Oxidative damage of DNA by chromium(V) complexes: relative importance of base versus sugar oxidation

Title

Oxidative damage of DNA by chromium(V) complexes: relative importance of base versus sugar oxidation

Creator

Bose R N; Moghaddas S; Mazzer P A; Dudones L P; Joudah L; Stroup D

Publisher

Nucleic Acids Research

Date

1999
1999-05

Description

Chromium(V)-mediated oxidative damage of deoxyribonucleic acids was investigated at neutral pH in aqueous solution by utilizing bis(2-ethyl-2-hydroxybutanato)oxochromate(V) (I) and bis(hydroxyethyl)amino-tris(hydroxymethyl)methane)oxochromate(V) (II). Single-stranded and double-stranded (ds) calf thymus and human placenta DNA, as well as two oligomers, 5'-GATCTAGTAGGAGGACAAATAGTGTPTG-3' and 5'-GATCCAAGCAAACACTATTTGTCCTCCTACTA-3', were reacted with the chromium(V) complexes. Most products were separated and characterized by chromatographic and spectroscopic methods, Polyacrylamide gel electrophoresis experiments reveal more damage at G sites in comparison to other bases. Three primary oxidation products, 5-methylene-2-furanone (5-MF), furfural and 8-oxo-2'-deoxyguanosine, were characterized, A minor product, which appears to be thymine propenal, was also observed. The dsDNA produces more furfural than furanone, The formation of these two products resulted from hydrogen abstraction dr hydride transfer from C1' and C5' positions of the ribose to the oxo-chromium(V) center. Since no enhancements of these products (except propenal) were observed in the presence of oxygen, mechanisms pertaining to the participation of activated oxygen species may be ruled out. The oxidation of the G base is most likely associated with an oxygen atom transfer from the oxo-metallates to the double bond between C8 and N7 of the purine ring. The formation of the propenal may be associated with an oxygen-activated species, since a marginal enhancement of this product was observed in the presence of oxygen, The formation of furfural in higher abundance over 5-MF for dsDNA was attributed to the ease of hydrogen abstraction (or hydride transfer) from the C5' compared to C1' position of the ribose within a Cr(V)-DNA intermediate in which the metal center is bound to the phosphate diester moiety.

Subject

Biochemistry & Molecular Biology; in-vitro; nucleic-acids; abstraction; aqueous-solution; carcinogen chromium(vi); hydrogen; molecular-oxygen; radical formation; redox potentials; singlet oxygen; strand breaks

Format

Journal Article or Conference Abstract Publication

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Rights

Article information provided for research and reference use only. All rights are retained by the journal listed under publisher and/or the creator(s).

Pages

2219-2226

Issue

10

Volume

27

Citation

Bose R N; Moghaddas S; Mazzer P A; Dudones L P; Joudah L; Stroup D, “Oxidative damage of DNA by chromium(V) complexes: relative importance of base versus sugar oxidation,” NEOMED Bibliography Database, accessed May 18, 2021, https://neomed.omeka.net/items/show/8680.

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