Guanylated Diamines, Triamines, and Polyamines: Chemistry and Biological Properties

The preparation methodologies and chemical properties of guanylated diamines, triamines, and polyamines are reported. The precursor for polyamine biosynthesis is ornithine, a nonproteic amino acid, an intermediate of the urea cycle, and derived from arginine by the action of arginase. Ornithine decarboxylase (ODC) is required for the first step in polyamine synthesis, in which ornithine is decarboxylated to produce putrescine. The degradation of ODC is regulated by the antizyme, a small protein induced by polyamine that regulates also the polyamine transporter. Spermidine/spermine N1-acetyl-transferase (SSAT) is a propylamine acetyltransferase that monoacetylates spermidine and may form either mono or diacetylates spermine. Guanethidine is a monoguanylated ethylendiamine whose amine moiety is constituted by an octahydro-1-azocyne. The synthesis of structurally simple monoguanylated diamines through direct guanylation of diamines with S-Me- or O-Me-iso(thio)ureas is an effective approach.