Development of Irreversible Inactivators of Spermine Oxidase and <i>N</i><sup>1</sup>-Acetylpolyamine Oxidase

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  • Moriya Shun-suke
    Translational Medical Research Center, Tokyo Metropolitan Institute of Medical Science
  • Miura Toshiyuki
    Translational Medical Research Center, Tokyo Metropolitan Institute of Medical Science
  • Takao Koichi
    Faculty of Pharmaceutical Sciences, Josai University
  • Sugita Yoshiaki
    Faculty of Pharmaceutical Sciences, Josai University
  • Samejima Keijiro
    Translational Medical Research Center, Tokyo Metropolitan Institute of Medical Science
  • Hiramatsu Kyoko
    Translational Medical Research Center, Tokyo Metropolitan Institute of Medical Science
  • Kawakita Masao
    Translational Medical Research Center, Tokyo Metropolitan Institute of Medical Science

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  • Development of Irreversible Inactivators of Spermine Oxidase and N¹-Acetylpolyamine Oxidase

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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 (N8-butadienyl Spd) and N-[3-(2,3-butadienylamino)propyl]-1,4-butanediamine (N1-butadienyl Spd) irreversibly inactivated human spermine oxidase (SMO) and N1-acetylpolyamine oxidase (APAO). Interestingly, N8-butadienyl Spd inactivated SMO far more potently than N,N′-di-2,3-butadienyl-1,4-butanediamine (MDL 72527).

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