Browsing by Author "Rautsola, Iiro"

Multimodality imaging is an efficient, non-invasive method for investigation of molecular and cellular processes in vivo. However, the potential of multimodality imaging in plant studies is yet to be fully realized, largely due to the lack of research into suitable molecular tracers and instrumentation. Iodine has PET- and SPECT-compatible radioisotopes that have significant advantages over other radioisotopes applied in plant radioisotope imaging, and can be incorporated into small molecules via a variety of reactions. In this master’s thesis, a radioiodination method exploiting a novel, Dowex® H+-mediated addition of iodine for terminal alkynes was optimized and tested on two D-glucose analogues. The goal of the sugar analogue radioiodination was to develop a radioiodinated molecular tracer for plant carbohydrate metabolism studies. The parameters under optimization were activation Dowex® by HCl, reaction temperature, carrier amount, solvent, and evaporation of excess water. The most optimal results were achieved under the following conditions: Dowex® HCl-activated, reaction temperature 95 °C, amount of carrier 3.0 µmol of carrier, cyclohexanol as solvent, and excess water evaporated. The Dowex® approach was compared to electrophilic reactions with Chloramine T and Iodogen, and it was concluded that the Dowex® approach leads to superior radiochemical yields under the optimized conditions. The Dowex® method was successfully tested on the sugar analogues, resulting in a single main product at a satisfactory 50 – 56 % radiochemical yield. The main products were successfully characterized with NMR, and in addition the method was indicated to be regioselective. It is plausible that the developed method may be improved further in terms of radiochemical yield and molar activity, and that the method could prove to be a useful tool for developing novel radiodinated molecular tracers for plant studies.