5′-(2-Phosphoryl-1,4-dioxobutane) as a product of 5′-oxidation of deoxyribose in DNA: Elimination as trans-1,4-dioxo-2-butene and approaches to analysis

Chemical Research in Toxicology

Volumn 17, Issue 11, 2004, Pages 1406-1413

  Chen, Bingzi ^a   Bohnert, Tonika ^a,b   Zhou, Xinfeng ^a   Dedon, Peter C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b BIOGEN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BLEOMYCIN; BUTANE; CALICHEAMICIN; CARBON; DEOXYRIBOSE; DNA; EDETIC ACID; HYDRAZINE; HYDROGEN; HYDROXYLAMINE; IRON; NUCLEIC ACID BASE; OXIME; PHOSPHATE; PYRIDAZINE; ZINOSTATIN; ALDEHYDE; MALEALDEHYDE; ORGANOPHOSPHORUS COMPOUND; OXIDIZING AGENT;

ARTICLE; CONTROLLED STUDY; DOSE RESPONSE; GAMMA RADIATION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY; CHEMISTRY; DNA ADDUCT; DNA DAMAGE; DRUG EFFECT; MASS FRAGMENTOGRAPHY; METHODOLOGY; OXIDATION REDUCTION REACTION;

ALDEHYDES; DEOXYRIBOSE; DNA; DNA ADDUCTS; DNA DAMAGE; DOSE-RESPONSE RELATIONSHIP, DRUG; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; ORGANOPHOSPHORUS COMPOUNDS; OXIDANTS; OXIDATION-REDUCTION;

EID: 4544293709     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx049818e     Document Type: Article

References (32)

1. Dedon, P. C., and Goldberg, I. H. (1992) Free-radical mechanisms involved in the formation of sequence-dependent bistranded DNA lesions by the antitumor antibiotics bleomycin, neocarzinostatin, and calicheamicin. Chem. Res. Toxicol, 5, 311-332.
2. Angeloff, A., Dubey, I., Pratviel, G., Bernadou, J., and Meunier, B. (2001) Characterization of a 5′-aldehyde terminus resulting from the oxidative attack at C5′ of a 2-deoxyribose on DNA. Chem. Res. Toxicol. 14, 1413-1420.
3. Kawabata, H., Takeshita, H., Fujiwara, T., Sugiyama, H., Matsuura, T., and Saito, I. (1989) Chemistry of neocarzinostatin-mediated degradation of d(GCATGC). Mechanism of spontaneous thymine release. Tetrahedron Lett. 30, 4263-4266.
4. Witz, G. (1989) Biological interaction of α- and β-unsaturated aldehydes. Free Radical Biol. Med. 7, 333-349.
5. Marnett, L. J. (1994) DNA adducts of alpha, beta-unsaturated aldehydes and dicarbonyl compounds. IARC Sci. Publ. 125, 151-163.
6. Chen, L. J., Hecht, S. S., and Peterson, L. A. (1997) Characterization of amino acid and glutathione adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem. Res. Toxicol. 10, 866-874.
7. Chen, L.-J., Hecht, S. S., and Peterson, L. A. (1995) Identification ofcis-2-butene-1,4-dial as a microsomal metabolite of furan. Chem. Res. Toxicol. 8, 903-906.
8. Maga, J. A. (1979) Furans in foods. CRC Crit. Rev. Food Sci. Nutr. 11, 355-400.
9. Egle, J. L., Jr., and Gochberg, B. J. (1979) Respiratory retention and acute toxicity of furan. Am. Ind. Hyg. Assoc. J. 40, 310-314.
10. Gingipalli, L., and Dedon, P. C. (2001) Reaction ofcis- and trans-2-butene-1,4-dial with 2′-deoxycytidine to form stable oxadiazabicyclooctaimine adducts. J. Am. Chem. Soc. 123, 2664-2665.
11. Byrns, M. C., Predecki, D. P., and Peterson, L. A. (2002) Characterization of nucleoside adducts of cis-2-butene-1,4-dial, a reactive metabolite of furan. Chem. Res. Toxicol. 15, 373-379.
12. Sheldrick, G. M., and Schnieder, T. R. (1997) SHELXL: High-resolution refinement. Macromol. Cryst. 277, 319-343.
13. Sheldrick, G. M. (1990) Phase annealing in SHELX-90-Direct methods for larger structures. Acta Crystallogr. 46, 467-473.
14. Letsinger, R. L., and Lasco, R. (1956) Pyrrolopyridazines. J. Am. Chem. Soc. 21, 764-766.
15. Hong, Y.-S., and Lee, H.-K. (1975) Structural studies on conjugated oximes (II). Nuclear magnetic resonance spectrial analysis on the configuration and hydrogen bond of cis-2-butenedialdioxime in solutions. J. Korean Chem. Soc. 19, 233-239.
16. Dedon, P. C., and Goldberg, I. H. (1990) Sequence-specific double-strand breakage of DNA by neocarzinostatin within a staggered cleavage site. J. Biol. Chem. 265, 14713-14716.
17. Dedon, P. C., Salzberg, A. A., and Xu, J. (1993) Exclusive production of bistranded DNA damage by calicheamicin. Biochemistry 32, 3617-3622.
18. Ausubel, F. M., Brent, R., Kingston, R. E., Moore, D. D., Seidman, J. G., Smith, J. A., and Struhl, K. (1989) Current Protocols in Molecular Biology, John Wiley and Sons, New York.
19. Milligan, J. R., Aguilera, J. A., and Ward, J. F. (1993) Variation of single-strand break yield with scavenger concentration for plasmid DNA irradiated in aqueous solution. Radiat. Res. 133, 151-157.
20. Sugiyama, H., Xu, C., Murugesan, N., and Hecht, S. M. (1985) Structure of the alkali-labile product formed during iron(II)-bleomycin-mediated DNA strand scission. J. Am. Chem. Soc. 107, 4104-4105.
21. Povirk, L. F., and Goldberg, I. H. (1985) Endonuclease-resistant apyrimidinic sites formed by neocarzinostatin at cytosine residues in DNA: Evidence for a possible role in mutagenesis. Proc. Natl. Acad. Sci. U.S.A. 82, 3182-3186.
22. Gal, A., Tamir, S., Kennedy, L. J., Tannenbaum, S. R., and Wogan, G. N. (1997) Nitrotyrosine formation, apoptosis, and oxidative damage: Relationships to nitric oxide production in SJL mice bearing the rcsx tumor. Cancer Res. 57, 1823-1828.
23. LaMarr, W. A., Sandman, K. M., Reeve, J. N., and Dedon, P. C. (1997) Differential effects of DNA supercoiling on radical-mediated DNA strand breaks. Chem. Res. Toxicol. 10, 1118-1122.
24. Kennedy, L. J., Moore, K., Jr., Caulfield, J. L., Tannenbaum, S. R., and Dedon, P. C. (1997) Quantitation of 8-oxoguanine and strand breaks produced by four oxidizing agents. Chem. Res. Toxicol. 10, 386-392.
25. 2-glyoxal adduct of deoxyguanosine by phosphoglycolaldehyde, a product of 3′-deoxyribose oxidation in DNA. Chem. Res. Toxicol. 14, 1247-1253.
26. Dedon, P. C., Plastaras, J. P., Rouzer, C. A., and Marnett, L. J. (1998) Indirect mutagenesis by oxidative DNA damage: Formation of the pyrimidopurinone adduct of deoxyguanosine by base propenal. Proc. Natl. Acad. Sci. U.S.A. 95, 11113-11116.
27. Bohnert, T., Gingipalli, L., and Dedon, P. C. (2004) Reaction of 2′-deoxyribonucleosides with cis- and trans-1,4-dioxo-2-butene. Biochem. Biophys. Res. Commun. 323, 838-844.
28. Stubbe, J., and Kozarich, J. W. (1987) Mechanisms of bleomycin-induced DNA degradation. Chem. Rev. 87, 1107-1136.
29. Chin, D.-H., Kappen, L. S., and Goldberg, I. H. (1987) 3′-Formyl phosphate-ended DNA: High energy intermediate in antibiotic-induced DNA sugar damage. Proc. Natl. Acad. Sci. U.S.A. 84, 7070-7074.
30. Dedon, P. C., Jiang, Z.-W., and Goldberg, I. H. (1992) Neocarzinostatin-mediated DNA damage in a model AGT-ACT site: Mechanistic studies of thiol-sensitive partitioning of C4′ DNA damage products. Biochemistry 31, 1917-1927.
31. Balasubramanian, B., Pogozelski, W. K., and Tullius, T. D. (1998) DNA strand breaking by the hydroxyl radical is governed by the accessible surface areas of the hydrogen atoms of the DNA backbone. Proc. Natl. Acad. Sci. U.S.A. 95, 9738-9743.
32. Collins, C., Awada, M. M., Zhou, X., and Dedon, P. C. (2003) Analysis of 3′-phosphoglycolaldehyde residues in oxidized DNA by gas chromatography/negative chemical ionization/mass spectrometry. Chem. Res. Toxicol. 16, 1560-1566.