Formaldehyde-mediated modification of natural deoxyguanosine with amines: one-pot cyclization as a molecular model for genotoxicity.
Stable cross-linked adducts, 3-(2-deoxy-beta-D-ribofuranosyl)-7-phenyl-5,6,7,8-tetrahydro[1,3,5]triazino[1,2-a]purin-10(3H)-one and 7-butyl-3-(2-deoxy-beta-D-ribofuranosyl)-5,6,7,8-tetrahydro[1,3,5]triazino[1,2-a]purin-10(3H)-one, that formed chemically from natural deoxyguanosine and aniline or buthyl amine in the presence of formaldehyde were identified. This reaction appears to be a general reaction of deoxyguanosine and primary amines, and it may be a model of DNA modification with carcinogenic aromatic amines without metabolic activation, if formaldehyde is present.
Institute of Molecular and Cellular Biosciences, University of Tokyo, Japan.
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H
Takahashi
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Hashimoto
D000588:Amines / Q000737:chemistry; D003500:Cyclization; D003849:Deoxyguanosine / Q000737:chemistry*; D005557:Formaldehyde / Q000737:chemistry* / Q000633:toxicity; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D015394:Molecular Structure
D000588:Amines; D005557:Formaldehyde; D003849:Deoxyguanosine