Ratiometric pH-Responsive 19F Magnetic Resonance Imaging Contrast Agents Based on Hydrazone Switches

Dawid Janasik; Krzysztof Jasiński; Władysław P Węglarz; Ivan Nemec; Pawel Jewula; Tomasz Krawczyk

doi:10.1021/acs.analchem.1c04978

Ratiometric pH-Responsive ¹⁹F Magnetic Resonance Imaging Contrast Agents Based on Hydrazone Switches

Anal Chem. 2022 Mar 1;94(8):3427-3431. doi: 10.1021/acs.analchem.1c04978. Epub 2022 Feb 14.

Authors

Dawid Janasik¹, Krzysztof Jasiński², Władysław P Węglarz², Ivan Nemec^{3

4}, Pawel Jewula³, Tomasz Krawczyk¹

Affiliations

¹ Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology Krzywoustego 4,44-100 Gliwice, Poland.
² Institute of Nuclear Physics Polish Academy of Sciences, 31-342 Krakow, Poland.
³ Central European Institute of Technology Brno University of Technology, Purkyňova 123, 612-00 Brno, Czech Republic.
⁴ Department of Inorganic Chemistry, Faculty of Science, Palacký University 17. Listopadu 1192/12, 771 46 Olomouc, Czech Republic.

Abstract

Hydrazone-based molecular switches serve as efficient ratiometric pH-sensitive agents that can be tracked with ¹⁹F NMR/MRI and ¹H NMR. Structural changes induced between pH 3 and 4 lead to signal appearance and disappearance at ¹H and ¹⁹F NMR spectra allowing ratiometric pH measurements. The most pronounced are resonances of the CF₃ group shifted by 1.8 ppm with ¹⁹F NMR and a hydrazone proton shifted by 2 ppm with ¹H NMR.

Publication types

Letter
Research Support, Non-U.S. Gov't

MeSH terms

Contrast Media* / chemistry
Hydrazones* / chemistry
Hydrogen-Ion Concentration
Magnetic Resonance Imaging / methods
Magnetic Resonance Spectroscopy

Substances

Contrast Media
Hydrazones