Formation of an 8-hydroxyguanine moiety in deoxyribonucleic acid on gamma-irradiation in aqueous solution
Isolation and characterization of a novel radiation-induced product, i.e., the 8-hydroxyguanine residue, produced in deoxyribonucleic acid (DNA), 2'-deoxyguanosine, and 2'-deoxyguanosine 5'-monophosphate by gamma-irradiation in aqueous solution, are described. For this purpose, gamma-irradiated DNA was first hydrolyzed with a mixture of four enzymes, i.e., DNase I, spleen and snake venom exonucleases, and alkaline phosphatase. Analysis of the resulting mixture by capillary gas chromatography-mass spectrometry after trimethylsilylation revealed the presence of a product, which was identified as 8-hydroxy-2'-deoxyguanosine on the basis of the typical fragment ions of its trimethylsilyl (Me3Si) derivative. This product was then isolated by using reversed-phase high-performance liquid chromatography. The UV and proton nuclear magnetic resonance spectra taken from the isolated product confirmed the structure suggested by the mass spectrum of its Me3Si derivative. The yield of 8-hydroxyguanine was also measured. Its mechanism of formation is believed to involve OH radical addition to the C-8 position of guanine followed by oxidation of the radical adduct.
- Research Organization:
- National Bureau of Standards, Gaithersburg, MD
- OSTI ID:
- 6293650
- Journal Information:
- Biochemistry; (United States), Vol. 16
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
DNA
BIOLOGICAL RADIATION EFFECTS
PURINES
NMR SPECTRA
ALKALINE PHOSPHATASE
AQUEOUS SOLUTIONS
CATTLE
DNA-ASE
GAMMA RADIATION
GAS CHROMATOGRAPHY
GUANINE
LIQUID COLUMN CHROMATOGRAPHY
MASS SPECTROSCOPY
NUCLEAR MAGNETIC RESONANCE
NUCLEASES
AMINES
ANIMALS
AROMATICS
AZAARENES
BIOLOGICAL EFFECTS
CHROMATOGRAPHY
DISPERSIONS
DOMESTIC ANIMALS
ELECTROMAGNETIC RADIATION
ENZYMES
ESTERASES
HETEROCYCLIC COMPOUNDS
HYDROLASES
HYDROXY COMPOUNDS
IONIZING RADIATIONS
MAGNETIC RESONANCE
MAMMALS
MIXTURES
NUCLEIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHOSPHATASES
PHOSPHODIESTERASES
RADIATION EFFECTS
RADIATIONS
RESONANCE
RUMINANTS
SEPARATION PROCESSES
SOLUTIONS
SPECTRA
SPECTROSCOPY
VERTEBRATES
560111* - Radiation Effects on Biochemicals- In Vitro- (-1987)