Carbohydrate-appended 2,2′-dipicolylamine metal complexes as potential imaging agents
Carbohydrate-appended 2,2′-dipicolylamine metal complexes as potential imaging agents
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DOI：
10.1021/ic048528i
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发表时间：
2005-04-18
影响因子：
4.6
通讯作者：
Orvig, C
中科院分区：
文献类型：
--
作者：
Storr, T;Sugai, Y;Orvig, C
三个离散的附接有碳水化合物的2，2 ′-吡啶二甲基胺配体与{M（CO）3}（+）（M = Tc-99 m/ Re）核心络合：2-（双（2-吡啶基甲基）氨基）乙基-β-D-吡喃葡萄糖苷（L-1）、2-（双（2-吡啶基甲基）氨基）乙基-β-D-吡喃木糖糖苷（L-2）和2-（双（2-吡啶基甲基）氨基）乙基-α-D-吡喃甘露糖苷（L-3）。乙烯间隔基用于分离所有三个配体中的碳水化合物部分和吡啶二甲基胺（DPA）官能团。配合物[Re（L1-3）（CO）（3）]Br的结构经H-1和C-13一维/二维核磁共振谱表征，证实了配合物在溶液中的侧链性质。NMR测量也建立了远程不对称效应的碳水化合物功能上的螯合部分的配体。一个类似物，[Re（L-1）（CO）（3）]Cl，其特征在于在固态的X-射线晶体学。通过红外光谱、元素分析、电导率和质谱法提供进一步表征。用[Tc-99 m（H_2O）（3）（CO）（3）]（+）标记L-1-L-3，得到高产率的与Re类似物性质相同的化合物。发现放射性标记的化合物在24小时内存在大量过量的半胱氨酸或组氨酸时对配体交换是稳定的。
Three discrete carbohydrate-appended 2,2'-dipicolylamine ligands were complexed to the {M(CO)3}(+) (M = Tc-99m/ Re) core: 2-(bis(2-pyridinylmethyl)amino)ethyl-beta-D-glucopyranoside (L-1), 2-(bis(2-pyridinylmethyl)amino)ethyl-beta-Dxylopyranoside (L-2), and 2-(bis(2-pyridinylmethyl)amino)ethyl-alpha-D-mannopyranoside (L-3). An ethylene spacer is used to separate the carbohydrate moiety and the dipicolylamine (DPA) function in all three ligands. The Re complexes [Re(L1-3)(CO)(3)]Br were characterized by H-1 and C-13 1D/2D NMR spectroscopies, which confirmed the pendant nature of the carbohydrate moieties in solution. NMR measurements also established the long-range asymmetric effect of the carbohydrate functions on the chelating portion of the ligand. One analogue, [Re(L-1)(CO)(3)]Cl, was characterized in the solid state by X-ray crystallography. Further characterization was provided by IR spectroscopy, elemental analysis, conductivity, and mass spectrometry. Radiolabeling of L-1-L-3 with [Tc-99m(H2O)(3)(CO)(3)](+) afforded high yield compounds of identical character to the Re analogues. The radiolabeled compounds were found to be stable toward ligand exchange in the presence of a large excess of either cysteine or histidine over a 24-h period.