Chemical and photochemical generated carbon-centered radical intermediate and its reaction with desoxyribonucleic acid.
The possible action of carbon-centered radicals in promoting damage to DNA is explored by generation of the 2-phenylethyl radical. The radical is generated during oxidation of phenelzine (2-phenylethyl hydrazine) by ferricyanide, as well as optically from phenylpropionic acid. Covalent binding of the 2-phenylethyl radical to DNA is suggested by studies with the plasmid pBR 322 DNA. Other sensitive techniques used to study DNA damage were the interaction with formaldehyde at 60 degrees C and the fluorescence of DNA-Tb(III) and DNA-DAPI complexes. Theoretical MNDO calculations indicated a preferential attack at position 8 of the guanine residues. This study shows that the 2-phenylethyl radical is able to induce primary effects on nucleic acid structure, leading to alkylated products, especially at purine rings.
Justo
G Z
GZ
Instituto de Química, Universidade Estadual de Campinas, Brazil.
Livotto
P R
PR
Durán
N
N
D000478:Alkylation; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D004249:DNA Damage; D004578:Electron Spin Resonance Spectroscopy; D005292:Ferricyanides / Q000737:chemistry; D005456:Fluorescent Dyes; D005609:Free Radicals; D007211:Indoles; D007364:Intercalating Agents; D010084:Oxidation-Reduction; D010624:Phenelzine / Q000737:chemistry*; D010666:Phenylpropionates / Q000737:chemistry / Q000528:radiation effects; D010782:Photolysis; D013050:Spectrometry, Fluorescence; D013725:Terbium
D005292:Ferricyanides; D005456:Fluorescent Dyes; D005609:Free Radicals; D007211:Indoles; D007364:Intercalating Agents; D010666:Phenylpropionates; D013725:Terbium; C007931:hexacyanoferrate III; C007293:DAPI; C067490:terbium chloride; D004247:DNA; D010624:Phenelzine