Carbohydrate Conjugates for Molecular Imaging and Radiotherapy:  99mTc(I) and 186Re(I) Tricarbonyl Complexes of N-(2‘-Hydroxybenzyl)-2-amino-2-deoxy-d-glucose

• Published in: Bioconjugate chemistry 2004-07, Vol.15 (4), p.923-926
• Main Authors: Bayly, Simon R, Fisher, Cara L, Storr, Tim, Adam, Michael J, Orvig, Chris
• Format: Article
• Language: English
• Subjects: Carbohydrates; Carbohydrates - chemistry; Chromatography, High Pressure Liquid; Glucosamine - analogs & derivatives; Glucosamine - chemical synthesis; Glucosamine - chemistry; Glucose; Labeling; Magnetic Resonance Imaging - instrumentation; Magnetic Resonance Spectroscopy; Molecular Structure; Molecules; Radioisotopes; Radiopharmaceuticals - chemistry; Rhenium - chemistry; Rhenium - therapeutic use; Scientific imaging; Technetium Compounds - chemical synthesis; Technetium Compounds - chemistry; Technetium Compounds - therapeutic use
• ISSN: 1043-1802; 1520-4812
• DOI: 10.1021/bc0499681

An approach to a new class of potential radiopharmaceuticals is demonstrated by the labeling of a glucosamine derivative with the tricarbonyls of 99mTc and 186Re. The proligand HL 2 (N-(2‘-hydroxybenzyl)-2-amino-2-deoxy-d-glucose) was produced by hydrogenation of the corresponding Schiff base and reacted with [NEt4]2[Re(CO)3Br3] to form the neutral complex [(L 2 )Re(CO)3] in 40% yield. 1H and 13C NMR spectra indicate that the {Re(CO)3} core is bound in a tridentate fashion via the amino N, phenolato O, and C-3 hydroxyl O atoms of the ligand. At the tracer-level, labeling of HL 2 with [99mTc(CO)3(H2O)3]+ and [186Re(CO)3(H2O)3]+ was achieved in aqueous conditions in 95 ± 2% and 94 ± 3% average radiochemical yields, respectively.