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

J Am Chem Soc. 2017 Dec 6;139(48):17431-17437. doi: 10.1021/jacs.7b08292. Epub 2017 Nov 17.


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.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Indicators and Reagents
  • Lactic Acid / analysis*
  • Lactic Acid / chemistry*
  • Lanthanoid Series Elements / chemistry*
  • Magnetic Resonance Spectroscopy / methods*


  • Indicators and Reagents
  • Lanthanoid Series Elements
  • Lactic Acid