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Browsing by Subject "Boron Neutron Capture Therapy"

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  • Synthesis of glycoconjugates for Boron Neutron Capture Therapy 
    Matović, Jelena (2019)
    Boron Neutron Capture Therapy is a binary cancer treatment based on the nuclear capture and fission reaction which occur when 10B is irradiated with low energy thermal neutrons. BNCT has throughout the years shown noticeable clinical results with the boron delivery agents that are currently available for testing. However, these delivery agents display deficiencies on multiple frontiers. My goal was to synthesize three different carbohydrate delivery agents for BNCT. Carbohydrate delivery agents have great potential for multiple reasons. They have low toxicity, high aqueous solubility and a high amount of boron atoms can be attached to a single molecule. These three synthesized molecules, 6-O-o-carboranylmethyl-D-glucopyranose, (O)-carboranylmethyl -D-glucopyranoside, (O)-carboranylmethyl -D-glucopyranoside, consist out of a glucose moiety and a carborane cage at both anomeric positions 1 as well as position 6. The synthetic pathways developed were 5-6 steps long and the overall yields varied between 13-15%. The synthesized molecules are currently undergoing biological evaluation.
  • Towards the synthesis of labeled glycoconjugates for boron neutron capture therapy 
    Stubb, Henrik (2021)
    Boron neutron capture therapy (BNCT) is an emerging cancer treatment method that is currently limited by suboptimal boron delivery strategies. A wide range of biomolecules have been investigated as potential tumor targeting boron carriers. Carbohydrates excel on several aspects by providing high solubility and low cytotoxicity. This work focuses on the synthesis of an orthogonally protected glycoconjugate for a GLUT1 targeting approach to BNCT. Knowledge of suitable glycoconjugate structures for this targeting strategy is emerging, and the aim of this work was to explore further functionalization of these structures, which will be necessary for future labeling of the boron carriers. The seven-step synthesis of an orthogonally protected mannopyranoside – and structural determination with NMR spectroscopy and mass spectrometry – is described in detail. The attachment of a boron cluster to the target molecule was performed, and early-stage fluorination trials were carried out. While important insights were obtained from these functionalization attempts, the functionalization of the target molecule will require some additional effort in the future. The protecting group strategies are currently being redesigned based on the information obtained through this work.

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