3-Nitrobenzanthrone (3-NBA) is compound which posseses high mutagenic potential and is present in diesel exhaust. 3-NBA forms aminobenzanthrone (ABA) DNA adducts with the major product occurring at the C8 position of guanine. The synthetic preparation of the C8-dG-ABA adduct has allowed for investigation into the structural and thermodynamic properties of this adduct in the context of a 12-mer deoxynucleotide sequence. Utilizing nuclear Overhauser effect spectroscopy (NOESY) and correlation spectroscopy (COSY) NMR experiments we have been able to conclude that the C8-dG-ABA duplex adopts one major conformation in which the adduct intercalates within the duplex displacing the opposing base. Neighboring base pairs remain intact. Determination of the C8-dG-ABA duplex melting temperature shows a decrease of nearly 11 �C compared to native DNA indicating a significant loss in thermodynamic stability. Supported by NIH grants CA-55678 (M.P.S.), ES-009127 (A.B.), and ES-021762 (A.B.).

Structural characteristics of a C8 guanine adduct formed by 3-nitrobenzanthrone

248th National Meeting (2014)

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