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

11 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
StatePublished - Dec 6 2017

ASJC Scopus subject areas

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

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    Zhang, L., Martins, A. F., Zhao, P., Tieu, M., Esteban-Gómez, D., McCandless, G. T., Platas-Iglesias, C., & Sherry, A. D. (2017). Enantiomeric Recognition of d - And l -Lactate by CEST with the Aid of a Paramagnetic Shift Reagent. Journal of the American Chemical Society, 139(48), 17431-17437. https://doi.org/10.1021/jacs.7b08292