用于分子成像和放射治疗的碳水化合物缀合物：N-(2'-羟基苄基)-2-氨基-2-脱氧-D-葡萄糖的99mTc(I)和186Re(I)三羰基配合物

Carbohydrate conjugates for molecular imaging and radiotherapy: 99mTc(I) and 186Re(I) tricarbonyl complexes of N-(2'-Hydroxybenzyl)-2-amino-2-deoxy-D-glucose.

作者信息

Bayly Simon R, Fisher Cara L, Storr Tim, Adam Michael J, Orvig Chris

机构信息

Department of Chemistry, University of British Columbia, 2036 Main Mall, Vancouver, V6T 1Z1, Canada.

出版信息

Bioconjug Chem. 2004 Jul-Aug;15(4):923-6. doi: 10.1021/bc0499681.

DOI:10.1021/bc0499681

PMID:15264883

Abstract

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.

摘要

通过用99mTc和186Re的三羰基对葡糖胺衍生物进行标记，展示了一种制备新型潜在放射性药物的方法。前体配体HL2（N-(2'-羟基苄基)-2-氨基-2-脱氧-D-葡萄糖）通过相应席夫碱的氢化反应制得，并与[NEt4]2[Re(CO)3Br3]反应，以40%的产率形成中性配合物[(L2)Re(CO)3]。1H和13C NMR光谱表明，[Re(CO)3]核心通过配体的氨基N、酚氧基O和C-3羟基O原子以三齿方式配位。在示踪剂水平上，在水性条件下，HL2分别与[99mTc(CO)3(H2O)3]+和[186Re(CO)3(H2O)3]+进行标记，平均放射化学产率分别为95±2%和94±3%。