Novel approach to design an isosteric charge-deficient analogue of spermine and its biochemically important derivatives.

The design and synthesis of SpmTrien (1,12-diamino-3,6,9-triazadodecane), an isosteric and charge-deficient analogue of spermine with excellent chelating properties towards Cu(2+) ions, as well as novel N(1)- and N(12)-Ac-SpmTriens and bis-Et-SpmTrien (N(1),N(12)-diethyl-1,12-diamino-3,6,9-triazadodecane) are described. Possible applications of SpmTrien and its derivatives to the investigation of the enzymes of polyamine metabolism and spermine cellular functions, including interaction with DNA, are discussed.