Synthesis and cross-linking activities of oligodeoxynucleotides containing a 4-oxoalkenal group.
The 4-oxoalkenal group, which has been characterized as part of a novel lipid-peroxidation-derived genotoxin, reacts with dG, dC, and dA, yielding etheno adducts. To develop a new interstrand cross-linking system based on the covalent bond formed between the 4-oxoalkenal group and DNA bases, we prepared 4-oxoalkenal-derivatized oligodeoxynucleotides. The protected 4-oxoalkenal derivative with a primary amino group was synthesized and incorporated to the 5' end of the oligodeoxynucleotide. In the presence of the complementary strand, cross-linking products were observed by HPLC and MALDI-MS analysis.
Kobori
Akio
A
Department of Biomolecular Engineering, Graduate School of Science and Technolog, Kyoto Institute of Technology, Gosyokaidocho, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.
Kobuchi
Takashi
T
Ikeda
Masato
M
Murakami
Akira
A
D002851:Chromatography, High Pressure Liquid; D003432:Cross-Linking Reagents / Q000138:chemical synthesis* / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D003432:Cross-Linking Reagents; D005663:Furans; D009838:Oligodeoxyribonucleotides