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Tricatecholamide Analogs of Enterobactin as Gallium- and Indium-Binding Radiopharmaceuticals

The Edward Mallinckrodt Institute of Radiology, Washington University School of Medicine, St. Louis, Missouri
University of California, Berkeley
Lawrence Berkeley Laboratory, University of California, Berkeley, California

Correspondence: For reprints contact: Michael J. Welch, PhD, Dept. of Radiology, Washington Univ. School of Medicine, 510 S. Kingshighway, St. Louis, MO 63110.

ABSTRACT

Isopropyl N-substituted tricatecholamide analogs of enterobactin have been found to form gallium and indium complexes with very high stability constants and to exhibit in vivo characteristics significantly different from gallium- or indium-transferrin and EDTA. The 3,4-DiP-LICAMS and TiP-MECAMS complexes were found to clear primarily through the kidneys, whereas the less polar 3,4-DiP-LICAM complex was eliminated through the liver. The rationale for developing new metal-binding analogs with larger organic groups attached to the amide nitrogens is discussed.