Thiol-dependent DNA cleavage by 3H-1,2-benzodithiol-3-one 1,1-dioxide

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 9, 2000, Pages 885-889

  Breydo, Leonid ^a   Gates, Kent S ^a,b  

^a UNIVERSITY OF MISSOURI   (United States)

^b University of Missouri   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LEINAMYCIN; SULFUR DERIVATIVE; THIOL;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; DNA CLEAVAGE; DNA DAMAGE; OXIDATION; REACTION ANALYSIS;

ANTIBIOTICS, ANTINEOPLASTIC; DNA DAMAGE; DNA, SUPERHELICAL; LACTAMS; MACROLIDES; OXIDATION-REDUCTION; PLASMIDS; SULFHYDRYL COMPOUNDS; THIAZOLES; THIONES;

EID: 0034193394     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(00)00125-6     Document Type: Article

References (30)

1. Behroozi S.B., Kim W., Gates K.S. J. Org. Chem. 60:1995;3964.
2. Behroozi S.J., Kim W., Dannaldson J., Gates K.S. Biochemistry. 35:1996;1768.
3. Asai A., Hara M., Kakita S., Kanda Y., Yoshida M., Saito H., Saitoh Y. J. Am. Chem. Soc. 118:1996;6802.
4. Mitra K., Kim W., Daniels J.S., Gates K.S. J. Am. Chem. Soc. 119:1997;11691.
5. Mitra K., Gates K.S. Recent Res. Devel. Org. Chem. 3:1999;311.
6. Chatterji T., Gates K.S. Bioorg. Med. Chem. Lett. 8:1998;535.
7. Davidson B.S., Molinski T.F., Barrows L.R., Ireland C.M. J. Am. Chem. Soc. 113:1991;4709.
8. Searle P.A., Molinski T.F. J. Org. Chem. 59:1994;6600.
9. Kohama Y., Iida K., Semba T., Mimura T., Inada A., Tanaka K., Nakanishi T. Chem. Pharm. Bull. 40:1992;2210.
10. Iyer R.P., Phillips L.R., Egan W., Regan J.B., Beaucage S.L. J. Org. Chem. 55:1990;4693.
11. Halliwell B., Gutteridge J.M.C. Methods Enzymol. 186:1990;1.
12. Graf E., Mahoney J.R., Bryant R.G., Eaton J.W. J. Biol. Chem. 259:1984;3620.
13. Fridovich I. Acc. Chem. Res. 5:1972;321.
14. In systems where addition of SOD inhibits DNA damage it is likely due to the fact that superoxide radical serves as a necessary reducing agent for trace metals involved in the Fenton reaction. In systems where other reducing agents (e.g., thiols) are present, addition of SOD can actually increase DNA-damage efficiency. See, for example: Eliot, H.; Gianni, L.; Myers, C. Biochemistry 1984, 23, 928. Parraga, A.; Orozco, M.; Portugal, J. Eur. J. Biochem. 1992, 208, 227. Weglarz, L.; Bartosz, G. Int. J. Biochem. 1991, 23, 663. Nagai, K.; Hecht, S. M. J. Biol. Chem. 1991, 266, 23994.
15. In systems where addition of SOD inhibits DNA damage it is likely due to the fact that superoxide radical serves as a necessary reducing agent for trace metals involved in the Fenton reaction. In systems where other reducing agents (e.g., thiols) are present, addition of SOD can actually increase DNA-damage efficiency. See, for example: Eliot, H.; Gianni, L.; Myers, C. Biochemistry 1984, 23, 928. Parraga, A.; Orozco, M.; Portugal, J. Eur. J. Biochem. 1992, 208, 227. Weglarz, L.; Bartosz, G. Int. J. Biochem. 1991, 23, 663. Nagai, K.; Hecht, S. M. J. Biol. Chem. 1991, 266, 23994.
16. In systems where addition of SOD inhibits DNA damage it is likely due to the fact that superoxide radical serves as a necessary reducing agent for trace metals involved in the Fenton reaction. In systems where other reducing agents (e.g., thiols) are present, addition of SOD can actually increase DNA-damage efficiency. See, for example: Eliot, H.; Gianni, L.; Myers, C. Biochemistry 1984, 23, 928. Parraga, A.; Orozco, M.; Portugal, J. Eur. J. Biochem. 1992, 208, 227. Weglarz, L.; Bartosz, G. Int. J. Biochem. 1991, 23, 663. Nagai, K.; Hecht, S. M. J. Biol. Chem. 1991, 266, 23994.
17. In systems where addition of SOD inhibits DNA damage it is likely due to the fact that superoxide radical serves as a necessary reducing agent for trace metals involved in the Fenton reaction. In systems where other reducing agents (e.g., thiols) are present, addition of SOD can actually increase DNA-damage efficiency. See, for example: Eliot, H.; Gianni, L.; Myers, C. Biochemistry 1984, 23, 928. Parraga, A.; Orozco, M.; Portugal, J. Eur. J. Biochem. 1992, 208, 227. Weglarz, L.; Bartosz, G. Int. J. Biochem. 1991, 23, 663. Nagai, K.; Hecht, S. M. J. Biol. Chem. 1991, 266, 23994.
18. Hertzberg R.P., Dervan P.B. Biochemistry. 23:1984;3934.
19. Compound 11 undergoes hydrolysis slowly compared to thiolysis. In the DNA-cleavage reactions reported here, 11 was the final component added to thiol-containing reaction mixtures to ensure that thiol-triggered chemistry predominates.
20. 4,9 Obtained as a mixture where n=0, 1, and 2 (90:9:1, 558 mg, 3.6 mmol).
21. Lüdersdorf, R.; Martens, J.; Pakzad, B.; Praefcke, K. Justus Liebig Ann. Chem. 1992, 1977.
22. Ozaki S., Yang H.-J., Matsui T., Goto Y., Watanabe Y. Tetrahedron: Asymmetry. 10:1999;183.
23. Overman L.E., Matzinger D., O'Connor E.M., Overman J.D. J. Am. Chem. Soc. 96:1974;6081.
24. Wentrup C., Bender H., Gross G. J. Org. Chem. 52:1987;3838.
25. Kice J.L., Rogers T.E. J. Am. Chem. Soc. 96:1974;8015.
26. Lees W.J., Whitesides G.M. J. Org. Chem. 58:1993;642.
27. Derbesy G., Harpp D.N. Sulfur Lett. 14:1992;199.
28. Kawamura S., Abe Y., Tsurugi J. J. Org. Chem. 34:1969;3633.
29. 10.
30. 22 and would not yield 'activated' leinamycin (2).