Formation of S-formyl-2'-deoxycytidine from 5-methyl-2'-deoxycytidine in duplex DNA by Fenton-type reactions and -irradiation | Zendy

Hiroyuki Kamiya | Zendy; N. Karino | Zendy; Yoshihito Ueno | Zendy; Hiroyuki Kaji | Zendy; Akira Matsuda | Zendy; Hiroshi Kasai | Zendy

Open Access

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

Author(s) -

Hiroyuki Kamiya,

N. Karino,

Yoshihito Ueno,

Hiroyuki Kaji,

Akira Matsuda,

Hiroshi Kasai

Publication year - 1999

Publication title -

nucleic acids research

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 9.008

H-Index - 537

eISSN - 1362-4954

pISSN - 0305-1048

DOI - 10.1093/nar/27.22.4385

Subject(s) - deoxycytidine , dna , biology , dna methylation , cpg site , microbiology and biotechnology , methylation , biochemistry , gene , gene expression , genetics , chemotherapy , gemcitabine

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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