Lysyl oxidase (LOX) is a copper dependent amino oxidase that converts the amine side chains of lysine amino acids to aldehydes in order to form cross-linkages necessary for the maturation of the connective tissues collagen and elastin. Unfortunately, research has shown that LOX is also involved in the metastasis of cancer, in that tumors that induce LOX are more likely to spread to other parts of the body. Research has shown that β-aminopropionitrile (BAPN) can inhibit the LOX enzyme and prevent the tumor from metastasizing. BAPN is toxic, however, so it cannot be directly introduced to the body without damaging connective and epidermal cells.The goal of this project is to synthesize small amide carrier molecules that can selectively deliver BAPN to hypoxic tumor cells. Aromatic amides were prepared that incorporate the BAPN structure. Previous reaction conditions produced low yeilds, so new reaction conditions were tested. The optimal reaction conditions as well as yields will be reported. These products were then purified via column chromatography and tested via gas chromatography – mass spectrometry (GCMS) and nuclear magnetic resonance (NMR) spectroscopy. Once purity has been established, these molecules are submitted to our collaborators for screening against lysyl oxidase.

Synthesis of small amide carrier molecules for the inhibition of lysyl oxidase

256th National Meeting (2018)

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