NDLI: DNA damage by oxo- and peroxo-chromium(v) complexes: insight into the mutation and carcinogenesis mechanisms

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DNA damage by oxo- and peroxo-chromium(v) complexes: insight into the mutation and carcinogenesis mechanisms

Content Provider	Royal Society of Chemistry (RSC)
Author	Wesdemiotis, Chrys Stroup, Diane Bose, Rathindra N. Marin, Roberto Judah, Lamis
Copyright Year	2014
Abstract	The carcinogenic and mutagenic properties of chromium(VI) compounds are attributed to hypervalent chromium species, especially metastable oxo- and peroxo-chromium(V)/(IV) complexes. To understand the nature of DNA damage induced by various hypervalent chromium complexes, reactions of sodium bis(2-ethyl-2-hydroxybutanato)oxochromate(V) (I) with single- and double-stranded DNA were investigated in the presence of hydrogen peroxide and a radical scavenger. In these reactions, three DNA damaging agents, oxo- and peroxo-chromium(V) complexes and hydroxyl radicals, were generated. Both double and single-stranded DNA cleavages were largely observed after piperidine treatment, indicating base-labile scissions. Although these cleavages appeared to be random in most cases, a modest selectivity towards the G base was observed for the double stranded oligonucleotides. A variety of sugar and base oxidation products were detected after enzymatic digestion of the reaction mixtures with exo- and endo-nucleases. These products include furfural, 5-methylene furanone, 8-oxo-7,8-dihydro-2′-guanosine (8-oxodGuo), thymine propenal, deoxyribonucleoside derivative of 5-guanidinohydantoin (dGh), cytosine glycol and 5-hydroxy cytosine. The first three mentioned products were observed for reactions of compound I with DNA in the absence of peroxide. Since compound I generated a persistent peroxo-chromium(V) complex in situ and oxidation of DNA by the oxo-chromium(V) was relatively slow, it appears that the peroxo-species was largely responsible for the formation of dGh through a four-electron oxidation of the guanine residue following the mechanism proposed by Meunier and coworkers. Likewise, the formation of propenals follows a similar pathway observed for bleomycine-mediated DNA oxidation that follows Hecht's mechanism. On the other hand, 5,6-dihydroxy-5,6-dihydro-2′-deoxycytidine (dCydGl) and 5-hydroxy-2′-deoxycytidine (5-OHdCyd) were most likely formed from the reactions of DNA with the hydroxyl radical. We hypothesize that base oxidations and the formation of abasic sites are most likely responsible for transverse DNA mutation.
Starting Page	56
Ending Page	66
Page Count	11
File Format	HTM / HTML PDF
ISSN	2045452X
Volume Number	3
Issue Number	1
Journal	Toxicology Research
DOI	10.1039/c3tx50061f
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Hydrogen peroxide Furfural Methylene bridge Guanosine Hypervalent molecule Guanine Metastability Hydroxy group Hecht Meunier Carbohydrate Cytosine Scavenger (chemistry) Piperidine Hydroxyl radical DGH Thymine 8-Oxo-2'-deoxyguanosine 2-Furanone Hexavalent chromium Sodium Deoxycytidine DNA Chromium Mutation
Content Type	Text
Resource Type	Article
Subject	Health, Toxicology and Mutagenesis Toxicology

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