Inactivation of bovine plasma amine oxidase by 1,1,1-trihalo-3-aminopropanes

In this paper, we report the inactivation of copper containing bovine plasma amine oxidase (BPAO) by a series of saturated alkylamines containing halogen atoms at gamma-position, which are 1,1,1-trihalo-3-aminopropane, 1,1,1-trifluoro-2-hydroxy-3-aminopropane, 1,1,1-trichloro-2-hydroxy-3-aminopropane, and 1,1,1-trichloro-2-(2-phenethyloxy)-3-aminopropane. The trihalo-2-hydroxypropylamine analogs exhibited a time-dependent inactivation behavior of BPAO, with 1,1,1-trifluoro-2-hydroxy-3-aminopro pane as the most efficient inactivator. The incorporation of a OH group at beta-position increased inactivation efficiency by 10-fold within the trifluoro analogs, and the incorporation of a phenethyloxy group at beta-position exhibited a higher efficiency by 3-fold within the trichloro analogs based on I-75 values. All four compounds were found to be irreversible inactivators for BPAO. (C) 2017 Elsevier Inc. All rights reserved.