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Rotaxane Probes for the Detection of Hydrogen Peroxide by 129 Xe HyperCEST NMR Spectroscopy
Author(s) -
Klass Sarah H.,
Truxal Ashley E.,
Fiala Tahoe A.,
Kelly Joseph,
Nguyen Dang,
Finbloom Joel A.,
Wemmer David E.,
Pines Alexander,
Francis Matthew B.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201903045
Subject(s) - chemistry , nuclear magnetic resonance spectroscopy , hydrogen peroxide , proton nmr , molecule , spectroscopy , nuclear magnetic resonance , stereochemistry , organic chemistry , physics , quantum mechanics
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 H 2 O 2 , which is upregulated in several disease states. Added H 2 O 2 was detected by 129 Xe hyperCEST NMR spectroscopy in the low micromolar range, as well as H 2 O 2 produced by HEK 293T cells activated with tumor necrosis factor.