877220-56-9

Upstream product

• 111-41-1 2-(2-Aminoethylamino)ethanol 
• 174626-34-7 N-(benzyloxycarbonyl)-3-amino-1-propyl methanesulfonate 
• 34637-22-4 3-[(N-benzyloxycarbonyl)amino]propanol 

Downstream Products

• 877220-57-0 N³,N⁶,N⁹-tris(benzyloxycarbonyl)-9-amino-3,6-diazanonan-1-ol 
• 877220-58-1 N⁶,N⁹,N¹²-tris(benzyloxycarbonyl)-1,12-diamino-3,6,9-triazadodecane 

Relevant academic research and scientific papers

Synthesis and biological characterization of novel charge-deficient spermine analogues

Biogenic polyamines, spermidine and spermine, are positively charged at physiological pH. They are present in all cells and essential for their growth and viability. Here we synthesized three novel derivatives of the isosteric charge-deficient spermine analogue 1,12-diamino-3,6,9-triazadodecane (SpmTrien, 5a) that are N1-Ac-SpmTrien (5c), N12-Ac-SpmTrien (5b), and N1,N12-diethyl-1,12-diamino-3,6,9-triazadodecane (N1,N12-Et2-SpmTrien, 5d). 5a and 5d readily accumulated in DU145 cells at the same concentration range as natural polyamines and moderately competed for the uptake with putrescine (1) but not with spermine (4a) or spermidine (2). 5a efficiently down-regulated ornithine decarboxylase and decreased polyamine levels, while 5d proved to be inefficient, compared with N1,N11-diethylnorspermine (6). None of the tested analogues were substrates for human recombinant spermine oxidase, but those having free aminoterminus, including 1,8-diamino-3,6-diazaoctane (Trien, 3a), were acetylated by mouse recombinant spermidine/spermine N 1-acetyltransferase. 5a was acetylated to 5c and 5b, and the latter was further metabolized by acetylpolyamine oxidase to 3a, a drug used to treat Wilson's disease. Thus, 5a is a bioactive precursor of 3a with enhanced bioavailability.

A charge-deficient analogue of spermine with chelating properties

1,12-Diamino-3,6,9-triazadodecane, a new isosteric and charge-deficient analogue of spermine, is synthesized. Unlike spermine, the new analogue is an excellent chelator of Cu2+ ions. Possible applications of this compound for studying enzymes o