Studies on the mechanism of action of azinomycin B: Definition of regioselectivity and sequence selectivity of DNA cross-link formation and clarification of the role of the naphthoate

Journal of the American Chemical Society

Volumn 124, Issue 44, 2002, Pages 13008-13017

  Coleman, Robert S ^a   Perez, Ronelito J ^a   Burk, Christopher H ^a   Navarro, Antonio ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KINETIC ASSAY;

ASSAYS; CROSSLINKING; VISCOSITY MEASUREMENT;

DNA;

AZINOMYCIN B; UNCLASSIFIED DRUG;

ARTICLE; COVALENT BOND; DNA CROSS LINKING; DNA DENATURATION; DRUG MECHANISM; ENERGY TRANSFER; PROTEIN DNA INTERACTION; SEQUENCE ANALYSIS; STRUCTURE ANALYSIS; VISCOMETRY;

ANTI-BACTERIAL AGENTS; ANTIBIOTICS, ANTINEOPLASTIC; CROSS-LINKING REAGENTS; DNA; GLYCOPEPTIDES; NAPHTHALENES; PEPTIDES; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 0037032256     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja025563k     Document Type: Article

References (38)

1. For references to synthetic work on the azinomycins, see: Coleman, R. S. Synlett 1998, 1031. Coleman, R. S.; Kong, J.-S.; Richardson, T. E. J. Am. Chem. Soc. 1999, 121, 9088. Hodgkinson, T. J.; Shipman, M. Tetrahedron 2001, 57, 4467.
2. For references to synthetic work on the azinomycins, see: Coleman, R. S. Synlett 1998, 1031. Coleman, R. S.; Kong, J.-S.; Richardson, T. E. J. Am. Chem. Soc. 1999, 121, 9088. Hodgkinson, T. J.; Shipman, M. Tetrahedron 2001, 57, 4467.
3. For references to synthetic work on the azinomycins, see: Coleman, R. S. Synlett 1998, 1031. Coleman, R. S.; Kong, J.-S.; Richardson, T. E. J. Am. Chem. Soc. 1999, 121, 9088. Hodgkinson, T. J.; Shipman, M. Tetrahedron 2001, 57, 4467.
4. (a) Hartley, J. A.; Hazrati, A.; Kelland, L. R.; Khanim, R.; Shipman, M.; Suzenet, F.; Walker, L. F. Angew. Chem., Int. Ed. 2000, 112, 3609.
5. (b) Hartley, J. A.: Hazrati, A.; Khanim, R. Hodgkinson, T. J.; Shipman, M.; Suzenet, F.; Kelland, L. R. Chem. Commun. 2000, 2325.
6. (c) Hodgkinson, T. J.; Kelland, L. R. Shipman, M.; Suzenet, F. Bioorg. Med. Chem. Lett. 2000, 10, 239.
7. Nagaoka, K.; Matsumoto, M.; Oono, J.; Yokoi, K.; Ishizeki, S.; Nakashima, T. J. Antibiot. 1986, 39, 1527. Yokoi, K.; Nagaoka. K.: Nakashima, T. Chem. Pharm. Bull. 1986, 34, 4554.
8. Nagaoka, K.; Matsumoto, M.; Oono, J.; Yokoi, K.; Ishizeki, S.; Nakashima, T. J. Antibiot. 1986, 39, 1527. Yokoi, K.; Nagaoka. K.: Nakashima, T. Chem. Pharm. Bull. 1986, 34, 4554.
9. 50 = 0.07 μg/mL (1a) and 0.11 μg/mL (1b) against L5178Y cells. In vivo antitumor activity: 193% ILS at 16 μg/kg 1b (3/7 survivors) against P388 leukemia; 161% ILS at 32 μg/kg 1b (5/8 survivors) against Erlich carcinoma. In the same system, mitomycin C exhibited a 204% ILS at 1 mg/kg against P388 leukemia.
10. Coleman, R. S.; Li, J.; Navarro, A. Angew. Chem., Int. Ed. 2001, 40, 1736.
11. For a review on the synthesis of DNA cross-linking agents, and a discussion of the historical development of DNA cross-linking agents, see: Coleman. R. S. Curr. Opin. Drug Discov. Dev. 2001, 4, 435. For a comprehensive review on DNA cross-linking agents, see: Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723. For a review of agents that covalently modify DNA, see: Gates K. S. Covalent Modification of DNA by Natural Products. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Pergamon Press/Elsevier Science: Oxford, U.K., 1999; Vol. 7, p 491.
12. For a review on the synthesis of DNA cross-linking agents, and a discussion of the historical development of DNA cross-linking agents, see: Coleman. R. S. Curr. Opin. Drug Discov. Dev. 2001, 4, 435. For a comprehensive review on DNA cross-linking agents, see: Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723. For a review of agents that covalently modify DNA, see: Gates K. S. Covalent Modification of DNA by Natural Products. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Pergamon Press/Elsevier Science: Oxford, U.K., 1999; Vol. 7, p 491.
13. For a review on the synthesis of DNA cross-linking agents, and a discussion of the historical development of DNA cross-linking agents, see: Coleman. R. S. Curr. Opin. Drug Discov. Dev. 2001, 4, 435. For a comprehensive review on DNA cross-linking agents, see: Rajski, S. R.; Williams, R. M. Chem. Rev. 1998, 98, 2723. For a review of agents that covalently modify DNA, see: Gates K. S. Covalent Modification of DNA by Natural Products. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Meth-Cohn, O., Eds.; Pergamon Press/Elsevier Science: Oxford, U.K., 1999; Vol. 7, p 491.
14. Lown, J. W.; Majumdar, K. C. Can. J. Biochem. 1977, 55, 630.
15. Hata, T.; Koga, F.; Sano, Y.; Kanamori, K.; Matsumae, A.; Sugawara, R.; Hoshi, T.; Shimi, T.; Ito, S.; Tomizawa, S. J. Antibiot., Ser. A. 1954, 7, 107.
16. Armstrong, R. W.; Salvati, M. E.; Nguyen, M. J. Am. Chem. Soc. 1992, 114, 3144.
17. Fujiwara, T.; Saito, I.; Sugiyama, H. Tetrahedron Lett. 1999, 40, 315.
18. Alcaro, S.; Coleman, R. S. J. Org. Chem. 1998, 63, 4620.
19. Alcaro, S.; Coleman, R. S. J. Med. Chem. 2000, 43, 2783.
20. Alcaro, S.; Ortuso, F.; Coleman, R. S. J. Med. Chem. 2002, 45, 861.
21. Zang, H.; Gates, K. S. Biochemistry 2000, 39, 14968.
22. Coleman, R. S.; Sarko, C. R.; Gittinger, J. P. Tetrahedron Lett. 1997, 38, 5917.
23. Coleman, R. S.; McKinley, J. D. Tetrahedron Lett. 1998, 39, 3433.
24. Sugiyama, H.; Saito, I. J. Am. Chem. Soc. 1996, 118, 7063.
25. For a similar report of steric hindrance of cross-link formation due to the C5-methyl group of thymine, see: Coleman, R. S.; Pires, R. M. Nucleic Acids Res. 1997, 25, 4771.
26. Gao, X.; Stassinopoulos, A.; Gu, J.; Goldberg, I. H. Bioorg. Med. Chem. 1995, 3, 795.
27. Shishido, K.; Omodani, T.; Shibuya, M. J. Chem. Soc., Perkin Trans. 1 1992, 2053.
28. Cohen, G.; Eisenberg, H. K. Biopolymers 1969, 8, 45.
29. For essentially identical data comparing ethidium bromide with the minor groove binder Hoechst 33258, see Figure 5 in ref 23.
30. LePeck, J. B.; Paoletti, C. J. Mol. Biol. 1967, 27, 87.
31. Suh, D.; Chaires, J. B. Bioorg. Med. Chem. 1995, 3, 723.
32. Förster, T. Ann. Phys. 1948, 2, 55.
33. Wilson, W. D.; Krishnamoorthy, C. R.; Wang, Y.-H.; Smithy, J. C. Biopolymers 1985, 24, 1941. Bresloff, J. L.; Crothers, D. M. Biochemistry 1981, 20, 3547.
34. Wilson, W. D.; Krishnamoorthy, C. R.; Wang, Y.-H.; Smithy, J. C. Biopolymers 1985, 24, 1941. Bresloff, J. L.; Crothers, D. M. Biochemistry 1981, 20, 3547.
35. For a recent review, see: Kane-Maguire, N. A. P.; Wheeler J. F. Coord. Chem. Rev. 2001, 211, 145, and references therein.
36. Coleman, R. S.; Burk, C. H.; Navarro, A.; Brueggemeier, R. W.; Diaz-Cruz, E. S. Org. Lett. 2002, 4, 3545.
37. Viola, G.; Uriarte, E,; Gia, O.; Moro, S. Farmaco 2000, 55, 276.
38. Coleman, R. S.; Richardson, T. E.; Carpenter, A. J. J. Org. Chem. 1998, 63, 5738.