Reaction of DNA with glycidaldehyde. Isolation and identification of a deoxyguanosine reaction product.
Glycidaldehyde, a bifunctional carcinogenic alkylating agent, has been found to react with calf thymus DNA in vitro under alkaline conditions. A product was isolated and identified to be the result of a fusion of a delta4-imidazoline ring to the pyrimidine ring of deoxyguanosine at the N-1 and 2-NH2 positions. Following reaction and dialysis, the DNA was hydrolyzed enzymatically to nucleosides. The structural assignment of the product was based on comparison of the elution volume from a Sephadex G-10 column, the ultraviolet spectra at various conditions of pH, and the thin layer chromatographic properties with respect to an authentic sample. The formation of the extended ring system with DNA-derived guanosine may be related to the mode of carcinogenic action of this difunctional alkylating agent.
D000447:Aldehydes; D000477:Alkylating Agents; D000818:Animals; D001665:Binding Sites; D002417:Cattle; D004247:DNA; D003853:Deoxyribonucleosides; D004852:Epoxy Compounds; D006151:Guanosine; D013950:Thymus Gland
D000447:Aldehydes; D000477:Alkylating Agents; D003853:Deoxyribonucleosides; D004852:Epoxy Compounds; D006151:Guanosine; D004247:DNA