Synthetic routes for C8-oxygen bonded deoxyguanosine adducts and photo-physical measurements of isomeric prodigiosin analogues

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La, Jamie Q.
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University of Guelph

Part I. This thesis is an investigation to devise a synthetic route for the biologically important 'O'-bound C8 adducted deoxyguanosine nucleoside. Here in, several methodological approaches are employed in an attempt to synthesize specifically oxygen bonded deoxyguanosine adducts. As shown by this research, palladium cross coupling reactions proved to be the most promising method for continuation and optimization of the project at hand. Future work will involve the incorporation of the oxygen bonded C8 adduct into duplex DNA and determine its biological effects. Part II. This thesis is an investigation of the synthetic routes, spectrophotometric measurements, fluorescent data, solvents effects, and 'keto-enol' equilibrium for compounds ' o'-hydroxy-phenyl-2-prodigiosin 42 and 'p'-hydroxy-phenyl-2-prodigiosin 43. Future work entails cytotoxicity studies against HL-b0 leukemia cells and the determination if the 'keto'-form contribution or even the phenolic moiety itself enhances biological activity of the prodigiosins.

synthetic route, O-bound C8 adducted deoxyguanosine nucleoside, oxygen bonded deoxyguanosine adducts, isomeric prodigiosin analogues