New substrates of polyamine oxidase. Dealkylation of N-alkyl-alpha, omega-diamines.
1) N-Alkyl-alpha, omega-diaminoalkanes are substrates of polyamine oxidase. 2) The compounds are oxidatively cleaved and form equimolar amounts of an aldehyde, a diamine, and H2O2. 3) Minimum structural requirements of a substrate of polyamine oxidase are two positively charged amino groups and an alkyl-substituent on one or both nitrogen atoms. 4) Dealkylation of N-alkyl derivatives by polyamine oxidase in vivo is a method to accumulate diamines in brain, and to release intracellularly an aldehyde from a stable prodrug.
Merrell Dow Research Institute, Strasbourg.
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Bolkenius
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Seiler
D000818:Animals; D001547:Benzaldehydes / Q000378:metabolism; D003959:Diamines / Q000138:chemical synthesis / Q000378:metabolism*; D066298:In Vitro Techniques; D008297:Male; D051379:Mice; D008956:Models, Chemical; D000587:Oxidoreductases Acting on CH-NH Group Donors / Q000378:metabolism*; D011700:Putrescine / Q000031:analogs & derivatives / Q000378:metabolism; D051381:Rats; D011915:Rats, Inbred BUF; D013552:Swine; D000097667:Polyamine Oxidase
D001547:Benzaldehydes; D003959:Diamines; D000587:Oxidoreductases Acting on CH-NH Group Donors; D011700:Putrescine; D000097667:Polyamine Oxidase; C061105:N,N'-bis(benzyl)-1,3-diaminopropane; C061106:N-benzylputrescine; C009475:trimethylenediamine; C032175:benzaldehyde