EPR spectroscopic reinvestigation of the activation of iron complexes of PMAH as a bleomycin model

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 780-784

  Lippai, István ^a   Magliozzo, Richard S ^a   Peisach, Jack ^a  

^a ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 [[N (AMINOETHYL)AMINO]METHYL] 4 [N [2 (4 IMIDAZOLYL)ETHYL]CARBAMOYL] 5 BROMOPYRIDINE; BENZENE DERIVATIVE; BLEOMYCIN; BLEOMYCIN A2; BLEOMYCIN DERIVATIVE; BLEOMYCIN SULFATE; HYDROPEROXIDE; IRON COMPLEX; METHANOL; PYRIDINE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CANCER INHIBITION; CHEMICAL MODIFICATION; DRUG MECHANISM; ELECTRON SPIN RESONANCE; MASS SPECTROMETRY; METAL BINDING; PROTEIN DOMAIN; TITRIMETRY;

EID: 0033518614     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja980458p     Document Type: Article

References (47)

1. Umezawa, H. In Bleomycin; Hecht, S. M., Ed.; Springer-Verlag: New York, 1979; pp 24-36.
2. Sausville, E. A.; Stein, R. W.; Peisach, J.; Horwitz, S. B. Biochemistry 1978, 17, 2746.
3. Burger, R. M.; Peisach, J.; Blumberg, W. E.; Horwitz, S. B. J. Biol. Chem. 1979, 254, 10906.
4. Burger, R. M.; Peisach, J.; Wittenberg, J. J. Biol. Chem. 1979, 254, 12299.
5. Suzuki, H.; Nagai, K.; Yamaki, H.; Tanaka, N.; Umezawa, H. J. Antibiot. 1969, 22, 446.
6. Burger, R. M.; Peisach, J.; Horwitz, S. J. Biol. Chem. 1981, 256, 11636.
7. Sam, J. W.; Tang, X.-J.; Peisach, J. J. Am. Chem. Soc. 1994, 116, 5250.
8. Wu, J. C.; Kozarich, J. W.; Stubbe, J. J. Biol. Chem. 1983, 256, 8606.
9. Wu, J. C.; Kozarich, J. W.; Stubbe, J. Biochemistry 1985, 24, 7562.
10. D'Andrea, A. D.; Hasseltine, W. A. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 3608.
11. Takeshita, M.; Grollman, A. P.; Ohtsubo, E.; Ohtsubo, H. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 5983.
12. Wu, W.; Vanderwall, D. E.; Lui, S. M.; Tang, X. J.; Turner, C. J.; Kozarich, J. W.; Stubbe, J. J. Am. Chem. Soc. 1996, 118, 1268.
13. Boger, D. L.; Ramsey, T. M.; Cai, H.; Hoehn, S. T.; Kozarich, J. W.; Stubbe, J. J. Am. Chem. Soc. 1998, 120, 53.
14. Sam, J. W.; Takahashi, S.; Lippai, I.; Peisach, J.; Rousseau, D. L. J. Biol. Chem. 1998, 273, 16090.
15. Guajardo, R. J.; Hudson, S. E.; Brown, S. J.; Mascharak, P. K. J. Am. Chem. Soc. 1993, 115, 7971.
16. 15 labeled this reaction the reversal of monooxygenase chemistry, implying the formation of an iron oxene preceding the formation of the ferric peroxide complex, Sauer-Masarwa et al. (Sauer-Masarwa, A.; Herron, N.; Fendrick, C. M.; Busch, D. H. Inorg. Chem. 1993, 32, 1086) argued that other mechanistic interpretations of this reaction are possible.
17. Dawson, J. H. Science 1988, 240, 433 and references therein.
18. Padbury, G.; Sligar, S. G.; Labeque, R.; Marnett, L. J. Biochemistry 1988, 27, 7846.
19. Magliozzo, R. S.; Peisach, J. Inorg. Chem. 1989, 28, 608.
20. Sam, J. W.; Tang, X.-J.; Magliozzo, R. S.; Peisach, J. J. Am. Chem. Soc. 1995, 117, 1012.
21. Brown, S. J.; Stephan, D. W.; Mascharak, P. K. J. Am. Chem. Soc. 1988, 110, 1996.
22. Newman, M. S. J. Am. Chem. Soc. 1940, 62, 2295.
23. Noller, C. R.; Bannerot, R. A. J. Am. Chem. Soc. 1934, 56, 1563.
24. Gerrard, W. J. Chem. Soc. 1939, 99.
25. Bissinger, W. E.; Kung, F. E. J. Am. Chem. Soc. 1947, 69, 2158.
26. Cotton, F. A.; Francis, R. J. Am. Chem. Soc. 1960, 82, 2986.
27. Saltzman, H.; Sharefkin, J. G. Org. Synth. 1963, 43, 60.
28. 3OH mixtures with v/v ratios of 1:1, 1.3:1, and 1:1.3.
29. 3OH. This has been confirmed by ionspray mass spectrometry.
30. Gupta, R. K.; Mildvan, A. S.; Schonbaum, G. R. Biochem. Biophys. Res. Commun. 1979, 89, 1334.
31. Burger, R. M.; Blanchard J. S.; Horwitz, S. B.; Peisach, J. J. Biol. Chem. 1985, 260, 15406.
32. IIIBLM in the presence of base (data not shown).
33. Sugiura, Y. J. Am. Chem. Soc. 1980, 102, 5208.
34. Lecomte, C.; Chadwick, D. L.; Coppens, P.; Stevens, E. D. Inorg. Chem. 1983, 22, 2982.
35. Hatano, K.; Uno, T. Bull. Chem. Soc. Jpn. 1990, 63, 1825.
36. Jonas, R. T.; Stack, T. D. P. J. Am. Chem. Soc. 1997, 119, 8566.
37. Boger, D. L.; Teramoto, S.; Honda, T.; Zhou, J. J. Am. Chem. Soc. 1995, 117, 7338 and references therein.
38. Schulz, C. E.; Devaney, P. W.; Winkler, H.; Debrunner, P. G.; Doan, N.; Chiang, R.; Rutter, R.; Hager, L. P. FEBS Lett. 1979, 103, 102.
39. Stang, P. Angew. Chem., Int. Ed. Engl. 1992, 31, 274.
40. Moriarty, R.; Prakash, O. Acc. Chem. Res. 1986, 19, 244.
41. Banks, D. Chem. Rev. 1966, 66, 243.
42. Murugesan, N.; Hecht, S. J. Am. Chem. Soc. 1985, 107, 493.
43. Murugesan, N.; Ehrenfeld, G.; Hecht, S. J. Biol. Chem. 1982, 257, 8600.
44. Ehrenfeld, G. M.; Rodrigez, L. O.; Hecht, S. M.; Chang, C.; Basus, V. J.; Oppenheimer, N. J. Biochemistry 1985, 24, 81.
45. Nam, W.; Valentine, J. S.; J. Am. Chem. Soc. 1990, 112, 4977.
46. Yang, Y.; Diederich, F.; Valentine, J. S. J. Am. Chem. Soc. 1990, 112, 7826.
47. Samnani, P. B.; Bhattacharya, P. K. J. Mol. Catal. 1997, 126, L1.