Browsing by Author "Rättö, Ronja"

In this master’s thesis biochemistry of cancer, glucose transporters in cancer therapy and the importance of imaging are explored, and the synthesis of applicable glycoconjugates is introduced. Bioorthogonal applications of functionalizable glycoconjugates, such as, drug delivery, imaging, cancer therapy and studying biological phenomenon inside living cells, are reviewed. The basic theories on biochemistry of cancer, cancer imaging with [18F]-2-fluoro-2- deoxy-D-glucose-Positron Emission Tomography (18FDG-PET) and glucose transporters are discussed in the literature review section. The databases used to scan relevant literature were SciFinder and Helsinki University Library (Helka) web article search. The first of the glycoconjugates synthesized, 1,2,3,4-Tetra-O-benzyl-6-O-propargyl-D- glucopyranose, is already published in the literature as an intermediate on the route towards improved delivery agents for BNCT. The final product has been assessed in in vitro studies, cellular uptake and cytotoxicity studies giving outstanding results. The boron delivery capacity of the molecule is prominently superior compared to the agents in clinical use at the moment. The glucoconjugate can also be functionalized for the use in other applications with the use of the propargyl conjugation site. The second synthesis covers two potential bioorthogonal chemistry glycoconjugates: α-D-Mannopyranoside, phenyl 6-azido-6-deoxy-3,4-O-[(1S,2S)-1,2- dimethoxy-1,2-dimethyl-1,2-ethanediyl]-1-thio-, 2-trifluoromethanesulfonate and -2-(4- methylbenzenesulfonate). These mannopyranoside derivatives are functionalizable glycoconjugates with a wide range of applications in biological research. They both contain three conjugation sites that can be functionalized for further applications. The carbohydrate part is recognized by cells, the azide functional group at C-6 can be modified through click chemistry, the thiol can be activated in glycosylation reactions and the triflate or tosylate in C-2 can be substituted in an SN2 reaction, for example with [18F] to enable imaging. This elegant toolkit offers a wide range of biorthogonal opportunities for chemists and biologists alike.