Glucosamine Conjugates of Tricarbonylcyclopentadienyl Rhenium(I) and Technetium(I) Cores

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• 作者：Cara L. Ferreira ; Charles B. Ewart ; Simon R. Bayly ; Brian O. Patrick ; Jennifer Steele ; Michael J. Adam ; Chris Orvig
• 刊名：Inorganic Chemistry
• 出版年：2006
• 出版时间：August 21, 2006
• 年：2006
• 卷：45
• 期：17
• 页码：6979 - 6987
• 全文大小：166K
• 年卷期：v.45,no.17(August 21, 2006)
• ISSN：1520-510X

文摘

To obtain a ^99mTc glucose conjugate for imaging, double-ligand transfer (DLT) and related reactions were examinedfor the preparation of CpM(CO)₃ (Cp = cyclopentadienyl; M = Re, Tc) complexes with pendant carbohydrates atCp. Tricarbonyl{N-(1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy--D-glucopyranose)cyclopentadienyl carboxamide}rhenium(I) (1a) and tricarbonyl{N-(2-amino-2-deoxy--D-glucopyranose)cyclopentadienyl carboxamide}rhenium(I) (2a) wereprepared. The compounds were fully characterized by mass spectrometry, elemental analysis, IR, and NMRspectroscopy. Full assignment of the NMR spectra verified the pendant nature of the glucosamine moieties in thesolution state and that 2a exists as both anomers. The solid-state structure of 2a was determined by X-raycrystallography, again confirming the pendant nature of the glucosamine, but differing from the solution state inthat the anomer crystallized preferentially (93%). Compound 2a was determined to be a high-affinity competitiveinhibitor (K_i = 330 ± 70 M) of the glucose metabolism enzyme hexokinase, demonstrating that it retains certainbiological activity. The ^99mTc analogues 1b and 2b were prepared in moderate radiochemical yields by means ofthe single-ligand transfer (SLT) route, which is more pertinent to radiopharmaceutical synthesis.