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Enantiomeric Recognition of d- and l-Lactate by CEST with the Aid of a Paramagnetic Shift Reagent
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2017-11-17 00:00:00 , DOI: 10.1021/jacs.7b08292
Lei Zhang 1 , André F. Martins 1, 2 , Piyu Zhao 1 , Michael Tieu 1 , David Esteban-Gómez 3 , Gregory T. McCandless 1 , Carlos Platas-Iglesias 3 , A. Dean Sherry 1, 2
Affiliation  

A previous report demonstrated that EuDO3A could be used as an NMR shift reagent for imaging extracellular lactate produced by cancer cells using CEST imaging. In this work, a series of heptadentate macrocyclic YbDO3A-trisamide complexes with δ-chiral carbons in the three pendant side-arms were examined as shift reagents for lactate detection. High resolution 1H NMR spectra and DFT calculations provided evidence for the formation of stereoselective lactate·YbDO3A-trisamide complexes each with a different CEST signature. This stereoselectivity allowed discrimination of d- versus l-lactate by both high-resolution NMR and CEST. This work demonstrates that lanthanide-based paramagnetic shift reagents can be designed to detect important metabolites by CEST MRI selectively.

中文翻译:

CEST在顺磁性位移试剂的帮助下对d和l乳酸酯的对映体识别

先前的报告表明EuDO3A可用作NMR移位试剂,用于使用CEST成像对癌细胞产生的细胞外乳酸进行成像。在这项工作中,研究了三个悬垂侧臂中带有δ手性碳的一系列七齿大环YbDO3A-三酰胺配合物作为乳酸检测的转移试剂。高分辨率的1 H NMR光谱和DFT计算为形成立体选择性的乳酸·YbDO3A-三酰胺复合物提供了证据,每种复合物具有不同的CEST标记。这种立体选择性可以区分d-l-通过高分辨率NMR和CEST进行乳酸酯化。这项工作表明,可以设计基于镧系元素的顺磁转移试剂,以通过CEST MRI选择性检测重要的代谢物。
更新日期:2017-11-19
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