Chemical and biological characterization of glycidamide-adducted adenine in DNA.

ABSTRACT: Acrylamide, a food contaminant, is metabolically converted to glycidamide (GA), which reacts with nucleobases in DNA. Although several GA adducts with dG, 2'-deoxyadenosine (dA), and dC are known, the mutagenic potency of each adduct remains unclear. Here, we focused on N⁶-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine (N⁶-GA-dA), which is produced by the Dimroth rearrangement of N1-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine. We separately prepared N1-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine and N⁶-GA-dA and measured their Dimroth rearrangement reaction rates. Since N⁶-GA-dA is the stable final product under physiological conditions (pH 7.0, at 37°C), we examined its presence in genomic DNA isolated from GA-treated cells. N⁶-GA-dA

SUBMITTER: Akagi JI 

PROVIDER: S-EPMC12769786 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature