Photo-oxidation of duplex DNA with the stable trioxatriangulenium ion.

ABSTRACT

We show that 5'-Gs in 5'-GG-3' duplex DNA dinucleotide steps are preferentially oxidized by the trioxatriangulenium ion (TOTA( plus sign in circle )) upon photo-activation, an oxidation pattern characteristic of guanine radical cation formation. Some photo-oxidation of the 3'G in 5'GG3' steps and of isolated guanines is also observed but reactions carried out in D(2)O reveal only a minor increase in oxidation damage at these sites, indicating that electron transfer is the primary mechanism of guanine oxidation.