Spectroscopic characterization of the initial C8 intermediate in the reaction of the 2-fluorenylnitrenium ion with 2'-deoxyguanosine

Journal of the American Chemical Society

Volumn 121, Issue 14, 1999, Pages 3303-3310

  McClelland, Robert A ^a   Ahmad, Abid ^a   Dicks, Andrew P ^a   Licence, Victoria E ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

2 FLUORENYLAMINE; DEOXYGUANOSINE; FLUORENE; N HYDROXY 2 FLUORENYLAMINE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; IRRADIATION; PH MEASUREMENT; PHOTOLYSIS; REACTION ANALYSIS; REACTION TIME; SPECTROSCOPY;

EID: 0033553130     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9836702     Document Type: Article

References (51)

1. Beland, F. A.; Kadlubar, F. F. In Handbook of Experimental Pharmacology; Cooper, C. S., Grover, P. L., Eds.; Springer-Verlag: Heidelberg, 1990; Vol. 94/I, pp 267-325. Kriek, E. J. Cancer Res. Clin. Oncol. 1992, 118, 481-189. (c) Heflich, R. H.; Neft, R. E. Mutat. Res. 1994, 318, 73-174. Hoffman, G. R.; Fuchs, R. P. P. Chem. Res. Toxicol. 1997, 10, 347-359. Patel, D. J.; Mao, B.; Gu, Z.; Hingerty, B. E.; Gorin, A.; Basu, A. K.; Broyde, S. Chem. Res. Toxicol. 1998, 11, 391-407.
2. Beland, F. A.; Kadlubar, F. F. In Handbook of Experimental Pharmacology; Cooper, C. S., Grover, P. L., Eds.; Springer-Verlag: Heidelberg, 1990; Vol. 94/I, pp 267-325. Kriek, E. J. Cancer Res. Clin. Oncol. 1992, 118, 481-189. (c) Heflich, R. H.; Neft, R. E. Mutat. Res. 1994, 318, 73-174. Hoffman, G. R.; Fuchs, R. P. P. Chem. Res. Toxicol. 1997, 10, 347-359. Patel, D. J.; Mao, B.; Gu, Z.; Hingerty, B. E.; Gorin, A.; Basu, A. K.; Broyde, S. Chem. Res. Toxicol. 1998, 11, 391-407.
3. Beland, F. A.; Kadlubar, F. F. In Handbook of Experimental Pharmacology; Cooper, C. S., Grover, P. L., Eds.; Springer-Verlag: Heidelberg, 1990; Vol. 94/I, pp 267-325. Kriek, E. J. Cancer Res. Clin. Oncol. 1992, 118, 481-189. (c) Heflich, R. H.; Neft, R. E. Mutat. Res. 1994, 318, 73-174. Hoffman, G. R.; Fuchs, R. P. P. Chem. Res. Toxicol. 1997, 10, 347-359. Patel, D. J.; Mao, B.; Gu, Z.; Hingerty, B. E.; Gorin, A.; Basu, A. K.; Broyde, S. Chem. Res. Toxicol. 1998, 11, 391-407.
4. Beland, F. A.; Kadlubar, F. F. In Handbook of Experimental Pharmacology; Cooper, C. S., Grover, P. L., Eds.; Springer-Verlag: Heidelberg, 1990; Vol. 94/I, pp 267-325. Kriek, E. J. Cancer Res. Clin. Oncol. 1992, 118, 481-189. (c) Heflich, R. H.; Neft, R. E. Mutat. Res. 1994, 318, 73-174. Hoffman, G. R.; Fuchs, R. P. P. Chem. Res. Toxicol. 1997, 10, 347-359. Patel, D. J.; Mao, B.; Gu, Z.; Hingerty, B. E.; Gorin, A.; Basu, A. K.; Broyde, S. Chem. Res. Toxicol. 1998, 11, 391-407.
5. Beland, F. A.; Kadlubar, F. F. In Handbook of Experimental Pharmacology; Cooper, C. S., Grover, P. L., Eds.; Springer-Verlag: Heidelberg, 1990; Vol. 94/I, pp 267-325. Kriek, E. J. Cancer Res. Clin. Oncol. 1992, 118, 481-189. (c) Heflich, R. H.; Neft, R. E. Mutat. Res. 1994, 318, 73-174. Hoffman, G. R.; Fuchs, R. P. P. Chem. Res. Toxicol. 1997, 10, 347-359. Patel, D. J.; Mao, B.; Gu, Z.; Hingerty, B. E.; Gorin, A.; Basu, A. K.; Broyde, S. Chem. Res. Toxicol. 1998, 11, 391-407.
6. Weissberger, J. H. In Carcinogenic and Mutagenic Responses to Aromatic Amines and Nitroarenes; King, C. M., Romano, L. J., Schueltze, D., Eds.; Elsevier: New York, pp 3-19. Sugimura, T. Science 1992, 258, 603-607. Vineis, P. Environ. Health Perspect. 1994, 102, 7-10. Layton, D. W.; Bogen, K. T.; Knize, M. G.; Hatch, F. T.; Johnson, V. M.; Felton, J. S. Carcinogenesis 1995, 16, 35-52.
7. Weissberger, J. H. In Carcinogenic and Mutagenic Responses to Aromatic Amines and Nitroarenes; King, C. M., Romano, L. J., Schueltze, D., Eds.; Elsevier: New York, pp 3-19. Sugimura, T. Science 1992, 258, 603-607. Vineis, P. Environ. Health Perspect. 1994, 102, 7-10. Layton, D. W.; Bogen, K. T.; Knize, M. G.; Hatch, F. T.; Johnson, V. M.; Felton, J. S. Carcinogenesis 1995, 16, 35-52.
8. Weissberger, J. H. In Carcinogenic and Mutagenic Responses to Aromatic Amines and Nitroarenes; King, C. M., Romano, L. J., Schueltze, D., Eds.; Elsevier: New York, pp 3-19. Sugimura, T. Science 1992, 258, 603-607. Vineis, P. Environ. Health Perspect. 1994, 102, 7-10. Layton, D. W.; Bogen, K. T.; Knize, M. G.; Hatch, F. T.; Johnson, V. M.; Felton, J. S. Carcinogenesis 1995, 16, 35-52.
9. Weissberger, J. H. In Carcinogenic and Mutagenic Responses to Aromatic Amines and Nitroarenes; King, C. M., Romano, L. J., Schueltze, D., Eds.; Elsevier: New York, pp 3-19. Sugimura, T. Science 1992, 258, 603-607. Vineis, P. Environ. Health Perspect. 1994, 102, 7-10. Layton, D. W.; Bogen, K. T.; Knize, M. G.; Hatch, F. T.; Johnson, V. M.; Felton, J. S. Carcinogenesis 1995, 16, 35-52.
10. Dipple, A. Carcinogenesis 1995, 16, 437-441.
11. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochim. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer. Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182: American Chemical Society: Washington, DC, 1984; Vol. 1, pp 175-276.
12. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochim. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer. Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182: American Chemical Society: Washington, DC, 1984; Vol. 1, pp 175-276.
13. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochim. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer. Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182: American Chemical Society: Washington, DC, 1984; Vol. 1, pp 175-276.
14. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochim. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer. Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182: American Chemical Society: Washington, DC, 1984; Vol. 1, pp 175-276.
15. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochim. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer. Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182: American Chemical Society: Washington, DC, 1984; Vol. 1, pp 175-276.
16. Miller, J. A. Cancer Res. 1970, 30, 559-576. Kriek, E. Biochim. Biophys. Acta 1974, 335, 177-203. Miller, E. C. Cancer. Res. 1978, 38, 1479-1496. Miller, E. C.; Miller, J. A. Cancer 1981, 47, 2327-2345. Miller, J. A.; Miller, E. C. Environ. Health Perspect. 1983, 49, 3-12. Garner, R. C.; Martin, C. N.; Clayson, D. B. In Chemical Carcinogens, 2nd ed.; Searle, C. E., Ed.; ACS Monograph 182: American Chemical Society: Washington, DC, 1984; Vol. 1, pp 175-276.
17. Novak, M.; Martin, K. A.; Heinrich, J. L. J. Org. Chem. 1989, 54, 5430-5431. Ulbrich, R.; Famulok, M.; Bosold, F.; Boche, G. Tetrahedron Lett. 1990, 31, 1689-1692. Helmick, J. S.; Martin, K. A.; Heinrich, J. L.; Novak, M. J. Am. Chem. Soc. 1991, 113, 3459-3466.
18. Novak, M.; Martin, K. A.; Heinrich, J. L. J. Org. Chem. 1989, 54, 5430-5431. Ulbrich, R.; Famulok, M.; Bosold, F.; Boche, G. Tetrahedron Lett. 1990, 31, 1689-1692. Helmick, J. S.; Martin, K. A.; Heinrich, J. L.; Novak, M. J. Am. Chem. Soc. 1991, 113, 3459-3466.
19. Novak, M.; Martin, K. A.; Heinrich, J. L. J. Org. Chem. 1989, 54, 5430-5431. Ulbrich, R.; Famulok, M.; Bosold, F.; Boche, G. Tetrahedron Lett. 1990, 31, 1689-1692. Helmick, J. S.; Martin, K. A.; Heinrich, J. L.; Novak, M. J. Am. Chem. Soc. 1991, 113, 3459-3466.
20. (a) Novak, M.; Kennedy, S. A. J. Am. Chem. Soc. 1995, 117, 574-575.
21. (b) Kennedy, S. A.; Novak, M.; Kolb, B. A. J. Am. Chem. Soc. 1997, 119, 7654-7664.
22. Novak, M.; Kennedy, S. A. J. Phys. Org. Chem. 1998, 11, 71-76.
23. (a) Davidse, P. A.; Kahley, M. J.; McClelland, R. A.; Novak, M. J. Am. Chem. Soc. 1994, 116, 4513-4514.
24. (b) McClelland, R. A.; Davidse, P. A.; Hadzialic, G. J. Am. Chem. Soc. 1995, 117, 4173-4174.
25. (c) McClelland, R. A.; Kahley, M. J.; Davidse, P. A. J. Phys. Org. Chem. 1996, 9, 355-360.
26. (d) McClelland, R. A.; Kahley, M. J.; Davidse, P. A.; Hadzialic, G. J. Am. Chem. Soc. 1996, 118, 4794-4803.
27. (e) Ren, D.; McClelland, R. A. Can. J. Chem. 1998, 76, 78-84.
28. (f) McClelland, R. A.; Gadosy, T. A.; Ren, D. Can. J. Chem. 1998, 76, 1327-1337.
29. (a) Arylnitrenium ions have also been studied by LFP by Falvey and co-workers.
30. (b) Anderson, G. B.; Falvey, D. E. J. Am. Chem. Soc. 1993, 115, 9870-9871.
31. (c) Robbins, R. J.; Yang, L. L.-N.; Anderson, G. B.; Falvey, D. E. J. Am. Chem. Soc. 1995, 117, 6544-6552.
32. (d) Srivasta, S.; Falvey, D. E. J. Am. Chem. Soc. 1995, 117, 10186-10193.
33. (e) Robbins, R. J.; Laman, D. M.; Falvey, D. E. J. Am. Chem. Soc. 1996, 118, 8127-8135.
34. (f) Moran, R. J.; Falvey, D. E. J. Am. Chem. Soc. 1996, 118, 8965-8966.
35. (g) Srivasta, S.; Toscane, J. P.; Moran, R. J.; Falvey, D. E. J. Am. Chem. Soc. 1997, 119, 11552-11553.
36. Humphreys, W. G.; Kadlubar, F. F.; Guengerich, F. P. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 8278-8282 and references therein.
37. 8f
38. Schuster, G. B.; Platz, M. S. Adv. Photochem. 1992, 17, 69-143.
39. This applies to wavelengths above 310 nm only. Below this wavelength, the dG present in the solution also absorbs.
40. 8d
41. Zoltewicz, J. A.; Clark, D. F., Sharpless, T. W.; Grahe, G. J. Am. Chem. Soc. 1970, 92, 1741-1750.
42. Haines, J. A.; Reese, C. B.; Todd, L. J. Chem. Soc. 5281-5288. Hecht, S. M.; Adams, B. L.; Kozarich, J. W. J. Org. Chem. 1976, 41, 2303-2311.
43. Haines, J. A.; Reese, C. B.; Todd, L. J. Chem. Soc. 5281-5288. Hecht, S. M.; Adams, B. L.; Kozarich, J. W. J. Org. Chem. 1976, 41, 2303-2311.
44. Tomasz, M.; Olson, J.; Mercado, C. M. Biochemistry 1972, 11, 1235-1241.
45. -1. This, moreover, is an upper limit, since the kinetics shows no sign that such a process is occurring.
46. Steenken, S.; McClelland, R. A. J. Am. Chem. Soc. 1990, 112, 9648-9649.
47. Mathivanan, N.; Cozens, F.; McClelland, R. A.; Steenken, S. J. Am. Chem. Soc. 1992, 114, 2198-2203.
48. 6b,8f
49. Tsang, P.; Vold, R. R.; Vold, R. L. J. Magn. Reson. 1987, 71, 276-283.
50. Kriek, E.; Westra, J. G. Carcinogenesis 1980, 1, 459.
51. Allen, A. A.; Kresge, A. J.; Schepp, N. P.; Tidwell, T. T. Can. J. Chem. 1987, 65, 1719.