Cleavage at 5-methylcytosine in DNA by photosensitized oxidation with 2-methyl-1,4-naphthoquinone tethered oligodeoxynucleotides

Hisatsugu Yamada; Kazuhito Tanabe; Sei-Ichi Nishimoto

doi:10.1016/j.bmcl.2004.11.038

Cleavage at 5-methylcytosine in DNA by photosensitized oxidation with 2-methyl-1,4-naphthoquinone tethered oligodeoxynucleotides

Bioorg Med Chem Lett. 2005 Feb 1;15(3):665-8. doi: 10.1016/j.bmcl.2004.11.038.

Authors

Hisatsugu Yamada¹, Kazuhito Tanabe, Sei-Ichi Nishimoto

Affiliation

¹ Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura Campus, Kyoto 615-8510, Japan.

PMID: 15664833
DOI: 10.1016/j.bmcl.2004.11.038

Abstract

Photosensitized one-electron oxidation of 5-methylcytosine in DNA by 2-methyl-1,4-naphthoquinone, attached to 5'-end of an oligodeoxynucleotide strand, produced 5-formylcytosine and led to selective DNA strand cleavage at the original 5-methylcytosine configuration. This specified photoreaction is useful for positive display of 5-methylcytosine in DNA on a sequencing gel.

MeSH terms

5-Methylcytosine / chemistry*
Autoradiography
DNA Damage*
Humans
Hydrolysis
Naphthoquinones / chemistry
Oligodeoxyribonucleotides / chemistry*
Oxidation-Reduction
Phosphorus Radioisotopes
Photochemistry
Structure-Activity Relationship
Vitamin K 3 / chemistry*

Substances

Naphthoquinones
Oligodeoxyribonucleotides
Phosphorus Radioisotopes
5-Methylcytosine
Vitamin K 3