Synthetic enterobactin analogues. Carboxamido-2,3-dihydroxyterephthalate conjugates of spermine and spermidine.
Two examples of a new class of synthetic polycatecholate ligands, the carboxamido-2,3-dihydroxyterephthalate conjugates of spermine (8) and of spermidine (10), have been synthesized via the generally useful synthon methyl-2,3-dimethoxyterephthaloyl chloride (6). Initial biological evaluation reveals tetrameric terephthalate (8) to be an extremely effective agent for sequestering and removing plutonium from mice; a single 25-mumol/kg (ip) dose of 8 removed 73% of the plutonium citrate previously injected (iv, 1 h earlier). Under the same conditions, trimeric terephthalate (10) excreted only 49% of injected plutonium. In vitro kinetic experiments have shown that 10 rapidly and quantitatively removed Fe from human transferrin. These results are discussed in relation to the design of metal-ion specific sequestering agents.
D000818:Animals; D002614:Chelating Agents / Q000138:chemical synthesis*; D004758:Enterobactin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005260:Female; D006801:Humans; D007501:Iron / Q000302:isolation & purification; D051379:Mice; D010795:Phthalic Acids / Q000138:chemical synthesis*; D011005:Plutonium / Q000302:isolation & purification; D012694:Serine / Q000031:analogs & derivatives*; D013095:Spermidine / Q000138:chemical synthesis*; D013096:Spermine / Q000138:chemical synthesis*
D002614:Chelating Agents; D010795:Phthalic Acids; D004758:Enterobactin; D013096:Spermine; D012694:Serine; D011005:Plutonium; D007501:Iron; D013095:Spermidine