The synthesis, physicochemical properties, and toxicological implications of a novel series of N-2-(azol-1(2)-yl)ethyliminodiacetic acids, useful as contrast agents for magnetic resonance imaging are reported. Compounds were prepared by alkylation of methyl iminodiacetate with N-2-bromoethylazoles and subsequent hydrolysis. Stability constants of the corresponding Gd(III) complexes and T1 and T2 relaxivities were determined and interpreted in terms of optimized geometries obtained by semiempirical PM3 calculations. Compounds show increased T2 relaxivity and decreased toxicity in vitro as compared to EDTA-Gd(III) complexes. Copyright (C) 1999 Elsevier Science Ltd.

This work was supported in part by grants D.G.I.C.Y.T (PB-93-0037, PB-94-0011 and Acciones Integradas HA95-14B and HA96-99B), D.G.E.S. PB96-011-C01, PB96-0864-CO2-02), Community of Madrid (AC-07/105/96, AC-08.1/0023/97).

Peer Reviewed