An Efficient, Site-Specific DNA Target for Bleomycin

Journal of the American Chemical Society

Volumn 107, Issue 25, 1985, Pages 7765-7767

  Sugiyama, Hiroshi ^a   Kilkuskie, Robert E ^a   Hecht, Sidney M ^a   Van Der Marel, Gijs A ^b   Van Boom, Jacques H ^b  

^a UNIVERSITY OF VIRGINIA   (United States)

^b LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

BLEOMYCIN; DNA FRAGMENT;

DODECANUCLEOTIDE; DRUG INTERACTION; DRUG MECHANISM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; PRELIMINARY COMMUNICATION; PRIORITY JOURNAL; THEORETICAL STUDY;

EID: 0022407545     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00311a092     Document Type: Article

References (12)

1. Hecht, S. M. In “Bleomycin: Chemical, Biochemical and Biological Aspects”; Hecht, S. M., Ed.; Springer-Verlag: New York, 1979; p 1 ff. (b) Umezawa, H. In “Medicinal Chemistry Series: Anticancer Agents Based on Natural Product Models”; Cassady, J. M., Dourous, J. D., Eds.; Academic Press; New York, 1980; Vol. XVI, p 148 ff. (c) Povirk, L. F. In “Molecular Aspects of Anti-cancer Drug Action”; Neidle, S., Waring, M. J., Eds.; Macmillan: London, 1983; p 157 ff.
2. Fe•BLM-mediated strand scission occurs preferentially at.GC.and.GT.sequences, (a) D’Andrea, A. D.; Haseltine, W. A. Proc. Natl. Acad. Sci. U.S.A. 1978, 75, 3608. (b) Takeshita, M.; Grollman, A.; Ohtsubo, E.; Ohtsubo, H. Proc. Natl. Acad. Sci. 1978, 75, 5983. (c) Mirabelli, C. K.; Ting, A.; Huang, C. H.; Mong, S.; Crooke, S. T. Cancer Res. 1982, 42, 2779.
3. Ishida, R.; Takahashi, T. Biochem. Biophys. Res. Commun. 1975, 66, 1432. (b) Sausville, E. A.; Peisach, J.; Horwitz, S. B. Biochemistry 1978, 17, 2740. (c) Oppenheimer, N., J.; Chang, C.; Rodriquez, L. O.; Hecht, S. M. J. Biol. Chem. 1981, 256, 1514. (d) Ehrenfeld, G. M.; Rodriguez, L. O.; Hecht, S. M.; Chang, C.; Basus, V. J.; Oppenheimer, N. J. Biochemistry 1985, 24, 81. (e) Ehrenfeld, G. M.; Murugesan, N.; Hecht, S. M. Inorg. Chem. 1984, 23, 1496.
4. III•BLM + hv has also been reported. See: Chang, C. H.; Meares, C. F. Biochemistry 1984, 23, 2268.
5. These include difficulties in (i) preparation of such species in quantity for degradation, (ii) separation of the products resulting from modification at each of several loci within a given sequence, and (iii) analysis of the resulting oligomeric products by routine spectral techniques due both to the size of the formed products and the modest extent of product formation at any given site. (7) See, e.g.: (a) Giloni, L.; Takeshita, M.; Johnson, F.; Iden, C.; Grollman, A. P. J. Biol. Chem. 1981, 256, 8608. (b) Murugesan, N.; Xu, C.; Ehrenfeld, G. M.; Sugiyama, H., Kilkuskie, R. E.; Rodriguez, L. O.; Chang, L.-H.; Hecht, S. M. Biochemistry 1985, 24, 5735. (c) Uesugi, S.; Shida, T., Ikehara, M.; Kobayashi, Y.; Kyogoku, Y. Nucleic Acids Res. 1984, 12, 1581.
6. Van Boom, J. H. Heterocycles 1977, 7, 1197. Matteucci, M. D.; Caruthers, M. H. J. Am. Chem. Soc. 1981, 103, 3185.
7. Johnson, F.; Pillai, K. M. R.; Grollman, A. P.; Tseng, L.; Takeshita, M. J. Med. Chem. 1984, 27, 954.
8. Burger, R. M.; Berkowitz, A. R.; Peisach, J.; Horwitz, S. B. J. Biol. Chem. 1980, 255, 11832.
9. Wu, J. C.; Kozarich, J. W.; Stubbe, J. J. Biol. Chem. 1983, 258, 4694. (b) Burger, R. M.; Peisach, J.; Horwitz, S. B. J. Biol. Chem. 1983, 257, 8612.
10. Sugiyama, H.; Xu, C.; Murugesan, N.; Hecht, S. M. J. Am. Chem. Soc. 1985, 107, 4104. (18) Distamycin A has been shown to bind to AT-rich regions of DNA. (a) Van Dyke, M. W.; Hertzberg, R. P.; Dervan, P. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 5470. (b) Sugiura, Y.; Suzuki, T. J. Biol. Chem. 1982, 257, 10544. (c) Kopka, M. L.; Yoon, C.; Goodsell, D.; Pjura, P.; Dickerson, R. E. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 1376.
11. 11in the presence of 42 μM distamycin A constituted <1% of the total reaction products, as judged by HPLC analysis.
12. Kuramochi, H.; Takahashi, K.; Takita, T.; Umezawa, H. J. Antibiot. 1981, 34, 576. (b) Burger, R. M.; Peisach, J.; Horwitz, S. B. J. Biol. Chem. 1981, 256, 11636. (c) Murugesan, N.; Hecht, S. M. J. Am. Chem. Soc. 1985, 107, 493.