Enantiomeric Recognition of d - And l -Lactate by CEST with the Aid of a Paramagnetic Shift Reagent

Lei Zhang, André F. Martins, Piyu Zhao, Michael Tieu, David Esteban-Gómez, Gregory T. McCandless, Carlos Platas-Iglesias, A. Dean Sherry

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)17431-17437
Number of pages7
JournalJournal of the American Chemical Society
Volume139
Issue number48
DOIs
Publication statusPublished - Dec 6 2017

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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