title: Development of irreversible inactivators of spermine oxidase and N1-acetylpolyamine oxidase.
abstract: Three functional groups (2-propenyl, 2-propynyl, and 2,3-butadienyl) were introduced onto one of the terminal amino groups of spermidine. Of the six compounds synthesized, N-(3-aminopropyl)-N'-2,3-butadienyl-1,4-butanediamine (N(8)-butadienyl Spd) and N-[3-(2,3-butadienylamino)propyl]-1,4-butanediamine (N(1)-butadienyl Spd) irreversibly inactivated human spermine oxidase (SMO) and N(1)-acetylpolyamine oxidase (APAO). Interestingly, N(8)-butadienyl Spd inactivated SMO far more potently than N,N'-di-2,3-butadienyl-1,4-butanediamine (MDL 72527).
authors.affiliation: Translational Medical Research Center, Tokyo Metropolitan Institute of Medical Science.
authors.forename: Shun-suke
authors.initials: SS
authors.lastname: Moriya
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Miura
authors.forename: Koichi
authors.initials: K
authors.lastname: Takao
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Sugita
authors.forename: Keijiro
authors.initials: K
authors.lastname: Samejima
authors.forename: Kyoko
authors.initials: K
authors.lastname: Hiramatsu
authors.forename: Masao
authors.initials: M
authors.lastname: Kawakita
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D006801:Humans; D000587:Oxidoreductases Acting on CH-NH Group Donors / Q000037:antagonists & inhibitors*; D013095:Spermidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology*; D013096:Spermine / Q000378:metabolism*; D000097667:Polyamine Oxidase
chemical_list: D004791:Enzyme Inhibitors; D000587:Oxidoreductases Acting on CH-NH Group Donors; D013095:Spermidine; D013096:Spermine; D000097667:Polyamine Oxidase