SYNTHESIS OF AN OPTICALLY PURE MULTIVALENT SCAFFOLD

Ryan Lacy , Nabila Brabez, and Victor Hruby

SYNTHESIS OF AN OPTICALLY PURE MULTIVALENT SCAFFOLD

 It was noted that cancer cells often over express various types of receptors on their surface. In an effort to combat these rapidly dividing cells, we theorized that the use of multivalent ligand-receptor interaction could increase specificity and effectiveness of current cancer treatment drugs. This project is focused on the design, synthesis, and testing of multivalent ligands and their use in early cancer detection and treatment. Tests were performed initially with homo trivalent ligands. This multivalent ligand was comprised of three ligands that individually were shown to have micromolar affinities. Yet, when these ligands were combined together into a trivalent construct, they showed a large increase in affinity into the nanomolar level. This large fold increase in affinity made us hopeful that a trivalent ligand composed of three different ligands, could cause an even larger affinity increase in addition to providing more specificity towards certain cancer cells. Our next step in this project is the synthesis of these heterotrivalent ligands. In order to be used in cancer treatment the scaffold of these ligands must be optically pure. This study focuses on the synthesis of this optically pure, heterovalent scaffold. The approach to synthesizing this optically pure scaffold is through the use of oppolozer sultam as an auxillary. This optically pure scaffold will be protected with three different protecting groups, which will allow the addition of three different ligands and consequentially the creation of an optically pure, heterotrivalent ligand.

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