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Structure and Stability of Oxygen-Linked DNA Adducts Derived from Phenolic Toxins

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dc.contributor.advisor Manderville, Richard A. Kuska, Michael S. 2013-05-17T18:20:32Z 2013-05-17T18:20:32Z 2013-05 2013-05-13 2013-05-17
dc.description.abstract A significant focus of nucleic acids research is on the reactivity of electrophilic species with DNA to form addition products (adducts). Phenols are known to be able to form adducts at the C8 site of deoxyguanosine (dG). This dissertation studies the oxygen (O)-linked class of phenolic dG adducts for their hydrolytic stability as well as their structural impact on the DNA duplex. To determine the effect of C8 O-linked phenolic dG adducts on glycosidic bond stability spectrophotometric determination of hydrolysis kinetics was performed. The kinetics establish the adducts to be less stable than native dG in acid, but surprisingly stable under physiological conditions. Then to assess the modified duplex structure, a C8 O-linked phenolic dG adduct was incorporated into a DNA duplex. Thermal melting analysis establish the adduct as having a destabilizing effect on the regularly paired duplex and the conformational analysis suggests the phenolic lesion to be weakly mutagenic. en_US
dc.description.sponsorship NSERC en_US
dc.language.iso en en_US
dc.rights Attribution-NoDerivs 2.5 Canada *
dc.rights.uri *
dc.subject DNA en_US
dc.subject Hydrolysis en_US
dc.subject Adduct en_US
dc.subject Modified DNA en_US
dc.subject DNA Duplex en_US
dc.subject DNA conformation en_US
dc.subject Kinetics en_US
dc.subject Acid Hydrolysis en_US
dc.subject C8-aryl adducts en_US
dc.subject C8 modified Guanosine en_US
dc.subject Guanosine en_US
dc.subject Phenols en_US
dc.subject Toxicity en_US
dc.subject Mutation en_US
dc.title Structure and Stability of Oxygen-Linked DNA Adducts Derived from Phenolic Toxins en_US
dc.type Thesis en_US Chemistry en_US Master of Science en_US Department of Chemistry en_US
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Attribution-NoDerivs 2.5 Canada Except where otherwise noted, this item's license is described as Attribution-NoDerivs 2.5 Canada