title: N-2-(azol-1(2)-yl)ethyliminodiacetic acids: a novel series of Gd(III) chelators as T2 relaxation agents for magnetic resonance imaging.
abstract: 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.
authors.affiliation: Dpto. Química Orgánica y Biología, Facultad de Ciencias, UNED, Madrid, Spain.
authors.forename: P
authors.initials: P
authors.lastname: López
authors.forename: C G
authors.initials: CG
authors.lastname: Seipelt
authors.forename: P
authors.initials: P
authors.lastname: Merkling
authors.forename: L
authors.initials: L
authors.lastname: Sturz
authors.forename: J
authors.initials: J
authors.lastname: Alvarez
authors.forename: A
authors.initials: A
authors.lastname: Dölle
authors.forename: M D
authors.initials: MD
authors.lastname: Zeidler
authors.forename: S
authors.initials: S
authors.lastname: Cerdán
authors.forename: P
authors.initials: P
authors.lastname: Ballesteros
mesh_terms: D000085:Acetates / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D002118:Calcium / Q000737:chemistry; D006528:Carcinoma, Hepatocellular / Q000201:enzymology / Q000473:pathology; D002614:Chelating Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D003287:Contrast Media / Q000737:chemistry*; D005682:Gadolinium / Q000737:chemistry*; D007770:L-Lactate Dehydrogenase / Q000378:metabolism; D008279:Magnetic Resonance Imaging; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013816:Thermodynamics; D014407:Tumor Cells, Cultured
chemical_list: D000085:Acetates; D002614:Chelating Agents; D003287:Contrast Media; D005682:Gadolinium; D007770:L-Lactate Dehydrogenase; D002118:Calcium