C4′ sugar oxidation of deoxyribonucleotide triphosphates by chromium(V) complexes

Mutation Research - Genetic Toxicology and Environmental Mutagenesis

Volumn 610, Issue 1-2, 2006, Pages 66-73

  Chowdhury, Tahmeena ^a   Jamieson, Elizabeth R ^a  

^a SMITH COLLEGE   (United States)

Author keywords

Chromium(V); Deoxyribonucleotide triphosphates; Sugar oxidation

Indexed keywords

[2,2-BIS(HYDROXYMETHYL)-2-[BIS(2-HYDROXYETHYL)AMINO]ETHANOLATO]OXOCHROMATE; BIS(2 ETHYL 2 HYDROXYBUTYRATO)OXOCHROMATE; CHROMIUM DERIVATIVE; DEOXYRIBONUCLEOSIDE TRIPHOSPHATE; DEOXYRIBOSE; DNA; HYDROGEN; NUCLEIC ACID BASE; PURINE NUCLEOTIDE; PYRIMIDINE NUCLEOTIDE; SUGAR; THIOBARBITURIC ACID REACTIVE SUBSTANCE; UNCLASSIFIED DRUG; DEOXYRIBONUCLEOTIDE;

ARTICLE; MEASUREMENT; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; OXIDATION REDUCTION REACTION;

CHROMIUM COMPOUNDS; DEOXYRIBONUCLEOTIDES; DEOXYRIBOSE; KINETICS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; OXIDATION-REDUCTION;

EID: 33749259226     PISSN: 13835718     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.mrgentox.2006.06.013     Document Type: Article

References (36)

1. Sugden K.D., and Stearns D.M. The role of chromium(V) in the mechanism of chromate-induced oxidative DNA damage and cancer. J. Environ. Pathol. Toxicol. Oncol. 19 (2000) 215-230
2. Connett P.H., and Wetterhahn K.E. Metabolism of the carcinogen chromate by cellular constituents. Struct. Bond. 54 (1983) 93-124
3. Costa M. Toxicity and carcinogenicity of Cr(VI) in animal models and humans. Crit. Rev. Toxicol. 27 (1997) 431-442
4. Krumpolc M., and Rocek J. Chromium(V) oxidations of organic compounds. Inorg. Chem. 24 (1985) 617-621
5. Stearns D.M., and Wetterhahn K.E. Reaction of Cr(VI) with ascorbate produces chromium(V), chromium(IV), and carbon-based radicals. Chem. Res. Toxicol. 7 (1994) 219-230
6. Fonkeng B.S., Gelerinter E., and Bose R.N. Electron paramagnetic resonance spectroscopic characterization of {2,2-bis(hydroxymethyl)-2-[bis(2-hydroxyethyl)amino]ethanolato}oxochromate(V). J. Chem. Soc. Dalton Trans. (1995) 4129-4130
7. Bose R.N., Fonkeng B.S., Moghaddas S., and Stroup D. Mechanisms of DNA damage by chromium(V) carcinogens. Nucl. Acids Res. 26 (1998) 1588-1596
8. Sugden K.D., and Wetterhahn K.E. Reaction of chromium(V) with the EPR spin traps 5,5-dimethylpyrroline N-oxide and phenyl-N-tert-butylnitrone resulting in direct oxidation. Inorg. Chem. 35 (1996) 651-657
9. Sugden K.D., and Wetterhahn K.E. Identification of the oxidized products formed upon reaction of chromium(V) with thymidine nucleotides. J. Am. Chem. Soc. 118 (1996) 10811-10818
10. Sugden K.D., and Wetterhahn K.E. Direct and hydrogen peroxide-induced chromium(V) oxidation of deoxyribose in single-stranded and double-stranded calf thymus DNA. Chem. Res. Toxicol. 10 (1997) 1397-1406
11. Sugden K.D. Formation of modified cleavage termini from the reaction of chromium(V) with DNA. J. Inorg. Biochem. 77 (1999) 177-183
12. Bose R.N., Moghaddas S., Mazzer P.A., Dudones L.P., Joudah L., and Stroup D. Oxidative damage of DNA by chromium(V) complexes: relative importance of base versus sugar oxidation. Nucl. Acids Res. 27 (1999) 2219-2226
13. Salnikow K., Zhitkovich A., and Costa M. Analysis of the binding sites of chromium to DNA and protein in vitro and in intact cells. Carcinogenesis 13 (1992) 2341-2346
14. Zhitkovich A., Voitkun V., and Costa M. Formation of the amino acid-DNA complexes by hexavalent and trivalent chromium in vitro: importance of trivalent chromium and the phosphate group. Biochemistry 35 (1996) 7275-7282
15. O'Brien T., Mandel H.G., Pritchard D.E., and Patierno S.R. Critical role of chromium (Cr)-DNA interactions in the formation of Cr-induced polymerase arresting lesions. Biochemistry 41 (2002) 12529-12537
16. Arakawa H., Ahmad R., Naoui M., and Tajmir-Riahi H.-A. A comparative study of calf thymus DNA binding to Cr(III) and Cr(VI) ions. Evidence for the guanine N-7-chromium-phosphate chelate formation. J. Biol. Chem. 275 (2000) 10150-10153
17. Tamino G., Peretta L., and Levis A.G. Effects of the trivalent and hexavalent chromium on the physicochemical properties of mammalian cell nucleic acids and synthetic polynucleotides. Chem.-Biol. Interact. 37 (1981) 309-319
18. Tsapakos M.J., and Wetterhahn K.E. The interaction of chromium with nucleic acids. Chem.-Biol. Interact. 46 (1983) 265-277
19. Borges K.M., and Wetterhahn K.E. Chromium cross-links glutathione and cysteine to DNA. Carcinogenesis 10 (1989) 2165-2168
20. Bridgewater L.C., Manning F.C.R., and Patierno S.R. Base-specific arrest of in vitro DNA replication by carcinogenic chromium: relationship to DNA interstrand cross-linking. Carcinogenesis 15 (1994) 2421-2427
21. Bridgewater L.C., Manning F.C.R., Woo E.S., and Patierno S.R. DNA polymerase arrest by adducted trivalent chromium. Mol. Carcinog. 9 (1994) 122-133
22. Krumpolc M., and Rocek J. Synthesis of stable chromium(V) complexes of tertiary hydroxy acids. J. Am. Chem. Soc. 101 (1979) 3206-3209
23. Greenwald R.A., Rush S.W., Moak S.A., and Weitz Z. Conversion of superoxide generated by polymorphonuclear leukocytes to hydroxyl radical: a direct spectrophotometric detection system based on degradation of deoxyribose. Free Rad. Biol. Med. 6 (1989) 385-392
24. Waravdekar V.S., and Saslaw L.D. A sensitive colorimetric method for the estimation of 2-deoxy sugars with the use of the malondialdehyde-thiobarbituric acid reaction. J. Biol. Chem. 234 (1959) 1945-1950
25. Giloni L., Takeshita M., Johnson F., Iden C., and Grollman A.P. Bleomycin-induced strand-scission of DNA. Mechanism of deoxyribose cleavage. J. Biol. Chem. 256 (1981) 8608-8615
26. Burger R.M., Berkowitz A.R., Peisach J., and Horwtiz S.B. Origin of malondialdehyde from DNA degraded by Fe(II) bleomycin. J. Biol. Chem. 255 (1980) 11832-11838
27. Crich D., and Mo X.-S. Nucleotide C4′ radical fragmentation is base-dependent. Tetrahedron Lett. 38 (1997) 8169-8172
28. Crich D., Suk D.-H., and Hao X. The effect of base in the fragmentation of nucleotide C4′ radicals. Tetrahedron 58 (2002) 5789-5801
29. Lin B.L., Fu Y., Liu L., and Guo Q.X. Effects of bases on the stabilities of nucleoside C4′ radicals. Chin. Chem. Lett. 14 (2003) 1073-1076
30. Grollman A.P., Takeshita M., Pillai K.M.R., and Johnson F. Origin and cytotoxic properties of base propenals derived from DNA. Cancer Res. 45 (1985) 1127-1131
31. Dedon P.C., Plastaras J.P., Rouzer C.A., and Marnett L.J. Indirect mutagenesis by oxidative DNA damage: formation of the pyrimidopurinone adduct of deoxyguanosine by base propenal. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 11113-11116
32. Pogozelski W.K., and Tullius T.D. Oxidative strand scission of nucleic acids: routes initiated by hydrogen abstraction from the sugar moiety. Chem. Rev. 98 (1998) 1089-1107
33. McGall G.H., Rabow L.E., Ashley G.W., Wu S.H., Kozarich J.W., and Stubbe J. New insight into the mechanism of base propenal formation during bleomycin-mediated DNA degradation. J. Am. Chem. Soc. 114 (1992) 4958-4967
34. Ajmera S., Wu J.C., Worth Jr. L., Rabow L.E., Stubbe J., and Kozarich J.W. DNA degradation by bleomycin: evidence for 2′R-proton abstraction and for C-O bond cleavage accompanying base propenal formation. Biochemistry 25 (1986) 6586-6592
35. Strittmatter H., Dussy A., Schwitter U., and Giese B. Differences between 4′-RNA and 4′-DNA radicals during anerobic and aerobic strand cleavage. Angew. Chem. Int. Ed. 38 (1999) 135-137
36. Witz G., Lawrie N.J., Zaccaria A., Ferran Jr. H.E., and Goldstein B.D. The reaction of 2-thiobarbituric acid with biologically active alpha, beta-unsaturated aldehydes. J. Free Rad. Biol. Med. 2 (1986) 33-39