| Popis: |
This study was focused on development of a novel glucosensor for continuous and noninvasive monitoring of tear glucose. This was an effort to relieve diabetic patients of pain while assaying their blood glucose by conventional invasive methods like finger pricking. The project consisted of two parts: synthesis of a catechol based dye and improvement of its properties through further modification; secondly, synthesis of a novel pyridinylboronic acid framework. The target dye was synthesized through a series of reactions. Subsequently, the dye was tested for its utility as an indicator by using dye-glucose-pyridinylboronic acid system; but it failed to respond positively at the physiologic pH of 7.4. In an interesting reaction, furfurylamine was ring expanded to a bromopyridinol. which was successfully converted to 3-allyloxy-5-bromopyridinol. Allyl functionality was introduced to serve two purposes, one being to utilize its C=C double bond as an anchoring site for a siloxane oligomer. The other purpose of protecting the hydroxyl group during sensitive reactions was badly defeated when both the alkyl lithium and palladium catalyzed cross-coupling route to pyridinylboronic acid synthesis failed. This interference by allyl group could be avoided by using acryloyl moiety. Anyway, in terms of future prospect, the idea of glucosensor seemed to be pretty much realizable. Proper fine-tuning of the dye system and pyridine moiety could lead to successful completion of the project. |
