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Synthesis of C8-N-acetylarylamine 2'-dG-adducts and their site-specifically incorporation into oligonucleotides.

Beside the predominately found C8-NH-arylamine-dG damages also C8-N-acetylarylamine-lesions of 2'-dG seems to play an important role in the induction of the chemical carcinogenesis. A new synthetic pathway leading to these DNA-adducts using different aromatic amines have been developed. The C8-dG-adducts were converted into the corresponding phosphoramidites and incorporated site-specifically into oligonucleotides giving damaged DNA-strands. With damaged DNA hybrids studies with respect to their thermal stability (UV melting temperature analysis) and circular dichroism were performed.