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.
Khomutov
A R
AR
Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov St, 32, Moscow, Russia. alexkhom@list.ru
Grigorenko
N A
NA
Skuridin
S G
SG
D000588:Amines / Q000032:analysis; D002614:Chelating Agents / Q000138:chemical synthesis / Q000494:pharmacology; D015195:Drug Design; D006863:Hydrogen-Ion Concentration; D008958:Models, Molecular; D013095:Spermidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D013096:Spermine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology
D000588:Amines; D002614:Chelating Agents; D013096:Spermine; D013095:Spermidine