Rotaxane Probes for the Detection of Hydrogen Peroxide by 129 Xe HyperCEST NMR Spectroscopy

Angew Chem Int Ed Engl. 2019 Jul 15;58(29):9948-9953. doi: 10.1002/anie.201903045. Epub 2019 Jun 11.

Abstract

The development of sensitive and chemically selective MRI contrast agents is imperative for the early detection and diagnosis of many diseases. Conventional responsive contrast agents used in 1 H MRI are impaired by the high abundance of protons in the body. 129 Xe hyperCEST NMR/MRI comprises a highly sensitive complement to traditional 1 H MRI because of its ability to report specific chemical environments. To date, the scope of responsive 129 Xe NMR contrast agents lacks breadth in the specific detection of small molecules, which are often important markers of disease. Herein, we report the synthesis and characterization of a rotaxane-based 129 Xe hyperCEST NMR contrast agent that can be turned on in response to H2 O2 , which is upregulated in several disease states. Added H2 O2 was detected by 129 Xe hyperCEST NMR spectroscopy in the low micromolar range, as well as H2 O2 produced by HEK 293T cells activated with tumor necrosis factor.

Keywords: NMR spectroscopy; cucurbit[6]uril; rotaxanes; sensors; xenon.

Publication types

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

MeSH terms

  • Hydrogen Peroxide / metabolism*
  • Magnetic Resonance Spectroscopy / methods*
  • Rotaxanes / therapeutic use*

Substances

  • Rotaxanes
  • Hydrogen Peroxide