DNA damage induced via independent generation of the radical resulting from formal hydrogen atom abstraction from the C1'-position of a nucleotide

Chemistry and Biology

Volumn 5, Issue 5, 1998, Pages 263-271

  Tronche, Christopher ^a   Goodman, Brian K ^a   Greenberg, Marc M ^a  

^a Immunology and Pathology   (United States)

Author keywords

DNA damage; Free radicals

Indexed keywords

EID: 0032078218     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(98)90619-6     Document Type: Article

References (41)

1. von Sonntag, C. (1987). The Chemical Basis of Radiation Biology. Taylor and Francis, London.
2. Breen, A.P. & Murphy, J.A. (1995). Reactions of oxyl radicals with DNA. Free Radical Biol. Med. 18, 1033-1077.
3. Pratviel, G., Bernadou, J. & Meunier, B. (1995). Carbon-hydrogen bonds of DNA sugar units as targets for chemical nucleases and drugs. Angew. Chem. Int. Ed. Engl. 34, 746-770.
4. Sigman, D.S., Mazumder, A. & Perrin, D.M. (1993). Chemical nucleases. Chem. Rev. 93, 2295-2316.
5. Goldberg, I.H. (1991). Mechanism of neocarzinostatin action: Role of DNA microstructure in determination of chemistry of bistranded oxidative cleavage. Accounts Chem. Res. 24, 191-198.
6. Lesiak, K.B. & Wheeler, K.T. (1990). Formation of α-deoxyadenosine in polydeoxynucleotides exposed to ionizing radiation under anoxic conditions. Radiation Res. 121, 328-337.
7. Ide, H., Yamaoka, T. & Kimura, Y. (1994). Replication of DNA templates containing the α-anomer of deoxyadenosine, a major adenine lesion produced by hydroxyl radicals. Biochemistry 33, 7127-7133.
8. Cheng, C-C., Goll, J.G., Neyhart, G.A., Welch, T.W., Singh, P. & Thorp, H.H. (1995). Relative rates and potentials of competing redox processes during DNA cleavage: oxidation mechanisms and sequence-specific catalysis of the self-inactivation of oxometal oxidants by DNA. J. Am. Chem. Soc. 117, 2970-2980.
9. Neyhart, G.A., Cheng, C-C. & Thorp, H.H. (1995). Kinetics and mechanism of the oxidation of sugars and nucleotides by oxoruthenium(IV): model studies for predicting cleavage patterns in polymeric DNA and RNA. J. Am. Chem. Soc. 117, 1463-1471.
10. 2H from C-1′ of the C residue in AGC·ICT by the radical center at C-2 of activated neocarzinostatin chromophore: structure of the drug/DNA complex responsible for bistranded lesion formation. Biochemistry 31, 9117-9121.
11. Kappen, L.S., Goldberg, I.H., Wu, S.H., Stubbe, J., Worth, L., Jr. & Kozarich, J.W. (1990). Isotope effects on the sequence-specific cleavage of dC in d(AGC) sequences by neocarzinostatin: elucidation of chemistry of minor lesions. J. Am. Chem. Soc. 112, 2797-2798.
12. Yu, L., Golik, J., Harrison, R. & Dedon, P. (1994). The deoxyfucose-anthranilate of esperamicin A1 confers intercalative DNA binding and causes a switch in the chemistry of bistranded DNA lesions. J. Am. Chem. Soc. 116, 9733-9738.
13. Greenberg, M.M., et al., & Venkatesan, H. (1997). DNA damage induced via 5,6-dihydrothymid-5-yl in single-stranded oligonucleotides. J. Am. Chem. Soc. 119, 1828-1839.
14. 2 glasses and frozen aqueous solutions. Int. J. Radiat. Biol. 70, 327-336.
15. Goodman, B.K. & Greenberg, M.M. (1996). Independent generation and reactivity of 2′-deoxyurid-1′-yl. J. Org. Chem. 61, 2-3.
16. Gimisis, T., Ialongo, G. & Chatgilialoglu, C. (1998). Generation of C-1′ radicals through a β-(acyloxy)alkyl rearrangement in modified purine and pyrimidine nucleosides. Tetrahedron 54, 573-592.
17. Boger, D.L., et al., & Turnbull, P. (1997). Duocarmycin SA shortened, simplified, and extended agents: a systematic examination of the role of the DNA binding subunit. J. Am. Chem. Soc. 119, 4977-4986.
18. Mitra, K., Kim, W., Daniels, J.S. & Gates, K.S. (1997). Oxidative DNA cleavage by the antitumor antibiotic leinamycin and simple 1,2-dithiolan-3-one 1-oxides: evidence for thiol-dependent conversion of molecular oxygen to DNA-cleaving oxygen radicals mediated by polysulfides. J. Am. Chem. Soc. 119, 11691-11692.
19. Greenberg, M.M., Yoo, D.J. & Goodman, B.K. (1997). C1′-Acylated derivatives of 2′-deoxyuridine. Photolabile precursors of 2′-deoxyuridin-1′-yl. Nucleosides Nucleotides 16, 33-40.
20. Schulhof, J.C., Molko, D. & Teoule, R. (1987). Facile removal of new base protecting groups useful in oligonucleotide synthesis. Tetrahedron Lett. 28, 51-54.
21. Tallman, K.T., Tronche, C., Yoo, D.J. & Greenberg, M.M. (1998). Release of superoxide from nucleoside peroxy radicals, a double edged sword? J. Am. Chem. Soc., in press.
22. Neta, P., Grodkowski, J. & Ross, A.B. (1996). Rate constants for reactions of aliphatic carbon-centered radicals in aqueous solution. J. Phys. Chem. Ref. Data 25, 709-964.
23. Tronche, C., Martinez, F.N., Horner, J.H., Newcomb, M., Senn, M. & Giese, B. (1996). Polar substituent and solvent effects on the kinetics of radical reactions with thiols. Tetrahedron Lett. 37, 5845-5848.
24. Dervan, P.B. (1986). Design of sequence-specific DNA-binding molecules. Science 232, 464-471.
25. Scaiano, J.C. (1980). Solvent effects on the photochemistry of xanthone. J. Am. Chem. Soc. 102, 7747-7753.
26. Gut, I.G., Wood, P.D. & Redmond, R.W. (1996). Interaction of triplet photosensitizers with nucleosides and DNA in aqueous solution at room temperature. J. Am. Chem. Soc. 118, 2366-2373.
27. Meijler, M.M., Zelenko, O. & Sigman, D.S. (1997). Chemical mechanism of DNA scission by (1,10-phenanthroline)copper. Carbonyl oxygen of 5-methylenefuranone is derived from water. J. Am. Chem. Soc. 119, 1135-1136.
28. Chen, T. & Greenberg, M.M. (1998). Model studies indicate that copper-phenanthroline induces direct strand breaks via β-elimination of the 2′-deoxyribonolactone intermediate observed in enediyne mediated DNA damage. J. Am. Chem. Soc., in press.
29. Hildenbrand, K. & Schulte-Frohlinde, D. (1997). Time-resolved EPR studies on the reaction rates of peroxyl radicals of poly(acrylic acid) and of calf thymus DNA with glutathione. Re-examination of a rate constant for DNA. Int. J. Radiat. Biol. 71, 377-385.
30. Newton, G.L., Aguilera, J.A., Ward, J.F., Fahey, R.C. (1996). Binding of radioprotective thiols and disulfides in Chinese hamster V79 cell nuclei. Radiation Res. 146, 298-305.
31. Crich, D. & Yao, Q. (1998). Free radical chemistry of nucleosides and nucleotides. Ring opening of C4′-radicals. Tetrahedron 54, 305-318.
32. Behrens, G., Koltzenburg, G. & Schulte-Frohlinde, D. (1982). Model reactions for the degradation of DNA-4′ radicals in aqueous solution. Fast hydrolysis of α-alkoxyalkyl radicals with a leaving group in β-position followed by radical rearrangement and elimination reactions. Z. Naturforsch. 37c, 1205-1227.
33. Giese, B., Beyrich-Graf, X., Erdmann, P., Petretta, M. & Schwitter, U. (1995). The chemistry of single-stranded 4′-DNA radicals: influence of the radical precursor on anaerobic and aerobic strand cleavage. Chem. Biol. 2, 367-375.
34. Crich, D. & Mo, X-S. (1997). Nucleotide C3′,4′-radical cations and the effect of a 2′-oxygen substituent. The DNA/RNA paradox. J. Am. Chem. Soc. 119, 249-250.
35. Giese, B., Dussy, A., Meggers, E., Petretta, M. & Schwitter, U. (1997). Conformation, lifetime, and repair of 4′-DNA radicals. J. Am. Chem. Soc. 119, 11130-11131.
36. McHugh, P.J. & Knowland, J. (1995). Novel reagents for chemical cleavage at abasic sites and UV photoproducts in DNA. Nucleic Acids Res. 23, 1664-1670.
37. Bailly, V. & Verly, W.G. (1988). Importance of thiols in the repair mechanisms of DNA containing AP (apurinic or apyrimidinic) sites. Nucleic Acids Res. 16, 9489-9496.
38. Razskazovskii, Y. & Sevilla, M.D. (1996). Reactions of sulphonyl peroxyl radicals with DNA and its components: hydrogen atom abstraction from the sugar backbone versus addition to pyrimidine double bonds. Int. J. Radiat. Biol. 69, 75-87.
39. Epstein, J.L., et al., & Kozarich, J.W. (1997). Interplay of hydrogen abstraction and radical repair in the generation of single- and double-strand DNA damage by the esperamicins. J. Am. Chem. Soc. 119, 6731-6738.
40. Sambrook, J., Fritsch, E.F. & Maniatis, T. (1989). Molecular Cloning: A Laboratory Manual. (2nd Ed.), Cold Spring Harbor Laboratory Press, NY.
41. Iverson, B.L. & Dervan, P.B. (1987). Adenine specific DNA chemical sequencing reaction. Nucleic Acids Res. 15, 7823-7830.