Apurinic DNA: Modelisation and Reactivity Towards 9-Aminoellipticine and Related Amines

Abstract

The mechanism of breakage of the model apurinic oliaonucieotide Tp(AP)pT by 9 aminoellipticine and the structurally related 3-aminocarbazole was investigated. Breakage results from the formation of an unstable Schiff base between the aldehyde group of the apurinic site and the aromatic amines. followed by fact β-elimination of 5′ -Dhasphate thymidine. An α.13-Othvlenic Schiff base is then formed which can account for the specific fluorescence observed during the reaction between apurinic DNA and 9-aminoellipticine.