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Hyperpolarization of 15N-pyridinium and 15N-aniline derivatives by using parahydrogen: new opportunities to store nuclear spin polarization in aqueous media

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Abstract

Hyperpolarization techniques hold the promise to improve the sensitivity of magnetic resonance imaging (MRI) contrast agents by over 10 000-fold. Among these techniques, para-hydrogen induced polarization (PHIP) allows for generating contrast agents within seconds. Typical hyperpolarized contrast agents are traceable for 2–3 minutes only, thus prolonging tracking-times holds great importance for the development of new ways to diagnose and monitor diseases. Here, we report on the design of perdeuterated 15N-containing molecules with longitudinal relaxation times (T1) of several minutes. T1 is a measure for how long hyperpolarization can be stored. In particular, we introduce two new hyperpolarizable families of compounds that we signal enhanced with para-hydrogen: tert-amine aniline derivatives and a quaternary pyridinium compound with 15N-T1 of about 8 minutes. Especially the latter compound has great potential for applicability since we achieved 15N-polarization up to 8% and the pyridinium motif is contained in a variety of drug molecules and is also used in drug delivery systems.

Graphical abstract: Hyperpolarization of 15N-pyridinium and 15N-aniline derivatives by using parahydrogen: new opportunities to store nuclear spin polarization in aqueous media

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Publication details

The article was received on 17 Jun 2019, accepted on 30 Jul 2019 and first published on 06 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC02970B
Chem. Sci., 2019, Advance Article
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    Hyperpolarization of 15N-pyridinium and 15N-aniline derivatives by using parahydrogen: new opportunities to store nuclear spin polarization in aqueous media

    A. P. Jagtap, L. Kaltschnee and S. Glöggler, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC02970B

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