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

Shun-suke Moriya; Toshiyuki Miura; Koichi Takao; Yoshiaki Sugita; Keijiro Samejima; Kyoko Hiramatsu; Masao Kawakita

doi:10.1248/bpb.b13-00913

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

Shun-suke Moriya, Toshiyuki Miura, Koichi Takao, Yoshiaki Sugita, Keijiro Samejima , Kyoko Hiramatsu, Masao Kawakita

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Keywords: spermine oxidase, N¹-acetylpolyamine oxidase, irreversible inhibitor, MDL 72527, polyamine catabolism

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2014 Volume 37 Issue 3 Pages 475-480

DOI https://doi.org/10.1248/bpb.b13-00913

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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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