Conjugation of a novel histidine derivative to biomolecules and labelling with [99mTc(OH2)3(CO)3]+

被引:47
作者
van Staveren, DR
Mundwiler, S
Hoffmanns, U
Pak, JK
Spingler, B
Metzler-Nolte, N
Alberto, R
机构
[1] Univ Zurich, Inst Inorgan Chem, CH-8057 Zurich, Switzerland
[2] Heidelberg Univ, Inst Pharm & Mol Biotechnol, D-69120 Heidelberg, Germany
关键词
D O I
10.1039/b405575f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The new histidine derivative 3-{1-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propyl]-1H-imidazol-4-yl}-2-(3-trimethylsilanyl- ethylcarboxyamino)-propionic acid methyl ester ( 7) has been prepared via alkylation of the histidine urea derivative (7S)-5,6,7,8-tetrahydro-7-(methoxycarbonyl)-5-oxoimidazo-[1,5-c]-pyrimidine ( 2) with Fmoc-protected 3-iodopropyl-amine, followed by ring opening with 2-trimethylsilylethanol. After Fmoc cleavage by HNEt2, the histidine amine derivative was coupled to biotin, to the pentapeptide leucine-enkephalin and to Vitamin B12-b-acid by amide formation, employing TBTU as the coupling reagent. In order to make the histidine accessible for labelling, the teoc protecting group was removed by either NBu4F ( for the biotin conjugate) or by TFA ( for the enkephalin and B12 conjugates). Reaction of a 10(-4) M solution of the bioconjugates with [Tc-99m(H2O)(3)(CO)(3)](+) at 50 degreesC for 30 min led to the formation of one single new peak in the HPLC radiochromatogram in each case, confirming quantitative labelling of the respective biomolecules. To assess the nature of the labelled compounds, the rhenium analogues with Re(CO)(3) were also synthesised and similar retention times confirmed the identity with the Tc-99m labelled conjugates.
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页码:2593 / 2603
页数:11
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