Highly potent propargylamine and allylamine inhibitors of bovine plasma amine oxidase.
Propargylamine was reported many years ago to be a mechanism-based inhibitor of bovine plasma amine oxidase (BPAO), though the potency was modest and allylamine was a substrate. Herein, selected 3-substituted propargylamines and allylamines were found to be potent time-dependent inactivators of BPAO, exhibiting IC(50) values of 2-13 microM at 30 degrees C, making them the most potent BPAO inhibitors reported to date. The most potent compound, trans-3-chloroallylamine, was previously found not to inhibit the flavin-dependent monoamine oxidase (the cis isomer did), and thus appears to be a highly selective inhibitor.
Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106, USA.
Heung-Bae
HB
Jeon
Lawrence M
LM
Sayre
D000499:Allylamine / Q000737:chemistry / Q000378:metabolism*; D006631:Amine Oxidase (Copper-Containing) / Q000037:antagonists & inhibitors / Q000378:metabolism*; D000818:Animals; D001665:Binding Sites; D001798:Blood Proteins / Q000378:metabolism; D002417:Cattle; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D008667:Metalloproteins / Q000378:metabolism; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism*; D010949:Plasma / Q000201:enzymology*; D011437:Propylamines / Q000737:chemistry / Q000378:metabolism*; D013997:Time Factors
D001798:Blood Proteins; D004791:Enzyme Inhibitors; D008667:Metalloproteins; D011437:Propylamines; C009054:propargylamine; D000499:Allylamine; D010293:Pargyline; D006631:Amine Oxidase (Copper-Containing)