DNA Photosensitization by an "Insider": Photophysics and Triplet Energy Transfer of 5‐Methyl‐2‐pyrimidone Deoxyribonucleoside. Issue 32 (1st July 2015)

• Record Type: Journal Article
• Authors: Bignon, Emmanuelle; Gattuso, Hugo; Morell, Christophe; Dumont, Elise; Monari, Antonio
• Is Part Of: Chemistry. Volume 21:Issue 32(2015)
• Page Start: 11509
• Page End: 11516
• Publication Date: 2015-07-01
• Subjects: DNA -- energy transfer -- molecular dynamics -- nucleobases -- photophysics; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201501212
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: The main chromophore of (6‐4) photoproducts, namely, 5‐methyl‐2‐pyrimidone (Pyo), is an artificial noncanonical nucleobase. This chromophore has recently been reported as a potential photosensitizer that induces triplet damage in thymine DNA. In this study, we investigate the spectroscopic properties of the Pyo unit embedded in DNA by means of explicit solvent molecular‐dynamics simulations coupled to time‐dependent DFT and quantum‐mechanics/molecular‐mechanics techniques. Triplet‐state transfer from the Pyo to the thymine unit was monitored in B‐DNA by probing the propensity of this photoactive pyrimidine analogue to induce a Dexter‐type triplet photosensitization and subsequent DNA damage. Abstract : Internal affairs : The structural and photophysical properties of the artificial nucleobase 5‐methyl‐2‐pyrimidone (Pyo) embedded in a B‐DNA representative pentadecamer are revealed by means of explicit solvent molecular‐dynamics simulations (see picture). Furthermore, the triplet‐state transfer of the Pyo unit in B‐DNA and its propensity to induce a Dexter‐type triplet photosensitization and subsequent DNA damage were monitored.