Literature DB >> 10536146

Formation of 5-formyl-2'-deoxycytidine from 5-methyl-2'-deoxycytidine in duplex DNA by Fenton-type reactions and gamma-irradiation.

N Murata-Kamiya1, H Kamiya, N Karino, Y Ueno, H Kaji, A Matsuda, H Kasai.   

Abstract

5-methyl-2'-deoxycytidine (5-Me-dC) is formed by the enzymatic methylation of dC, primarily in CpG sequences in DNA, and is involved in the regulation of gene expression. In the present study, 5-Me-dC and double-stranded DNA fragments containing 5-Me-dC were either gamma-irradiated or aerobically treated with Fenton-type reagents, Fe(II)-EDTA, Fe(II)-nitrilotriacetic acid, Fe(III)-EDTA-H(2)O(2)-catechol or ascorbic acid-H(2)O(2) under neutral conditions. The formation of 5-formyl-2'-deoxycytidine (5-CHO-dC) was observed upon treatment of both 5-Me-dC and DNA fragments containing 5-Me-dC. The yields of 5-CHO-dC from 5-Me-dC and those of 5-formyl-2'-deoxyuridine from dT were comparable. These results suggest that 5-Me-dC in DNA is as susceptible to oxidation as dT in cells, and raise the possibility that 5-CHO-dC may contribute to the high mutagenic rate observed in CpG sequences in genomic DNA.

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Year:  1999        PMID： 10536146      PMCID： PMC148720          DOI： 10.1093/nar/27.22.4385

Source DB:  PubMed          Journal:  Nucleic Acids Res        ISSN： 0305-1048            Impact factor:   16.971


  7 in total

1.  Synthesis and properties of oligonucleotides containing 5-formyl-2'-deoxycytidine: in vitro DNA polymerase reactions on DNA templates containing 5-formyl-2'-deoxycytidine.

Authors:  N Karino; Y Ueno; A Matsuda
Journal:  Nucleic Acids Res       Date:  2001-06-15       Impact factor: 16.971

2.  Thymine DNA glycosylase can rapidly excise 5-formylcytosine and 5-carboxylcytosine: potential implications for active demethylation of CpG sites.

Authors:  Atanu Maiti; Alexander C Drohat
Journal:  J Biol Chem       Date:  2011-08-23       Impact factor: 5.157

3.  Synthesis of stable-isotope enriched 5-methylpyrimidines and their use as probes of base reactivity in DNA.

Authors:  Artur Burdzy; Katherine T Noyes; Victoria Valinluck; Lawrence C Sowers
Journal:  Nucleic Acids Res       Date:  2002-09-15       Impact factor: 16.971

4.  Oxidative DNA damage induced by copper and hydrogen peroxide promotes CG-->TT tandem mutations at methylated CpG dinucleotides in nucleotide excision repair-deficient cells.

Authors:  Dong-Hyun Lee; Timothy R O'Connor; Gerd P Pfeifer
Journal:  Nucleic Acids Res       Date:  2002-08-15       Impact factor: 16.971

Review 5.  Mutagenic potentials of damaged nucleic acids produced by reactive oxygen/nitrogen species: approaches using synthetic oligonucleotides and nucleotides: survey and summary.

Authors:  Hiroyuki Kamiya
Journal:  Nucleic Acids Res       Date:  2003-01-15       Impact factor: 16.971

6.  New functions for DNA modifications by TET-JBP.

Authors:  Yun Huang; Anjana Rao
Journal:  Nat Struct Mol Biol       Date:  2012-11       Impact factor: 15.369

7.  Hydroxyl-radical-induced oxidation of 5-methylcytosine in isolated and cellular DNA.

Authors:  Guru S Madugundu; Jean Cadet; J Richard Wagner
Journal:  Nucleic Acids Res       Date:  2014-05-22       Impact factor: 16.971
  7 in total

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