Reactions of ester derivatives of carcinogenic N-(4-biphenylyl)hydroxylamine and the corresponding hydroxamic acid with purine nucleosides

Journal of the American Chemical Society

Volumn 119, Issue 33, 1997, Pages 7654-7664

  Kennedy, Sonya A ^a   Novak, Michael ^a   Kolb, Brent A ^a  

^a MIAMI UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE; CARCINOGEN; GUANOSINE; INOSINE; PURINE NUCLEOSIDE;

ARTICLE; CARCINOGENESIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; DNA ADDUCT; KINETICS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030929002     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970698p     Document Type: Article

References (55)

1. (a) Kriek, E. Chem.-Biol. Interact. 1969, 1, 3-17.
2. (b) Kriek, E. Chem.-Biol. Interact. 1971, 3, 19-28.
3. (c) Meerman, J. H. N.; Beland, F. A.; Mulder, G. J. Carcinogenesis 1981, 2, 413-416.
4. (d) Fuchs, R. P. P. Anal. Biochem. 1978, 91, 663-673.
5. (e) Beland, F. A.; Dooley, K. L.; Jackson, C. D. Cancer Res. 1982, 42, 1348-1354.
6. (f) Tamura, N.; King, C. M. Carcinogenesis 1990, 11, 535-540.
7. (g) Kriek, E.; Miller, J. A.; Juhl, U.; Miller, E. C. Biochemistry 1967, 6, 177-182.
8. (h) Nelson, J. H.; Grunberger, D.; Cantor, C. R.; Weinstein, I. B. J. Mol. Biol. 1971, 62, 331-346.
9. (i) Evans, F. E.; Miller, D. W.; Levine, R. A. J. Am. Chem. Soc. 1984, 106, 396-401.
10. Underwood, G. R.; Price, M. F.; Shapiro, R. Carcinogenesis 1988, 9, 1817-1821. Lee, M.-S.; King, C. M. Chem.-Biol. Interact. 1981, 34, 239-248. Van de Poll, M. L. M.; Van der Hulst, D. A. M.; Tates, A. D.; Meerman, J. Carcinogenesis 1990, 11, 333-339. Shapiro, R.; Underwood, G. R.; Zawadzka, H.; Broyde, S.; Hingerty, B. Biochemistry 1986, 25, 2198-2205.
11. Underwood, G. R.; Price, M. F.; Shapiro, R. Carcinogenesis 1988, 9, 1817-1821. Lee, M.-S.; King, C. M. Chem.-Biol. Interact. 1981, 34, 239-248. Van de Poll, M. L. M.; Van der Hulst, D. A. M.; Tates, A. D.; Meerman, J. Carcinogenesis 1990, 11, 333-339. Shapiro, R.; Underwood, G. R.; Zawadzka, H.; Broyde, S.; Hingerty, B. Biochemistry 1986, 25, 2198-2205.
12. Underwood, G. R.; Price, M. F.; Shapiro, R. Carcinogenesis 1988, 9, 1817-1821. Lee, M.-S.; King, C. M. Chem.-Biol. Interact. 1981, 34, 239-248. Van de Poll, M. L. M.; Van der Hulst, D. A. M.; Tates, A. D.; Meerman, J. Carcinogenesis 1990, 11, 333-339. Shapiro, R.; Underwood, G. R.; Zawadzka, H.; Broyde, S.; Hingerty, B. Biochemistry 1986, 25, 2198-2205.
13. Underwood, G. R.; Price, M. F.; Shapiro, R. Carcinogenesis 1988, 9, 1817-1821. Lee, M.-S.; King, C. M. Chem.-Biol. Interact. 1981, 34, 239-248. Van de Poll, M. L. M.; Van der Hulst, D. A. M.; Tates, A. D.; Meerman, J. Carcinogenesis 1990, 11, 333-339. Shapiro, R.; Underwood, G. R.; Zawadzka, H.; Broyde, S.; Hingerty, B. Biochemistry 1986, 25, 2198-2205.
14. Novak, M.; Kennedy, S. A. J. Am. Chem. Soc. 1995, 117, 574-575.
15. Humphreys, W. G.; Kadlubar, F. F.; Guengerich, F. P. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 8278-8282.
16. (a) Beland, F. A.; Kadlubar, F. F. Environ. Health Perspect. 1985, 62, 19-30.
17. (b) Beland, F. A.; Kadlubar, F. F. In Chemical Carcinogenesis and Mutagenesis I; Cooper, C. S., Grover, P. L., Eds.; Springer-Verlag: Berlin, 1990; pp 267-326.
18. (c) Swaminathan, S.; Frederickson, S. M.; Hatcher, J. F. Carcinogenesis 1994, 14, 611-617.
19. (d) Scribner, J. D.; Smith, P. L.; McCloskey, J. A. J. Org. Chem. 1978, 43, 2085-2087.
20. (e) Scribner, J. D.; Naimy, N. K. Cancer Res. 1975, 35, 1416-1421.
21. Novak, M.; Pelecanou, M.; Roy, A. K.; Andronico, A. F.; Plourde, F. M.; Olefirowicz, T. M.; Curtin, T. J. J. Am. Chem. Soc. 1984, 106, 5623-5631.
22. Novak, M.; Kahley, M. J.; Eiger, E.; Helmick, J. S.; Peters, H. E. J. Am. Chem. Soc. 1993, 115, 9453-9460.
23. Helmick, J. S.; Martin, K. A.; Heinrich, J. L.; Novak, M. J. Am. Chem. Soc. 1991, 113, 3459-3466. Novak, M.; Helmick, J. S.; Oberlies, N.; Rangappa, K. S.; Clark, W. M.; Swenton, J. S. J. Org. Chem. 1993, 53, 867-878.
24. Helmick, J. S.; Martin, K. A.; Heinrich, J. L.; Novak, M. J. Am. Chem. Soc. 1991, 113, 3459-3466. Novak, M.; Helmick, J. S.; Oberlies, N.; Rangappa, K. S.; Clark, W. M.; Swenton, J. S. J. Org. Chem. 1993, 53, 867-878.
25. Maeda, M.; Nushi, K.; Kawazoe, Y. Tetrahedron 1974, 30, 2677-2682.
26. Hazlet, S. E.; Dornfeld, C. A. J. Am. Chem. Soc. 1544, 66, 1781-1782.
27. Chenon, M.-T.; Pugmire, R. J.; Grant, D. M.; Panzica, R. P.; Townsend, L. B. J. Am. Chem. Soc. 1975, 97, 4627-4636.
28. Albright, J. D.; Lieberman, D. F. J. Heterocycl. Chem. 1994, 31, 537-539.
29. (a) Lange, W.; Tückmantel, W. Chem. Ber. 1989, 122, 1765-1776.
30. (b) Vogel, E.; Altenbach, H.-J.; Drossard, J.-M.; Schmickler, H.; Stegelmeier, H. Angew. Chem., Int. Ed. Engl. 1980, 19, 1016-1018.
31. (a) Davidse, P. A.; Kahley, M. J.; McClelland, R. A.; Novak, M. J. Am. Chem. Soc. 1994, 116, 4513-4514.
32. (b) McClelland, R. A.; Davidse, P. A.; Hadzialic, G. J. Am. Chem. Soc. 1995, 117, 4173-4174.
33. s determined for different products in the same reaction were in good agreement (±15%). Average values obtained from all products are reported in this paper.
34. Dunn, D. B.; Hall, R. H. In CRC Handbook of Biochemistry and Molecular Biology, Nucleic Acids, 3rd ed.; Fasman, G. D., Ed.; CRC Press: Inc.; Cleveland, OH, 1975; Vol. 1, pp 65-215.
35. Sigel, H.; Massoud, S. S.; Corfu, N. A. J. Am. Chem. Soc. 1994, 116, 2958-2971. Evans, F. E.; Sarma, R. H. J. Mol. Biol. 1974, 89, 249-253. Martin, R. B. Acc. Chem. Res. 1985, 18, 32-38. Lönnberg, H.; Vihanto, P. Inorg. Chim. Acta 1981, 56, 157-161. Rawitscher, M.; Sturtevant, J. J. Am. Chem. Soc. 1960, 82, 3739-3740. Jencks, W. P.; Regenstein, J. In CRC Handbook of Biochemistry and Molecular Biology, Physical and Chemical Data, 3rd ed.; Fasman, G. D., Ed.; CRC Press: Inc.; Cleveland, OH, 1975; Vol. 1, pp 305-352.
36. Sigel, H.; Massoud, S. S.; Corfu, N. A. J. Am. Chem. Soc. 1994, 116, 2958-2971. Evans, F. E.; Sarma, R. H. J. Mol. Biol. 1974, 89, 249-253. Martin, R. B. Acc. Chem. Res. 1985, 18, 32-38. Lönnberg, H.; Vihanto, P. Inorg. Chim. Acta 1981, 56, 157-161. Rawitscher, M.; Sturtevant, J. J. Am. Chem. Soc. 1960, 82, 3739-3740. Jencks, W. P.; Regenstein, J. In CRC Handbook of Biochemistry and Molecular Biology, Physical and Chemical Data, 3rd ed.; Fasman, G. D., Ed.; CRC Press: Inc.; Cleveland, OH, 1975; Vol. 1, pp 305-352.
37. Sigel, H.; Massoud, S. S.; Corfu, N. A. J. Am. Chem. Soc. 1994, 116, 2958-2971. Evans, F. E.; Sarma, R. H. J. Mol. Biol. 1974, 89, 249-253. Martin, R. B. Acc. Chem. Res. 1985, 18, 32-38. Lönnberg, H.; Vihanto, P. Inorg. Chim. Acta 1981, 56, 157-161. Rawitscher, M.; Sturtevant, J. J. Am. Chem. Soc. 1960, 82, 3739-3740. Jencks, W. P.; Regenstein, J. In CRC Handbook of Biochemistry and Molecular Biology, Physical and Chemical Data, 3rd ed.; Fasman, G. D., Ed.; CRC Press: Inc.; Cleveland, OH, 1975; Vol. 1, pp 305-352.
38. Sigel, H.; Massoud, S. S.; Corfu, N. A. J. Am. Chem. Soc. 1994, 116, 2958-2971. Evans, F. E.; Sarma, R. H. J. Mol. Biol. 1974, 89, 249-253. Martin, R. B. Acc. Chem. Res. 1985, 18, 32-38. Lönnberg, H.; Vihanto, P. Inorg. Chim. Acta 1981, 56, 157-161. Rawitscher, M.; Sturtevant, J. J. Am. Chem. Soc. 1960, 82, 3739-3740. Jencks, W. P.; Regenstein, J. In CRC Handbook of Biochemistry and Molecular Biology, Physical and Chemical Data, 3rd ed.; Fasman, G. D., Ed.; CRC Press: Inc.; Cleveland, OH, 1975; Vol. 1, pp 305-352.
39. Sigel, H.; Massoud, S. S.; Corfu, N. A. J. Am. Chem. Soc. 1994, 116, 2958-2971. Evans, F. E.; Sarma, R. H. J. Mol. Biol. 1974, 89, 249-253. Martin, R. B. Acc. Chem. Res. 1985, 18, 32-38. Lönnberg, H.; Vihanto, P. Inorg. Chim. Acta 1981, 56, 157-161. Rawitscher, M.; Sturtevant, J. J. Am. Chem. Soc. 1960, 82, 3739-3740. Jencks, W. P.; Regenstein, J. In CRC Handbook of Biochemistry and Molecular Biology, Physical and Chemical Data, 3rd ed.; Fasman, G. D., Ed.; CRC Press: Inc.; Cleveland, OH, 1975; Vol. 1, pp 305-352.
40. Sigel, H.; Massoud, S. S.; Corfu, N. A. J. Am. Chem. Soc. 1994, 116, 2958-2971. Evans, F. E.; Sarma, R. H. J. Mol. Biol. 1974, 89, 249-253. Martin, R. B. Acc. Chem. Res. 1985, 18, 32-38. Lönnberg, H.; Vihanto, P. Inorg. Chim. Acta 1981, 56, 157-161. Rawitscher, M.; Sturtevant, J. J. Am. Chem. Soc. 1960, 82, 3739-3740. Jencks, W. P.; Regenstein, J. In CRC Handbook of Biochemistry and Molecular Biology, Physical and Chemical Data, 3rd ed.; Fasman, G. D., Ed.; CRC Press: Inc.; Cleveland, OH, 1975; Vol. 1, pp 305-352.
41. Kim, S.-H.; Martin, R. B. Inorg. Chim. Acta 1984, 91, 19-24.
42. 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.
43. 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.
44. Novak, M.; Rangappa, K. S. J. Org. Chem. 1992, 57, 1285-1290. Novak, M.; Rangappa, K. S.; Manitsas, R. K. J. Org. Chem. 1993, 58, 7813-7821.
45. Novak, M.; Rangappa, K. S. J. Org. Chem. 1992, 57, 1285-1290. Novak, M.; Rangappa, K. S.; Manitsas, R. K. J. Org. Chem. 1993, 58, 7813-7821.
46. Novak, M.; Lin, J. J. Am. Chem. Soc. 1996, 118, 1302-1308.
47. Novak, M.; Pelecanou, M. Unpublished results.
48. McClelland, R. A. Personal communication.
49. Novak, M.; Kennedy, S. A. J. Phys. Org. Chem. 1997, in press.
50. Novak, M.; Kahley, M. J.; Lin, J.; Kennedy, S. A.; Swanegan, L. A. J. Am. Chem. Soc. 1995, 117, 574-575. Novak, M.; Kahley, M. J.; Lin, J.; Kennedy, S. A.; James, T. G. J. Org. Chem. 1995, 60, 8294-8304.
51. Novak, M.; Kahley, M. J.; Lin, J.; Kennedy, S. A.; Swanegan, L. A. J. Am. Chem. Soc. 1995, 117, 574-575. Novak, M.; Kahley, M. J.; Lin, J.; Kennedy, S. A.; James, T. G. J. Org. Chem. 1995, 60, 8294-8304.
52. Dipple, A. Carcinogenesis 1995, 16, 437-441.
53. Kriek, E. Cancer Res. 1972, 32, 2042-2048. Westra, J. G.; Kriek, E.; Hittenhausen, H. Chem.-Biol. Interact. 1976, 15, 149-164.
54. Kriek, E. Cancer Res. 1972, 32, 2042-2048. Westra, J. G.; Kriek, E.; Hittenhausen, H. Chem.-Biol. Interact. 1976, 15, 149-164.
55. Kriek, E.; Hengeveld, G. M. Chem.-Biol. Interact. 1978, 21, 179-201.