One-electron oxidation of a pyrenyl photosensitizer covalently attached to DNA and competition between its further oxidation and DNA hole injection.

ABSTRACT: The photosensitized hole injection and guanine base damage phenomena have been investigated in the DNA sequence, 5'-d(CATG(1)(Py)CG(2)TCCTAC) with a site-specifically positioned pyrene-like (Py) benzo[a]pyrene 7,8-diol 9,10-epoxide-derived N(2)-guanine adduct (G(1)(Py)). Generation of the Py radical cation and subsequent hole injection into the DNA strand by a 355 nm nanosecond laser pulses (approximately 4 mJ cm(-2)) results in the transformation of G(1)(Py) to the imidazolone derivative Iz(1)(Py) and a novel G(1)(Py*) photoproduct that has a mass larger by 16 Da (M+16) than the mass (M) of G(1)(Py). In addition, hole transfer and the irreversible oxidation of G(2), followed by the formation of Iz(2) was observed (Yun et al. [2007], J. Am. Chem. Soc., 129, 9321). Oxygen-18 and deuterium i

SUBMITTER: Yun BH 

PROVIDER: S-EPMC3705723 | biostudies-literature | 2010 May-Jun

REPOSITORIES: biostudies-literature