(A) Time course of the oxidation of spermine by SMOX as measured by hydrogen peroxide production coupled to HRP catalyzed oxidation of luminol over 10 min. All compounds (1–7) were assayed in triplicate at a concentration of 20 μM. Compounds were not pre-incubated with enzyme prior to reading. Luminescence was compared to vehicle control (shown in red) and MDL-72527 (shown in blue). Assay conditions: 0.083 M glycine buffer, pH = 8, 0.3 µg/mL of purified SMOX enzyme, 2 mM of spermine substrate, 25 °C. (B) Zoomed in view of data from panel A for compounds 1–7. (C) Lineweaver–Burk plot of compound 6 across three doses (0, 0.1, and 1 µM) and varying concentrations of substrate [spermine] Ki = 1.6 µM. All R2 values for kinetic analysis were >0.98. (D) Lineweaver–Burk plot of compound 7 across three doses (0, 0.1, and 1 µM) and varying concentrations of substrate [spermine] Ki = 0.46 µM. All R2 values for kinetic analysis were > 0.98.