Synthetic Enterobactin Analogues. Carboxamido-2,3-dihydroxyterephthalate Conjugates of Spermine and Spermidine

Article abstract of DOI:10.1021/jm00134a015

Two examples of a new class of synthetic polycatecholate ligands, the carboxamido-2,3-dihydroxyterephthalate conjugates of spermine (8) and 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-μmol/kg (ip) dose of 8 removed 73percent of the plutonium citrate previously injected (iv,1h earlier).Under the same conditions, trimeric terephthalate (10) ex creted only 49percent 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.