Carbohydrate conjugates for molecular imaging and radiotherapy: 99mTc(I) and 186Re(I) tricarbonyl complexes of N-(2'-Hydroxybenzyl)-2-amino-2-deoxy-D-glucose.
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 HL2 (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 [(L2)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 HL2 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.
Bayly
Simon R
SR
Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, V6T 1Z1, Canada.
Fisher
Cara L
CL
Storr
Tim
T
Adam
Michael J
MJ
Orvig
Chris
C
D002241:Carbohydrates / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*; D008279:Magnetic Resonance Imaging / Q000295:instrumentation*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011868:Radioisotopes; D019275:Radiopharmaceuticals / Q000737:chemistry*; D012211:Rhenium / Q000737:chemistry* / Q000627:therapeutic use; D017556:Technetium Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use
D002241:Carbohydrates; C495579:N-(2'-hydroxybenzyl)-2-amino-2-deoxyglucose; D011868:Radioisotopes; D019275:Radiopharmaceuticals; D017556:Technetium Compounds; D012211:Rhenium; D005944:Glucosamine