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  • Title: Phenolic ethylenediamine derivatives: a study of orally effective iron chelators.
    Author: Hershko C, Grady RW, Link G.
    Journal: J Lab Clin Med; 1984 Mar; 103(3):337-46. PubMed ID: 6699459.
    Abstract:
    Of 35 potential iron chelators screened for in vivo activity in rats, a group of phenolic compounds with excellent chelating properties were identified. These included N,N'-ethylene-bis(o-hydroxyphenylglycine) (EHPG), N,N'-Bis(o-hydroxybenzyl)-ethylenediamine diacetic acid (HBED), and their respective dimethyl esters (dmEHPG and dmHBED). All four phenolic compounds produced a marked increase in the fecal excretion of hepatocellular radioiron. This amounted to 42% of total body radioactivity with dmEHPG, 58% with EHPG, 63% with HBED, and 80% with dmHBED after a single injection of 40 mg/animal. At a dose of 5 mg/animal, EHPG, HBED, and dmHBED were 9, 12, and 15 times more potent, respectively, than deferoxamine. Both dimethyl esters showed significant oral activity; oral dmEHPG retained 1/3 and dmHBED retained 2/3 of the effect of the same dose given by intramuscular injection. The ester dmHBED combines oral effectiveness with superior chelating ability, selective hepatocellular action, and low apparent toxicity. It may represent a significant advance in the development of new iron chelating drugs.
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