Formation of an 8-hydroxyguanine moiety in deoxyribonucleic acid on gamma-irradiation in aqueous solution

Journal Article · Tue Jul 30 04:00:00 EDT 1985 · Biochemistry; (United States)

DOI:https://doi.org/10.1021/bi00337a032· OSTI ID:6293650

Dizdaroglu, M

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), Journal Name: Biochemistry; (United States) Vol. 16; ISSN BICHA
• Country of Publication: United States
• Language: English

Related Subjects

560111* -- Radiation Effects on Biochemicals-- In Vitro-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
ALKALINE PHOSPHATASE
AMINES
ANIMALS
AQUEOUS SOLUTIONS
AROMATICS
AZAARENES
BIOLOGICAL EFFECTS
BIOLOGICAL RADIATION EFFECTS
CATTLE
CHROMATOGRAPHY
DISPERSIONS
DNA
DNA-ASE
DOMESTIC ANIMALS
ELECTROMAGNETIC RADIATION
ENZYMES
ESTERASES
GAMMA RADIATION
GAS CHROMATOGRAPHY
GUANINE
HETEROCYCLIC COMPOUNDS
HYDROLASES
HYDROXY COMPOUNDS
IONIZING RADIATIONS
LIQUID COLUMN CHROMATOGRAPHY
MAGNETIC RESONANCE
MAMMALS
MASS SPECTROSCOPY
MIXTURES
NMR SPECTRA
NUCLEAR MAGNETIC RESONANCE
NUCLEASES
NUCLEIC ACIDS
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PHOSPHATASES
PHOSPHODIESTERASES
PURINES
RADIATION EFFECTS
RADIATIONS
RESONANCE
RUMINANTS
SEPARATION PROCESSES
SOLUTIONS
SPECTRA
SPECTROSCOPY
VERTEBRATES