Mechanism of DNA strand scission induced by (1,10- phenanthroline)copper complex: Major direct DNA cleavage is not through 1',2'-dehydronucleotide intermediate nor β-elimination of forming ribonolactone [14]

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6313-6314

  Oyoshi, Takanori ^a   Sugiyama, Hiroshi ^a  

^a TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; LACTONE DERIVATIVE; NUCLEOTIDE DERIVATIVE; PHENANTHROLINE DERIVATIVE;

CHEMICAL REACTION; COMPLEX FORMATION; DNA CLEAVAGE; DNA DEGRADATION; DNA STRAND; LETTER; OXIDATION; REACTION ANALYSIS;

EID: 0034608974     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9919130     Document Type: Letter

References (37)

1. (a) For reviews, see: Sigman, D. S.; Chen C.-h. B. Annu. Rev. Biochem. 1990, 59, 207.
2. (b) Sigman, D. S.; Mazumder, A.; Perrin, P. M. Chem. Rev. 1993, 93, 2295.
3. (c) Pratviel, G.; Bernadou, J.; Meunier, B. Angew. Chem., Int Ed. Engl. 1995, 34, 746.
4. (d) Pogozelski, W. K.; Tullius, D. Chem. Rev. 1998, 98, 1089.
5. (e) Sigman, D. S.; Graham, D. R.; D'Aurora, V.; Stern, A. M. J. Biol. Chem. 1979, 254, 12269.
6. (f) Veal, J.; Rill, R. L. Biochemistry 1988, 27, 1822.
7. (g) Veal, J.; Rill, R. L. Biochemistry 1989, 28, 3243.
8. (h) Kuwabara, M.; Yoon, C.; Goyane, T.; Thederahn, T.; Sigman, D. S. Biochemistry 1986, 25, 7401.
9. (i) Pan, C. Q.; Johnson, R. C., Sigman, D. S. Biochemistry 1996, 35, 4326.
10. (j) Perrin, D. M.; Chen, C-H. B.; Xu, Y.; Pearson, L.; Sigman, D. S. J. Am. Chem. Soc. 1997, 119, 5746.
11. (k) Bullard, J. M.; van Waes, M. A.; Bucklin, D. J.; Hill W. E. EMBO J. 1995, 252, 572.
12. (l) Hill, W. E.; Bucklin, D. J.; Bullard, J. M.; Galbraith, A. L.; Jammi, N. V. Rettberg, C. C.; Sawyer, B. S.; van Waes, M. A. Biochem. Cell Biol. 1995, 73, 1033.
13. (m) Bullard. J. M.; van Waes, M. A.; Bucklin, D. J.; Rice, M. J.; Hill, W. E. Biochemistry 1998, 37, 1350.
14. (n) Muth, G. W.; Thompson, C. M.; Hill, W. E. Nucleic Acids Res. 1999, 27, 1906.
15. Goyne, T. E.; Sigman, D. S. J. Am. Chem. Soc: 1987, 109, 2846.
16. Meijier, M. M.; Zelenko, O.; Sigman, D. S. J. Am. Chem. Soc. 1997, 119, 1135.
17. Chen, T.; Greenberg, M. M. J. Am. Chem. Soc 1998, 120, 3815.
18. 2 in 50 mM Tris HCl (pH 7.5) showed typical B-form conformation under reaction conditions (Figure IS).
19. Structures of 1, 2, and 3 were characterized by ion spray MS and heat treatment. ESMS (negative): 1, calcd 1673.1, found 1673.0; 2, calcd 1697.1, found 1696.8 (Figure 2S): 3, calcd 1657.1, found 1656.8 (Figure 6S(a)). Heat treatment of 1, 2, and 3 provided corresponding fragments with phosphate termini and 5-methylenefuranone.
20. (a) Urata, H.; Yamamoto, K.; Akagi, M.; Hiroaki, H.; Uesugi, S. Biochemistry 1989, 28, 9566.
21. (b) Sugiyama, H.; Tsutsumi, Y.; Saito, I. J. Am. Chem. Soc. 1990, 112, 6720.
22. (c) Sugiyama, H.; Tsutsumi, Y.; Fujimoto, K.; Saito, I. J. Am. Chem. Soc. 1993, 115, 4443.
23. (d) Kotera, M.; Bourdat, A.-G.; Defrancq, E.; Lhomme, J. J. Am. Chem. Soc. 1998, 120, 11810.
24. (e) Jourdan, M.; Garcia, J.; Defrancq, E.; Kotera, M.; Lhomme, J. Biochemistry 1999, 38, 3985.
25. Structures of 1a and 2a were characterized by ESMS and heat treatment. ESMS (negative): 1a, calcd 1036.7, found 1036.6; 2a, calcd 1349.9, found 1349.8. Heat treatment (90 °C, 30 min) of 1a and 2a provided d(CGT)p and d(CGTA)p, respectively, together with 5-methylenefuranone.
26. 2Cu and MPA were 4.2 and 6.2 h, respectively.
27. Structures of 4 and 5 were characterized by ESMS as well as by comparison with authentic materials after dephosphorylation with alkaline phosphatase. ESMS (negative): 4, calcd 940.6, found 940.4; 5, calcd 1253.8, found 1253.4 (Figure 6S).
28. (a) Kappen, L. S.; Goldberg, I. H. Biochemistry 1983, 22, 4872.
29. (b) Kawabata, H.; Takeshita, H.; Fujiwara, T.; Sugiyama, H.; Matsuura, T.; Saito, I. Tetrahedron Lett. 1989, 30, 4263.
30. 13 respectively. Snake venom phosphodiesterase and alkaline phosphatase treatment gave dC-, dG-, dT-, and dA-phosphoroglycolate in a ratio of 1:1:1:1. Hydrazine treatment and successive enzymatic digestion gave dC-, dG-, dT-, and dA-pyridazine in a ratio of 1:2:1:1.
31. 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. (a) Sugiyama, H.; Xu, C.; Murugesan, N.; Hecht, S. M.; van der Martel, G.; van Boom, J. H. Biochemistry 1988, 27, 58. (b) Sugiyama, H.; Kawabata, H.; Fujiwara, T.; Dannoue, Y.; Saito. I. J. Am. Chem. Soc. 1990, 112, 5252.
32. 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. (a) Sugiyama, H.; Xu, C.; Murugesan, N.; Hecht, S. M.; van der Martel, G.; van Boom, J. H. Biochemistry 1988, 27, 58. (b) Sugiyama, H.; Kawabata, H.; Fujiwara, T.; Dannoue, Y.; Saito. I. J. Am. Chem. Soc. 1990, 112, 5252.
33. 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. (a) Sugiyama, H.; Xu, C.; Murugesan, N.; Hecht, S. M.; van der Martel, G.; van Boom, J. H. Biochemistry 1988, 27, 58. (b) Sugiyama, H.; Kawabata, H.; Fujiwara, T.; Dannoue, Y.; Saito. I. J. Am. Chem. Soc. 1990, 112, 5252.
34. Sigman's group previously pointed out that C4′ oxidation is also operating, but they assumed this contribution for direct DNA strand scission is not so large. Kuwabara, M.; Yoon, C.; Goyne, T.; Theerahn, T.; Sigman, D. S. Biochemistry 1986, 25, 7401.
35. Tronche, C.; Goodman, B. K.; Greenberg, M. M. Chem., Biol. 1998, 5, 263.
36. 13a The contributions of A-, G-, C-, and T-phosphoroglycolate are 1.1%, 0.6%, 1.0%, and 1.0%, respectively.
37. Dizdaroglu, M.; Aruoma, O. I.; Halliwell, B. Biochemistry 1990, 29, 8447.