Abstract
We describe studies of aziridine-2-carboxamide (Leakadine) reactivity with N-, O-, and S-nucleophiles in aqueous solutions using NMR spectroscopy and chemical synthesis. The results show that nucleophilic ring opening reactions of Leakadine with N- and O-nucleophiles take place only in acidic solutions, while reactions with S-nucleophiles occur irrespective of the pH and at a significantly higher reaction rate. These data suggest that the antitumor and immunostimulating activity of Leakadine may be associated with inhibition of extracellular cysteine proteases of cancer cells.
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