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

3 Citations (Scopus)

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

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Lactic Acid
Nuclear magnetic resonance
Imaging techniques
Stereoselectivity
Lanthanoid Series Elements
Metabolites
Rare earth elements
Discrete Fourier transforms
Magnetic resonance imaging
Carbon
Cells
Neoplasms
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

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

Cite this

Enantiomeric Recognition of d - And l -Lactate by CEST with the Aid of a Paramagnetic Shift Reagent. / Zhang, Lei; Martins, André F.; Zhao, Piyu; Tieu, Michael; Esteban-Gómez, David; McCandless, Gregory T.; Platas-Iglesias, Carlos; Sherry, A. Dean.

In: Journal of the American Chemical Society, Vol. 139, No. 48, 06.12.2017, p. 17431-17437.

Research output: Contribution to journalArticle

Zhang, L, Martins, AF, Zhao, P, Tieu, M, Esteban-Gómez, D, McCandless, GT, Platas-Iglesias, C & Sherry, AD 2017, 'Enantiomeric Recognition of d - And l -Lactate by CEST with the Aid of a Paramagnetic Shift Reagent', Journal of the American Chemical Society, vol. 139, no. 48, pp. 17431-17437. https://doi.org/10.1021/jacs.7b08292
Zhang, Lei ; Martins, André F. ; Zhao, Piyu ; Tieu, Michael ; Esteban-Gómez, David ; McCandless, Gregory T. ; Platas-Iglesias, Carlos ; Sherry, A. Dean. / Enantiomeric Recognition of d - And l -Lactate by CEST with the Aid of a Paramagnetic Shift Reagent. In: Journal of the American Chemical Society. 2017 ; Vol. 139, No. 48. pp. 17431-17437.
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