. Org. Chem., 1979, 44, 4652
19. (b) T.M. Harris, M.P. Stone and C.M. Harris, Chem. Res. Toxicol., 1988, 1, 79.
20. R.G. Harvey, and F.B. Dunne, Nature, 1978, 273, 566.
21. J.P. Glusker, D.E. Zacharias, H.L. Carrell, P.P. Fu and R.G. Harvey, Cancer Res., 1976, 36, 3951.
22. G.L. Borosky, J. Org. Chem., 2000, 64, 7738.
23. P.J. Lowe and B.D. Silverman, Acc. Chem. Res., 1984, 17, 532.
24. K.H. Stansbury, J.W. Flesher and R.C. Gupta, Chem. Res. Toxicol., 1994, 7, 254
25. (a) R.E. Royer, G.H. Daub and D.L. Vander Jagt, J. Org. Chem., 1979, 44, 3196
26. (b) R.E. Royer, T.A. Lyle, G.G. Moy, G.H. Daub and D.L. Vander Jagt, J. Org. Chem., 1979, 44, 3202
27. (c) L.M. Deck and G.H. Daub, J. Org. Chem., 1983, 48, 3577.
28. (a) R.E. Lehr, C.W. Taylor, S. Kumar, H.D. Mah and D.M. Jerina, J. Org. Chem., 1978, 43, 3462
29. (b) R.G. Harvey, H.M. Lee and N. Shyamasunda, J. Org. Chem., 1979, 44, 78.
30. (a) A.W. Wood, W. Levin, D.R. Thakker, H. Yagi, R.L. Chang, D.E. Ryan, P.E. Thomas, P.M. Dansette, N. Whittaker, S. Turujman, R.E. Lehr, S. Kumar, D.M. Jerina and A.H. Conney, J. Biol. Chem., 1979, 254, 4408
31. (b) M.C. MacLeod, W. Levin, A.H. Conney, R.E. Lehr, B.K. Mansfield, D.M. Jerina and J.K. Selkirk, Carcinogenesis, 1980, 1, 165.
32. L. von Szentpaly and I. L. Shamovsky, Int. J. Quantum Chem., 1995, 191
33. L. von Szentpaly and I. L. Shamovsky, Mol. Pharmacol., 1995, 47, 624.
34. (a) K. K. Laali, P. E. Hansen, J. J. Houser and M. Zander, J. Chem. Soc., Perkin Trans. 2, 1995, 1781
35. (b) K. K. Laali, S. Hollenstein, R. G. Harvey and P. E. Hansen, J. Org. Chem., 1997, 62, 4023
36. (c) K. K. Laali and P. E. Hansen, J. Org. Chem., 1997, 62, 5804
37. (d) K. K. Laali, M. Tanaka, S. Hollenstein and M. Cheng, J. Org. Chem., 1997, 62, 7752.
38. (a) K. K. Laali and M. Tanaka, J. Org. Chem., 1998, 63, 7280
39. (b) K. K. Laali, M. Tanaka and P. E. Hansen, J. Org. Chem., 1998, 63, 8217
40. (c) K. K. Laali and S. Hollenstein, J. Chem. Soc., Perkin Trans. 2, 1998, 897.
41. (a) K. K. Laali, S. Hollenstein, S. E. Galembeck and M. M. Coombs, J. Chem. Soc., Perkin Trans. 2, 2000, 211
42. (b) K. K. Laali, T. Okazaki and M. M. Coombs, J. Org. Chem., 2000, 65, 7399.
43. (a) F. Oesch, G. Stillger, H. Frank and K. L. Platt, J. Org. Chem., 1982, 47, 568
44. (b) S. E. Klassen, G. H. Daub and D. L. Vander Jagt, J. Org. Chem., 1983, 48, 4361.
45. B. Zajc, J. Org. Chem., 1999, 64, 1902.
46. S. Kumar, P. L. Kole and R. K. Sehgal, J. Org. Chem., 1989, 54, 5272.
47. P. Cremonesi, E. L. Cavalieri and E. G. Rogan, J. Org. Chem., 1989, 54, 3561.
48. G. A. Olah, P. W. Westerman and D. A. Forsyth, J. Am. Chem. Soc., 1975, 97, 3419.
49. G. A. Olah and P. W. Westerman, J. Am. Chem. Soc., 1973, 95, 3706.
50. V. P. Reddy, D. R. Bellow and G. K. S. Prakash, J. Fluorine Chem., 1992, 56, 195.
51. Gaussian 98, Revision A. 9, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery Jr., R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, A. G. Baboul, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1998.
52. (a) I. Moežk and B. Šket, Synth. Commun., 1992, 2513
53. D. Dolenc and B. Šket, Synlett, 1995, 327
54. (b) P. Anandasundaresan, V. S. Panchatsharam, K. Nagarajan, V. Balasubramanian and N. Venkatasubramanian, Indian J. Chem. Sect. A: Inorg., Bio-inorg., Phys., Theor. Anal. Chem., 1980, 19, 576.
55. V. J. Melendez-Colon, A. Luch, A. Seidel and W. M. Baird, Chem. Res. Toxicol., 2000, 13, 10
56. A. Luch, W. Schoder, H. Grein, J. Doehmer, J. Jacob, A. Seidel and W. M. Baird, Polycyclic Aromat. Compd., 2000, 21, 1.