Synthesis and evaluation of the thiosemicarbazone, dithiocarbazonate, and 2'-pyrazinylhydrazone of pyrazinecarboxaldehyde as agents for the treatment of iron overload

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Abstract
Three prototype tridentate ligands (i.e., pyrazinecarboxaldehyde thiosemicarbazone, sodium pyrazinecarboxaldehyde dithiocarbazonate and pyrazinecarboxaldehyde 2''-pyrazinylhydrazone) were prepared and evaluated for their relative abilities to remove Fe from model systems designed to mimic particular aspects of chronic transfusional Fe overload. These compounds were synthesized by condensation of pyrazinecarboxaldehyde with the appropriate substituted hydrazide. Fe binding properties were determined, and the ability to remove Fe from the proteins transferrin and ferritin was ascertained. An in vivo model system employing Fe-loaded mice was used to demonstrate that all 3 compounds were effective at reducing tissue Fe levels.

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